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Sample records for benzaldehyde thiosemicarbazone derivatives

  1. Benzaldehyde thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Xiu-Ping Ju

    2008-12-01

    Full Text Available The title compound, C8H9N3S, contains two molecules in the asymmetric unit. One molecule is close to being planar (r.m.s. deviation from the mean plane = 0.06 Å for the non-H atoms, while the other exhibits a dihedral angle of 21.7 (1° between the benzene ring and the mean plane of the thiosemicarbazone unit. Intermolecular N—H...S hydrogen bonds link the molecules into layers parallel to the (010 plane.

  2. Antitrypanosomal Activity of Novel Benzaldehyde-Thiosemicarbazone Derivatives from Kaurenoic Acid †

    OpenAIRE

    2011-01-01

    A series of new thiosemicarbazones derived from natural diterpene kaurenoic acid were synthesized and tested against the epimastigote forms of Trypanosoma cruzi to evaluate their antitrypanosomal potential. Seven of the synthesized thiosemicarbazones were more active than kaurenoic acid with IC50 values between 2-24.0 mM. The o-nitro-benzaldehyde-thiosemicarbazone derivative was the most active compound with IC50 of 2.0 mM. The results show that the structural modifications accomplished enhan...

  3. Antitrypanosomal Activity of Novel Benzaldehyde-Thiosemicarbazone Derivatives from Kaurenoic Acid †

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    Cecília M. A. de Oliveira

    2011-01-01

    Full Text Available A series of new thiosemicarbazones derived from natural diterpene kaurenoic acid were synthesized and tested against the epimastigote forms of Trypanosoma cruzi to evaluate their antitrypanosomal potential. Seven of the synthesized thiosemicarbazones were more active than kaurenoic acid with IC50 values between 2-24.0 mM. The o-nitro-benzaldehyde-thiosemicarbazone derivative was the most active compound with IC50 of 2.0 mM. The results show that the structural modifications accomplished enhanced the antitrypanosomal activity of these compounds. Besides, the thiocyanate, thiosemicarbazide and the p- methyl, p-methoxy, p-dimethylamine, m-nitro and o-chlorobenzaldehyde-thiosemicarbazone derivatives displayed lower toxicity for LLMCK2 cells than kaurenoic acid, exhibing an IC50 of 59.5 mM.

  4. Benzaldehyde Thiosemicarbazone Derived from Limonene Complexed with Copper Induced Mitochondrial Dysfunction in Leishmania amazonensis

    OpenAIRE

    Britta, Elizandra Aparecida; Barbosa Silva, Ana Paula; Ueda-Nakamura, Tânia; Dias-Filho, Benedito Prado; Silva, Cleuza Conceição; Sernaglia, Rosana Lázara; Nakamura, Celso Vataru

    2012-01-01

    Background Leishmaniasis is a major health problem that affects more than 12 million people. Treatment presents several problems, including high toxicity and many adverse effects, leading to the discontinuation of treatment and emergence of resistant strains. Methodology/Principal Findings We evaluated the in vitro antileishmanial activity of benzaldehyde thiosemicarbazone derived from limonene complexed with copper, termed BenzCo, against Leishmania amazonensis. BenzCo inhibited the growth o...

  5. Simultaneous second derivative spectrophotometric determination of cobalt and vanadium using 2-hydroxy-3-methoxy benzaldehyde thiosemicarbazone

    International Nuclear Information System (INIS)

    2-Hydroxy-3-methoxy benzaldehyde thiosemicarbazone reacts with cobalt(II) and vanadium(V) at pH 6.0 forming respectively brown and green coloured complexes in aqueous dimethyl formamide. The second derivative spectrum of Co(II) complex shows zero amplitude at 434.5 nm and considerably large amplitude at 409.5 nm, while V(V) complex shows sufficient amplitude at 434.5 nm and zero amplitude at 409.5 nm. Further, the derivative amplitudes obey Beer's law at 409.5 and 434.5 nm for Co(II) and V(V) in the range 0.059-3.535 and 0.051-4.074 μg/ml, respectively. This enables the simultaneous determination of Co(II) and V(V) without separation. A large number of foreign ions do not interfere in the present method. The method is applied to the simultaneous determination of Co(II) and V(V) in synthetic mixtures and alloy steel samples

  6. Benzaldehyde Thiosemicarbazone Derived from Limonene Complexed with Copper Induced Mitochondrial Dysfunction in Leishmania amazonensis

    Science.gov (United States)

    Britta, Elizandra Aparecida; Barbosa Silva, Ana Paula; Ueda-Nakamura, Tânia; Dias-Filho, Benedito Prado; Silva, Cleuza Conceição; Sernaglia, Rosana Lázara; Nakamura, Celso Vataru

    2012-01-01

    Background Leishmaniasis is a major health problem that affects more than 12 million people. Treatment presents several problems, including high toxicity and many adverse effects, leading to the discontinuation of treatment and emergence of resistant strains. Methodology/Principal Findings We evaluated the in vitro antileishmanial activity of benzaldehyde thiosemicarbazone derived from limonene complexed with copper, termed BenzCo, against Leishmania amazonensis. BenzCo inhibited the growth of the promastigote and axenic amastigote forms, with IC50 concentrations of 3.8 and 9.5 µM, respectively, with 72 h of incubation. Intracellular amastigotes were inhibited by the compound, with an IC50 of 10.7 µM. BenzCo altered the shape, size, and ultrastructure of the parasites. Mitochondrial membrane depolarization was observed in protozoa treated with BenzCo but caused no alterations in the plasma membrane. Additionally, BenzCo induced lipoperoxidation and the production of mitochondrial superoxide anion radicals in promastigotes and axenic amastigotes of Leishmania amazonensis. Conclusion/Significance Our studies indicated that the antileishmania activity of BenzCo might be associated with mitochondrial dysfunction and oxidative damage, leading to parasite death. PMID:22870222

  7. Benzaldehyde thiosemicarbazone derived from limonene complexed with copper induced mitochondrial dysfunction in Leishmania amazonensis.

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    Elizandra Aparecida Britta

    Full Text Available BACKGROUND: Leishmaniasis is a major health problem that affects more than 12 million people. Treatment presents several problems, including high toxicity and many adverse effects, leading to the discontinuation of treatment and emergence of resistant strains. METHODOLOGY/PRINCIPAL FINDINGS: We evaluated the in vitro antileishmanial activity of benzaldehyde thiosemicarbazone derived from limonene complexed with copper, termed BenzCo, against Leishmania amazonensis. BenzCo inhibited the growth of the promastigote and axenic amastigote forms, with IC(50 concentrations of 3.8 and 9.5 µM, respectively, with 72 h of incubation. Intracellular amastigotes were inhibited by the compound, with an IC(50 of 10.7 µM. BenzCo altered the shape, size, and ultrastructure of the parasites. Mitochondrial membrane depolarization was observed in protozoa treated with BenzCo but caused no alterations in the plasma membrane. Additionally, BenzCo induced lipoperoxidation and the production of mitochondrial superoxide anion radicals in promastigotes and axenic amastigotes of Leishmania amazonensis. CONCLUSION/SIGNIFICANCE: Our studies indicated that the antileishmania activity of BenzCo might be associated with mitochondrial dysfunction and oxidative damage, leading to parasite death.

  8. Synthesis, Characterization, and In Vitro Cytotoxic Activities of Benzaldehyde Thiosemicarbazone Derivatives and Their Palladium (II) and Platinum (II) Complexes against Various Human Tumor Cell Lines

    Science.gov (United States)

    Hernándeza, Wilfredo; Paz, Juan; Vaisberg, Abraham; Spodine, Evgenia; Richter, Rainer; Beyer, Lothar

    2008-01-01

    The palladium (II) bis-chelate Pd (L1−3)2 and platinum (II) tetranuclear Pt4(L4)4 complexes of benzaldehyde thiosemicarbazone derivatives have been synthesized, and characterized by elemental analysis and IR, FAB(+)-mass and NMR (1H, 13C) spectroscopy. The complex Pd(L2)2 [HL2 = m-CN-benzaldehyde thiosemicarbazone] shows a square-planar geometry with two deprotonated ligands (L) coordinated to PdII through the nitrogen and sulphur atoms in a transarrangement, while the complex Pt4(L4)4 [HL4 = 4-phenyl-1-benzaldehyde thiosemicarbazone] has a tetranuclear geometry with four tridentate ligands coordinated to four PtII ions through the carbon (aromatic ring), nitrogen, and sulphur atoms where the ligands are deprotonated at the NH group. The in vitro antitumor activity of the ligands and their complexes was determined against different human tumor cell lines, which revealed that the palladium (II) and platinum (II) complexes are more cytotoxic than their ligands with IC50 values at the range of 0.07–3.67 μM. The tetranuclear complex Pt4(L4)4, with the phenyl group in the terminal amine of the ligand, showed higher antiproliferative activity (CI50 = 0.07–0.12 μM) than the other tested palladium (II) complexes. PMID:19148285

  9. Synthesis, Characterization, and In Vitro Cytotoxic Activities of Benzaldehyde Thiosemicarbazone Derivatives and Their Palladium (II and Platinum (II Complexes against Various Human Tumor Cell Lines

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    Lothar Beyer

    2009-01-01

    Full Text Available The palladium (II bis-chelate Pd (L1−32 and platinum (II tetranuclear Pt4(L44 complexes of benzaldehyde thiosemicarbazone derivatives have been synthesized, and characterized by elemental analysis and IR, FAB(+-mass and NMR (1H,13C spectroscopy. The complex Pd(L22 [HL2=m-CN-benzaldehyde thiosemicarbazone] shows a square-planar geometry with two deprotonated ligands (L coordinated to PdII through the nitrogen and sulphur atoms in a transarrangement, while the complex Pt4(L44 [HL4=4-phenyl-1-benzaldehyde thiosemicarbazone] has a tetranuclear geometry with four tridentate ligands coordinated to four PtII ions through the carbon (aromatic ring, nitrogen, and sulphur atoms where the ligands are deprotonated at the NH group. The in vitro antitumor activity of the ligands and their complexes was determined against different human tumor cell lines, which revealed that the palladium (II and platinum (II complexes are more cytotoxic than their ligands with IC50 values at the range of 0.07–3.67 μM. The tetranuclear complex Pt4(L44, with the phenyl group in the terminal amine of the ligand, showed higher antiproliferative activity (CI50 = 0.07–0.12 μM than the other tested palladium (II complexes.

  10. Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis.

    Science.gov (United States)

    de Melos, Jorge Luiz R; Torres-Santos, Eduardo Caio; Faiões, Viviane dos S; Del Cistia, Catarina de Nigris; Sant'Anna, Carlos Maurício R; Rodrigues-Santos, Cláudio Eduardo; Echevarria, Aurea

    2015-10-20

    A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC₅₀ = 20.74 μM and 16.40 μM, respectively. The intracellular amastigotes assays showed IC₅₀ = 22.00 μM (22) and 17.00 μM (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. PMID:26375353

  11. Coordination compounds of titanium (4), zirconium (4) and hafnium (4) with thiosemicarbazone of benzaldehyde

    International Nuclear Information System (INIS)

    Adducts of titanium (4), zirconium (4) and hafnium (4) tetrachlorides with thiosemicarbazone of benzaldehyde of the MCl4xLig and MCl4x2Lig composition are extracted from solutions in nonaqueous ethylacetate. On the basis of infrared spectra in the range of 250-4000 cm-1 a conclusion is drawn about participation of azomethine nitrogen and sulfur atoms in coordination with metal. Studied is the behaviour of synthetized adducts and their components in absolute methanol with the help of paper chromatography, measurement of electric conductivity and pH. It is established that adduct decomposition and simultaneous metal tetrachloride solvolysis take place at dissolving in the alcohol

  12. Structural, thermal and optical characterization of an organic NLO material—Benzaldehyde thiosemicarbazone monohydrate single crystals

    Science.gov (United States)

    Santhakumari, R.; Ramamurthi, K.

    2011-02-01

    Single crystals of the organic NLO material, benzaldehyde thiosemicarbazone (BTSC) monohydrate, were grown by slow evaporation method. Solubility of BTSC monohydrate was determined in ethanol at different temperatures. The grown crystals were characterized by single crystal X-ray diffraction analysis to determine the cell parameters and by FT-IR technique to study the presence of the functional groups. Thermogravimetric and differential thermal analyses reveal the thermal stability of the crystal. UV-vis-NIR spectrum shows excellent transmission in the region of 200-1100 nm. Theoretical calculations were carried out to determine the linear optical constants such as extinction coefficient and refractive index. Further the optical nonlinearities of BTSC have been investigated by Z-scan technique with He-Ne laser radiation of wavelength 632.8 nm. Mechanical properties of the grown crystal were studied using Vickers microhardness tester. Second harmonic generation efficiency of the powdered BTSC monohydrate was tested using Nd:YAG laser and it is found to be ˜5.3 times that of potassium dihydrogen orthophosphate.

  13. Vibrational, NMR and UV-visible spectroscopic investigation and NLO studies on benzaldehyde thiosemicarbazone using computational calculations

    Science.gov (United States)

    Moorthy, N.; Prabakar, P. C. Jobe; Ramalingam, S.; Pandian, G. V.; Anbusrinivasan, P.

    2016-04-01

    In order to investigate the vibrational, electronic and NLO characteristics of the compound; benzaldehyde thiosemicarbazone (BTSC), the XRD, FT-IR, FT-Raman, NMR and UV-visible spectra were recorded and were analysed with the calculated spectra by using HF and B3LYP methods with 6-311++G(d,p) basis set. The XRD results revealed that the stabilized molecular systems were confined in orthorhombic unit cell system. The cause for the change of chemical and physical properties behind the compound has been discussed makes use of Mulliken charge levels and NBO in detail. The shift of molecular vibrational pattern by the fusing of ligand; thiosemicarbazone group with benzaldehyde has been keenly observed. The occurrence of in phase and out of phase molecular interaction over the frontier molecular orbitals was determined to evaluate the degeneracy of the electronic energy levels. The thermodynamical studies of the temperature region 100-1000 K to detect the thermal stabilization of the crystal phase of the compound were investigated. The NLO properties were evaluated by the determination of the polarizability and hyperpolarizability of the compound in crystal phase. The physical stabilization of the geometry of the compound has been explained by geometry deformation analysis.

  14. Nickel Complexes of Thiosemicarbazone Derivatives of Lawsone

    OpenAIRE

    Sanjay Gaikwad

    2013-01-01

    Thiosemicarbazone derivative at 1 position of the Lawsone ( 2-hydroxy-1,4-naphthalenedione ) i.e. 1-TSCND is an important derivative, Which possesses a powerful chelating ability, appreciable analytical utility and significant biological activity[1]. Its Nickel (II) complex is newly reported here

  15. Nickel Complexes of Thiosemicarbazone Derivatives of Lawsone

    Directory of Open Access Journals (Sweden)

    Sanjay Gaikwad

    2013-06-01

    Full Text Available Thiosemicarbazone derivative at 1 position of the Lawsone ( 2-hydroxy-1,4-naphthalenedione i.e. 1-TSCND is an important derivative, Which possesses a powerful chelating ability, appreciable analytical utility and significant biological activity[1]. Its Nickel (II complex is newly reported here

  16. Synthesis, structural, antibacterial and spectral studies of Co (II) complexes with salicylaldehyde and p-chloro-benzaldehyde 4-phenyl thiosemicarbazone

    International Nuclear Information System (INIS)

    The Co(II) complexes derived from salicylaldehyde 4-phenyl thiosemicarbazone; SaOHtsc, p-chlorobenzaldehyde 4-phenyl thiosemicarbazone; ph-HClbtsc is reported and characterized based on elemental analysis, IR, magnetic susceptibility measurement, 1H and 13C NMR spectra. The Co(II) complexes have the molecular formula CoL2 where the ligand corresponding to SaOHtsc and ph-HClbtsc. The elemental analysis for the ligands and complexes were in a good agreement with the theoretical values. The ligands coordinate to metal ions in different ways which is through mono negative bidentate or di negative tridentate. The magnetic susceptibility measurements showed that the CoL2 complexes with ligand SaOHtsc are diamagnetic thus making this complexes suitable for NMR studies. The signals at the 10.04 ppm were assigned to N2H in the 1H-NMR spectra of the free ligands was absent in the spectra of the complexes due to the deprotonation of the N2H and coordination to the metal centres. The absence of the band in IR spectrum which is assigned to v(N2-H) in the spectra of CoL2 complexes is due to the deprotonation of the ligands upon complexation through azomethine nitrogen and thionic sulphur atom to metal ion. The thiosemicarbazones and its Co(II) complexes showed moderate inhibitory against bacteria Bacillus Subtilis, Staphylococcus Epidermis, Escherichia Coli and Proteus Mirabilis in 10 μg/ disc. (author)

  17. Effect of 4-(N,N-diethylamino)benzaldehyde thiosemicarbazone on the corrosion of aged 18 Ni 250 grade maraging steel in phosphoric acid solution

    International Nuclear Information System (INIS)

    Highlights: → DEABT as corrosion inhibitor for maraging steel in phosphoric acid. → Inhibition efficiency increases with increase in inhibitor concentration. → Inhibition efficiency decreases with increase in temperature. → Adsorption obeys Langmuir adsorption isotherm. - Abstract: 4-(N,N-diethylamino)benzaldehyde thiosemicarbazone (DEABT) was studied for its corrosion inhibition property on the corrosion of aged 18 Ni 250 grade maraging steel in 0.67 M phosphoric acid at 30-50 deg. C by potentiodynamic polarization, EIS and weight loss techniques. Inhibition efficiency of DEABT was found to increase with the increase in DEABT concentration and decrease with the increase in temperature. The activation energy Ea and other thermodynamic parameters (ΔGads0, ΔHads0, ΔSads0) have been evaluated and discussed. The adsorption of DEABT on aged maraging steel surface obeys the Langmuir adsorption isotherm model and the inhibitor showed mixed type inhibition behavior.

  18. Benzaldehyde thiosemicarbazone monohydrate

    Directory of Open Access Journals (Sweden)

    Sheng-Jiu Gu

    2008-08-01

    Full Text Available In the title compound, C8H9N3S·H2O, intramolecular N—H...N hydrogen bonding contributes to the molecular conformation. Water molecules are involved in intermolecular N—H...O and O—H...S hydrogen bonds, which link the molecules into ribbons extended along the a axis. Weak intermolecular N—H...S hydrogen bonds link these ribbons into layers parallel to the ab plane with the phenyl rings pointing up and down.

  19. A theoretical study of benzaldehyde derivatives as tyrosinase inhibitors using Ab initio calculated NQCC parameters

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    Marjan Rafiee

    2015-09-01

    Full Text Available Tyrosinase is a multifunctional copper-containing enzyme. It can catalyze two distinct reactions of melanin synthesis and benzaldehyde derivatives, which are potential tyrosinase inhibitors. To find the relationships between charge distributions of benzaldehyde and their pharmaceutical behavior, the present study aimed at investigating nuclear quadrupole coupling constants of quadrupolare nuclei in the functional benzaldehyde group and calculating some its derivatives. In addition, the differences between the electronic structures of various derivatives of this depigmenting drug were examined. All ab initio calculations were carried out using Gaussian 03. The results predicted benzaldehyde derivatives to be bicentral inhibitors; nevertheless, the oxygen or hydrogen contents of the aldehyde group were not found to be the only active sites. Furthermore with the presence of the aldehyde group, the terminal methoxy group in C4 was found to contribute to tyrosinase inhibitory activities. In addition, an oxygen atom with high charge density in the side chain was found to play an important role in its inhibitory effect.

  20. Reactions with Visnaginone: Synthesis, Cyclisation and Microbial Evaluation of Some Visnaginone Thiosemicarbazone Derivatives

    OpenAIRE

    Sadek Elsayed Abdou; Salah Mohamed El-Qusy; Sami Selim Ghabrial; Mahmoud Ibrahim Haggag

    2011-01-01

    Several new visnaginone ethers were prepared and their thiosemicarbazone derivatives  are  synthesized. The behavior of the thiosemicarbazones in methanolic sodium methoxide and hydrochloric acid is discussed. Structures were established on the bases of elemental and spectral data studies. Some of the thiosemicarbazones were tested for their antimicrobial activity. The structures of the synthesized derivatives (5a-g,6a-g) were confirmed by means of IR, 1H NMR, MS and elemental analyses. The s...

  1. The Effect of the Serum Amino Acid Levels Thiosemicarbazone Derivatives and its Metal Complexes on Rats

    OpenAIRE

    Karatepe, Mustafa; Kaman, Dilara

    2013-01-01

    Advers biological activities of Thiosemicarbazone (TSC) and Schiff base (SB) derivatives have been widely studied in rats and in other animal species using different doses, times and routes of administration. To date, no attempt has been made to study alterations occurring in the amino acid profile in the effects of the thiosemicarbazone derivative and its metal complexes on the rats. At this study, the rats were injected subcutaneously with a new thiosemicarbazone and its LH-Zn and LH-Cu com...

  2. The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives

    OpenAIRE

    Marina Azevedo Souza; Susana Johann; Luciana Alves Rodrigues dos Santos Lima; Fernanda Fraga Campos; Isolda Castro Mendes; Heloisa Beraldo; Elaine Maria de Souza-Fagundes; Patricia Silva Cisalpino; Carlos Augusto Rosa; Tania Maria de Almeida Alves; Nivea Pereira de Sa; Carlos Leomar Zani

    2013-01-01

    Lapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antimicrobial activity against the bacteria Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentrations (MICs) of 0.05 and 0.10 µmol/mL, respectively. The thiosemicarbazone an...

  3. A combined experimental and quantum chemical studies on molecular structure, spectral properties, intra and intermolecular interactions and first hyperpolarizability of 4-(benzyloxy)benzaldehyde thiosemicarbazone and its dimer

    Science.gov (United States)

    Kumar, Amit; Rawat, Poonam; Baboo, Vikas; Verma, Divya; Singh, R. N.; Saxena, Deepti; Gauniyal, H. M.; Pandey, Anoop Kumar; Pal, Harish

    2013-02-01

    In the present work, a detailed spectroscopic analysis of 4-(benzyloxy)benzaldehyde thiosemicarbazone (3) has been carried out using 1H NMR, 13C NMR, UV-Visible and FT-IR spectroscopic techniques. The quantum chemical calculations have been carried out using DFT level of theory, B3LYP functional and 6-31G(d,p) basis set. The calculated thermodynamic parameters show that the formation of 3 is an exothermic and spontaneous reaction at 25 °C. The vibrational analysis indicates the formation of dimer in the solid state by intermolecular hydrogen bonding (Nsbnd H⋯Sdbnd C) and the binding energy of dimer is calculated to be 11.2 kcal/mol, using DFT calculation. NBO analysis is carried out to investigate the charge transfer in various intra and intermolecular interactions involved in dimer. Topological parameters at bond critical points (BCPs) are calculated to analyze the strength and nature of various intra and intermolecular interactions in dimer by Bader's 'Atoms in molecules' AIM theory in detail. The local reactivity descriptors such as Fukui functions (fk+, fk-), local softnesses (sk+, sk-) and electrophilicity indices (ωk+, ωk-) analysis are performed to determine the reactive sites within molecule. Non linear optical (NLO) behavior of title compound is investigated by the computed value of first hyperpolarizability (β0).

  4. The binding of β-d-glucopyranosyl-thiosemicarbazone derivatives to glycogen phosphorylase: A new class of inhibitors.

    Science.gov (United States)

    Alexacou, Kyra-Melinda; Tenchiu Deleanu, Alia-Cristina; Chrysina, Evangelia D; Charavgi, Maria-Despoina; Kostas, Ioannis D; Zographos, Spyros E; Oikonomakos, Nikos G; Leonidas, Demetres D

    2010-11-15

    Glycogen phosphorylase (GP) is a promising target for the treatment of type 2 diabetes. In the process of structure based drug design for GP, a group of 15 aromatic aldehyde 4-(β-d-glucopyranosyl)thiosemicarbazones have been synthesized and evaluated as inhibitors of rabbit muscle glycogen phosphorylase b (GPb) by kinetic studies. These compounds are competitive inhibitors of GPb with respect to α-d-glucose-1-phosphate with IC(50) values ranging from 5.7 to 524.3μM. In order to elucidate the structural basis of their inhibition, the crystal structures of these compounds in complex with GPb at 1.95-2.23Å resolution were determined. The complex structures reveal that the inhibitors are accommodated at the catalytic site with the glucopyranosyl moiety at approximately the same position as α-d-glucose and stabilize the T conformation of the 280s loop. The thiosemicarbazone part of the studied glucosyl thiosemicarbazones possess a moiety derived from substituted benzaldehydes with NO(2), F, Cl, Br, OH, OMe, CF(3), or Me at the ortho-, meta- or para-position of the aromatic ring as well as a moiety derived from 4-pyridinecarboxaldehyde. These fit tightly into the β-pocket, a side channel from the catalytic site with no access to the bulk solvent. The differences in their inhibitory potency can be interpreted in terms of variations in the interactions of the aldehyde-derived moiety with protein residues in the β-pocket. In addition, 14 out of the 15 studied inhibitors were found bound at the new allosteric site of the enzyme. PMID:20947361

  5. DNA binding, DNA cleavage, antioxidant and cytotoxicity studies on ruthenium(II) complexes of benzaldehyde 4-methyl-3-thiosemicarbazones

    Science.gov (United States)

    Sampath, Krishnan; Sathiyaraj, Subbaiyan; Jayabalakrishnan, Chinnasamy

    2013-03-01

    Four new ruthenium(II) complexes with N(4)-methyl thiosemicarbazone ligands, (E)-2-(2-chlorobenzylidene)-N-methylhydrazinecarbothioamide (HL1) and (E)-N-methyl-2-(2-nitrobenzylidene)hydrazinecarbothioamide (HL2), were prepared and fully characterized by various spectro-analytical techniques. The Schiff bases act as bidentate, monobasic chelating ligands with S and N as the donor sites and are preferably found in the thiol form in all the complexes studied. The molecular structure of HL1 and HL2 were determined by single crystal X-ray diffraction method. DNA binding of the compounds was investigated by absorption spectroscopy which indicated that the complexes bind to DNA via intercalation. The oxidative cleavage of the complexes with CT-DNA inferred that the effects of cleavage are dose dependent. Antioxidant studies of the ligands and complexes showed the significant antioxidant activity against DPPH radical. In addition, the in vitro cytotoxicity of the ligands and complexes against MCF-7 cell line was assayed which showed higher cytotoxic activity with the lower IC50 values indicating their efficiency in killing the cancer cells even at low concentrations.

  6. The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives

    Directory of Open Access Journals (Sweden)

    Marina Azevedo Souza

    2013-05-01

    Full Text Available Lapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antimicrobial activity against the bacteria Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentrations (MICs of 0.05 and 0.10 µmol/mL, respectively. The thiosemicarbazone and semicarbazone derivatives were also active against the pathogenic yeast Cryptococcus gattii (MICs of 0.10 and 0.20 µmol/mL, respectively. In addition, the lapachol thiosemicarbazone derivative was active against 11 clinical isolates of Paracoccidioides brasiliensis, with MICs ranging from 0.01-0.10 µmol/mL. The lapachol-derived thiosemicarbazone was not cytotoxic to normal cells at the concentrations that were active against fungi and bacteria. We synthesised, for the first time, thiosemicarbazone and semicarbazone derivatives of lapachol. The MICs for the lapachol-derived thiosemicarbazone against S. aureus, E. faecalis, C. gattii and several isolates of P. brasiliensis indicated that this compound has the potential to be developed into novel drugs to treat infections caused these microbes.

  7. The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives

    Science.gov (United States)

    Souza, Marina Azevêdo; Johann, Susana; Lima, Luciana Alves Rodrigues dos Santos; Campos, Fernanda Fraga; Mendes, Isolda Castro; Beraldo, Heloisa; de Souza-Fagundes, Elaine Maria; Cisalpino, Patrícia Silva; Rosa, Carlos Augusto; Alves, Tânia Maria de Almeida; de Sá, Nívea Pereira; Zani, Carlos Leomar

    2013-01-01

    Lapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antimicrobial activity against the bacteria Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentrations (MICs) of 0.05 and 0.10 µmol/mL, respectively. The thiosemicarbazone and semicarbazone derivatives were also active against the pathogenic yeast Cryptococcus gattii (MICs of 0.10 and 0.20 µmol/mL, respectively). In addition, the lapachol thiosemicarbazone derivative was active against 11 clinical isolates of Paracoccidioides brasiliensis, with MICs ranging from 0.01-0.10 µmol/mL. The lapachol-derived thiosemicarbazone was not cytotoxic to normal cells at the concentrations that were active against fungi and bacteria. We synthesised, for the first time, thiosemicarbazone and semicarbazone derivatives of lapachol. The MICs for the lapachol-derived thiosemicarbazone against S. aureus, E. faecalis, C. gattii and several isolates of P. brasiliensis indicated that this compound has the potential to be developed into novel drugs to treat infections caused these microbes. PMID:23778660

  8. ONE-POT SYNTHESIS OF FUNCTIONALIZED 2-THIAZOLIDIN-4-ONES FROM THIOSEMICARBAZONE DERIVATIVES AND ACETYLENIC ESTERS IN WATER Ein-Topf-Synthese funktionalisierter 2-THIAZOLIDIN-4-one FROM Thiosemicarbazone DERIVATE UND Acetylenische ESTERS IM WASSER.

    Directory of Open Access Journals (Sweden)

    Sayed Ali Ahmadi*, Dadkhoda Ghazanfari

    2013-07-01

    Full Text Available Some derivatives of 2-thiazolidin-4-ones were synthesized from dialkyl acetylenedicarboxylates and thiosemicarbazone derivatives of chalchones in the presence of triphenylphosphine in water

  9. Aryl- and heteroaryl-thiosemicarbazone derivatives and their metal complexes: a pharmacological template.

    Science.gov (United States)

    Moorthy, Narayana S H N; Cerqueira, Nuno M F S A; Ramos, Maria J; Fernandes, Pedro A

    2013-05-01

    In this review, we discuss the current patents concerning aryl/heteroaryl thiosemicarbazone derivatives as regards to their activities and properties, including coordination (chelation) properties. The mode of action of the aryl/heteroaryl thiosemicarbazone derivatives involves metal coordination with proteins or biological fluids that have metal ions in their structure. Additionally, these molecules can also form multiple hydrogen bonds through their (thio) amide and N3 nitrogen that ensure a strong interaction with the receptor. In some cases, strong π-π interactions can be observed too. Special attention is given to pyridyl, bis-pyridyl, benzoylpyridyl and isatin thiosemicarbazone derivatives that exhibit significant anticancer, antiviral and other activities in free and in metal complexed forms. This key biological role is often related with their capability to inhibit the enzyme ribonucleotide reductase, similar to what is observed with potent anticancer drugs such as Triapine and methisazone. Recent studies have revealed that thiosemicarbazone can also inhibit topoisomerase II α enzyme. Thiosemicarbazone derivatives form coordination complex with various metals such as Zn, Cu, Fe, Co, Ni, Pt, Pd, etc., and these complexes provide better activities than the free thiosemicarbazones. Recent patents show that the controlled or sustained release dosage form of the thiosemicarbazone derivatives along with ionizing radiations is used for the treatment of proliferative diseases (US20110152281, US20110245304, US20120172217). PMID:22963201

  10. Isatin based thiosemicarbazone derivatives as potential bioactive agents: Anti-oxidant and molecular docking studies

    Science.gov (United States)

    Haribabu, J.; Subhashree, G. R.; Saranya, S.; Gomathi, K.; Karvembu, R.; Gayathri, D.

    2016-04-01

    A new series of isatin based thiosemicarbazones has been synthesized from benzylisatin and unsubstituted/substituted thiosemicarbazides (1-5). The synthesized compounds were characterized by elemental analyses, and UV-Visible, FT-IR, 1H &13C NMR and mass spectroscopic techniques. Three dimensional molecular structure of three compounds (1, 3 and 4) was determined by single crystal X-ray crystallography. Anti-oxidant activity of the thiosemicarbazone derivatives showed their excellent scavenging effect against free radicals. In addition, all the compounds showed good anti-haemolytic activity. In silico molecular docking studies were performed to screen the anti-inflammatory and anti-tuberculosis properties of thiosemicarbazone derivatives.

  11. Synthesis of Novel Highly Functionalized 4-Thiazolidinone Derivatives from 4-Phenyl-3-thiosemicarbazones

    Directory of Open Access Journals (Sweden)

    Abdelmadjid Benmohammed

    2014-03-01

    Full Text Available We present herein the synthesis in good yields of two series of highly functionalized thiazolidinone derivatives from the reactions of various 4-phenyl-3-thio-semicarbazones with ethyl 2-bromoacetate and diethyl acetylenedicarboxylate, respectively.

  12. The antimicrobial activity of lapachol and its thiosemicarbazone and semicarbazone derivatives

    OpenAIRE

    2013-01-01

    Lapachol was chemically modified to obtain its thiosemicarbazone and semicarbazone derivatives. These compounds were tested for antimicrobial activity against several bacteria and fungi by the broth microdilution method. The thiosemicarbazone and semicarbazone derivatives of lapachol exhibited antimicrobial activity against the bacteria Enterococcus faecalis and Staphylococcus aureus with minimal inhibitory concentrations (MICs) of 0.05 and 0.10 µmol/mL, respectively. The thiosemicarbazo...

  13. Corrosion inhibition of 6061 Al-15 vol. pct. SiC(p) composite and its base alloy in a mixture of sulphuric acid and hydrochloric acid by 4-(N,N-dimethyl amino) benzaldehyde thiosemicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Pinto, Geetha Mable [Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasnagar 575 025, Mangalore, Karnataka (India); Nayak, Jagannath [Department of Metallurgical and Materials Engineering, National Institute of Technology Karnataka, Surathkal, Srinivasnagar 575 025, Karnataka (India); Shetty, A. Nityananda, E-mail: nityashreya@gmail.com [Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasnagar 575 025, Mangalore, Karnataka (India)

    2011-02-15

    Research highlights: {yields} Corrosion inhibition of Al-SiC composite. {yields} DMABT as corrosion inhibitor. {yields} Inhibition through physisorption of DMABT. - Abstract: The corrosion inhibition characteristics of 4-(N,N-dimethylamino) benzaldehyde thiosemicarbazone (DMABT) on the corrosion behavior of 6061 Al-15 vol. pct. SiC(p) composite and its base alloy were studied at different temperatures in acid mixture medium containing varying concentrations of hydrochloric acid and sulphuric acid using Tafel extrapolation technique and ac impedance spectroscopy (EIS). The effect of inhibitor concentration, temperature and concentration of the acid mixture media on the inhibitor action was investigated. It was found that inhibition efficiencies increase with the increase in inhibitor concentration, but decrease with the increase in temperature and with the increase in concentration of the acid media. Thermodynamic parameters for dissolution process were determined. The adsorption of DMABT on both the composite and base alloy was found to be through physisorption obeying Freundlich adsorption isotherm.

  14. Intermolecular interaction of thiosemicarbazone derivatives to solvents and a potential Aedes aegypti target

    Science.gov (United States)

    da Silva, João Bosco P.; Hallwass, Fernando; da Silva, Aluizio G.; Moreira, Diogo Rodrigo; Ramos, Mozart N.; Espíndola, José Wanderlan P.; de Oliveira, Ana Daura T.; Brondani, Dalci José; Leite, Ana Cristina L.; Merz, Kenneth M.

    2015-08-01

    DFT calculations were used to access information about structure, energy and electronic properties of series of phenyl- and phenoxymethyl-(thio)semicarbazone derivatives with demonstrated activity against the larvae of Aedes aegypti in stage L4. The way as the thiosemicarbazone derivatives can interact with solvents like DMSO and water were analyzed from the comparison between calculated and experimental 1H NMR chemical shifts. The evidences of thiosemicarbazone derivatives making H-bond interaction to solvent have provide us insights on how they can interact with a potential A. aegypti's biological target, the Sterol Carrier Protein-2.

  15. Synthesis, characterization and antibacterial studies of some metal complexes of a schiff base derived from benzaldehyde and sulfonamide

    International Nuclear Information System (INIS)

    Neutral complexes of Cu(II), Ni(II), and Co(II) with a schiff base derived from benzaldehyde and sulfonamide have been synthesized and characterized the basis of on FTIR, UV-VIS, molar conductance and atomic absorption spectroscopic data. These metal complexes were also screened for their antibacterial activity against two bacterial species E.coli and Salmonella typhae. The metal complexes showed enhanced antibacterial activity as compared to uncomplexed ligand. (author)

  16. Insights into the binding of thiosemicarbazone derivatives with human serum albumin: spectroscopy and molecular modelling studies.

    Science.gov (United States)

    Karthikeyan, Subramani; Bharanidharan, Ganesan; Kesherwani, Manish; Mani, Karthik Ananth; Srinivasan, Narasimhan; Velmurugan, Devadasan; Aruna, Prakasarao; Ganesan, Singaravelu

    2016-06-01

    4-[(1Z)-1-(2-carbamothioylhydrazinylidene)ethyl]phenyl acetate [Ace semi],4-[(1Z)-1-(2-carbamothioylhydrazinylidene)ethyl]phenyl propanoate [Pro semi] from the family of thiosemicarbazones derivative has been newly synthesized. It has good anticancer activity as well as antibacterial and it is also less toxic in nature, its binding characteristics are therefore of huge interest for understanding pharmacokinetic mechanism of the drug. The binding of thiosemicarbazone derivative to human serum albumin (HSA) has been investigated by studying its quenching mechanism, binding kinetics and the molecular distance (r) between donor (HSA) and acceptor (thiosemicarbazone derivative) was estimated according to Forster's theory of non-radiative energy transfer using fluorescence spectroscopy. The binding dynamics has been elaborated using synchronous fluorescence spectroscopy, and the feature of thiosemicarbazone derivative induced structural changes of HSA has been studied by circular dichorism, Fourier transform infrared spectroscopy. Molecular modelling simulations explore the hydrophobic interaction and hydrogen bonding which stabilizes the interaction. PMID:26368536

  17. Some lanthanide complexes of semicarbazone and thiosemicarbazone derived from fluorenone

    International Nuclear Information System (INIS)

    A new series of lanthanide chloride complexes with the ligands fluorenone semicarbazone (FSC) and fluorenone thiosemicarbazone (FTSC) of composition [LnLCl2(H2O)2](Ln = La, Pr, Nd, Sm, Gd) were synthesised and characterized by microanalytical, spectral, magnetic and conductivity data. These ligands act as monovalent bidentate and bond through carbonyl oxygen/thiocarbonyl sulfur and the azomethine nitrogen atom. (author). 18 refs., 2 tabs

  18. Oxidation of benzaldehydes to benzoic acid derivatives by three Desulfovibrio strains.

    OpenAIRE

    Zellner, G; Kneifel, H; De Winter, J.

    1990-01-01

    Desulfovibrio vulgaris Marburg, "Desulfovibrio simplex" XVI, and Desulfovibrio sp. strain MP47 used benzaldehydes such as vanillin, 3,4,5-trimethoxybenzaldehyde, protocatechualdehyde, syringaldehyde, p-anisaldehyde, p-hydroxybenzaldehyde, and 2-methoxybenzaldehyde as electron donors for sulfate reduction and carbon dioxide and/or components of yeast extract as carbon sources for cell synthesis. The aldehydes were oxidized to their corresponding benzoic acids. The three sulfate reducers oxidiz...

  19. Synthesis, molecular modeling, and biological evaluation of novel chiral thiosemicarbazone derivatives as potent anticancer agents.

    Science.gov (United States)

    Taşdemir, Demet; Karaküçük-İyidoğan, Ayşegül; Ulaşli, Mustafa; Taşkin-Tok, Tuğba; Oruç-Emre, Emİne Elçİn; Bayram, Hasan

    2015-02-01

    A series of new chiral thiosemicarbazones derived from homochiral amines in both enantiomeric forms were synthesized and evaluated for their in vitro antiproliferative activity against A549 (human alveolar adenocarcinoma), MCF-7 (human breast adenocarcinoma), HeLa (human cervical adenocarcinoma), and HGC-27 (human stomach carcinoma) cell lines. Some of compounds showed inhibitory activities on the growth of cancer cell lines. Especially, compound exhibited the most potent activity (IC50 4.6 μM) against HGC-27 as compared with the reference compound, sindaxel (IC50 10.3 μM), and could be used as a lead compound to search new chiral thiosemicarbazone derivatives as antiproliferative agents. PMID:25399965

  20. Dioxouranium (VI) complexes of N4- substituted aryl thiosemicarbazones derived from 2,6- diacetylpyridine

    International Nuclear Information System (INIS)

    Some seven-coordinated dioxouranium(VI) complexes of 4N-aryl substituted thiosemicarbazones derived from 2,6-diacetylpyridine were prepared in non-aqueous solvent. All the complexes were characterised by infrared, electronic and 1H NMR spectra. In all the cases the ligands behave as di basic quinquedentate (N3S2) ligands. The complexes may have distorted pentagonal bipyramidal geometry. (author)

  1. Electrochemical and positron annihilation studies of semicarbazones and thiosemicarbazones derived from ferrocene

    International Nuclear Information System (INIS)

    A series of six ferrocene derivates containing a semicarbazone or thiosemicarbazone side chain was investigated by cyclic voltammetry and positron annihilation lifetime measurements. Both the redox and the electron capture processes took place on the Fe atom. Correlations between the two methods were proposed. taking into account the substituents on the side chain of the compounds, their redox potentials and the probabilities of o-positronium (o-Ps), formation. (author)

  2. Synthesis and In Vitro Evaluation of New Thiosemicarbazone Derivatives as Potential Antimicrobial Agents

    OpenAIRE

    Zafer Asım Kaplancıklı; Mehlika Dilek Altıntop; Belgin Sever; Zerrin Cantürk; Ahmet Özdemir

    2016-01-01

    In an effort to develop potent antimicrobial agents, new thiosemicarbazone derivatives were synthesized via the reaction of 4-[4-(trifluoromethyl)phenyl]thiosemicarbazide with aromatic aldehydes. The compounds were evaluated for their inhibitory effects on pathogenic bacteria and yeasts using the CLSI broth microdilution method. Microplate Alamar Blue Assay was also carried out to determine the antimycobacterial activities of the compounds against Mycobacterium tuberculosis H37Rv. Among these...

  3. Bivalent transition metal complexes of coumarin-3-yl thiosemicarbazone derivatives: Spectroscopic, antibacterial activity and thermogravimetric studies

    Science.gov (United States)

    Refat, Moamen S.; El-Deen, Ibrahim M.; Anwer, Zeinab M.; El-Ghol, Samir

    2009-02-01

    Schiff base complexes of Cu(II), Co(II) and Ni(II) with two coumarin-3-yl thiosemicarbazone derivatives (1E)-1-(1-(2-oxo-2H-chromen-3-yl)ethylidene)thiosemicarbazide (OCET) and (1E)-1-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene)thiosemicarbazide (BOCET) were synthesized by the reaction of Cu(II), Co(II) and Ni(II) chlorides with each mentioned ligand with molar ratio 1:2 metal-to-ligand. Both ligands and their metal complexes were characterized by different physicochemical methods, elemental analysis, molar conductivity, (UV-vis, Mass, Infrared, 1H NMR spectra) and also thermal analysis (TG and DTG) techniques. The discussion of the outcome data of the prepared complexes indicate that the coumarin-3-yl thiosemicarbazone derivatives ligands behave as a bidentate ligand through both thione sulphur and azomethine nitrogen with 1:2 (metal:ligand) stoichiometry for all complexes. The molar conductance measurements proved that the complexes are electrolytes. The kinetic thermodynamic parameters such as: E∗, Δ H∗, Δ S∗and Δ G∗are calculated from the DTG curves, all complexes are more ordered except Ni(II) complexes. The antibacterial activity of the coumarin-3-yl thiosemicarbazone derivatives and their metal complexes was evaluated against some kinds of Gram positive and Gram negative bacteria.

  4. Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose

    Institute of Scientific and Technical Information of China (English)

    Xiao Ming JI; He Ping SUN; Hai Wei XU; Hong Min LIU

    2006-01-01

    1,2-O-Isopropylidene-5-O-p-toluenesulfonyl-α-D-erythro-pentofuranos-3-ulose 1 was treated with thiourea and aminothiourea to give a D-ribose derivative 2 bearing a 2-amino 1,3-thiazine ring and a thiosemicarbazone derivative 5, respectively. 2 was acylated with Ac2O and propandioic acid to afford two acylation derivatives 3 and 4, respectively. Reduction of 5with NaBH4 in methanol produced a hydrothiosemicarbazone derivative 6. The absolute configuration of 2 was confirmed by X-ray crystallographic analysis. The structures of all products were elucidated by IR, NMR and HRMS spectra.

  5. Mixed ligand ruthenium(III) complexes of benzaldehyde 4-methyl-3-thiosemicarbazones with triphenylphosphine/triphenylarsine co-ligands: Synthesis, DNA binding, DNA cleavage, antioxidative and cytotoxic activity

    Science.gov (United States)

    Sampath, K.; Sathiyaraj, S.; Raja, G.; Jayabalakrishnan, C.

    2013-08-01

    The new ruthenium(III) complexes with 4-methyl-3-thiosemicarbazone ligands, (E)-2-(2-chlorobenzylidene)-N-methylhydrazinecarbothioamide (HL1) and (E)-2-(2-nitrobenzylidene)-N-methylhydrazinecarbothioamide (HL2), were prepared and characterized by various physico-chemical and spectroscopic methods. The title compounds act as bidentate, monobasic chelating ligands with S and N as the donor sites and are preferably found in the thiol form in all the complexes studied. The molecular structure of HL1 and HL2 were determined by single crystal X-ray diffraction method. DNA binding of the ligands and complexes were investigated by absorption spectroscopy and IR spectroscopy. It reveals that the compounds bind to nitrogenous bases of DNA via intercalation. The oxidative cleavage of the complexes with CT-DNA inferred that the effects of cleavage are dose dependent. Antioxidant study of the ligands and complexes showed the significant antioxidant activity against DPPH radical. In addition, the in vitro cytotoxicity of the ligands and complexes against MCF-7 cell line was assayed which showed higher cytotoxic activity with the lower IC50 values indicating their efficiency in killing the cancer cells even at low concentrations.

  6. Evaluation of DNA-binding, DNA cleavage, antioxidant and cytotoxic activity of mononuclear ruthenium(II) carbonyl complexes of benzaldehyde 4-phenyl-3-thiosemicarbazones

    Science.gov (United States)

    Sampath, Krishnan; Sathiyaraj, Subbaiyan; Jayabalakrishnan, Chinnasamy

    2013-11-01

    Two 4-phenyl-3-thiosemicarbazone ligands, (E)-2-(2-chlorobenzylidene)-N-phenylhydrazinecarbothioamide (HL1) and (E)-2-(2-nitrobenzylidene)-N-phenylhydrazinecarbothioamide (HL2), and its ruthenium(II) complexes were synthesized and characterized by physico-chemical and spectroscopic methods. The Schiff bases act as bidentate, monobasic chelating ligands with S and N as the donor sites and are preferably found in the thiol form in all the complexes studied. The molecular structure of HL1 and HL2 were determined by single crystal X-ray diffraction method. DNA binding of the compounds was investigated by absorption spectroscopy which indicated that the compounds bind to DNA via intercalation. The oxidative cleavage of the complexes with CT-DNA inferred that the effects of cleavage are dose dependent. Antioxidant study of the ligands and complexes showed significant antioxidant activity against DPPH radical. In addition, the in vitro cytotoxicity of the ligands and complexes assayed against HeLa and MCF-7 cell lines showed higher cytotoxic activity with the lower IC50 values indicating their efficiency in killing the cancer cells even at low concentrations.

  7. Dioxouranium (VI) complexes of macrocyclic ligands derived from 2.6-diacetyl pyridine-bis(thiosemicarbazone)

    International Nuclear Information System (INIS)

    The dioxouranium(VI) complex of 2.6-diacetylpyridine-bis(thiosemicarbazone), (DAPTC), [UO2(DAPTC) (NO3)2] and its reactions with diketones are described. The complexes so obtained have been characterized on the basis of elemental analyses, electrical conductance and spectral (i.r. and electronic) data. The parent complex reacts with β-diketones to form a complex of the type [UO2(mac)(NO3)2], where mac is a macrocyclic ligand derived by the condensation of DAPTC and a β-diketone. The ligand, DAPTC, acts as a neutral, terdentate ligand having coordination sites at pyridine nitrogen and two azomethine nitrogens. 27 refs

  8. Preparation and evaluation of copper-67 labeled copper(II) bis(thiosemicarbazone) derivatives as potential blood flow tracers

    International Nuclear Information System (INIS)

    A series of bis(thiosemicarbazone) derivatives of diketones and dialdehydes has been synthesized and labelled with copper-67. The biodistributions of these complexes in rats has been determined following femoral vein injection. Brain and heart levels of the complexes were determined at elapsed times of 1 minute, 5 minutes, and 2 hours as a function of % injected dose per organ

  9. Lignin-derived oxygenate reforming on a bimetallic surface: The reaction of benzaldehyde on Zn/Pt(111)

    Science.gov (United States)

    Shi, Daming; Vohs, John M.

    2016-08-01

    Temperature programmed desorption (TPD) and high-resolution electron energy loss spectroscopy (HREELS) were used to characterize the adsorption and reaction of benzaldehyde (C6H5CHO) on hydrogen-covered Pt(111) and Zn-modified Pt(111) surfaces. Benzaldehyde was found to interact with Pt(111) via both the phenyl ring and carbonyl of the aldehyde group. This bonding configuration facilitates unselective decomposition of the benzaldehyde to produce CO, H2, and small hydrocarbon fragments at relatively low temperatures. On the other hand, benzaldehyde was found to bond to Zn-decorated Pt(111) surface exclusively via the carbonyl group in an η2(C, O) configuration, with the phenyl ring tilted away from the surface. This configuration weakens Csbnd O bond in the carbonyl facilitating its cleavage and helps prevent hydrogenation of the phenyl ring.

  10. Palladium(II) Complexes of NS Donor Ligands Derived from Steroidal Thiosemicarbazones as Antibacterial Agents

    OpenAIRE

    Abdullah M. Asiri; Khan, Salman A

    2010-01-01

    We have investigated the antibacterial activity of some new steroidal thiosemicarbazones and their Pd(II) metal complexes were prepared by the reaction of the thiosemicarbazones with [Pd(DMSO)2Cl2]. The steroidal thiosemicarbazones were prepared by the reaction of thiosemicarbazides with a steroidal ketone. The structures of these compounds were elucidated by IR, 1H-NMR, 13C-NMR, FAB mass spectroscopic methods, elemental analyses and TGA analysis. The antibacterial activity of these compounds...

  11. Spectroscopic study one thiosemicarbazone derivative with ctDNA using ethidium bromide as a fluorescence probe.

    Science.gov (United States)

    Geng, Shaoguang; Wu, Qing; Shi, Lei; Cui, Fengling

    2013-09-01

    In this study, a thiosemicarbazone derivative (E)-2-((1,4-dihydroxy-9,10-anthraquinone-2-yl)methylene)-N-(4-fluorophenyl)hydrazinecarbothioamide (DAFPT) was synthesized, and the interaction of DAFPT with calf thymus DNA (ctDNA) was explored using ethidium bromide (EB) as a fluorescence probe. The binding mode between DAFPT and ctDNA was investigated by UV absorption spectroscopy, fluorescence spectroscopy and molecular docking. The fluorescence quenching mechanism of EB-ctDNA by DAFPT might be a combined quenching type. Thermodynamic parameters showed that the reaction was spontaneous. According to ionic strength, fluorescence polarization and melting temperature (T(m)) curve results, DAFPT-ctDNA interaction was groove binding. The molecular modeling results indicated that DAFPT could slide into the A-T rich region of ctDNA. PMID:23769721

  12. Dioxouranium (VI) complexes of macrocyclic ligands derived from 2. 6-diacetyl pyridine-bis(thiosemicarbazone)

    Energy Technology Data Exchange (ETDEWEB)

    Yadav, H.D.S.; Sengupta, S.K.; Tripathi, S.C.

    The dioxouranium(VI) complex of 2.6-diacetylpyridine-bis(thiosemicarbazone), (DAPTC), (UO/sub 2/(DAPTC) (NO/sub 3/)/sub 2/) and its reactions with diketones are described. The complexes so obtained have been characterized on the basis of elemental analyses, electrical conductance and spectral (i.r. and electronic) data. The parent complex reacts with ..beta..-diketones to form a complex of the type (UO/sub 2/(mac)(NO/sub 3/)/sub 2/), where mac is a macrocyclic ligand derived by the condensation of DAPTC and a ..beta..-diketone. The ligand, DAPTC, acts as a neutral, terdentate ligand having coordination sites at pyridine nitrogen and two azomethine nitrogens. 27 refs.

  13. Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities

    Science.gov (United States)

    Ali, Amna Qasem; Teoh, Siang Guan; Salhin, Abdussalam; Eltayeb, Naser Eltaher; Khadeer Ahamed, Mohamed B.; Majid, A. M. S. Abdul

    New derivatives of thiosemicarbazone Schiff base with isatin moiety were synthesized L1-L6. The structures of these compounds were characterized based on the spectroscopic techniques. Compound L6 was further characterized by XRD single crystal. The interaction of these compounds with calf thymus (CT-DNA) exhibited high intrinsic binding constant (kb = 5.03-33.00 × 105 M-1) for L1-L3 and L5 and (6.14-9.47 × 104 M-1) for L4 and L6 which reflect intercalative activity of these compounds toward CT-DNA. This result was also confirmed by the viscosity data. The electrophoresis studies reveal the higher cleavage activity of L1-L3 than L4-L6. The in vitro anti-proliferative activity of these compounds against human colon cancer cell line (HCT 116) revealed that the synthesized compounds (L3, L6 and L2) exhibited good anticancer potency.

  14. Cu, Pt, and Pd complexes of the 3-deoxy-1,2-bis(thiosemicarbazone) derived from D-glucose.

    Science.gov (United States)

    Horton, D; Varela, O

    2000-09-22

    3-Deoxy-D-erythro-hexos-2-ulose bis(thiosemicarbazone) (1) acts as a tetradentate ligand of the N2S2 type which forms stable coordination complexes with metal(II) cations. The Cu(II), Pt(II), and Pd(II) chelates (2, 4, and 6, respectively) of 1 were synthesized and characterized by elemental analysis and NMR spectroscopy. The NMR spectra of the Pt complex (4) showed the coupling of H-1 and C-1, C-2 of the bis(thiosemicarbazone) with 195Pt (33.7% naturally occurring), which supports the structure proposed for the chelate. The complexes 2, 4, and 6 were acetylated to give the corresponding tri-O-acetyl derivatives 3, 5, and 7. Elimination of Cu(II) from 3 with hydrogen sulfide afforded 8, the tri-O-acetyl derivative of 1. Preliminary studies have shown antiviral activity of chelates 2, 4, and 6 against poliovirus type 1. PMID:11072850

  15. Synthesis and biological evaluation of new naphthalene substituted thiosemicarbazone derivatives as potent antifungal and anticancer agents.

    Science.gov (United States)

    Altıntop, Mehlika Dilek; Atlı, Özlem; Ilgın, Sinem; Demirel, Rasime; Özdemir, Ahmet; Kaplancıklı, Zafer Asım

    2016-01-27

    New thiosemicarbazone derivatives (1-10) were obtained via the reaction of 4-(naphthalen-1-yl)thiosemicarbazide with fluoro-substituted aromatic aldehydes. The synthesized compounds were evaluated for their in vitro antifungal effects against pathogenic yeasts and molds using broth microdilution assay. Ames and umuC assays were carried out to determine the genotoxicity of the most effective antifungal derivatives. Furthermore, all compounds were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and NIH/3T3 mouse embryonic fibroblast cell lines using XTT test. Among these derivatives, 4-(naphthalen-1-yl)-1-(2,3-difluorobenzylidene)thiosemicarbazide (1) and 4-(naphthalen-1-yl)-1-(2,5-difluorobenzylidene)thiosemicarbazide (3) can be identified as the most promising antifungal derivatives due to their notable inhibitory effects on Candida species and no cytotoxicity against NIH/3T3 mouse embryonic fibroblast cell line. According to Ames and umuC assays, compounds 1 and 3 were classified as non-mutagenic compounds. On the other hand, 4-(naphthalen-1-yl)-1-(2,4-difluorobenzylidene)thiosemicarbazide (2) can be considered as the most promising anticancer agent against A549 cell line owing to its notable inhibitory effect on A549 cells with an IC50 value of 31.25 μg/mL when compared with cisplatin (IC50 = 16.28 μg/mL) and no cytotoxicity against NIH/3T3 cells. PMID:26706351

  16. Synthesis and In Vitro Evaluation of New Thiosemicarbazone Derivatives as Potential Antimicrobial Agents

    Directory of Open Access Journals (Sweden)

    Zafer Asım Kaplancıklı

    2016-01-01

    Full Text Available In an effort to develop potent antimicrobial agents, new thiosemicarbazone derivatives were synthesized via the reaction of 4-[4-(trifluoromethylphenyl]thiosemicarbazide with aromatic aldehydes. The compounds were evaluated for their inhibitory effects on pathogenic bacteria and yeasts using the CLSI broth microdilution method. Microplate Alamar Blue Assay was also carried out to determine the antimycobacterial activities of the compounds against Mycobacterium tuberculosis H37Rv. Among these derivatives, compounds 5 and 11 were more effective against Enterococcus faecalis (ATCC 29212 than chloramphenicol, whereas compounds 1, 2, and 12 and chloramphenicol showed the same level of antibacterial activity against E. faecalis. Moreover, compound 2 and chloramphenicol exhibited the same level of antibacterial activity against Staphylococcus aureus. On the other hand, the most potent anticandidal derivatives were found as compounds 2 and 5. These derivatives and ketoconazole exhibited the same level of antifungal activity against Candida glabrata. According to the Microplate Alamar Blue Assay, the tested compounds showed weak to moderate antitubercular activity.

  17. Synthesis and characterization of some novel antimicrobial thiosemicarbazone O-carboxymethyl chitosan derivatives.

    Science.gov (United States)

    Mohamed, Nadia A; Mohamed, Riham R; Seoudi, Rania S

    2014-02-01

    Three novel thiosemicarbazone O-carboxymethyl chitosan derivatives were obtained via a condensation reaction of thiosemicarbazide O-carboxymethyl chitosan with o-hydroxybenzaldehyde, p-methoxybenzaldehyde, and p- chlorobenzaldehyde respectively. Their structures were characterized by elemental analysis, FTIR, (13)C NMR and X-ray diffraction. The antimicrobial behaviors of the prepared derivatives against three types of bacteria Staphylococcus aureus (S. aureus, RCMBA 2004), Bacillus subtilis (B. subtilis, RCMBA 6005), and Escherichia coli (E. Coli, RCMBA 5003) and three crops-threatening pathogenic fungi Aspergillus fumigatus (A. fumigatus, RCMBA 06002), Geotrichum candidum (G. candidum, RCMB 05098), and Candida albicans (C. albicans, RCMB 05035) were investigated. The results indicated that the antibacterial and antifungal activities of the investigated derivatives are much higher than those of the parent O-carboxymethyl chitosan. They were more potent in case of Gram-positive bacteria than Gram-negative bacteria. The presence of electron withdrawing chlorine atom on the aryl moiety of the aldehyde portion improved greatly antimicrobial activity to be nearly equivalent to the used standard drugs. PMID:24211430

  18. Palladium(II Complexes of NS Donor Ligands Derived from Steroidal Thiosemicarbazones as Antibacterial Agents

    Directory of Open Access Journals (Sweden)

    Abdullah M. Asiri

    2010-07-01

    Full Text Available We have investigated the antibacterial activity of some new steroidal thiosemicarbazones and their Pd(II metal complexes were prepared by the reaction of the thiosemicarbazones with [Pd(DMSO2Cl2]. The steroidal thiosemicarbazones were prepared by the reaction of thiosemicarbazides with a steroidal ketone. The structures of these compounds were elucidated by IR, 1H-NMR, 13C-NMR, FAB mass spectroscopic methods, elemental analyses and TGA analysis. The antibacterial activity of these compounds were tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria. The results showed that steroidal complexes are better inhibitors of both types of the bacteria (Gram-positive and Gram-negative as compared to steroidal thiosemicarbazones. Compound Ia displays remarkable antibacterial activity as compared to amoxicillin.

  19. Copper(II) complexes with 2-pyridineformamide-derived thiosemicarbazones: Spectral studies and toxicity against Artemia salina

    Science.gov (United States)

    Ferraz, Karina O.; Wardell, Solange M. S. V.; Wardell, James L.; Louro, Sonia R. W.; Beraldo, Heloisa

    2009-07-01

    The copper(II) complexes [Cu(H2Am4DH)Cl 2] ( 1), [Cu(H2Am4Me)Cl 2] ( 2), [Cu(H2Am4Et)Cl 2] ( 3) and [Cu(2Am4Ph)Cl] ( 4) with 2-pyridineformamide thiosemicarbazone (H2Am4DH) and its N(4)-methyl (H2Am4Me), N(4)-ethyl (H2Am4Et) and N(4)-phenyl (H2Am4Ph) derivatives were studied by means of infrared and EPR spectral techniques. The crystal structure of 4 was determined. The studied compounds proved to be toxic to Artemia salina, suggesting that they could present cytotoxic activity against solid tumors. Among the free thiosemicarbazones H2Am4Ph presented higher toxicity than all other compounds, which showed comparable effects. In the case of complexes 2 and 3 toxicity is probably attributable to the complex as an entity or to a synergistic effect involving the thiosemicarbazone and copper. H2Am4Ph and complexes 2 and 3 revealed to be the most promising compounds as potential antineoplasic agents.

  20. In vitro evaluation of the activity of thiosemicarbazone derivatives against mycotoxigenic fungi affecting cereals.

    Science.gov (United States)

    Degola, Francesca; Morcia, Caterina; Bisceglie, Franco; Mussi, Francesca; Tumino, Giorgio; Ghizzoni, Roberta; Pelosi, Giorgio; Terzi, Valeria; Buschini, Annamaria; Restivo, Francesco Maria; Lodi, Tiziana

    2015-05-01

    With a steadily increasing world population, a more efficient system of food production is of paramount importance. One of the major causes of food spoilage is the presence of fungal pathogens and the production and accumulation of mycotoxins. In the present work we report a study on the activity of a series of functionalized thiosemicarbazones (namely cuminaldehyde, trans-cinnamaldehyde, quinoline-2-carboxyaldehyde, 5-fluoroisatin thiosemicarbazone and 5-fluoroisatin N(4)-methylthiosemicarbazone), as antifungal and anti-mycotoxin agents, against the two major genera of cereal mycotoxigenic fungi, i.e. Fusarium and Aspergillus. These thiosemicarbazones display different patterns of efficacy on fungal growth and on mycotoxin accumulation depending on the fungal species. Some of the molecules display a greater effect on mycotoxin synthesis than on fungal growth. PMID:25702884

  1. Spectroscopic evaluation of manganese(II) complexes derived from semicarbazones and thiosemicarbazones

    Science.gov (United States)

    Chandra, Sulekh; Gupta, Lokesh Kumar

    2005-09-01

    Manganese(II) complexes having the general composition Mn(L) 2X 2 [where L = isopropyl methyl ketone semicarbazone (LLA), isopropyl methyl ketone thiosemicarbazone (LLB), 4-aminoacetophenone semicarbazone (LLC) and 4-aminoacetophenone thiosemicarbazone (LLD) and X = Cl -, 1/2SO 42-] have been synthesized. All the complexes were characterized by elemental analyses, molar conductance, magnetic moment susceptibility, EI-mass, 1H NMR, IR, EPR and electronic spectral studies. All the complexes show magnetic moments corresponding to five unpaired electrons. The possible geometries of the complexes were assigned on the basis of EPR, electronic and infrared spectral studies.

  2. Synthesis, characterization, and thermal stability of novel poly(azomethine-urethane)s and polyphenol derivatives derived from 2,4-dihydroxy benzaldehyde and toluene-2,4-diisocyanate

    Energy Technology Data Exchange (ETDEWEB)

    Kaya, Ismet, E-mail: kayaismet@hotmail.com [Canakkale Onsekiz Mart University, Faculty of Sciences and Arts, Department of Chemistry, 17020, Canakkale (Turkey); Avc Latin-Small-Letter-Dotless-I , Ali [Celal Bayar University, Faculty of Sciences and Arts, Department of Chemistry, 45040, Manisa (Turkey)

    2012-03-15

    Graphical abstract: Black-Right-Pointing-Triangle Synthesis, characterization, and thermal stability of novel poly(azomethine-urethane)s and polyphenol derivatives derived from 2,4-dihydroxy benzaldehyde and toluene-2,4-diisocyanate. Highlights: Black-Right-Pointing-Pointer New pol(azomethine-urethane)s were synthesized. Black-Right-Pointing-Pointer PAMUs were converted to their polyphenol species by oxidative polymerization reaction with NaOCl. Black-Right-Pointing-Pointer The synthesized compounds were characterized by solubility tests, TGA and DSC. Black-Right-Pointing-Pointer T{sub g} values of PAMUs were between 137 and 178 Degree-Sign C and thermal stabilities of them were very good. Black-Right-Pointing-Pointer Obtained compounds can be promising candidates for aerospace applications. - Abstract: Up to date, only a few kinds of poly(azomethine-urethane)s (PAMUs) were synthesized and studied with thermal degradation steps. However, polyphenol based PAMUs including azomethine linkages have not been investigated yet. The polyurethanes were prepared by condensation reaction of 2,4-dihydroxybenzaldehyde (2,4-DHBA) with toluene-2,4-diisocyanate (TDI) under argon atmosphere. Synthesized polyurethane was converted to its poly(azomethine urethane) species (TP-2AP, TP-3AP, and TP-4AP) by graft copolymerization reactions with amino phenols (2-amino phenol, 3-amino phenol, and 4-amino phenol). Obtained poly(azomethine urethane)s were converted to their polyphenol species (P-TP-2AP, P-TP-3AP, and P-TP-4AP) by oxidative polymerization reaction (OP) using NaOCl as the oxidant. The structures of the obtained compounds were confirmed by FT-IR, UV-vis, {sup 1}H NMR, and {sup 13}C NMR techniques. The molecular weight distribution parameters of the synthesized compounds were determined by the size exclusion chromatography (SEC). The synthesized compounds were also characterized by solubility tests, TG-DTA, and DSC. Fluorescence measurements were carried out in various

  3. Structural studies on acetophenone- and benzophenone-derived thiosemicarbazones and their zinc(II) complexes

    Science.gov (United States)

    Ferraz, Karina S. O.; Silva, Nayane F.; Da Silva, Jeferson G.; Speziali, Nivaldo L.; Mendes, Isolda C.; Beraldo, Heloisa

    2012-01-01

    In the present work N(3)- meta-chlorophenyl-(HAc3 mCl, 1) and N(3)- meta-fluorphenyl-(HAc3 mF, 2) acetophenone thiosemicarbazone, and N(3)- meta-chlorophenyl-(HBz3 mCl, 3) and N(3)- meta-fluorphenyl-(HBz3 mF, 4) benzophenone thiosemicarbazone were obtained, as well as their zinc(II) complexes [Zn(Ac3 mCl) 2] ( 5), [Zn(Ac3 mF) 2] ( 6), [Zn(Bz3 mCl) 2] ( 7) and [Zn(Bz3 mF) 2] ( 8). Upon re-crystallization in DMSO:acetone conversion of 8 into [Zn(Bz3 mF) 2]·(DMSO) ( 8a) occurred. The crystal structures of 2, 5 and 8a were determined.

  4. α-N-heterocyclic thiosemicarbazone derivatives as potential antitumor agents: A structure-activity relationships approach

    OpenAIRE

    Matesanz, Ana I.; Souza, Pilar

    2009-01-01

    α-N-Heterocyclic thiosemicarbazones, (N)-TSCs, are potent inhibitors of ribonucleotide reductase (RR). This enzyme plays a critical role in DNA synthesis and repair, and is a well-recognized target for cancer chemotherapeutic agents. In this review the structural features of (N)-TSCs, required for maximum antitumour activity have been explored. Special attention is given to the mechanisms of action and structure-activity relationships

  5. Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells.

    Science.gov (United States)

    Lovejoy, David B; Richardson, Des R

    2002-07-15

    We previously demonstrated that 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone (311) and other aroylhydrazone chelators possess potent antineoplastic activity because of their ability to bind iron (Fe). From these studies, we identified structural components of the hydrazones that provide antineoplastic activity, namely the salicylaldehyde and 2-hydroxy-1-naphthylaldehyde moieties. A related group of chelators known as the thiosemicarbazones also show pronounced antitumor activity because of their ability to inhibit ribonucleotide reductase. Considering this, we designed a new series of "hybrid ligands" by condensation of the aldehydes described above with a range of thiosemicarbazides. The parent compound of these ligands is 2-hydroxy-1-naphthylaldehyde thiosemicarbazone (NT). Of 8 NT analogues, 3 chelators, namely NT, N4mT (2-hydroxy-1-naphthylaldehyde-4-methyl-3-thiosemicarbazone), and N44mT (2-hydroxy-1-naphthylaldehyde-4,4-dimethyl-3-thiosemicarbazone), showed high antiproliferative activity against SK-N-MC neuroepithelioma cells (50% inhibitory concentration [IC(50)] = 0.5-1.5 microM). Indeed, their activity was significantly (P <.0001) greater than that of desferrioxamine (DFO) (IC(50) = 22 microM). We demonstrate that 311, a 311 analogue (311m), and several NT-series chelators have significantly (P <.001) greater antiproliferative activity against tumor cells than against a range of normal cell types. For example, the IC(50) values of NT and N4mT in SK-N-MC neuroepithelioma cells were 0.5 microM, whereas for fibroblasts the IC(50) values were greater than 25 microM. Further, the effect of one of the most potent chelators (311m) on preventing the growth of bone marrow stem cell cultures was far less than that of doxorubicin and similar to that of cisplatin. These studies support the further development of these chelators as antiproliferative agents. PMID:12091363

  6. Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities.

    Science.gov (United States)

    de Oliveira, Jamerson Ferreira; da Silva, Anekécia Lauro; Vendramini-Costa, Débora Barbosa; da Cruz Amorim, Cezar Augusto; Campos, Júlia Furtado; Ribeiro, Amélia Galdino; Olímpio de Moura, Ricardo; Neves, Jorge Luiz; Ruiz, Ana Lúcia Tasca Gois; Ernesto de Carvalho, João; Alves de Lima, Maria do Carmo

    2015-11-01

    A series of thiophene-2-thiosemicarbazones derivatives (5-14) was synthesized, characterized and evaluated for their antitumor activity. They were tested in vitro against human tumor cell lines through the colorimetric method. The results revealed that compounds 7 and 9 were the most effective in inhibiting 50% of the cell growth after 48 h of treatment. As compound 7 showed a potent antiproliferative profile, it has been chosen for further studies in 786-0 cell line by flow cytometry. Treatments with compound 7 (50 μM) induced early phosphatidylserine exposure after 18 h of exposure and this process progressed phosphatidylserine exposure with loss of cell membrane integrity after 24 h of treatment, suggesting a time-dependent cell death process. Regarding the cell cycle profile, no changes were observed after treatment with compound 7 (25 μM), suggesting a mechanism of cell death independent on the cell cycle. The in vivo studies show that compound 7 possess low acute toxicity, being the doses of 30-300 mgKg(-1) chosen for studies in Ehrlich solid tumor model in mice. All doses were able to inhibit tumor development being the lowest one the most effective. Our findings highlight thiophene-2-thiosemicarbazones as a promising class of compounds for further studies concerning new anticancer therapies. PMID:26454648

  7. Stereochemical trends of metal derivatives of some heterocyclic-2-thiones and thiosemicarbazones

    Indian Academy of Sciences (India)

    Tarlok S Lobana

    2000-06-01

    The interaction of heterocyclic thiones/thiosemicarbazones with metals has been the subject of several investigations as these ligands contain chemically active groups, -N(H)-C(=S)- -N=C(-SH)- ,and are useful model compounds for sulphur-containing analogues of purine and pyrimidine bases. Heterocylic-2-thiones bind to metals in several ways and lead to the formation of monomeric or polymeric complexes. For example, the simplest prototype of heterocylic-2-thiones, namely, pyridine-2-thione has several ways of binding, notably, terminal S-bonding and S-bridging (in neutral form), while in anionic form the modes are terminal S-bonding, S-bridging, N,S-chelation, N,S-bridging, N,S-chelation-cum-S-bridging and N,S-bridging-cum-S-bridging. Similarly, thiosemicarbazones bind to metals as S-bonded unidentates or N,S-chelates. In this paper, the chemistry of pyridine-2-thione, its N-oxide, 2-(benzylthio)pyridine-1-oxide thione with metals like iron(II), ruthenium(II), nickel(II), palladium(II), platinum(II), copper(I), copper(II), silver(I) and mercury(II) is briefly described. As regards thiosemicarbazones, focus is only on two compounds, namely organomercury(II) and organothallium(III). A variety of new molecules, well characterised by NMR and X-ray crystallography, is introduced.

  8. Influence of anthraquinone scaffold on E/Z isomer distribution of two thiosemicarbazone derivatives. 2D NMR and DFT studies

    Science.gov (United States)

    Marković, Violeta; Joksović, Milan D.; Marković, Svetlana; Jakovljević, Ivan

    2014-01-01

    A distribution of possible isomeric and tautomeric forms of two tautomerizable anthraquinone-thiosemicarbazones with pronounced cytotoxic potential was investigated using 2D NMR and DFT studies. Conformational analysis of the E and Z isomers of both thiosemicarbazones was performed to find out the most stable conformation for each molecule. It was found that superior stability of E-isomers results from ten-membered intramolecular hydrogen bond between thiosemicarbazone N2H and anthraquinone carbonyl group. This hydrogen bond is stronger than that between thiosemicarbazone N2H and ester oxygen, owing to the large partial negative charge on the anthraquinone oxygen.

  9. Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: Insights from fluorescence, (1)H NMR titration and molecular docking studies.

    Science.gov (United States)

    Xie, Juan; Dong, Huanhuan; Yu, Yanying; Cao, Shuwen

    2016-01-01

    Three structurally similar aromatic heterocyclic compounds 2-thiophenecarboxaldehyde (a), 2-furaldehyde (b), 2-pyrrolecarboxaldehyde (c) were chosen and a series of their thiosemicarbazone derivatives(1a-3a, 1b-3b and 1c-3c) were synthesized to evaluate their biological activities as mushroom tyrosinase inhibitors. The inhibitory effects of these compounds on tyrosinase were investigated by using spectrofluorimetry, (1)H NMR titration and molecular docking techniques. From the results of fluorescence spectrum and (1)H NMR titration, it was found that forming complexes between the sulfur atom from thiourea and copper ion of enzyme center may play a key role for inhibition activity. Moreover, investigation of (1)H NMR spectra further revealed that formation of hydrogen bond between inhibitor and enzyme may be helpful to above complexes formation. The results were well coincident with the suggestion of molecular docking and obviously showed that 2-thiophone N(4)-thiosemicarbazone (1a), 2-furfuran N(4)-thiosemicarbazone (1b) and 2-pyrrole N(4)-thiosemicarbazone (1c) are potential inhibitors which deserves further investigation. PMID:26213029

  10. Synthesis and evaluation of naphthalene-based thiosemicarbazone derivatives as new anticancer agents against LNCaP prostate cancer cells.

    Science.gov (United States)

    Altintop, Mehlika Dilek; Sever, Belgin; Özdemir, Ahmet; Kuş, Gökhan; Oztopcu-Vatan, Pinar; Kabadere, Selda; Kaplancikli, Zafer Asim

    2016-06-01

    Fourteen new naphthalene-based thiosemicarbazone derivatives were designed as anticancer agents against LNCaP human prostate cancer cells and synthesized. MTT assay indicated that compounds 6, 8 and 11 exhibited inhibitory effect on LNCaP cells. Among these compounds, 4-(naphthalen-1-yl)-1-[1-(4-hydroxyphenyl)ethylidene)thiosemicarbazide (6), which caused more than 50% death on LNCaP cells, was chosen for flow cytometric analysis of apoptosis. Flow cytometric analysis pointed out that compound 6 also showed apoptotic effect on LNCaP cells. Compound 6 can be considered as a promising anticancer agent against LNCaP cells owing to its potent cytotoxic activity and apoptotic effect. PMID:25826149

  11. Spectroscopic evaluation of Co(II), Ni(II) and Cu(II) complexes derived from thiosemicarbazone and semicarbazone

    Science.gov (United States)

    Chandra, Sulekh; Kumar, Anil

    2007-12-01

    Co(II), Ni(II) and Cu(II) complexes were synthesized with thiosemicarbazone (L 1) and semicarbazone (L 2) derived from 2-acetyl furan. These complexes were characterized by elemental analysis, molar conductance, magnetic moment, mass, IR, electronic and EPR spectral studies. The molar conductance measurement of the complexes in DMSO corresponds to non-electrolytic nature. All the complexes are of high-spin type. On the basis of different spectral studies six coordinated geometry may be assigned for all the complexes except Co(L) 2(SO 4) and Cu(L) 2(SO 4) [where L = L 1 and L 2] which are of five coordinated square pyramidal geometry.

  12. Antioxidant, antimicrobial, and theoretical studies of the thiosemicarbazone derivative Schiff base 2-(2-imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide (IMHC)

    OpenAIRE

    Al-Amiery, Ahmed A.; Al-Majedy, Yasmien K; Ibrahim, Heba H; Al-Tamimi, Ali A

    2012-01-01

    Background Adverse antimicrobial activities of thiosemicarbazone (TSC) and Schiff base derivatives have widely been studied by using different kinds of microbes, in addition different methods were used to assay the antioxidant activities using DPPH, peroxids, or ntrosyl methods. However, there are no studies describing the synthesis of TSC derived from creatinine. Results In this study, 2-(2-imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide (IMHC) was synthesized by the reaction of...

  13. Synthesis and Crystal Structure of a Mn(Ⅱ) Complex with Thiosemicarbazone Derivative of Pyridine-3-carbaldehyde Showing Unusual Coordination Mode of Tridentate Thiosemicarbazone

    Institute of Scientific and Technical Information of China (English)

    LI Ming-Xue; ZHOU Jing; WANG Jing-Ping; WANG Zi-Liang

    2006-01-01

    The title complex Mn(HL)4(NCS)2(CH3CH2OH)2 has been achieved via selfassembly by incorporating manganese(Ⅱ) into pyridine-3-carbaldehyde thiosemicarbazonate ligand,and characterized by elemental analysis and single-crystal X-ray diffraction study. The crystal crystallizes in triclinic, space group P1 with a = 8.896(2), b = 9.530(2), c = 14.520(4) (A), α =87.035(4), β= 88.112(4), γ= 69.434(4)°, V= 1150.9(5) (A)3, Z = 1, Mr = 984.17, Dc = 1.420 g/cm3,μ(MoKα) = 0.612 mm-1, F(000) = 511, the final R = 0.0574 and wR = 0.1547 for 2855 observed reflections with I > 2σ(I). The complex contains one six-coordinated manganese ion connected by two thiosemicarbazide ligands, in which the thiosemicarbazone ligand acts as a monodentate ligand and coordinates to the center metal atoms via the pyridyl nitrogen atoms, two ethanol molecules and two isothiocyanic anions to give rise to a mononuclear structure. The coordination of a potentially tridentate thiosemicarbazone in manganese(Ⅱ) complex without using its sulfur and imine nitrogen sites is unusual. Hydrogen bonds existing in the complex link the different components to stabilize the crystal structure.

  14. Thermodynamics of complexation of isatin-3-thiosemicarbazone (HIT and other related derivatives with some metal ions

    Directory of Open Access Journals (Sweden)

    H. H. MENA

    2002-04-01

    Full Text Available Proton-ligand formation constants of isatin-3-thiosemicarbazone (HIT ; N-acetylisatin-3-thiosemicarbazone (HAIT and 5-(p-nitrobenzoyl-1,2,4-triazino[5,6-b]indole-3-thione (HBITr ligands and their corresponding metal-ligand formation constants with Mn2+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, UO22+ and Th2+ ions were determined pH-metrically at 10, 20, 30 and 40°C in 75 %(v/v ethanol–water. The thermodynamic parameters (DG, DH and DS were also evaluated. It was found that both log K1 and –DH1, for HIT and HAIT-complexes are somewhat larger than log K2and –DH2, indicating a change in the dentate character of these ligands from tridentate (ONN-donors in 1:1 chelates to bidentate (ON-donors in 1:2; M:L chelates. In contrast, the values of log K2 and – DH2 for HBITr-complexes are somewhat larger than log K1 and –DH1, indicating a strong trans-effect for the second coordination. The dissociation process is non-spontaneous, endothermic and entropically unfavourable while the complexation process is spontaneous, exothermic and entropically favourable. The thermodynamic parameters were separated into their electrostatic (el and non-electrostatic (non constituents.

  15. Inhibition of Bovine Viral Diarrhea Virus RNA Synthesis by Thiosemicarbazone Derived from 5,6-Dimethoxy-1-Indanone▿

    Science.gov (United States)

    Castro, Eliana F.; Fabian, Lucas E.; Caputto, María E.; Gagey, Dolores; Finkielsztein, Liliana M.; Moltrasio, Graciela Y.; Moglioni, Albertina G.; Campos, Rodolfo H.; Cavallaro, Lucía V.

    2011-01-01

    In the present work, we described the activity of the thiosemicarbazone derived from 5,6-dimethoxy-1-indanone (TSC), which we previously characterized as a new compound that inhibits bovine viral diarrhea virus (BVDV) infection. We showed that TSC acts at a point of time that coincides with the onset of viral RNA synthesis and that it inhibits the activity of BVDV replication complexes (RCs). Moreover, we have selected five BVDV mutants that turned out to be highly resistant to TSC but still susceptible to ribavirin (RBV). Four of these resistant mutants carried an N264D mutation in the viral RNA-dependent RNA polymerase (RdRp). The remaining mutant showed an A392E mutation within the same protein. Some of these mutants replicated slower than the wild-type (wt) virus in the absence of TSC, whereas others showed a partial reversion to the wt phenotype over several passages in the absence of the compound. The docking of TSC in the crystal structure of the BVDV RdRp revealed a close contact between the indane ring of the compound and several residues within the fingers domain of the enzyme, some hydrophobic contacts, and hydrogen bonds with the thiosemicarbazone group. Finally, in the mutated RdRp from resistant BVDV, these interactions with TSC could not be achieved. Interestingly, TSC inhibited BVDV replication in cell culture synergistically with RBV. In conclusion, TSC emerges as a new nonnucleoside inhibitor of BVDV RdRp that is synergistic with RBV, a feature that turns it into a potential compound to be evaluated against hepatitis C virus (HCV). PMID:21430053

  16. Diphenyllead(IV) chloride complexes with benzilthiosemicarbazones. The first bis(thiosemicarbazone) derivatives.

    Science.gov (United States)

    Calatayud, David G; López-Torres, Elena; Mendiola, M Antonia

    2007-11-26

    Reactions of diphenyllead(IV) chloride with benzil bis(thiosemicarbazone) (L1H6) and benzil bis(4-methyl-3-thiosemicarbazone) (L1Me2H4) afforded the first complexes containing the diphenyllead(IV) moiety with bis(thiosemicarbazone) ligands. The new complexes show diverse structural characteristics depending on the ligand and the working conditions. Complexes [PbPh2Cl(L1H5)].3H2O (1) and [PbPh2Cl(L1Me2H3)] (3) are mononuclear species in which the ligands are partially deprotonated and the lead atom has a C2N2S2Cl environment in a distorted pentagonal bipyramid coordination geometry. Complex [PbPh(L1Me2H2)](2).2H2O (4) was also obtained, which contains two lead atoms in a binuclear structure with a C2N2S3 coordination sphere for each lead atom, since both dideprotonated ligands act as N2S2 chelate and as sulfur bridge. Reaction from L1H6, in the same conditions in which complex 4 was prepared, gave a mixture of products: the lead (II) complex [Pb(L1H4)]2 (2) and [PbPh3Cl]n. Reactions with the cyclic molecules 5-methoxy-5,6-diphenyl-4,5-dihydro-2H-[1,2,4]-triazine-3-thione (L2H2OCH3) and 5-methoxy-4-methyl-5,6-diphenyl-4,5-dihydro-2H-[1,2,4]-triazine-3-thione (L2MeHOCH3) were also explored. In all the complexes, the ligands are deprotonated. The complexes [PbPh2(L2)2] (5) and [PbPh2(L2MeOCH3)2] (7) present the same characteristics. The X-ray structure of 5 shows a distorted octahedral geometry around the lead atom, with the ligand molecules acting as NS chelates, but the nitrogen bonded to the metal is different; one of the triazines shows a novel behavior, since the nitrogen atom of the new imine group formed is the one that is bonded to the lead center, being a good example of linkage isomerism. The complex [PbPh2Cl(L2)] (6), which was also isolated, could not be crystallized. All the complexes were characterized by elemental analysis, mass spectrometry, IR and 1H, 13C, and 207Pb NMR spectroscopy and some of them by X-ray diffraction studies. PMID:17939655

  17. Synthesis, Characterization and Molecular Structures of some Bismuth(III) Complexes with Thiosemicarbazones and Dithiocarbazonic Acid Methylester Derivatives with Activity against Helicobacter Pylori

    OpenAIRE

    Diemer, Rolf; Dittes, Uwe; Nuber, Bernhard; Seifried, Volker; Opferkuch, Wolfgang; Keppler, Bernhard K.

    1995-01-01

    The reactions of bismuth(III) nitrate pentahydrate and bismuth(III) chloride with heterocyclic thiosemicarbazones and derivatives of dithiocarbazonic acid methylester were used to synthesize the respective bismuth(III) complexes, which could be divided into five groups D-H because of their stoichiometrical properties and their molecular structures. The molecular structure and the near coordination sphere of the bismuth(III) central atom of four representative compounds were determined by sing...

  18. QSAR study of some 5-methyl/trifluoromethoxy- 1H-indole-2,3-dione-3-thiosemicarbazone derivatives as anti-tubercular agents

    OpenAIRE

    Shahlaei, M.; Fassihi, A.; Nezami, A.

    2009-01-01

    In the present study, quantitative relationships between molecular structure and anti-tubercular activity of some 5-methyl/trifluoromethoxy-1H-indole-2,3-dione-3-thiosemicarbazone derivatives were discovered. The detailed application of an efficient linear method and principal component regression (PCR) for the evaluation of quantitative structure activity relationships of the studied compounds is demonstrated. Components produced by principal component analysis were used as the input for a l...

  19. Platinum and palladium complexes of thiosemicarbazones derived of 2-acetylthiophene: Synthesis and spectral studies

    Science.gov (United States)

    Neto, J. L.; de Lima, G. M.; Beraldo, H.

    2006-03-01

    The reaction of 2-acetylthiophene thiosemicarbazone (2-HATT) and 2-acetylthiophene 4-phenylthiosemicarbazone (2-HAT-4-FT) with Pd(COD)Cl 2 (COD = 1,5-cyclooctadiene) and trans-Pt 2PEt 3Cl 4 yielded four new metal complexes: [Pd(2-HATT)Cl 2] ( 1), [Pd(2-ATT) 2] ( 2), [Pd(2-AT-4-FT)Cl] ( 3) and [Pt(2-ATT)(PEt 3)Cl] ( 4). Apart from compound 3 all the others were characterised by 1H and 13C{ 1H} NMR, infrared spectroscopy, and elemental analysis. Multinuclear NMR experiments of 31P{ 1H} and 195Pt{ 1H} of complex 4 have revealed that the ligand 2-HATT behaves as a bidentate chelating agent towards Pd(COD)Cl 2 and trans-Pt 2PEt 3Cl 4 whereas ligand 2-HAT-4-FT forms a tridentate chelating complex with Pd(COD)Cl 2.

  20. Design and synthesis of novel 5,6-disubstituted pyridine-2,3-dione-3-thiosemicarbazone derivatives as potential anticancer agents.

    Science.gov (United States)

    Xie, Wenlin; Xie, Shimin; Zhou, Ying; Tang, Xufu; Liu, Jian; Yang, Wenqian; Qiu, Minghua

    2014-06-23

    A series of 5,6-disubstituted pyridine-2,3-dione-3-thiosemicarbazone derivatives(2a-2n) and 5,6-disubstituted pyridine-2,3-dione S-benzyl-3-thiosemicarbazones(3a-3g) were synthesized starting from 2,3-dihydroxypyridine via oxidation-Michael additions, condensations and nucleophilic substitutions. The structures of the compounds were established by IR, (1)H NMR, (13)C NMR, and HRMS. All newly synthesized compounds were screened for their anticancer activity against Breast cancer (MCF-7), Colon cancer (HCT-116) and hepatocellular cancer (BEL7402) cell lines. Bioassay results indicated that most of the prepared compounds exhibited cytotoxicity against various cancer cells in vitro. Some of the compounds exhibited promising antiproliferative activity, which were comparable to the positive control (5-fluorouracil). The structure-activity relationship was discussed. PMID:24819956

  1. Effect of N(4)-substituent groups on transfer of 2-benzoylpyridine thiosemicarbazone derivates at the water/1,2-dichloroethane interface

    International Nuclear Information System (INIS)

    Dependent on the pH of the aqueous phase, the transfer of protonated forms of 2-benzoylpyridine N(4)-phenyl thiosemicarbazone (BPPT) (which has antimicrobial, antifungal and anticytotoxic activities) and 2-benzoylpyridine N(4)-ethyl thiosemicarbazone (BPET) across water/1,2-dichloroethane (1,2-DCE) interface has been studied by cyclic voltammetry. The protonation constants of the ligands (pKa1w and pKa2w) were determined by spectrophotometry. The standard partition coefficients (logPi0) and the standard Gibbs energies of ionic (cationic) species of ligands (ΔGtr,i0,w→o) were calculated from the standard transfer potentials (Δowφi0). The standard Gibbs energies of their transfer (ΔGtr,i0,w→o) and partition coefficients of neutral species (log PN) were determined by shake-flask method. These thermodynamic parameters were evaluated as a quantitative and qualitative measure of the lipophilicities of two compounds. The differences between the partition coefficients of cationic and neutral form of compounds [diff(logPI+-N)] were interpreted by results obtained from voltammetric data. Effect of N(4)-phenyl and ethyl groups for transfer of 2-benzoylpyridine thiosemicarbazone derivatives at macro-liquid/liquid interface was investigated. The antimicrobial activity of BPET was tested against four types of bacteria and found to be active against Staphlylococcus aureus

  2. Ruthenium(II) complexes of 2-benzoylpyridine-derived thiosemicarbazones with cytotoxic activity against human tumor cell lines

    Science.gov (United States)

    Graminha, Angelica E.; Rodrigues, Cláudia; Batista, Alzir A.; Teixeira, Letícia R.; Fagundes, Elaine S.; Beraldo, Heloisa

    2008-04-01

    Reaction of [RuCl 3(dppb)H 2O] (dppb = 1,4 bis(diphenylphospine)butane) with 2-benzoylpyridine thiosemicarbazone (H2Bz4DH) and its N(4)-methyl (H2Bz4M) and N(4)-phehyl (H2Bz4Ph) derivatives gave [RuCl(dppb)(H2Bz4DH)]Cl ( 1), [RuCl(dppb)(H2Bz4M)]Cl ( 2) and [RuCl(dppb)(H2Bz4Ph)]Cl ( 3). The cytotoxic activity of the studied compounds was tested against the MCF-7, TK-10 and UACC-62 human tumor cell lines. The precursor [RuCl 3(dppb)H 2O] exhibits cytocidal activity against the tree cell lines. H2BzDH, H2Bz4M, and [RuCl(dppb)(H2Bz4M)]Cl ( 2) show a selective cytocidal effect against the UACC-62 cell line which makes them the most promising compounds.

  3. Ruthenium(II) complexes containing 2-pyridineformamide- and 2-benzoylpyridine-derived thiosemicarbazones and PPh 3: NMR and electrochemical studies of cis- trans-isomerization

    Science.gov (United States)

    Graminha, Angelica E.; Batista, Alzir A.; Mendes, Isolda C.; Teixeira, Letícia R.; Beraldo, Heloisa

    2008-04-01

    [RuCl(L)(PPh 3) 2] complexes with 2-benzoylpyridine- and 2-pyridineformamide-derived thiosemicarbazones (HL) were obtained and fully characterized. The complexes form cis- trans isomers. The cis isomer is disfavored by the sterical effect of two bulky groups close to each other whereas the trans isomer is disfavored by the electronic effect of competition of two phosphorous for π-bonding d orbitals of the metal. Our results suggest that, although both factors may be operating simultaneously, in CH 2Cl 2 solution the balance of these counterpoising effects favors the formation of the trans isomer.

  4. Pterostilbene carboxaldehyde thiosemicarbazone, a resveratrol derivative inhibits 17β-Estradiol induced cell migration and proliferation in HUVECs.

    Science.gov (United States)

    Nikhil, Kumar; Sharan, Shruti; Wishard, Rohan; Palla, Srinivasa Rao; Krishna Peddinti, Rama; Roy, Partha

    2016-04-01

    Angiogenesis plays important roles in tumor growth and metastasis, thus development of a novel angiogenesis inhibitor is essential for the improvement of therapeutics against cancer. Thrombospondins-1 (TSP-1) is a potent endogenous inhibitor of angiogenesis that acts through direct effects on endothelial cell migration, proliferation, survival, and activating apoptotic pathways. TSP-1 has been shown to disrupt estrogen-induced endothelial cell proliferation and migration. Here we investigated the potential of pterostilbene carboxaldehyde thiosemicarbazone (PTERC-T), a novel resveratrol (RESV) derivative, to inhibit angiogenesis induced by female sex steroids, particularly 17β-Estradiol (E2), on Human umbilical vein endothelial cells (HUVECs) and to elucidate the involvement of TSP-1 in PTERC-T action. Our results showed that PTERC-T significantly inhibited 17β-E2-stimulated proliferation of HUVECs and induced apoptosis as determined by annexin V/propidium iodide staining and cleaved caspase-3 expression. Furthermore, PTERC-T also inhibited endothelial cell migration, and invasion in chick chorioallantoic membrane (CAM) assay. In contrast, RESV failed to inhibit 17β-E2 induced HUVECs proliferation and invasion at similar dose. PTERC-T was also found to increase TSP-1 protein expression levels in a dose-dependent manner which, however, was counteracted by co-incubation with p38MAPK or JNK inhibitors, suggesting involvement of these pathways in PTERC-T action. These results suggest that the inhibitory effect of PTERC-T on 17β-E2 induced angiogenesis is associated, at least in part, with its induction of endothelial cell apoptosis and inhibition of cell migration through targeting TSP-1. Thus, PTERC-T could be considered as a potential lead compound for developing a class of new drugs targeting angiogenesis-related diseases. PMID:26850466

  5. Evaluation of the potential application of 2-acetylpyridine N4- phenyl thiosemicarbazones derivatives for cancer therapy and diagnosis

    International Nuclear Information System (INIS)

    Despite the wide range of antineoplastic agents available, resistance of some types of cancer and toxicity to normal cells have been identified as the main causes of treatment failure and death. The lack of early and precise diagnosis is also responsible for reducing survival of cancer patients. In this context, the development of substances with low toxicity and therapeutic potential and/or diagnosis purpose, is the major tool in an attempt to increase the survival of patients and assure the safety and efficacy of treatment. Thiosemicarbazones (TSC) are a class of synthetic compounds that have several biological activities, including antitumor. Although several studies have shown the great potential of TSC as therapeutic and / or diagnostic agents, different chemical modifications performed on this class of molecules indicate new possibilities for applications and still require further studies. The objective of this study was to evaluate the potential applicability of 2-acetylpyridine N-4-phenyl thiosemicarbazones derivatives for cancer therapy and diagnosis. The results showed that all 13 TSC tested were cytotoxic to breast and glioblastoma tumor cell lines, presenting higher in vitro antitumor activity than etoposide, an antineoplastic and inhibitor of topoisomerase II frequently used for cancer therapy. The TSC that have halogen or nitro on ortho position showed higher antitumor activity in vitro than their isomers with halogen or nitro on meta or para position of the phenyl group. H2Ac4oFPh and H2Ac4oClPh compounds showed the highest antitumor activity among all tested compounds, with IC50 in nanomolar order. These TSC induced cell death by apoptosis and oxidative stress was responsible, at least in part, for this type of cell death. The 5 mg.kg-1 H2Ac4oFPh dose, administered s.c., for 4 consecutive days, did not induce important toxicity; however, the same treatment protocol was not effective for tumor growth reduction in an animal model of brain tumor

  6. ANTIMICROBIAL ACTIVITY OF DIFFERENT THIOSEMICARBAZONE COMPOUNDS AGAINST MICROBIAL PATHOGENS

    OpenAIRE

    Negi Parul; Nandy Subhangkar; Mahato Arun

    2012-01-01

    Thiosemicarbazone belongs to a large group of thiourea derivatives, whose biological activities are a function of parent aldehyde or ketone moiety. They have been evaluated over the last 50 year as antiviral, antibacterial, antifungal, antimalarial, anticancer, leprosy, rheumatism, trypanosomiasis and coccidiodis. Thiosemicarbazones were prepared by simple process in which N4-thiosemicarbazone moiety was replaced by aliphatic, arylic and cyclic amines. Present study reported the anti-microbia...

  7. ANTIMICROBIAL ACTIVITY OF DIFFERENT THIOSEMICARBAZONE COMPOUNDS AGAINST MICROBIAL PATHOGENS

    Directory of Open Access Journals (Sweden)

    Negi Parul

    2012-05-01

    Full Text Available Thiosemicarbazone belongs to a large group of thiourea derivatives, whose biological activities are a function of parent aldehyde or ketone moiety. They have been evaluated over the last 50 year as antiviral, antibacterial, antifungal, antimalarial, anticancer, leprosy, rheumatism, trypanosomiasis and coccidiodis. Thiosemicarbazones were prepared by simple process in which N4-thiosemicarbazone moiety was replaced by aliphatic, arylic and cyclic amines. Present study reported the anti-microbial activity of different thiosemicarbazone compounds against certain bacterial and fungal pathogens viz. Bacillus cereus, Staphylococcus epidermis, Moraxella cattarhalis, Staph. Saprophyticus, Candida albicans and Aspergillus flavans.

  8. Spectroscopic, thermal and antibacterial studies on Mn(II) and Co(II) complexes derived from thiosemicarbazone

    OpenAIRE

    SULEKH CHANDRA; MONIKA TYAGI; Moamen S. Refat

    2009-01-01

    Mn(II) and Co(II) complexes having the general composition [M(L)2X2] (where L = 2-pyridinecarboxaldehyde thiosemicarbazone, M = Mn(II) and Co(II), X = Cl- and NO3-) were synthesized. All the metal complexes were characterized by elemental analysis, molar conductance, magnetic susceptibility measurements, mass, IR, EPR, electronic spectral studies and thermogravimetric analysis (TG). Based on the spectral studies, an octahedral geometry was assigned for all the complexes. Thermal studies of th...

  9. Cell death and ultrastructural alterations in Leishmania amazonensis caused by new compound 4-Nitrobenzaldehyde thiosemicarbazone derived from S-limonene

    OpenAIRE

    Britta, Elizandra Aparecida; Scariot, Débora Botura; Falzirolli, Hugo; Ueda-Nakamura, Tânia; Silva, Cleuza Conceição; Filho, Benedito Prado Dias; Borsali, Redouane; Nakamura, Celso Vataru

    2014-01-01

    Background The treatment of leishmaniasis with pentavalent antimonials is problematic because of their toxicity. Investigations of potentially active molecules are important to discover less toxic drugs that are viable economic alternatives for the treatment of leishmaniasis. Thiosemicarbazones are a group of molecules that are known for their wide versatility and biological activity. In the present study, we examined the antileishmania activity, mechanism of action, and biochemical alteratio...

  10. Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

    OpenAIRE

    Sinara Mônica Vitalino de Almeida; Elizabeth Almeida Lafayette; Lúcia Patrícia Bezerra Gomes da Silva; Cézar Augusto da Cruz Amorim; Tiago Bento de Oliveira; Ana Lucia Tasca Gois Ruiz; João Ernesto de Carvalho; Ricardo Olímpio de Moura; Eduardo Isidoro Carneiro Beltrão; Maria do Carmo Alves de Lima; Luiz Bezerra de Carvalho Júnior

    2015-01-01

    In this work, the acridine nucleus was used as a lead-compound for structural modification by adding different substituted thiosemicarbazide moieties. Eight new (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide derivatives (3a–h) were synthesized, their antiproliferative activities were evaluated, and DNA binding properties were performed with calf thymus DNA (ctDNA) by electronic absorption and fluorescence spectroscopies. Both hyperchromic and hypochromic effects, as well as re...

  11. Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

    Directory of Open Access Journals (Sweden)

    Sinara Mônica Vitalino de Almeida

    2015-06-01

    Full Text Available In this work, the acridine nucleus was used as a lead-compound for structural modification by adding different substituted thiosemicarbazide moieties. Eight new (Z-2-(acridin-9-ylmethylene-N-phenylhydrazinecarbothioamide derivatives (3a–h were synthesized, their antiproliferative activities were evaluated, and DNA binding properties were performed with calf thymus DNA (ctDNA by electronic absorption and fluorescence spectroscopies. Both hyperchromic and hypochromic effects, as well as red or blue shifts were demonstrated by addition of ctDNA to the derivatives. The calculated binding constants ranged from 1.74 × 104 to 1.0 × 106 M−1 and quenching constants from −0.2 × 104 to 2.18 × 104 M−1 indicating high affinity to ctDNA base pairs. The most efficient compound in binding to ctDNA in vitro was (Z-2-(acridin-9-ylmethylene-N- (4-chlorophenyl hydrazinecarbothioamide (3f, while the most active compound in antiproliferative assay was (Z-2-(acridin-9-ylmethylene-N-phenylhydrazinecarbothioamide (3a. There was no correlation between DNA-binding and in vitro antiproliferative activity, but the results suggest that DNA binding can be involved in the biological activity mechanism. This study may guide the choice of the size and shape of the intercalating part of the ligand and the strategic selection of substituents that increase DNA-binding or antiproliferative properties.

  12. Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives.

    Science.gov (United States)

    de Almeida, Sinara Mônica Vitalino; Lafayette, Elizabeth Almeida; da Silva, Lúcia Patrícia Bezerra Gomes; Amorim, Cézar Augusto da Cruz; de Oliveira, Tiago Bento; Ruiz, Ana Lucia Tasca Gois; de Carvalho, João Ernesto; de Moura, Ricardo Olímpio; Beltrão, Eduardo Isidoro Carneiro; de Lima, Maria do Carmo Alves; de Carvalho Júnior, Luiz Bezerra

    2015-01-01

    In this work, the acridine nucleus was used as a lead-compound for structural modification by adding different substituted thiosemicarbazide moieties. Eight new (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide derivatives (3a-h) were synthesized, their antiproliferative activities were evaluated, and DNA binding properties were performed with calf thymus DNA (ctDNA) by electronic absorption and fluorescence spectroscopies. Both hyperchromic and hypochromic effects, as well as red or blue shifts were demonstrated by addition of ctDNA to the derivatives. The calculated binding constants ranged from 1.74 × 10(4) to 1.0 × 10(6) M(-1) and quenching constants from -0.2 × 10(4) to 2.18 × 10(4) M(-1) indicating high affinity to ctDNA base pairs. The most efficient compound in binding to ctDNA in vitro was (Z)-2-(acridin-9-ylmethylene)-N- (4-chlorophenyl) hydrazinecarbothioamide (3f), while the most active compound in antiproliferative assay was (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide (3a). There was no correlation between DNA-binding and in vitro antiproliferative activity, but the results suggest that DNA binding can be involved in the biological activity mechanism. This study may guide the choice of the size and shape of the intercalating part of the ligand and the strategic selection of substituents that increase DNA-binding or antiproliferative properties. PMID:26068233

  13. Anti-parasitic action and elimination of intracellular Toxoplasma gondii in the presence of novel thiosemicarbazone and its 4-thiazolidinone derivatives

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    C.S. Carvalho

    2010-02-01

    Full Text Available Toxoplasma, which infects all eukaryotic cells, is considered to be a good system for the study of drug action and of the behavior of infected host cells. In the present study, we asked if thiosemicarbazone derivatives can be effective against tachyzoites and which morphological and ultrastructural features of host cells and parasites are associated with the destruction of Toxoplasma. The compounds were tested in infected Vero cell culture using concentration screens (0.1 to 20 mM. The final concentration of 1 mM was chosen for biological assay. The following results were obtained: 1 These new derivatives decreased T. gondii infection with an in vitro parasite IC50% of 0.2-0.7 mM, without a significant effect on host cells and the more efficient compounds were 2, 3 (thiosemicarbazone derivatives and 4 (thiazolidinone derivative; 2 The main feature observed during parasite elimination was continuous morphological disorganization of the tachyzoite secretory system, progressive organelle vesiculation, and then complete disruption; 3 Ultrastructural assays also revealed that progressive vesiculation in the cytoplasm of treated parasites did not occur in the host cell; 4 Vesiculation inside the parasite resulted in death, but this feature occurred asynchronously in different intracellular tachyzoites; 5 The death and elimination of T. gondii was associated with features such as apoptosis-like stage, acidification and digestion of parasites into parasitophorous vacuoles. Our results suggest that these new chemical compounds are promising for the elimination of intracellular parasites by mainly affecting tachyzoite development at 1 mM concentration for 24 h of treatment.

  14. Inhibitory Effects of Benzaldehyde Derivatives from the Marine Fungus Eurotium sp. SF-5989 on Inflammatory Mediators via the Induction of Heme Oxygenase-1 in Lipopolysaccharide-Stimulated RAW264.7 Macrophages

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    Kyoung-Su Kim

    2014-12-01

    Full Text Available Two benzaldehyde derivatives, flavoglaucin (1 and isotetrahydro-auroglaucin (2, were isolated from the marine fungus Eurotium sp. SF-5989 through bioassay- and 1H NMR-guided investigation. In this study, we evaluated the anti-inflammatory effects of these compounds in lipopolysaccharide (LPS-stimulated RAW264.7 macrophages. We demonstrated that compounds 1 and 2 markedly inhibited LPS-induced nitric oxide (NO and prostaglandin E2 (PGE2 production by suppressing inducible nitric oxide synthase (iNOS and cyclooxygenase-2 (COX-2 protein expression without affecting cell viability. We also demonstrated that the compounds reduced the secretion of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α, interleukin-1β (IL-1β and interleukin-6 (IL-6. Furthermore, compounds 1 and 2 inhibited LPS-induced nuclear factor-κB (NF-κB activation by suppressing phosphorylation of IkappaB (IκB. These results indicated that the anti-inflammatory effects of these benzaldehyde derivatives in LPS-stimulated RAW264.7 macrophages were due to the inactivation of the NF-κB pathway. In addition, compounds 1 and 2 induced heme oxygenase-1 (HO-1 expression through the nuclear transcription factor-E2–related factor 2 (Nrf2 translocation. The inhibitory effects of compounds 1 and 2 on the production of pro-inflammatory mediators and on NF-κB binding activity were reversed by HO-1 inhibitor tin protoporphyrin (SnPP. Thus, the anti-inflammatory effects of compounds 1 and 2 also correlated with their ability of inducing HO-1 expression.

  15. QSAR study of some 5-methyl/trifluoromethoxy- 1H-indole-2,3-dione-3-thiosemicarbazone derivatives as anti-tubercular agents

    Science.gov (United States)

    Shahlaei, M.; Fassihi, A.; Nezami, A.

    2009-01-01

    In the present study, quantitative relationships between molecular structure and anti-tubercular activity of some 5-methyl/trifluoromethoxy-1H-indole-2,3-dione-3-thiosemicarbazone derivatives were discovered. The detailed application of an efficient linear method and principal component regression (PCR) for the evaluation of quantitative structure activity relationships of the studied compounds is demonstrated. Components produced by principal component analysis were used as the input for a linear model development. Results indicate a linear relationship between the principal components obtained from molecular descriptors and the inhibitory activity of this set of molecules. The maximum variance in the activity of the molecules in PCR method was 73%. The performance of the developed model was tested by several validation methods. PMID:21589807

  16. A simple colorimetric method for determination of the specific activity of spallation-produced copper-67 using phenylglyoxal (PG) bis-(4N-methyl)thiosemicarbazone (TSC) derivatives

    International Nuclear Information System (INIS)

    Copper-67 (67Cu) is a useful radioisotope for therapeutic applications and is usually available from high-energy spallation of zinc targets. Since spallation-produced 67Cu can also contain undesirable levels of nonradioactive copper (63Cu and 65Cu), which may interfere with antibody labelling, the availability of a simple inexpensive technique to determine the specific activity of 67Cu would be useful. Bis-thiosemicarbazone (TSC) derivatives of 1,2-diketones or α-ketoaldehydes such as phenylglyoxal (PG) form orange-colored complexes with copper(II) that exhibit an absorption maximum at 480 mm. Analysis of HCl target solutions of 67Cu produced at the Brookhaven National Laboratory (one sample) and the Los Alamos Scientific Laboratory (four samples) by this method gave specific activity values which corresponded very well with values obtained by ion coupling plasma analysis (ICP). (Author)

  17. Spectral studies on Co(II), Ni(II) and Cu(II) complexes with thiosemicarbazone (L 1) and semicarbazone (L 2) derived from 2-acetyl furan

    Science.gov (United States)

    Chandra, Sulekh; Kumar, Anil

    2007-04-01

    Co(II), Ni(II) and Cu(II) complexes are synthesized with thiosemicarbazone (L 1) and semicarbazone (L 2) derived from 2-acetyl furan. These complexes are characterized by elemental analysis, molar conductance, magnetic susceptibility measurements, mass, IR, electronic and EPR spectral studies. The molar conductance measurements of the complexes in DMSO correspond to non-electrolytic nature except Ni(L) 2(NO 3) 2, which is 1:2 electrolyte. All the complexes are of high-spin type. On the basis of spectral studies an octahedral geometry may be assigned for Co(II) and Ni(II) complexes except nitrato complexes of Ni(II) which is of tetrahedral geometry, whereas tetragonal geometry for Cu(II) complexes.

  18. CNDO/2 calculations for α-oximino-acetoacetanilide thiosemicarbazone and synthesis and characterization of some metal chelates derived from it

    International Nuclear Information System (INIS)

    Solid complexes of α-oximinoacetoacetanilide thiosemicarbazone (OAATS) with Ni(II), Co(II), Zn(II), Mn(II), Cd(II), Hg(II) and UO2(II) have been prepared and characterized on the basis of their elemental analyses, conductivity, differential scanning calorimetry, thermogravimetric analysis, infrared and electronic spectral measurements, in conjunction with magnetic susceptibility measurements. Molecular orbital calculations employing the CNDO/2 method have been made for a number of conformations of the ligand molecule to ascertain the most stable one. (author). 24 refs., 3 figs., 2 tabs

  19. [Spectroscopic studies on the formation of metal complexes and on the protein binding of antiviral thiosemicarbazone derivatives (author's transl)].

    Science.gov (United States)

    Heinisch, L; Kramarczyk, K; Tonew, M; Hesse, G

    1981-04-01

    The complexation of some thiosemicarbazones and isothiosemicarbazones of isatin and quinolin-2-aldehydes with Cu2+, Zn2+ and Mn2+ ions was spectrometrically investigated. Semiquantitative data, obtained from extinction values, about the relative complexing tendencies within some groups of homologous substances were brought in relation to their antiviral effects and binding to bovine serum albumin. The complexing tendencies were greatest in compounds with methyl substituents and decreased for higher alkyl substituents. whereas the binding to protein increased in the same order. The well-known maxima of the antiviral observed with medium alkyl groups may be explained by a superposition of these effects. PMID:7255526

  20. New Oxidovanadium Complexes Incorporating Thiosemicarbazones and 1, 10-Phenanthroline Derivatives as DNA Cleavage, Potential Anticancer Agents, and Hydroxyl Radical Scavenger.

    Science.gov (United States)

    Ying, Peng; Zeng, Pengfei; Lu, Jiazheng; Chen, Hongyuan; Liao, Xiangwen; Yang, Ning

    2015-10-01

    Four novel oxidovanadium(IV) complexes, [VO(hntdtsc)(PHIP)] (1) (hntdtsc = 2-hydroxy-1-naphthaldehyde thiosemicarbazone, PHIP= 2-phenyl-imidazo[4,5-f]1,10-phenanthroline), [VO(hntdtsc)(DPPZ)](2)(DPPZ= dipyrido[3,2-a:2',3'-c]phenazine), [VO(satsc)(PHIP)](3) (satsc=salicylaldehyde thiosemicarbazone), and [VO(satsc)(DPPZ)](4), have been prepared and characterized. The chemical nuclease activities and photocleavage reactions of the complexes were tested. All four complexes can efficiently cleave pBR322 DNA, and complex 1 has the best cleaving ability. The antitumor properties of these complexes were examined with three different tumor cell lines using MTT assay. Their antitumor mechanism has been analyzed using cell cycle analysis, fluorescence microscopy of apoptosis, and Annexin V-FITC/PI assay. The results showed that the growth of human neuroblastoma (SH-SY5Y, SK-N-SH) and human breast adenocarcinoma (MCF-7) cells were inhibited significantly with very low IC50 values. Complex 1 was found to be the most potent antitumor agent among the four complexes. It can cause G0/G1 phase arrest of the cell cycle and exhibited significant induced apoptosis in SK-N-SH cells and displayed typical morphological apoptotic characteristics. In addition, they all displayed reasonable abilities to scavenge hydroxyl radical, and complex 1 was the best inhibitor. PMID:25659415

  1. Spectroscopic, thermal and antibacterial studies on Mn(II and Co(II complexes derived from thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    SULEKH CHANDRA

    2009-08-01

    Full Text Available Mn(II and Co(II complexes having the general composition [M(L2X2] (where L = 2-pyridinecarboxaldehyde thiosemicarbazone, M = Mn(II and Co(II, X = Cl- and NO3- were synthesized. All the metal complexes were characterized by elemental analysis, molar conductance, magnetic susceptibility measurements, mass, IR, EPR, electronic spectral studies and thermogravimetric analysis (TG. Based on the spectral studies, an octahedral geometry was assigned for all the complexes. Thermal studies of the compounds suggest that the complexes are more stable than the free ligand. This fact was supported by the kinetic parameters calculated using the Horowitz–Metzger (H–M and Coats–Redfern (C–R equations. The antibacterial properties of the ligand and its metal complexes were also examined and it was observed that the complexes are more potent bactericides than the free ligand.

  2. Synthesis, Spectral and Thermal Properties of Some Penta-Coordinated Complexes of Oxovanadium(IV) Derived from Thiosemicarbazones of 4-Aminoantipyrine

    OpenAIRE

    Ram K. Agarwal; PRASAD, Surendra; GAHLOT, Neetu

    2004-01-01

    The paper reports the synthesis of crystalline oxovanadium(IV), VO2+, complexes of thiosemicarbazones, i.e. 4[N-(4'-nitrobenzalidene)amino]antipyrine thiosemicarbazone (4'-NO2BAAPTS) and 4[N-(furan-2'-aldimine)amino]antipyrine thiosemicarbazone (FFAAPTS) with general composition VOX2L (X = Cl, Br, I, NO3 or NCS) and VO(ClO4)2(L)H2O (L = 4'-NO2BAAPTS or FFAAPTS). All the complexes were characterized by elemental analyses, molar mass, molar conductance, magnetic susc...

  3. Characterization of the anti tumoral activity of the thiosemicarbazones derived from N(4)-methyl-tolyl-2acetylpyridine And 2-pyridinoformamide and its metal complex: evaluation of the radiopharmaceutical potential

    International Nuclear Information System (INIS)

    Thiosemicarbazones have attracted great pharmacological interest because of their biological properties, such as cytotoxic activity against multiple strains of human tumors. The most studied compounds are pyridine-based because of their resemblance to pyridoxal metabolites that attach to co-enzyme B6-dependant enzymes. This work aimed the characterization of the anti tumoral effect of N(4)-methyl-tolyl-2-acetylpyridine and 2-pyridinoformamide-derived thiosemicarbazones and the development of a radiopharmaceutical based on a thiosemicarbazone metal complex for positron emission tomography. In the first phase of this study were synthesized twenty-one thiosemicarbazones, derived from N(4)methyl-2 acetylpyridine and 2-pyridine formamide, as well as their metal complexes (Sn, Ga and Cu). Their cytotoxic potential were evaluated against brain and breast tumor cells in vitro. Our results showed all of them presented powerful cytotoxic and antiproliferative activities against glioblastoma multiform and breast adenocarcinoma at very low concentrations (nanomolar range). Morphological alterations characteristic of apoptosis, such as cell shrinkage, chromatin condensation were observed. Copper chloride was used as control and has presented IC50 at millimolar range suggesting that copper complexation with thiosemicarbazone significantly increases (more than 1 million) the anti tumoral effect of this metal. Due to the potent anti tumoral activity of N(4)-methyl-tolyl-2-acetylpyridine derived thiosemicarbazones and the excellent properties of 64Cu (T1/2 = 12.7 hours, β+, β-, and EC decay), at the second part for this work it was developed a new imaging agent (radiopharmaceutical) for tumor detection by positron emission tomography (PET). The radiopharmaceuticals were produced in the nuclear reactor TRIGA-IPR-R1 from CDTN, via neutron capture reaction 63Cu (n,γ) 64Cu, of the copper complex N(4)-ortho-toluyl-2-acetylpyridine thiosemicarbazone (Culac). The induced specific

  4. The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells

    International Nuclear Information System (INIS)

    We have investigated the antitumor functions and mechanisms of 1,2-naphthoquinone-2-thiosemicarbazone (NQTS) and its metal complexes (Cu2+, Pd2+, and Ni2+) against MCF-7 human breast cancer cells. The cells were dosed with these complexes at varying concentrations, and cell viability was measured by a sulforhodamine B (SRB) method. To study mechanisms of action, the complexes were incubated with topoisomerase II (topo II) and supercoiled DNA, linear DNA, nicked open DNA, and relaxed DNA were detected by agarose gel electrophoresis. The results revealed that these complexes are effective antitumor chemicals in inhibiting MCF-7 cell growth, with Ni-NQTS being the most effective among the complexes studied. Our data also indicated that Ni-NQTS is more effective than the commercial antitumor drug, etoposide, based on IC50 values. The mechanistic study of action showed that metal complexes of NQTS, NQ, and NQTS can only stabilize the single-strand nicked DNA, but not double-strand breakage intermediates. In addition, metal derivatives of these ligands, but not the parent NQ and NQTS, exerted an antagonizing effect on topoisomerase II activity. In summary, chemicals with or without metal derivatives might possess different chemical-topoisomerase II-DNA interactions

  5. Antioxidant, antimicrobial, and theoretical studies of the thiosemicarbazone derivative Schiff base 2-(2-imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide (IMHC)

    Science.gov (United States)

    2012-01-01

    Background Adverse antimicrobial activities of thiosemicarbazone (TSC) and Schiff base derivatives have widely been studied by using different kinds of microbes, in addition different methods were used to assay the antioxidant activities using DPPH, peroxids, or ntrosyl methods. However, there are no studies describing the synthesis of TSC derived from creatinine. Results In this study, 2-(2-imino-1-methylimidazolidin-4-ylidene)hydrazinecarbothioamide (IMHC) was synthesized by the reaction of creatinine with thiosemicarbazide. The novel molecule was characterized by FT-IR, UV-VIS, and NMR spectra in addition of the elemental analysis. The free radical scavenging ability of the IMHC was determined by it interaction with the stable-free radical 2,2"-diphenyl-1-picrylhydrazyl (or nitric oxide or hydrogen peroxide) and showed encouraging antioxidant activities. Density functional theory calculations of the IMHC performed using molecular structures with optimized geometries. Molecular orbital calculations provide a detailed description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms. Highest occupied molecular orbital-lowest unoccupied molecular orbital energies and structures are shown. Conclusions IMHC shows considerable antibacterial and antifungal activities. The free radical scavenging activity of synthesized compound was screened for in vitro antioxidant activity. PMID:22373542

  6. Benzaldehyde thio­semicarbazone

    OpenAIRE

    Xiu-Ping Ju; Ji-Dong Zhang; Yan Qiao; Lingqian Kong

    2008-01-01

    The title compound, C8H9N3S, contains two molecules in the asymmetric unit. One molecule is close to being planar (r.m.s. deviation from the mean plane = 0.06 Å for the non-H atoms), while the other exhibits a dihedral angle of 21.7 (1)° between the benzene ring and the mean plane of the thiosemicarbazone unit. Intermolecular N—H...S hydrogen bonds link the molecules into layers parallel to the (010) plane.

  7. 4-Nitrobenzaldehyde thiosemicarbazone: a new compound derived from S-(-)-limonene that induces mitochondrial alterations in epimastigotes and trypomastigotes of Trypanosoma cruzi.

    Science.gov (United States)

    Britta, Elizandra Aparecida; Scariot, Débora Botura; Falzirolli, Hugo; da Silva, Cleuza Conceição; Ueda-Nakamura, Tânia; Dias Filho, Benedito Prado; Borsali, Redouane; Nakamura, Celso Vataru

    2015-06-01

    Trypanosoma cruzi is the causative agent of Chagas' disease, a parasitic disease that remains a serious health concern with unsatisfactory treatment. Drugs that are currently used to treat Chagas' disease are partially effective in the acute phase but ineffective in the chronic phase of the disease. The aim of the present study was to evaluate the antitrypanosomal activity and morphological, ultrastructural and biochemical alterations induced by a new molecule, 4-nitrobenzaldehyde thiosemicarbazone (BZTS), derived from S-(-)-limonene against epimastigote, trypomastigote and intracellular amastigote forms of T. cruzi. BZTS inhibited the growth of epimastigotes (IC50 = 9·2 μ m), intracellular amastigotes (IC50 = 3·23 μ m) and inhibited the viability of trypomastigotes (EC50 = 1·43 μ m). BZTS had a CC50 of 37·45 μ m in LLCMK2 cells. BZTS induced rounding and distortion of the cell body and severely damaged parasite mitochondria, reflected by extensive swelling and disorganization in the inner mitochondrial membrane and the presence of concentric membrane structures inside the organelle. Cytoplasmic vacuolization, endoplasmic reticulum that surrounded organelles, the loss of mitochondrial membrane potential, and increased mitochondrial O2 •- production were also observed. Our results suggest that BZTS alters the ultrastructure and physiology of mitochondria, which could be closely related to parasite death. PMID:25711881

  8. Thiosemicarbazone p-Substituted Acetophenone Derivatives Promote the Loss of Mitochondrial Δψ, GSH Depletion, and Death in K562 Cells.

    Science.gov (United States)

    Pessoto, Felipe S; Yokomizo, Cesar H; Prieto, Tatiana; Fernandes, Cleverton S; Silva, Alan P; Kaiser, Carlos R; Basso, Ernani A; Nantes, Iseli L

    2015-01-01

    A series of thiosemicarbazone (TSC) p-substituted acetophenone derivatives were synthesized and chemically characterized. The p-substituents appended to the phenyl group of the TSC structures were hydrogen, fluor, chlorine, methyl, and nitro, producing compounds named TSC-H, TSC-F, TSC-Cl, TSC-Me, and TSC-NO2, respectively. The TSC compounds were evaluated for their capacity to induce mitochondrial permeability, to deplete mitochondrial thiol content, and to promote cell death in the K562 cell lineage using flow cytometry and fluorescence microscopy. TSC-H, TSC-F, and TSC-Cl exhibited a bell-shaped dose-response curve for the induction of apoptosis in K562 cells due to the change from apoptosis to necrosis as the principal mechanism of cell death at the highest tested doses. TSC-Me and TSC-NO2 exhibited a typical dose-response profile, with a half maximal effective concentration of approximately 10 µM for cell death. Cell death was also evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, which revealed lower toxicity of these compounds for peripheral blood mononuclear cells than for K562 cells. The possible mechanisms leading to cell death are discussed based on the observed effects of the new TSC compounds on the cellular thiol content and on mitochondrial bioenergetics. PMID:26075034

  9. Effects on rat testes of the thiosemicarbazone derivative Schiff base (4-(1-phenylmethylcyclobutane-3-yl)-2-(2-hydroxybenzylidenehydrazino)thiazole) and its cadmium(II) complex.

    Science.gov (United States)

    Oner, Hakan; Karatepe, Mustafa; Karatas, Fikret; Oner, Jale; Yilmaz, Ibrahim; Cukurovali, Alaaddin

    2005-01-01

    The aim of this study was to investigate structural and biochemical changes in testes of rats treated with the thiosemicarbazone derivative thiazole ring Schiff base, (4-(1-phenyl-methylcyclobutane-3-yl)-2-(2-hydroxybenzylidene-hydrazino) thiazole (L), and its Cd(II) complex (CdL(2)). The animals were divided into three groups. Group I was designated as control. The rats in groups II and III were injected subcutaneously with L or CdL(2) respectively at 150-mg kg(-1) doses at 3-day intervals for 15 days. At the end of the study, blood samples were collected for biochemical analysis, and testes were removed for histological examinations. Serum levels of vitamin A, E and MDA of the L-injected group were similar to the control group. While CdL(2) treatment decreased serum vitamin A and E levels, it increased the MDA level compared to other groups. Histologically, the testes structures of L-treated animals were similar to the control. Spermatogenic cells in seminiferous tubules of CdL(2)-treated animals displayed necrosis. Nuclei of spermatogonia and primary spermatocytes were pyknotic and heterochromatic. Homogenous pink particles were present in place of the spermatids. The interstitial areas were oedematous and intertubular vessels were plugged. In conclusion, the present results indicate that L does not cause biochemical and morphological alterations, but its Cd(II) complex has degenerative effects in normal rat testes. PMID:15540255

  10. Thiosemicarbazone p-Substituted Acetophenone Derivatives Promote the Loss of Mitochondrial Δψ, GSH Depletion, and Death in K562 Cells

    Directory of Open Access Journals (Sweden)

    Felipe S. Pessoto

    2015-01-01

    Full Text Available A series of thiosemicarbazone (TSC p-substituted acetophenone derivatives were synthesized and chemically characterized. The p-substituents appended to the phenyl group of the TSC structures were hydrogen, fluor, chlorine, methyl, and nitro, producing compounds named TSC-H, TSC-F, TSC-Cl, TSC-Me, and TSC-NO2, respectively. The TSC compounds were evaluated for their capacity to induce mitochondrial permeability, to deplete mitochondrial thiol content, and to promote cell death in the K562 cell lineage using flow cytometry and fluorescence microscopy. TSC-H, TSC-F, and TSC-Cl exhibited a bell-shaped dose-response curve for the induction of apoptosis in K562 cells due to the change from apoptosis to necrosis as the principal mechanism of cell death at the highest tested doses. TSC-Me and TSC-NO2 exhibited a typical dose-response profile, with a half maximal effective concentration of approximately 10 µM for cell death. Cell death was also evaluated using the 3-(4,5-dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide (MTT assay, which revealed lower toxicity of these compounds for peripheral blood mononuclear cells than for K562 cells. The possible mechanisms leading to cell death are discussed based on the observed effects of the new TSC compounds on the cellular thiol content and on mitochondrial bioenergetics.

  11. Evaluation of anti-inflammatory effect of derivative (E)-N-(4-bromophenyl)-2-(thiophen-2-ylmethylene)-thiosemicarbazone.

    Science.gov (United States)

    de Oliveira, Jamerson Ferreira; Nonato, Fabiana Regina; Zafred, Rafael Rosolen Teixeira; Leite, Nayara Maria Siqueira; Ruiz, Ana Lúcia Tasca Gois; de Carvalho, João Ernesto; da Silva, Anekécia Lauro; de Moura, Ricardo Olímpio; Alves de Lima, Maria do Carmo

    2016-05-01

    The present study aimed to further investigate the anti-inflammatory activity of (E)-N-(4-bromophenyl)-2-(thiophen-2-ylmethylene)-thiosemicarbazone (BTTSC) as well as its antinociceptive effects. The anti-inflammatory activity was assessed using the model of ear edema induced by croton oil-induced and also evaluated in models of paw edema carrageenan-induced and by compound 48/80. Evaluation of the antinociceptive effect was performed through formalin test. In the nociception test induced by formalin the BTTSC showed activity in both phases of the pain, highlighting inflammatory pain, where it was able to reduce the time to paw lick 62.3, 84.30 and 100% at doses of 30, 100 and 300mgkg(-1). The anti-inflammatory activity was performed ear edema induced by croton oil, where none of the doses tested was capable of significantly regress edema. The paw edema carrageenan-induced showed activity compound, where the edema was reduced by 81.9 and 83.2% in the first two times of the experiment at the highest dose used. The paw edema assay induced by compound 48/80, showed that BTTSC after 15min of the inoculum phlogistic agent showed significant reduction of edema with values of 56.53% at a dose of 30mgkg(-1). Our results suggesting this compound exerts its antinociception effects connected with peripheral mechanisms. Furthermore, the compound was able to act in two phases of inflammation carrageenan-induced, highlighting the initial phase. This suggests an action on the early mediators of inflammation. The paw edema assay induced by compound 48/80 confirmed our hypothesis indicating action of the compound via histamine. PMID:27133079

  12. N-methylisatin-beta-thiosemicarbazone derivative (SCH 16) is an inhibitor of Japanese encephalitis virus infection in vitro and in vivo

    Science.gov (United States)

    Sebastian, Liba; Desai, Anita; Shampur, Madhusudana N; Perumal, Yogeeswari; Sriram, D; Vasanthapuram, Ravi

    2008-01-01

    Background During the early and mid part of 20th century, several reports described the therapeutic effects of N-methylisatin-β-Thiosemicarbazone (MIBT) against pox viruses, Maloney leukemia viruses and recently against HIV. However, their ability to inhibit flavivirus replication has not been investigated. Hence the present study was designed to evaluate the antiviral activity of 14 MIBT derivatives against Flaviviruses that are prevalent in India such as Japanese Encephalitis Virus (JEV), Dengue-2 (Den-2) and West Nile viruses (WNV). Results Amongst the fourteen Mannich bases of MIBT derivatives tested one compound – SCH 16 was able to completely inhibit in vitro Japanese encephalitis virus (JEV) and West Nile virus (WNV) replication. However no antiviral activity of SCH 16 was noted against Den-2 virus replication. This compound was able to inhibit 50% of the plaques (IC50) produced by JEV and WNV at a concentration of 16 μgm/ml (0.000025 μM) and 4 μgm/ml (0.000006 μM) respectively. Furthermore, SCH 16 at a concentration of 500 mg/kg body weight administered by oral route twice daily was able to completely (100%) prevent mortality in mice challenged with 50LD50 JEV by the peripheral route. Our experiments to understand the mechanism of action suggest that SCH 16 inhibited JEV replication at the level of early protein translation. Conclusion Only one of the 14 isatin derivatives -SCH 16 exhibited antiviral action on JEV and WNV virus infection in vitro. SCH 16 was also found to completely inhibit JEV replication in vivo in a mouse model challenged peripherally with 50LD50 of the virus. These results warrant further research and development on SCH 16 as a possible therapeutic agent. PMID:18498627

  13. N-methylisatin-beta-thiosemicarbazone derivative (SCH 16 is an inhibitor of Japanese encephalitis virus infection in vitro and in vivo

    Directory of Open Access Journals (Sweden)

    Sriram D

    2008-05-01

    Full Text Available Abstract Background During the early and mid part of 20th century, several reports described the therapeutic effects of N-methylisatin-β-Thiosemicarbazone (MIBT against pox viruses, Maloney leukemia viruses and recently against HIV. However, their ability to inhibit flavivirus replication has not been investigated. Hence the present study was designed to evaluate the antiviral activity of 14 MIBT derivatives against Flaviviruses that are prevalent in India such as Japanese Encephalitis Virus (JEV, Dengue-2 (Den-2 and West Nile viruses (WNV. Results Amongst the fourteen Mannich bases of MIBT derivatives tested one compound – SCH 16 was able to completely inhibit in vitro Japanese encephalitis virus (JEV and West Nile virus (WNV replication. However no antiviral activity of SCH 16 was noted against Den-2 virus replication. This compound was able to inhibit 50% of the plaques (IC50 produced by JEV and WNV at a concentration of 16 μgm/ml (0.000025 μM and 4 μgm/ml (0.000006 μM respectively. Furthermore, SCH 16 at a concentration of 500 mg/kg body weight administered by oral route twice daily was able to completely (100% prevent mortality in mice challenged with 50LD50 JEV by the peripheral route. Our experiments to understand the mechanism of action suggest that SCH 16 inhibited JEV replication at the level of early protein translation. Conclusion Only one of the 14 isatin derivatives -SCH 16 exhibited antiviral action on JEV and WNV virus infection in vitro. SCH 16 was also found to completely inhibit JEV replication in vivo in a mouse model challenged peripherally with 50LD50 of the virus. These results warrant further research and development on SCH 16 as a possible therapeutic agent.

  14. Thiosemicarbazone complexes of technetium

    International Nuclear Information System (INIS)

    One aproach to the design of new sup(99m)Tc-radiopharmaceuticals consists in the preparation of bifunctional radio-pharmaceuticals [1]. In this approach, a bifunctional molecule is synthesized which possesses a chelating functional group (capable of forming a stable complex with sup(99m)Tc) attached to a second functional group which is expected to have a useful biological distribution. Thiosemicarbazones are compounds that possess great chelating capacity [2] and are easily obtainable by condensation of the theosemicarbazide (H2N-NH-CS-NH2) or substituted thiosemicarbazide with the carbonyl groups of aldehydes or ketones. Consequently transformation of molecules of biological interest that the carbonyl group possess in thiosemicarbazones is simple and these modified molecules could act a bifunctional radiopharmaceuticals. For this reason a series of thiosemicarbazone complexes of 99Tc was prepared. This is the first report on technetium complexes with thiosemicarbazones. (orig.)

  15. Thiosemicarbazone complexes of technetium

    Energy Technology Data Exchange (ETDEWEB)

    Grases, F.; Genestar, C.

    1985-01-01

    One aproach to the design of new sup(99m)Tc-radiopharmaceuticals consists in the preparation of bifunctional radio-pharmaceuticals (1). In this approach, a bifunctional molecule is synthesized which possesses a chelating functional group (capable of forming a stable complex with sup(99m)Tc) attached to a second functional group which is expected to have a useful biological distribution. Thiosemicarbazones are compounds that possess great chelating capacity (2) and are easily obtainable by condensation of the theosemicarbazide (H/sub 2/N-NH-CS-NH/sub 2/) or substituted thiosemicarbazide with the carbonyl groups of aldehydes or ketones. Consequently transformation of molecules of biological interest that the carbonyl group possess in thiosemicarbazones is simple and these modified molecules could act as bifunctional radiopharmaceuticals. For this reason a series of thiosemicarbazone complexes of /sup 99/Tc was prepared. This is the first report on technetium complexes with thiosemicarbazones.

  16. Spectrophotometric, voltammetric and cytotoxicity studies of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)-substituted derivatives: A combined experimental-computational study

    Science.gov (United States)

    Akgemci, Emine Guler; Saf, Ahmet Ozgur; Tasdemir, Halil Ugur; Türkkan, Ercan; Bingol, Haluk; Turan, Suna Ozbas; Akkiprik, Mustafa

    2015-02-01

    In this study, 2-hydroxy-5-methoxyacetophenone thiosemicarbazone (HMAT) and its novel N(4) substituted derivatives were synthesized and characterized by different techniques. The optical band gap of the compounds and the energy of HOMO were experimentally examined by UV-vis spectra and cyclic voltammetry measurements, respectively. Furthermore, the conformational spaces of the compounds were scanned with molecular mechanics method. The geometry optimization, HOMO and LUMO energies, the energy gap of the HOMO-LUMO, dipole moment of the compounds were theoretically calculated by the density functional theory B3LYP/6-311++G(d,p) level. The minimal electronic excitation energy and maximum wavelength calculations of the compounds were also performed by TD-DFT//B3LYP/6-311++G(d,p) level of theory. Theoretically calculated values were compared with the related experimental values. The combined results exhibit that all compounds have good electron-donor properties which affect anti-proliferative activity. The cytotoxic effects of the compounds were also evaluated against HeLa (cervical carcinoma), MCF-7 (breast carcinoma) and PC-3 (prostatic carcinoma) cell lines using the standard MTT assay. All tested compounds showed antiproliferative effect having IC50 values in different range. In comparison with that of HMAT, it was obtained that while ethyl group on 4(N)-substituted position decreased in potent anti-proliferative effect, the phenyl group on the position increased in anti-proliferative effect for the tested cancer cell line. Considering the molecular energy parameters, the cytotoxicity activities of the compounds were discussed.

  17. Synthesis, nuclear magnetic resonance and infrared studies of zinc(II) and cadmium(II) complexes of thiosemicarbazones derived from fluorenone and p-anisaldehyde

    International Nuclear Information System (INIS)

    Fluorenone (FTSCH) and p-anisaldehyde (ATSCH) thiosemicarbazones react with zinc(II) and cadmium(II) acetates forming M:L 1:2 complexes, characterized by IR, 1H and 13C NMR spectra and elemental analyses. The coordination mode of the ligands is discussed and four-coordinate, pseudo-tetrahedral structures are suggested. (author)

  18. Spectral and structural studies of copper(II) complexes of thiosemicarbazones derived from salicylaldehyde and containing ring incorporated at N(4)-position

    Science.gov (United States)

    Latheef, Leji; Kurup, Maliyeckal R. Prathapachandra

    2008-06-01

    Mononuclear and binuclear copper(II) complexes ( 1- 8) with two ONS donor thiosemicarbazone ligands {salicylaldehyde 3-hexamethyleneiminyl thiosemicarbazone [H 2L 1] and salicylaldehyde 3-tetramethyleneiminyl thiosemicarbazone [H 2L 2]} have been prepared and physico-chemically characterized. IR, electronic and EPR spectra of the complexes have been obtained. The thiosemicarbazones bind to metal as dianionic ONS donor ligands in all the complexes except in [Cu(HL 1) 2] ( 2) and [Cu(HL 2) 2] ( 6). In compounds 2 and 6 the ligands are coordinated as monoanionic HL - ones. The magnetic susceptibility measurements indicate that all the complexes are paramagnetic. In complex [(CuL 1) 2] ( 1), the magnetic moment value is lower than the expected spin only value. In all the complexes g|| > g⊥ > 2.0023 and G values within the range 2.5-3.5 are consistent with d ground state. The complexes were given the formula as [(CuL 1) 2] ( 1); [Cu(HL 1) 2] ( 2); [CuL 1bpy] ( 3); [CuL 1phen] ( 4); [CuL 1γ-pic]·2H 2O ( 5); [Cu(HL 2) 2] ( 6); [CuL 2py]·3H 2O ( 7); [CuL 2bipy] ( 8). The structure of the compound 8 have been solved by single crystal X-ray crystallography and was found to be distorted square pyramid around copper(II) ion.

  19. Thiosemicarbazone complexes of the platinum metals. A story of variable coordination modes

    Indian Academy of Sciences (India)

    Indrani Pal; Falguni Basuli; Samaresh Bhattacharya

    2002-08-01

    Salicylaldehyde thiosemicarbazone (H2saltsc) reacts with [M(PPh3)3X2] (M = Ru, Os; X = Cl, Br) to afford complexes of type [M(PPh3)2(Hsaltsc)2], in which the salicylaldehyde thiosemicarbazone ligand is coordinated to the metal as a bidentate N,S-donor forming a four-membered chelate ring. Reaction of benzaldehyde thiosemicarbazones (Hbztsc-R) with [M(PPh3)3X2] also affords complexes of similar type, viz. [M(PPh3)2(bztsc-R)2], in which the benzaldehyde thiosemicarbazones have also been found to coordinate the metal as a bidentate N,S-donor forming a fourmembered chelate ring as before. Reaction of the Hbztsc-R ligands has also been carried out with [M(bpy)2X2] (M = Ru, Os; X = Cl, Br), which has afforded complexes of type [M(bpy)2(bztsc-R)]+, which have been isolated as perchlorate salts. Coordination mode of bztsc-R has been found to be the same as before. Structure of the Hbztsc-OMe ligand has been determined and some molecular modelling studies have been carried out determine the reason for the observed mode of coordination. Reaction of acetone thiosemicarbazone (Hactsc) has then been carried out with [M(bpy)2X2] to afford the [M(bpy)2(actsc)]ClO4 complexes, in which the actsc ligand coordinates the metal as a bidentate N,S-donor forming a five-membered chelate ring. Reaction of H2saltsc has been carried out with [Ru(bpy)2Cl2] to prepare the [Ru(bpy)2(Hsaltsc)]ClO4 complex, which has then been reacted with one equivalent of nickel perchlorate to afford an octanuclear complex of type [{Ru(bpy)2(saltsc-H)}4Ni4](ClO4)4.

  20. Overtone spectroscopy of some benzaldehyde derivatives

    Indian Academy of Sciences (India)

    P K Srivastava; D K Rai; S B Rai

    2001-06-01

    Overtone spectrum of , and -nitrobenzaldehydes and -chlorobenzaldehyde has been studied in 2000–12000 cm-1 region. Vibrational frequencies and anharmonicity constants for aryl as well as alkyl CH stretch vibrations have been determined. We have also determined the internuclear distances for the aryl CH bond in the different molecules. The small variation observed in these distances is an indication of the substitution effect. It is observed that in the case of -disubstituted benzenes, the shift in aryl CH bond is proportional to sum of the Hammet of the substituents. However in the case of -disubstituted benzenes it is only 80% of the para-substituted shift.

  1. Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities

    OpenAIRE

    Karaküçük-İyidoğan, Ayşegül; Taşdemir, Demet; Oruç-Emre, Emine Elçin; Balzarini, Jan

    2011-01-01

    A series of thiosemicarbazones and their platinum(II) and palladium(II) complexes have been synthesized. The chemical structures of ligands and their complexes were characterized by UV-Vis, IR, (1)H NMR, (13)C NMR, MS spectra, elemental analysis and TGA. The antiviral and cytotoxic activities of all compounds have been tested. Results of broad antiviral evaluation showed that none of the compounds evaluated endowed with anti-DNA or -RNA virus activity at subtoxic concentrations except for the...

  2. Synthesis, Spectral, and Biological Properties of Copper(II) Complexes of Thiosemicarbazones of Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes

    OpenAIRE

    2006-01-01

    We have synthesized a novel series of Schiff bases by condensation of 4-aminoantipyrine and various aromatic aldehydes followed by reaction with thiosemicarbazide. These thiosemicarbazones are potential ligands toward transition metal ions. The reaction of copper(II) salts with 4[N-(benzalidene)amino]antipyrinethiosemicarbazone (BAAPTS), 4[N-(4′-methoxybenzalidene) amino] antipyrinethiosemicarbozone (MBAAPTS), 4[N-(4′-dimethylamino benzalidene) amino] antipyrinethiosemicarbazone (DA...

  3. Microwave synthesis of mixed ligand diimine–thiosemicarbazone complexes of ruthenium(ii): biophysical reactivity and cytotoxicity†

    OpenAIRE

    Beckford, Floyd A.; Shaloski, Michael; LeBlanc, Gabriel; Thessing, Jeffrey; Lewis-Alleyne, Lesley C.; Holder, Alvin A.; LI, LIYA; Seeram, Navindra P.

    2009-01-01

    A novel microwave-assisted synthetic method has been used to synthesise a series of mixed ligand ruthenium(ii) compounds containing diimine as well as bidentate thiosemicarbazone ligands. The compounds contain the diimine 1,10-phenanthroline (phen) or 2,2′-bipyridine (bpy) and the thiosemicarbazone is derived from 9-anthraldehyde. Based on elemental analyses and spectroscopic data, the compounds are best formulated as [(phen)2Ru(thiosemicarbazone)](PF6)2 and [(phen)2Ru(thiosemicarbazone)](PF6...

  4. 3-Methoxybenzaldehyde thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Jian Zhang

    2009-04-01

    Full Text Available The title compound, C9H11N3OS, was prepared by the reaction of 3-methoxybenzaldehyde and thiosemicarbazide. The benzylidene ring and the thiosemicarbazone fragment are slightly twisted, making a dihedral angle of 14.1 (1°. A weak intramolecular N—H...N hydrogen bond may influence the conformation of the molecule. Intermolecular N—H...S hydrogen bonds build up a three-dimensional network.

  5. Pyridine-2-carbaldehyde thiosemicarbazone

    OpenAIRE

    Sheng-Xiang Yang; Kun Jiang; Xiang Zhang; Li-Hua Song

    2009-01-01

    The asymmetric unit of the title compound, C7H8N4S, contains two independent molecules with slightly different conformations; the dihedral angles between the pyridine ring and mean plane of the thiosemicarbazone unit in the two molecules are 2.88 (5) and 6.30 (5)°. Intermolecular N—H...N and N—H...S hydrogen bonds link the molecules into layers parallel to the ab plane.

  6. 3-Methoxybenzaldehyde thiosemicarbazone

    OpenAIRE

    Jian Zhang; Lin-ping Wu; Ling-hua Zhuang; Guo-wei Wang

    2009-01-01

    The title compound, C9H11N3OS, was prepared by the reaction of 3-methoxybenzaldehyde and thiosemicarbazide. The benzylidene ring and the thiosemicarbazone fragment are slightly twisted, making a dihedral angle of 14.1 (1)°. A weak intramolecular N—H...N hydrogen bond may influence the conformation of the molecule. Intermolecular N—H...S hydrogen bonds build up a three-dimensional network.

  7. Pyridine-2-carbaldehyde thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Sheng-Xiang Yang

    2009-02-01

    Full Text Available The asymmetric unit of the title compound, C7H8N4S, contains two independent molecules with slightly different conformations; the dihedral angles between the pyridine ring and mean plane of the thiosemicarbazone unit in the two molecules are 2.88 (5 and 6.30 (5°. Intermolecular N—H...N and N—H...S hydrogen bonds link the molecules into layers parallel to the ab plane.

  8. NMR spectral and structural studies on some xanthenones and their thiosemicarbazone derivatives: Crystal and molecular structure of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one

    Science.gov (United States)

    Sethukumar, A.; Vithya, V.; Udhaya Kumar, C.; Arul Prakasam, B.

    2012-01-01

    A series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones [ 1a- 9a] were prepared employing a three component one-pot reaction of aryl aldehyde, 2-naphthol and 1,3-cyclohexanedione using BF 3·OEt 2 as catalyst. Thiosemicarbazone derivatives [ 1b- 5b] were also prepared in the presence of acid catalyst. All the synthesized compounds have been characterized by IR and NMR. The structure of 5b was confirmed by HSQC spectral analysis. Single crystal X-ray structural analysis of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one evidences the envelope and flattened-boat conformations of cyclohexenone and pyran rings respectively.

  9. Electronic, epr and magnetic studies of Co(II), Ni(II) and Cu(II) complexes with thiosemicarbazone (L 1) and semicarbazone (L 2) derived from pyrole-2-carboxyaldehyde

    Science.gov (United States)

    Chandra, Sulekh; Kumar, Anil

    2007-07-01

    Co(II), Ni(II) and Cu(II) complexes are synthesized with thiosemicarbazone (L 1) and semicarbazone (L 2) derived from pyrole-2-carboxyaldehyde. These complexes are characterized by elemental analysis, molar conductance, magnetic susceptibility measurements, mass, IR, electronic and EPR spectral studies .The molar conductance measurements of the complexes in DMSO correspond to non-electrolytic nature except Co(L 1) 2(NO 3) 2 and Ni(L 1) 2(NO 3) 2 complexes which are 1:2 electrolytes. All the complexes are of high-spin type. On the basis of spectral studies an octahedral geometry may be assigned for Co(II) and Ni(II) complexes except Co(L 1) 2(NO 3) 2 and Ni(L 1) 2(NO 3) 2 which are of tetrahedral geometry. A tetragonal geometry may be suggested for Cu(II) complexes.

  10. A simple colorimetric method for determination of the specific activity of spallation-produced copper-67 using phenylglyoxal (PG) bis-([sup 4]N-methyl)thiosemicarbazone (TSC) derivatives

    Energy Technology Data Exchange (ETDEWEB)

    McPherson, D.W.; Lee, T.W.; Knapp, F.F. Jr. (Oak Ridge National Lab., TN (United States))

    1990-01-01

    Copper-67 ([sup 67]Cu) is a useful radioisotope for therapeutic applications and is usually available from high-energy spallation of zinc targets. Since spallation-produced [sup 67]Cu can also contain undesirable levels of nonradioactive copper ([sup 63]Cu and [sup 65]Cu), which may interfere with antibody labelling, the availability of a simple inexpensive technique to determine the specific activity of [sup 67]Cu would be useful. Bis-thiosemicarbazone (TSC) derivatives of 1,2-diketones or [alpha]-ketoaldehydes such as phenylglyoxal (PG) form orange-colored complexes with copper(II) that exhibit an absorption maximum at 480 mm. Analysis of HCl target solutions of [sup 67]Cu produced at the Brookhaven National Laboratory (one sample) and the Los Alamos Scientific Laboratory (four samples) by this method gave specific activity values which corresponded very well with values obtained by ion coupling plasma analysis (ICP). (Author).

  11. Microwave assisted synthesis, X-ray crystallography and DFT calculations of selected aromatic thiosemicarbazones

    Science.gov (United States)

    Serda, Maciej; Małecki, Jan G.; Mrozek-Wilczkiewicz, Anna; Musioł, Robert; Polański, Jarosław

    2013-04-01

    Series of four benzaldehyde thiosemicarbazones has been synthesized under microwave irradiation and characterized structurally by means of infrared and NMR spectroscopies and mass spectrometry. Their crystal structures were determined by single crystal X-ray analysis followed by DFT calculations. Partial charges on the molecular surface and dipole moments of the structures were calculated. Crystal structures are stabilized by intramolecular hydrogen bonding and stacking interactions. Studied compounds are interesting as antiproliferative and antifungal agents acting through interactions with iron. Thus presented results may be useful in design new more active or specific structures.

  12. The radiosensitizing effect of a N(4)-tolyl-2-acetylpyridine derived thiosemicarbazone and its metallic complex against a glioblastoma cell line

    International Nuclear Information System (INIS)

    Cancer is one of the most prevalent and difficult diseases to be treated. Despite the efforts at improving diagnose and treatment, the success is still very limited. One of the factors implicated in such limitation is the inherent radioresistance of most tumors, specially the cerebral ones. They are poorly vascularized due to the rapid growth of cells and disorganized angiogenesis that leads to hypoxic tissue that increases radioresistance. Also another issue is the side effects of exposition to high levels of radiation and chemicals. Combined approaches using both chemo and radiotherapy are one of the most effective strategies applied to maximize the results and decrease the side effects of the treatment to the patient. One of the drugs that are commonly used is cisplatin that has some, yet limited result. Given this context, our group has been testing several synthetic compounds of the thiosemicarbazone class. These chemicals have broad pharmacologic profile including antitumoral effect. We have shown in previous works the effective reduction of cell viability and proliferation using very low concentrations of thiosemicarbazones both in free form and complexed with metals like copper. In this work we present another application of this compound that can also be used as a radiosensitization agent in glioblastoma multiform cell line RT-2 present that the combined approach increases de effect of gamma radiation. Also, that the coordination to copper apparently does not increase this activity. (author)

  13. Synthesis, spectral characterization and biological evaluation of copper(II) and nickel(II) complexes with thiosemicarbazones derived from a bidentate Schiff base

    Science.gov (United States)

    Chandra, Sulekh; Bargujar, Savita; Nirwal, Rita; Yadav, Neesha

    2013-04-01

    Complexes of copper(II) and nickel(II) of general composition M(L)2X2, have been synthesized with the ligand 1-Tetralone thiosemicarbazone (where L = 1-Tetralone thiosemicarbazone and X=Cl,1/2SO42-). The molar conductance of the complexes in fresh solution of DMSO lies in the range of 10-20 Ω-1 cm2 mol-1 indicating their non-electrolytic behavior. Thus, the complexes may be formulated as [M(L2)X2]. Ligand was characterized by mass, NMR, IR and single crystallographic studies. All the complexes were characterized by elemental analyses, magnetic moments, IR, electronic and EPR spectral studies. The IR spectral data of ligand indicated the involvement of sulfur and azomethine nitrogen in coordination to the central metal ion. The copper(II) and nickel(II) complexes were found to have magnetic moments1.93-1.96 BM and 2.91-2.94 BM corresponding to one and two unpaired electrons respectively. On the basis of molar conductance, EPR, electronic and infrared spectral studies, a tetragonal geometry has been assigned for Cu(II) chloride complex and trigonal bipyramidal to Cu(II) sulfate complex but an octahedral geometry for Ni(II) complexes. Newly synthesized ligand and its Cu(II) and Ni(II) complexes have also been screened against different bacterial and fungal species.

  14. The radiosensitizing effect of a N(4)-tolyl-2-acetylpyridine derived thiosemicarbazone and its metallic complex against a glioblastoma cell line

    Energy Technology Data Exchange (ETDEWEB)

    Vilas Boas, Fabricio A.S.; Hudson, Luiza O.; Santos, Raquel G. dos [Centro de Desenvolvimento da Tecnologia Nuclear (CDTN/CNEN-MG), Belo Horizonte, MG (Brazil). Lab. de Radiobiologia], e-mail: fasvb@cdtn.br, e-mail: luluhud@yahoo.com.br, e-mail: santosr@cdtn.br; Mendes, Isolda C.; Beraldo, Heloisa O. [Universidade Federal de Minas Gerais (UFMG), Belo Horizonte, MG (Brazil). Dept. de Quimica], e-mail: Isolda.mendes@terra.com.br, e-mail: hberaldo@pq.cnpq.br

    2009-07-01

    Cancer is one of the most prevalent and difficult diseases to be treated. Despite the efforts at improving diagnose and treatment, the success is still very limited. One of the factors implicated in such limitation is the inherent radioresistance of most tumors, specially the cerebral ones. They are poorly vascularized due to the rapid growth of cells and disorganized angiogenesis that leads to hypoxic tissue that increases radioresistance. Also another issue is the side effects of exposition to high levels of radiation and chemicals. Combined approaches using both chemo and radiotherapy are one of the most effective strategies applied to maximize the results and decrease the side effects of the treatment to the patient. One of the drugs that are commonly used is cisplatin that has some, yet limited result. Given this context, our group has been testing several synthetic compounds of the thiosemicarbazone class. These chemicals have broad pharmacologic profile including antitumoral effect. We have shown in previous works the effective reduction of cell viability and proliferation using very low concentrations of thiosemicarbazones both in free form and complexed with metals like copper. In this work we present another application of this compound that can also be used as a radiosensitization agent in glioblastoma multiform cell line RT-2 present that the combined approach increases de effect of gamma radiation. Also, that the coordination to copper apparently does not increase this activity. (author)

  15. Synthesis and Characterization of New Palladium(II Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

    Directory of Open Access Journals (Sweden)

    Wilfredo Hernández

    2013-01-01

    Full Text Available The palladium(II bis-chelate complexes of the type [Pd(TSC1-52] (6–10, with their corresponding ligands 4-phenyl-1-(acetone-thiosemicarbazone, HTSC1 (1, 4-phenyl-1-(2′-chloro-benzaldehyde-thiosemicarbazone, HTSC2 (2, 4-phenyl-1-(3′-hydroxy-benzaldehyde-thiosemicarbazone, HTSC3 (3, 4-phenyl-1-(2′-naphthaldehyde-thiosemicarbazone, HTSC4 (4, and 4-phenyl-1-(1′-nitro-2′-naphthaldehyde-thiosemicarbazone, HTSC5 (5, were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H- and 13C-NMR. The molecular structure of HTSC3, HTSC4, and [Pd(TSC12] (6 have been determined by single crystal X-ray crystallography. Complex 6 shows a square planar geometry with two deprotonated ligands coordinated to PdII through the azomethine nitrogen and thione sulfur atoms in a cis arrangement. The in vitro cytotoxic activity measurements indicate that the palladium(II complexes (IC50=0.01–9.87 μM exhibited higher antiproliferative activity than their free ligands (IC50=23.48–70.86 and >250 μM against different types of human tumor cell lines. Among all the studied palladium(II complexes, the [Pd(TSC32] (8 complex exhibited high antitumor activity on the DU145 prostate carcinoma and K562 chronic myelogenous leukemia cells, with low values of the inhibitory concentration (0.01 and 0.02 μM, resp..

  16. Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

    Science.gov (United States)

    Hernández, Wilfredo; Paz, Juan; Carrasco, Fernando; Spodine, Evgenia; Manzur, Jorge; Sieler, Joachim; Blaurock, Steffen; Beyer, Lothar

    2013-01-01

    The palladium(II) bis-chelate complexes of the type [Pd(TSC1-5)2] (6–10), with their corresponding ligands 4-phenyl-1-(acetone)-thiosemicarbazone, HTSC1 (1), 4-phenyl-1-(2′-chloro-benzaldehyde)-thiosemicarbazone, HTSC2 (2), 4-phenyl-1-(3′-hydroxy-benzaldehyde)-thiosemicarbazone, HTSC3 (3), 4-phenyl-1-(2′-naphthaldehyde)-thiosemicarbazone, HTSC4 (4), and 4-phenyl-1-(1′-nitro-2′-naphthaldehyde)-thiosemicarbazone, HTSC5 (5), were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H- and 13C-NMR). The molecular structure of HTSC3, HTSC4, and [Pd(TSC1)2] (6) have been determined by single crystal X-ray crystallography. Complex 6 shows a square planar geometry with two deprotonated ligands coordinated to PdII through the azomethine nitrogen and thione sulfur atoms in a cis arrangement. The in vitro cytotoxic activity measurements indicate that the palladium(II) complexes (IC50 = 0.01–9.87 μM) exhibited higher antiproliferative activity than their free ligands (IC50 = 23.48–70.86 and >250 μM) against different types of human tumor cell lines. Among all the studied palladium(II) complexes, the [Pd(TSC3)2] (8) complex exhibited high antitumor activity on the DU145 prostate carcinoma and K562 chronic myelogenous leukemia cells, with low values of the inhibitory concentration (0.01 and 0.02 μM, resp.). PMID:24391528

  17. (E-4-Octyloxybenzaldehyde thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    M. A. A. A. A. Islam

    2010-01-01

    Full Text Available In the title compound, C16H25N3OS, the thiosemicarbazone group adopts an E configuration with respect to the C=N bond and is almost coplanar with the benzene ring, forming a dihedral angle of 9.3 (1°. In the crystal packing, the molecules lie along the a axis in an antiparallel arrangement and are held in place by van der Waals interactions. As a consequence, there is relatively low anisotropic thermal motion in the terminal atoms of the n-octyl chain.

  18. Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities.

    Science.gov (United States)

    Karaküçük-İyidoğan, Ayşegül; Taşdemir, Demet; Oruç-Emre, Emine Elçin; Balzarini, Jan

    2011-11-01

    A series of thiosemicarbazones and their platinum(II) and palladium(II) complexes have been synthesized. The chemical structures of ligands and their complexes were characterized by UV-Vis, IR, (1)H NMR, (13)C NMR, MS spectra, elemental analysis and TGA. The antiviral and cytotoxic activities of all compounds have been tested. Results of broad antiviral evaluation showed that none of the compounds evaluated endowed with anti-DNA or -RNA virus activity at subtoxic concentrations except for the palladium complex 1b. This compound exhibited slightly selective inhibition against cytomegalovirus. The platinum complex 4a exhibited the best cytostatic activities against human cervix carcinoma. Ligands 2, 4 and 5 showed cytostatic potential. The palladium complexes were in general less cytostatic than the corresponding platinum complexes or unliganded congeners. PMID:21993152

  19. Preparation of 35S labelled thiosemicarbazone

    International Nuclear Information System (INIS)

    A 35S labelled thiosemicarbazone is prepared, on a millimole scale by reacting labelled thiocyanate with hydrazine sulfate in ethanolic medium. The hydrazine thiocyanate so formed is then condensed with aldehyde to form the thiosemicarbazone

  20. 2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate

    OpenAIRE

    Tuncer Hökelek; Ertan Şahin; knur Babahan; Nursabah Sarıkavaklı

    2008-01-01

    In the title thiosemicarbazone derivative, C9H10N4OS·H2O, intramolecular N—H...N hydrogen bonds result in the formation of two nearly coplanar five- and six-membered rings, which are also almost coplanar with the adjacent phenyl ring. The oxime group has an E configuration and is involved in intermolecular O—H...O hydrogen bonding as a donor. In the crystal structure, intramolecular O—H...S and N—H...N and intermolecular O—H...O and N—H...S hydrogen bo...

  1. Cyclopalladated organosilane-tethered thiosemicarbazones: novel strategies for improving antiplasmodial activity.

    Science.gov (United States)

    Adams, Muneebah; Barnard, Linley; de Kock, Carmen; Smith, Peter J; Wiesner, Lubbe; Chibale, Kelly; Smith, Gregory S

    2016-04-01

    Two series of ferrocenyl- and aryl-derived cyclopalladated organosilane thiosemicarbazone complexes were synthesised via C-H bond activation. Selected compounds were evaluated for in vitro antiplasmodial activity against the chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains of the human malaria parasite Plasmodium falciparum. Cyclopalladation of the thiosemicarbazones resulted in antiplasmodial activities in the low micromolar range. PMID:26911403

  2. Characterization of the anti tumoral activity of the thiosemicarbazones derived from N(4)-methyl-tolyl-2acetylpyridine And 2-pyridinoformamide and its metal complex: evaluation of the radiopharmaceutical potential; Caracterizacao da atividade antitumoral das tiossemicarbazonas derivadas de N(4)-metil-toluil-2-acetilpiridina e 2-piridinoformamida e seus complexos metalicos: avaliacao do potencial radiofarmaceutico

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Paulo Roberto Ornelas da

    2008-07-01

    Thiosemicarbazones have attracted great pharmacological interest because of their biological properties, such as cytotoxic activity against multiple strains of human tumors. The most studied compounds are pyridine-based because of their resemblance to pyridoxal metabolites that attach to co-enzyme B{sub 6}-dependant enzymes. This work aimed the characterization of the anti tumoral effect of N(4)-methyl-tolyl-2-acetylpyridine and 2-pyridinoformamide-derived thiosemicarbazones and the development of a radiopharmaceutical based on a thiosemicarbazone metal complex for positron emission tomography. In the first phase of this study were synthesized twenty-one thiosemicarbazones, derived from N(4)methyl-2 acetylpyridine and 2-pyridine formamide, as well as their metal complexes (Sn, Ga and Cu). Their cytotoxic potential were evaluated against brain and breast tumor cells in vitro. Our results showed all of them presented powerful cytotoxic and antiproliferative activities against glioblastoma multiform and breast adenocarcinoma at very low concentrations (nanomolar range). Morphological alterations characteristic of apoptosis, such as cell shrinkage, chromatin condensation were observed. Copper chloride was used as control and has presented IC50 at millimolar range suggesting that copper complexation with thiosemicarbazone significantly increases (more than 1 million) the anti tumoral effect of this metal. Due to the potent anti tumoral activity of N(4)-methyl-tolyl-2-acetylpyridine derived thiosemicarbazones and the excellent properties of {sup 64}Cu (T{sub 1/2} = 12.7 hours, {beta}{sup +}, {beta}{sup -}, and EC decay), at the second part for this work it was developed a new imaging agent (radiopharmaceutical) for tumor detection by positron emission tomography (PET). The radiopharmaceuticals were produced in the nuclear reactor TRIGA-IPR-R1 from CDTN, via neutron capture reaction {sup 63}Cu (n,{gamma}) {sup 64}Cu, of the copper complex N(4)-ortho-toluyl-2

  3. Synthesis, Spectral, and Biological Properties of Copper(II Complexes of Thiosemicarbazones of Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes

    Directory of Open Access Journals (Sweden)

    Deepak Kumar Sharma

    2006-06-01

    Full Text Available We have synthesized a novel series of Schiff bases by condensation of 4-aminoantipyrine and various aromatic aldehydes followed by reaction with thiosemicarbazide. These thiosemicarbazones are potential ligands toward transition metal ions. The reaction of copper(II salts with 4[N-(benzalideneamino]antipyrinethiosemicarbazone (BAAPTS, 4[N-(4′-methoxybenzalidene amino] antipyrinethiosemicarbozone (MBAAPTS, 4[N-(4′-dimethylamino benzalidene amino] antipyrinethiosemicarbazone (DABAAPTS, and 4[N-(cinnamalidene amino] antipyrinethiosemicarbazone (CAAPTS resulted in the formation of solid complexes with the general composition CuX2⋅(H2O(L(X = Cl, Br, NO3, NCS, or CH3COO; L = BAAPTS, MBAAPTS, DABAAPTS, or CAAPTS. These complexes were characterized through elemental analysis, molecular weight, electrical conductance, infrared, electronic spectra, and magnetic susceptibilities at room temperature. Copper(II complexes with BAAPTS and MBAAPTS were screened for antibacterial and antifungal properties and have exhibited potential activity. Thermal stabilities of two representative complexes were also investigated.

  4. Adsorption, mobility, and dimerization of benzaldehyde on Pt(111)

    DEFF Research Database (Denmark)

    Rasmussen, Anton Michael Havelund; Hammer, Bjørk

    2012-01-01

    Building on results for the adsorption of benzene on Pt(111), the adsorption of benzaldehyde is investigated using density functional theory. Benzaldehyde is found to chemisorb preferentially with its aromatic ring in the flat-lying bridge geometry that is also preferred for benzene. Across the...

  5. Stability of the resistance to the thiosemicarbazone derived from 5,6-dimethoxy-1-indanone, a non-nucleoside polymerase inhibitor of bovine viral diarrhea virus.

    Directory of Open Access Journals (Sweden)

    Eliana F Castro

    Full Text Available Bovine viral diarrhea virus (BVDV is the prototype Pestivirus. BVDV infection is distributed worldwide and causes serious problems for the livestock industry. The thiosemicarbazone of 5,6-dimethoxy-1-indanone (TSC is a non-nucleoside polymerase inhibitor (NNI of BVDV. All TSC-resistant BVDV variants (BVDV-TSCr T1-5 present an N264D mutation in the NS5B gene (RdRp whereas the variant BVDV-TSCr T1 also presents an NS5B A392E mutation. In the present study, we carried out twenty passages of BVDV-TSCr T1-5 in MDBK cells in the absence of TSC to evaluate the stability of the resistance. The viral populations obtained (BVDV R1-5 remained resistant to the antiviral compound and conserved the mutations in NS5B associated with this phenotype. Along the passages, BVDV R2, R3 and R5 presented a delay in the production of cytopathic effect that correlated with a decrease in cell apoptosis and intracellular accumulation of viral RNA. The complete genome sequences that encode for NS2 to NS5B, Npro and Erns were analyzed. Additional mutations were detected in the NS5B of BVDV R1, R3 and R4. In both BVDV R2 and R3, most of the mutations found were localized in NS5A, whereas in BVDV R5, the only mutation fixed was NS5A V177A. These results suggest that mutations in NS5A could alter BVDV cytopathogenicity. In conclusion, the stability of the resistance to TSC may be due to the fixation of different compensatory mutations in each BVDV-TSCr. During their replication in a TSC-free medium, some virus populations presented a kind of interaction with the host cell that resembled a persistent infection: decreased cytopathogenicity and viral genome synthesis. This is the first report on the stability of antiviral resistance and on the evolution of NNI-resistant BVDV variants. The results obtained for BVDV-TSCr could also be applied for other NNIs.

  6. Evaluation of thiosemicarbazone derivative as chelating agent for the simultaneous removal and trace determination of Cd(II) and Pb(II) in food and water samples.

    Science.gov (United States)

    Koduru, Janardhan Reddy; Lee, Kap Duk

    2014-05-01

    In the present investigation, prepared N-ethyl-3-carbazolecarbaxaldehyde-3-thiosemicarbazone (ECCT) and employed for the simultaneous removal and determination of trace amounts of Cd(II) and Pb(II) from food and water samples. Cd(II) and Pb(II) gave yellow and orange colored complexes with ECCT in acetate buffer at pH 6.0 with λmax, 380 and 440nm, respectively. Both complexes were easily extractable into kerosene at 1:1(M:L) composition. It was in accordance with Beer's law in the range of 0.0-12.0 and 0.0-10.0μgmL(-1) with 0.999 and 0.997 correlation coefficient for Cd(II) and Pb(II) complexes, respectively, indicated a good linearity between the two variables. The molar absorptivity and Sandell's sensitivity were found to be 0.740×10(4)Lmol(-1)cm(-1), 1.52×10(-3)μgcm(-2) for Cd(II) and 1.809×10(4)L mol(-1)cm(-1), 1.15×10(-3)μgcm(-2) for Pb(II). The precision and accuracy of the method was checked for both metal ions by finding the relative standard deviations (n=8), which were 0.689% and 0.443%, with detection limits of 0.00151μgL(-1) and 0.00264μgL(-1) for Cd(II) and Pb(II), respectively. Further validation using certified reference material, NIST 1568b, resulted in determined concentrations of 0.028±0.253μgg(-1) for Cd(II) and 0.046±0.325μgg(-1) for Pb(II). These determined values agree well with the certified values in the reference materials. The interfering effects of various cations and anions were also studied. The proposed method performance was also evaluated in terms of Student 'T' test and Variance 'F' test, which indicated the significance of the present method parameters, as an inter comparison of the experimental values using ICP-OES. PMID:24360411

  7. Stability of the resistance to the thiosemicarbazone derived from 5,6-dimethoxy-1-indanone, a non-nucleoside polymerase inhibitor of bovine viral diarrhea virus.

    Science.gov (United States)

    Castro, Eliana F; Campos, Rodolfo H; Cavallaro, Lucía V

    2014-01-01

    Bovine viral diarrhea virus (BVDV) is the prototype Pestivirus. BVDV infection is distributed worldwide and causes serious problems for the livestock industry. The thiosemicarbazone of 5,6-dimethoxy-1-indanone (TSC) is a non-nucleoside polymerase inhibitor (NNI) of BVDV. All TSC-resistant BVDV variants (BVDV-TSCr T1-5) present an N264D mutation in the NS5B gene (RdRp) whereas the variant BVDV-TSCr T1 also presents an NS5B A392E mutation. In the present study, we carried out twenty passages of BVDV-TSCr T1-5 in MDBK cells in the absence of TSC to evaluate the stability of the resistance. The viral populations obtained (BVDV R1-5) remained resistant to the antiviral compound and conserved the mutations in NS5B associated with this phenotype. Along the passages, BVDV R2, R3 and R5 presented a delay in the production of cytopathic effect that correlated with a decrease in cell apoptosis and intracellular accumulation of viral RNA. The complete genome sequences that encode for NS2 to NS5B, Npro and Erns were analyzed. Additional mutations were detected in the NS5B of BVDV R1, R3 and R4. In both BVDV R2 and R3, most of the mutations found were localized in NS5A, whereas in BVDV R5, the only mutation fixed was NS5A V177A. These results suggest that mutations in NS5A could alter BVDV cytopathogenicity. In conclusion, the stability of the resistance to TSC may be due to the fixation of different compensatory mutations in each BVDV-TSCr. During their replication in a TSC-free medium, some virus populations presented a kind of interaction with the host cell that resembled a persistent infection: decreased cytopathogenicity and viral genome synthesis. This is the first report on the stability of antiviral resistance and on the evolution of NNI-resistant BVDV variants. The results obtained for BVDV-TSCr could also be applied for other NNIs. PMID:24950191

  8. The determination of furaldehyde and benzaldehyde in plum brandy

    Directory of Open Access Journals (Sweden)

    Rajković Miloš B.

    2005-01-01

    Full Text Available Among all alcohol liqueurs, brandies from drupaceous plants are characterized with the highest level of hydro cyanic acid, benzaldehyde and ethylcarbamate. In fruit brandies ethylcarbamate mainly originates from hydro cyanic acid during the processes of alcohol fermentation of crushed fruit and its preservation, distillation and ripening of the brandy. Hydro cyanic acid and benzaldehyde arise from the hydrolysis of amygdaline that is found exist in the heart of fruit stones and seeds, as well as from the hydrolysis of prunasine from the skin and flesh of drupaceous plants. The content of amygdaline and prunazine depends on the type of fruit, which corresponds to the potential content of hydro cyanic acid and benzaldehyde in the brandy that corresponds the stoichiometric ratio 1:3.94. The content of the aldehydes: furfural and benzaldehyde in plum brandy, strong plum brandy, young brandy, of domestic production in the various regions of Serbia were analyzed in this paper.

  9. The determination of furaldehyde and benzaldehyde in plum brandy

    OpenAIRE

    Rajković Miloš B.; Perić Lazar

    2005-01-01

    Among all alcohol liqueurs, brandies from drupaceous plants are characterized with the highest level of hydro cyanic acid, benzaldehyde and ethylcarbamate. In fruit brandies ethylcarbamate mainly originates from hydro cyanic acid during the processes of alcohol fermentation of crushed fruit and its preservation, distillation and ripening of the brandy. Hydro cyanic acid and benzaldehyde arise from the hydrolysis of amygdaline that is found exist in the heart of fruit stones and seeds, as well...

  10. 2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate

    Directory of Open Access Journals (Sweden)

    Tuncer Hökelek

    2008-03-01

    Full Text Available In the title thiosemicarbazone derivative, C9H10N4OS·H2O, intramolecular N—H...N hydrogen bonds result in the formation of two nearly coplanar five- and six-membered rings, which are also almost coplanar with the adjacent phenyl ring. The oxime group has an E configuration and is involved in intermolecular O—H...O hydrogen bonding as a donor. In the crystal structure, intramolecular O—H...S and N—H...N and intermolecular O—H...O and N—H...S hydrogen bonds generate edge-fused R22(8 and R41(11 ring motifs. The hydrogen-bonded motifs are linked to each other to form a three-dimensional supramolecular network.

  11. Synthesis and spectral characterization of mono- and binuclear copper(II) complexes derived from 2-benzoylpyridine-N⁴-methyl-3-thiosemicarbazone: crystal structure of a novel sulfur bridged copper(II) box-dimer.

    Science.gov (United States)

    Jayakumar, K; Sithambaresan, M; Aiswarya, N; Kurup, M R Prathapachandra

    2015-03-15

    Mononuclear and binuclear copper(II) complexes of 2-benzoylpyridine-N(4)-methyl thiosemicarbazone (HL) were prepared and characterized by a variety of spectroscopic techniques. Structural evidence for the novel sulfur bridged copper(II) iodo binuclear complex is obtained by single crystal X-ray diffraction analysis. The complex [Cu2L2I2], a non-centrosymmetric box dimer, crystallizes in monoclinic C2/c space group and it was found to have distorted square pyramidal geometry (Addison parameter, τ=0.238) with the square basal plane occupied by the thiosemicarbazone moiety and iodine atom whereas the sulfur atom from the other coordinated thiosemicarbazone moiety occupies the apical position. This is the first crystallographically studied system having non-centrosymmetrical entities bridged via thiolate S atoms with Cu(II)I bond. The tridentate thiosemicarbazone coordinates in mono deprotonated thionic tautomeric form in all complexes except in sulfato complex, [Cu(HL)(SO4)]·H2O (1) where it binds to the metal centre in neutral form. The magnetic moment values and the EPR spectral studies reflect the binuclearity of some of the complexes. The spin Hamiltonian and bonding parameters are calculated based on EPR studies. In all the complexes g||>g⊥>2.0023 and the g values in frozen DMF are consistent with the d(x2-y2) ground state. The thermal stabilities of some of the complexes were also determined. PMID:25546494

  12. Synthesis and spectral characterization of mono- and binuclear copper(II) complexes derived from 2-benzoylpyridine-N4-methyl-3-thiosemicarbazone: Crystal structure of a novel sulfur bridged copper(II) box-dimer

    Science.gov (United States)

    Jayakumar, K.; Sithambaresan, M.; Aiswarya, N.; Kurup, M. R. Prathapachandra

    2015-03-01

    Mononuclear and binuclear copper(II) complexes of 2-benzoylpyridine-N4-methyl thiosemicarbazone (HL) were prepared and characterized by a variety of spectroscopic techniques. Structural evidence for the novel sulfur bridged copper(II) iodo binuclear complex is obtained by single crystal X-ray diffraction analysis. The complex [Cu2L2I2], a non-centrosymmetric box dimer, crystallizes in monoclinic C2/c space group and it was found to have distorted square pyramidal geometry (Addison parameter, τ = 0.238) with the square basal plane occupied by the thiosemicarbazone moiety and iodine atom whereas the sulfur atom from the other coordinated thiosemicarbazone moiety occupies the apical position. This is the first crystallographically studied system having non-centrosymmetrical entities bridged via thiolate S atoms with Cu(II)sbnd I bond. The tridentate thiosemicarbazone coordinates in mono deprotonated thionic tautomeric form in all complexes except in sulfato complex, [Cu(HL)(SO4)]·H2O (1) where it binds to the metal centre in neutral form. The magnetic moment values and the EPR spectral studies reflect the binuclearity of some of the complexes. The spin Hamiltonian and bonding parameters are calculated based on EPR studies. In all the complexes g|| > g⊥ > 2.0023 and the g values in frozen DMF are consistent with the dx2-y2 ground state. The thermal stabilities of some of the complexes were also determined.

  13. Evaluation of the potential application of 2-acetylpyridine N4- phenyl thiosemicarbazones derivatives for cancer therapy and diagnosis; Avaliacao da potencial aplicacao de derivados de 2-acetilpiridina N-4 fenil tiossemicarbazonas em terapia e diagnostico oncologico

    Energy Technology Data Exchange (ETDEWEB)

    Soares, Marcella Araugio

    2013-08-01

    Despite the wide range of antineoplastic agents available, resistance of some types of cancer and toxicity to normal cells have been identified as the main causes of treatment failure and death. The lack of early and precise diagnosis is also responsible for reducing survival of cancer patients. In this context, the development of substances with low toxicity and therapeutic potential and/or diagnosis purpose, is the major tool in an attempt to increase the survival of patients and assure the safety and efficacy of treatment. Thiosemicarbazones (TSC) are a class of synthetic compounds that have several biological activities, including antitumor. Although several studies have shown the great potential of TSC as therapeutic and / or diagnostic agents, different chemical modifications performed on this class of molecules indicate new possibilities for applications and still require further studies. The objective of this study was to evaluate the potential applicability of 2-acetylpyridine N-4-phenyl thiosemicarbazones derivatives for cancer therapy and diagnosis. The results showed that all 13 TSC tested were cytotoxic to breast and glioblastoma tumor cell lines, presenting higher in vitro antitumor activity than etoposide, an antineoplastic and inhibitor of topoisomerase II frequently used for cancer therapy. The TSC that have halogen or nitro on ortho position showed higher antitumor activity in vitro than their isomers with halogen or nitro on meta or para position of the phenyl group. H2Ac4oFPh and H2Ac4oClPh compounds showed the highest antitumor activity among all tested compounds, with IC{sub 50} in nanomolar order. These TSC induced cell death by apoptosis and oxidative stress was responsible, at least in part, for this type of cell death. The 5 mg.kg{sup -1} H2Ac4oFPh dose, administered s.c., for 4 consecutive days, did not induce important toxicity; however, the same treatment protocol was not effective for tumor growth reduction in an animal model of brain

  14. Manganese(II) complexes of substituted di-2-pyridyl ketone thiosemicarbazones: Structural and spectral studies

    Science.gov (United States)

    Philip, Varughese; Suni, V.; Kurup, Maliyeckal R. Prathapachandra; Nethaji, Munirathinam

    2006-05-01

    The reaction between manganese(II) acetate and two substituted thiosemicarbazones derived from di-2-pyridyl ketone (HL) in 1:2 molar ratio produces new complexes of general formula [MnL 2]. The thiosemicarbazone moiety in HL deprotonates and gets coordinated to Mn(II) through the azomethine nitrogen, one of the pyridyl nitrogens, and the thiolate sulfur in both the complexes. The crystal structure of [ MnL21] was established by single crystal X-ray diffraction and the compound crystallizes into a monoclinic lattice with P2 1/ c space group. Manganese(II) exists in a distorted octahedral geometry in the complexes.

  15. ESR, electrochemical and reactivity studies of antitrypanosomal palladium thiosemicarbazone complexes

    Science.gov (United States)

    Otero, Lucía; Folch, Christian; Barriga, Germán; Rigol, Carolina; Opazo, Lucia; Vieites, Marisol; Gambino, Dinorah; Cerecetto, Hugo; Norambuena, Ester; Olea-Azar, Claudio

    2008-08-01

    Cyclic voltammetry (CV) and electron spin resonance (ESR) techniques were used in the investigation of novel palladium complexes with bioactive thiosemicarbazones derived from 5-nitrofurane or 5-nitrofurylacroleine. Sixteen palladium complexes grouped in two series of the formula [PdCl 2HL] or [PdL 2] were studied. ESR spectra of the free radicals obtained by electrolytic reduction were characterized and analyzed. The ESR spectra showed two different hyperfine patterns. The stoichiometry of the complexes does not seem to affect significantly the hyperfine constants however we observed great differences between 5-nitrofurane and 5-nitrofurylacroleine derivatives. The scavenger properties of this family of compounds were lower than Trolox.

  16. Structural and spectral studies of an iron(III) complex [Fe(Pranthas) 2][FeCl 4] derived from 2-acetylpyridine- N(4), N(4)-(butane-1, 4-diyl) thiosemicarbazone (HPranthas)

    Science.gov (United States)

    Sreekanth, A.; Fun, Hoong-Kun; Prathapachandra Kurup, M. R.

    2005-02-01

    A novel iron(III) complex of 2-acetylpyridine N(4), N(4)-(butyl-1, 4-diyl) thiosemicarbazone (HPranthas), [Fe(Pranthas) 2]FeCl 4 was synthesized and physico-chemically characterized by means of partial elemental analysis, magnetic measurements (polycrystalline state), UV-Vis and IR spectroscopies. The presence of spin-paired iron(III) cation with dxz2dyz2dxy1 ground state is revealed by the EPR and Mössbauer spectral data. Structure of the free ligand HPranthas and the complex [Fe(Pranthas) 2]FeCl 4 were solved by single crystal X-ray diffraction. The framework of iron(III) complex consists of a discrete monomeric cationic entity containing low spin iron(III) in a slightly distorted octahedral environment. The metal ion is bonded to one sulfur and two nitrogens of each thiosemicarbazone molecule. The tetrachloroferrate(III) ion acts as counterion.

  17. 2-Phenyl-tetrahydropyrimidine-4(1H-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

    Directory of Open Access Journals (Sweden)

    Markus Nahrwold

    2009-09-01

    Full Text Available Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R-β2-homoaspartate.

  18. Metal complexes with paramagnetic thiosemicarbazone

    International Nuclear Information System (INIS)

    The complexes of Ni(2), Fe(2), Zn(2), Cd(2), Pd(2) and Pt(2) with the stable nitroxyl radical of thiosemicarbazone 4-formyl- 2, 2, 5, 5-tetramethyl-3-imidazoline-1-oxyl of the composition ML2 are synthesized. In the basis of the data of physical methods (IR, EPR, electron spectroscopy) a conclusion is made on the way of the ligand coordination. The study of the magnetic properties of the complexes has shown that in the compounds prepared a weak exchange interaction between unpaired electrons of paramagnetic centres takes place

  19. A simple colorimetric method for determination of the specific activity of spallation-produced copper-67 (Cu-67) using the bis-(N4-methyl)thiosemicarbazone (TSC) derivative of phenylglyoxal

    International Nuclear Information System (INIS)

    A method for determining the specific activity of spallation-produced copper-67 based on the complexation of the radioisotope with bis-(N4-methyl)thiosemicarbazone. The complex, which has a strong absorbance in the visible region, is measured at 480 nm, 15 minutes after beginning of reaction. The standard curve is linear to 40 ppm with a lower limit of detection of 0.4 ppm. A zinc chloride complex was also evaluated at 100-fold excess and found to have no interference with the copper-67 complex

  20. Synthesis and structure-activity correlation studies of metal complexes of alpha-N-heterocyclic carboxaldehyde thiosemicarbazones in Shewanella oneidensis.

    Science.gov (United States)

    Wilson, Barbara A; Venkatraman, Ramaiyer; Whitaker, Cedrick; Tillison, Quintell

    2005-04-01

    This investigation involved the synthesis of metal complexes to test the hypothesis that structural changesand metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced reactivity exhibited by metal complexes of heterocyclic thiosemicarbazones, synthesis and structural characterization of di-2-pyridylketone 4N-phenyl thiosemicarbazone and diphenyl tin (Sn) and platinum (Pt) complexes were undertaken. Shewanella oneidensis MR-1, a metal ion-reducing bacterium, was used as a model organism to explore the biological activity under aerobic conditions. A comparision of the cytotoxic potential of selected ligand and metal-complex thiosemicarbazones on cell growth in wild type MR-1 and mutant DSP-010 Shewanella oneidensis strains at various concentrations (0, 5, 10, 15, 20 or 25 ppm) was performed. The wild type (MR-1) grown in the presence of increasing concentrations of Sn- thiosemicarbazone complexes was comparatively more sensitive (mean cell number = 4.8 X 10(8) +/- 4.3 X 10(7) SD) than the DSP-010, a spontaneous rifampicillin derivative of the parent strain (mean cell number = 5.6 x 10(8) +/- 6.4 X 10(7) SD) under comparable aerobic conditions (p = 0.0004). No differences were observed in the sensitivity of the wild and mutant types when exposed to various concentrations of diphenyl Pt- thiosemicarbazone complex (p = 0.425) or the thiosemicarbazone ligand (p = 0.313). Growth of MR-1 in the presence of diphenyl Sn-thiosemicarbazone was significantly different among treatment groups (p = 0.012). MR-1 cell numbers were significantly higher at 5ppm than at 10 to 20ppm (p = 0.05). The mean number of DSP-010 variant strain cells also differed among

  1. Synthesis and Structure-Activity Correlation Studies of Metal Complexes of α-N-heterocyclic Carboxaldehyde Thiosemicarbazones in Shewanella oneidensis

    Science.gov (United States)

    Wilson, Barbara A.; Venkatraman, Ramaiyer; Whitaker, Cedrick; Tillison, Quintell

    2005-01-01

    This investigation involved the synthesis of metal complexes to test the hypothesis that structural changes and metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced reactivity exhibited by metal complexes of heterocyclic thiosemicarbazones, synthesis and structural characterization of di-2-pyridylketone 4N-phenyl thiosemicarbazone and diphenyl tin (Sn) and platinum (Pt) complexes were undertaken. Shewanella oneidensis MR-1, a metal ion-reducing bacterium, was used as a model organism to explore the biological activity under aerobic conditions. A comparision of the cytotoxic potential of selected ligand and metal-complex thiosemicarbazones on cell growth in wild type MR-1 and mutant DSP-010 Shewanella oneidensis strains at various concentrations (0, 5, 10, 15, 20 or 25 ppm) was performed. The wild type (MR-1) grown in the presence of increasing concentrations of Sn- thiosemicarbazone complexes was comparatively more sensitive (mean cell number = 4.8 × 108 ± 4.3 × 107 SD) than the DSP-010, a spontaneous rifampicillin derivative of the parent strain (mean cell number = 5.6 × 108 ± 6.4 × 107 SD) under comparable aerobic conditions (p=0.0004). No differences were observed in the sensitivity of the wild and mutant types when exposed to various concentrations of diphenyl Pt- thiosemicarbazone complex (p= 0.425) or the thiosemicarbazone ligand (p=0.313). Growth of MR-1 in the presence of diphenyl Sn- thiosemicarbazone was significantly different among treatment groups (p=0.012). MR-1 cell numbers were significantly higher at 5ppm than at 10 to 20ppm (p = 0.05). The mean number of DSP-010 variant strain cells also differed among diphenyl Sn

  2. Antifungal activities of thiosemicarbazones and semicarbazones against mycotoxigenic fungi

    Directory of Open Access Journals (Sweden)

    Rojane de Oliveira Paiva

    2014-12-01

    Full Text Available Mycotoxigenic fungi can compromise the quality of food, exposing human and animal health at risk. The antifungal activity of eight thiosemicarbazones (1-8 and nine semicarbazones (9-17 was evaluated against Aspergillus flavus, A. nomius, A. ochraceus, A. parasiticus and Fusarium verticillioides. Thiosemicarbazones had MIC values of 125-500 µg/ml. The thiosemicarbazones 1 and 2 exerted fungistatic activity against Aspergillus spp., and thiosemicarbazone 2 exerted fungicidal activity against F. verticillioides. Compound 2 showed an iron chelating effect of 63%. The ergosterol content of A. parasiticus had a decrease of 28 and 71% for the 31.2 and 62.5 µg/ml concentrations of thiosemicarbazone 2 compared to the control. The obtained results of antifungal activity revealed that thiosemicarbazone class was more active when compared to semicarbazone class and, the thiosemicarbazone 2 was the most active compound, specially, against Aspergillus spp.

  3. Synthesis, Spectroscopic and Toxicity Studies of Titanocene Chelates of Isatin-3-Thiosemicarbazones

    OpenAIRE

    Garima Vatsa; Pandey, O. P.; S. K. Sengupta

    2004-01-01

    The reactions of bis(cyclopentadienyl)titanium(IV) dichloride with a new class of thiosemicarbazone (LH2), derived by condensing isatin with different N(4)-substituted thiosemicarbazides, have been studied and products of type [Cp2Ti(L)] have been isolated. On the basis of various physico-chemical and spectral studies, five coordinate structures have been assigned to these derivatives. Toxicity studies of titanocene complexes at tbur different concentrations have been carried out against snai...

  4. Biomass pyrolysis: Thermal decomposition mechanisms of furfural and benzaldehyde

    Science.gov (United States)

    Vasiliou, AnGayle K.; Kim, Jong Hyun; Ormond, Thomas K.; Piech, Krzysztof M.; Urness, Kimberly N.; Scheer, Adam M.; Robichaud, David J.; Mukarakate, Calvin; Nimlos, Mark R.; Daily, John W.; Guan, Qi; Carstensen, Hans-Heinrich; Ellison, G. Barney

    2013-09-01

    The thermal decompositions of furfural and benzaldehyde have been studied in a heated microtubular flow reactor. The pyrolysis experiments were carried out by passing a dilute mixture of the aromatic aldehydes (roughly 0.1%-1%) entrained in a stream of buffer gas (either He or Ar) through a pulsed, heated SiC reactor that is 2-3 cm long and 1 mm in diameter. Typical pressures in the reactor are 75-150 Torr with the SiC tube wall temperature in the range of 1200-1800 K. Characteristic residence times in the reactor are 100-200 μsec after which the gas mixture emerges as a skimmed molecular beam at a pressure of approximately 10 μTorr. Products were detected using matrix infrared absorption spectroscopy, 118.2 nm (10.487 eV) photoionization mass spectroscopy and resonance enhanced multiphoton ionization. The initial steps in the thermal decomposition of furfural and benzaldehyde have been identified. Furfural undergoes unimolecular decomposition to furan + CO: C4H3O-CHO (+ M) → CO + C4H4O. Sequential decomposition of furan leads to the production of HC≡CH, CH2CO, CH3C≡CH, CO, HCCCH2, and H atoms. In contrast, benzaldehyde resists decomposition until higher temperatures when it fragments to phenyl radical plus H atoms and CO: C6H5CHO (+ M) → C6H5CO + H → C6H5 + CO + H. The H atoms trigger a chain reaction by attacking C6H5CHO: H + C6H5CHO → [C6H6CHO]* → C6H6 + CO + H. The net result is the decomposition of benzaldehyde to produce benzene and CO.

  5. Microwave synthesis of mixed ligand diimine–thiosemicarbazone complexes of ruthenium(ii): biophysical reactivity and cytotoxicity†

    Science.gov (United States)

    Beckford, Floyd A.; Shaloski, Michael; Leblanc, Gabriel; Thessing, Jeffrey; Lewis-Alleyne, Lesley C.; Holder, Alvin A.; Li, Liya; Seeram, Navindra P.

    2010-01-01

    A novel microwave-assisted synthetic method has been used to synthesise a series of mixed ligand ruthenium(ii) compounds containing diimine as well as bidentate thiosemicarbazone ligands. The compounds contain the diimine 1,10-phenanthroline (phen) or 2,2′-bipyridine (bpy) and the thiosemicarbazone is derived from 9-anthraldehyde. Based on elemental analyses and spectroscopic data, the compounds are best formulated as [(phen)2Ru(thiosemicarbazone)](PF6)2 and [(phen)2Ru(thiosemicarbazone)](PF6)2 where thiosemicarbazone = 9-anthraldehydethiosemicarbazone, 9-anthraldehyde-N(4)-methylthiosemicarbazone, and 9-anthraldehyde-N(4)-ethylthiosemicarbazone. Fluorescence competition studies with ethidium bromide, along with viscometric measurements suggests that the complexes bind calf thymus DNA (CTDNA) relatively strongly via an intercalative mode possibly involving the aromatic rings of the diimine ligands. The complexes show good cytotoxic profiles against MCF-7 and MDA-MB-231 (breast adenocarcinoma) as well as HCT 116 and HT-29 (colorectal carcinoma) cell lines. PMID:20023905

  6. Inhibitory Kinetics of p-Substituted Benzaldehydes on Polyphenol Oxidase from the Fifth Instar of Pieris Rapae L.

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Polyphenol oxidase (PPO) is the enzyme responsible for enzymatic browning during the growth of insects. It is also involved in defense reactions and is related with immunities in insects. PPO,a metalloenzyme oxidase, catalyzes the oxidation of o-diphenol to o-quinone. The present paper describes the effects of benzaldehyde and its p-substituted derivatives on the activity of PPO from the fifth instar of Pieris rapae L. PPO from the fifth instar of Pieris rapae L. was purified using ammonium sulfate fractionation and chromatography on Sephadex G-100. The enzyme kinetics was characterized using L-3,4-dihydroxyphenylalanine (L-DOPA) as substrate. The results show that benzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, and p-cyanobenzaldehyde can inhibit the PPO activity for the oxidation of L-DOPA. The inhibitor concentration leading to 50% activity lost, IC50, was estimated to be 5.90, 5.62, 2.83, and 2.91 mmol/L for the four tested inhibitors, respectively. Kinetic analyses show that the inhibitory effects of these compounds are reversible. Benzaldehyde, p-hydroxybenzaldehyde, and p-chlorobenzaldehyde are noncompetitive inhibitors while p-cyanobenzaldehyde is a mixed-type inhibitor. The inhibition constants were determined for all four inhibitors.p-chlorobenzaldehyde and p-cyanobenzaldehyde were more potent inhibitors than the other compounds. These results provide a basis for developing PPO inhibition-based pesticides.

  7. Biodistribution of /sup 59/Fe-thiosemicarbazones

    Energy Technology Data Exchange (ETDEWEB)

    Hanson, R.N.; Davis, M.A.

    1982-01-01

    The /sup 59/Fe-iron(II) chelates of 2-formylpyridine thiosemicarbazone (I), 5-dimethylamino-2-formylpyridine thiosemicarbazone (II), and 5-hydroxy-2-formylpyridine thiosemicarbazone (III) were prepared and their biodistribution determined in normal rats. Early accumulation of these complexes occurred in the liver, muscle and pelt with lesser amounts in the blood, kidneys and other organs. The tissue levels decreased with a 1 to 2-h half-life with the exception of the liver and intestines. The liver level tended to remain constant over the 2-h period. Accumulation in the gut resulting from hepatobiliary excretion increased over the first 60 min and then leveled off. In rats bearing a subcutaneous glioblastoma the uptake of compound I increased during the first 24 h after administration, and tumor to normal tissue ratios of 2 to 3.3 were obtained.

  8. [Differentiation activity of pyridoxal thiosemicarbazone and its copper and cobalt complexes on Friend erythroleukemia cells].

    Science.gov (United States)

    Albertini, R; Gasparri Fava, G; Pinelli, S; Tarasconi, P; Starcich, B

    1991-07-01

    Thiosemicarbazones are a wide group of organic derivatives whose biological activities are a function of the parent aldehyde or ketone and of the coordination metal type. Some thiosemicarbazones possess a broad spectrum of potentially useful chemotherapeutic properties (antitumor, antibacterial, antiviral, antimalarial). The present study reports the biological effects of pyridoxal thiosemicarbazone, H2L, and relative complexes with copper, [(Cu(HL)(OH2))2]++ and with cobalt, [Co(III)(L)(HL)] on the differentiation of Friend erythroleukemia cells (FLC). They are murine proerythroblasts chronically infected by a producing Friend leukemia virus complex; their exposure to dimethylsulfoxide (Me2SO) or other chemical agents induces these cells to terminal erythroid differentiation, therefore these cells represent a good model of differentiation in vitro. Here we describe induction differentiation experiment of pyridoxal thiosemicarbazone and relative complexes of copper and cobalt on FLC performed with concentrations of 50 ug/ml (ligand), 2 ug/ml (complexes). These have little effects on cell proliferation at doses used in these experiments. Higher doses have evident cytotoxic effects. The treatment with the copper complex induces a moderate differentiation of FLC and enhances effects on erythroid differentiation of Me2SO-induced FLC. On the contrary H2L and [Co(III)(L)(HL)] haven't inducing effects or enhancing effects on Me2SO-induced FLC hemopoietic differentiation. In conclusion, the present study shows that copper complexes of pyridoxal thiosemicarbazone exert action of inducing agent and are able to enhance Me2SO-induced FLC hemopoietic differentiation. PMID:1818592

  9. Synthesis, spectroscopic studies and crystal structure of ( E)-2-(2,4-dihydroxybenzylidene)thiosemicarbazone and ( E)-2-[(1 H-indol-3-yl)methylene]thiosemicarbazone

    Science.gov (United States)

    Yıldız, Mustafa; Ünver, Hüseyin; Erdener, Diğdem; Kiraz, Aşkın; İskeleli, Nazan Ocak

    2009-02-01

    Thiosemicarbazone Schiff bases ( 1 and 2) derived from 2,4-dihydroxybenzaldehyde, indoline-3-carbaldehyde and thiosemicarbazone have been synthesized and their structures were elucidated by elemental analysis, FT-IR, 1H NMR, 13C NMR and UV-visible spectroscopic techniques. The structures of compounds 1 and 2 have also been examined cyrstallographically. The title compounds 1 and 2 crystallize in the monoclinic space group C2/ c and triclinic space group P1¯, with unit cell parameters: a = 21.421(1) and 7.233(1), b = 4.131(1) and 11.166(1), c = 24.942(2) and 13.648(1) Å, V = 1856.1(2) and 1019.5(1) Å 3, D x = 1.512 and 1.422 g cm -3 and Z = 8 and 4, respectively.

  10. Theoretical study of corrosion inhibition of amides and thiosemicarbazones

    International Nuclear Information System (INIS)

    An examination of quantum chemical and corrosion inhibition studies were carried out to investigate whether any clear links exist between the results of quantum chemical calculations and the experimental efficiencies of urea (U), thiourea (TU), acetamide (A), thioacetamide (TA), semicarbazide (SC), thiosemicarbazide (TSC), methoxybenzaldehydethiosemicarbazone (MBTSC), 2-acetylpyridine-(4phenyl) thiosemicarbazone (2AP4PTSC), 2-acetylpyridine-(4-methyl) thiosemicarbazone (2AP4MTSC), benzointhiosemicarbazone (BZOTSC) and benzilthiosemicarbazone (BZITSC) being corrosion inhibitors. The quantum chemical calculations have been performed by using DFT, ab-initio molecular orbital and semi-empirical methods for some amides and thiosemicarbozone derivatives being corrosion inhibitors. The highest occupied molecular orbital energy (E HOMO), lowest unoccupied molecular orbital energy (E LUMO), the energy gap between E HOMO and E LUMO (ΔE HOMO-LUMO), dipole moments (μ), charges on the C, O, N, S atoms, the total energies of the molecules and the polarizabilities , the coefficients of the development of the MO over the atomic orbital (AO) corresponding to the between atoms which a new bond is established have been calculated. The results of quantum chemical calculations and experimental efficiencies of inhibitors were subjected to correlation analysis. We have reached the conclusion that the synthesis of better corrosion inhibitors can be achieved by controlling all electronic properties and parameters of a selected group of molecules

  11. 3-Hydroxy-4-methoxybenzaldehyde thiosemicarbazone hemihydrate

    OpenAIRE

    S. M. Dharmaprakash; Patil, P. S.; E. Deepak D'Silva; Reza Kia; Hoong-Kun Fun

    2008-01-01

    The asymmetric unit of the title compound, C9H11N3O2S·0.5H2O, comprises two crystallograpically independent thiosemicarbazone molecules (A and B) and a water molecule of crystallization. In each of the thiosemicarbazone molecules, intramolecular O—H...O and N—H...N hydrogen bonds form five-membered rings, producing S(5) ring motifs. Intermolecular O—H...S and N—H...O interactions between molecule B and the water molecule form a six-membered ring, producing an R22(...

  12. Antiretroviral activity of thiosemicarbazone metal complexes.

    Science.gov (United States)

    Pelosi, Giorgio; Bisceglie, Franco; Bignami, Fabio; Ronzi, Paola; Schiavone, Pasqualina; Re, Maria Carla; Casoli, Claudio; Pilotti, Elisabetta

    2010-12-23

    Thiosemicarbazones display a wide antimicrobial activity by targeting bacteria, fungi, and viruses. Here, we report our studies on the antiviral activity of two thiosemicarbazone metal complexes, [bis(citronellalthiosemicarbazonato)nickel(II)] and [aqua(pyridoxalthiosemicarbazonato)copper(II)] chloride monohydrate, against the retroviruses HIV-1 and HTLV-1/-2. Both compounds exhibit antiviral properties against HIV but not against HTLVs . In particular, the copper complex shows the most potent anti-HIV activity by acting at the post-entry steps of the viral cycle. PMID:21121632

  13. Spectroscopic, thermal and electrochemical studies on some nickel(II) thiosemicarbazone complexes

    Science.gov (United States)

    El-Shazly, R. M.; Al-Hazmi, G. A. A.; Ghazy, S. E.; El-Shahawi, M. S.; El-Asmy, A. A.

    2005-01-01

    Several complexes of thiosemicarbazone derivatives with Ni(II) have been prepared. Structural investigation of the ligands and their complexes has been made based on elemental analysis, magnetic moment, spectral (UV-Vis, i.r., 1H NMR, ms), and thermal studies. The i.r. spectra suggest the bidentate mononegative and tridentate (neutral, mono-, and binegative) behavior of the ligands. Different stereochemistries were suggested for the isolated complexes. The thermogravimetry (TG) and derivative thermogravimetry (DTG) have been used to study the thermal decomposition and kinetic parameters of some ligands and complexes using the Coats-Redfern and Horowitz-Metzger equations. The redox properties and stability of the complexes toward oxidation waves explored by cyclic voltammetry are related to the electron withdrawing or releasing ability of the substituent of thiosemicarbazone moiety. The samples displayed Ni II/Ni I couples irreversible waves associated with Ni III/Ni II process.

  14. Heterocyclyl linked anilines and benzaldehydes as precursors for biologically significant new chemical entities

    Indian Academy of Sciences (India)

    Raman K Verma; Vijay Kumar; Prithwish Ghosh; Lalit K Wadhwa

    2012-09-01

    Benzylidene and benzyl thiazolidinediones, oxazolidinediones, isoxazolidinediones and their acyclic analogs like alpha alkylthio/alkoxy phenylpropanoic acids, beta-keto esters and tyrosine-based compounds possess broad therapeutic potential in general and as Peroxisome Proliferator Activated Receptors (PPARs) agonists in particular in the management of hyperglycemia and hyperlipidaemia for the treatment of Type 2 Diabetes (T2D). We have synthesised and characterized some novel and suitably substituted heterocyclyl linked benzaldehydes and anilines, which can be easily and very readily derivatized to all the above mentioned classes to generate new chemical entities of broader biological significance. Synthesis of their benzylidene thiazolidinedione and diethyl malonate and also benzyl diethyl malonate and alpha-bromoesters derivatives is reported in some of the cases in the present work.

  15. Complexes of 3dn Metal Ions with Thiosemicarbazones: Synthesis and Antimicrobial Activity

    Directory of Open Access Journals (Sweden)

    Tudor Rosu

    2007-04-01

    Full Text Available The chelating behavior of the thiosemicarbazone derivatives of 2-hydroxy-8-R-tricyclo[7.3.1.0.2,7]tridecane-13-one (where R = H, CH3, C6H5 towards Co(II, Ni(II and Cu(II has been investigated by elemental analysis, molar conductivity measurements, UV-VIS, IR, ESR spectroscopy and thermal studies. It was deduced from the experiments performed that the ligands coordinate to metal ions in different ways – neutral bidentate or mononegative bidentate – depending on the nature of R. Also, if metal acetates are used instead of metal chlorides, the ligands coordinate in a mononegative bidentate fashion, regardless of the nature of R or the thiosemicarbazone type ligand. The antimicrobial activity of the ligands and of the complexes towards samples of Acinetobacter boumanii, Klebsiella pneumoniae, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa was determined.

  16. Monitoring cellular uptake and cytotoxicity of copper(II) complex using a fluorescent anthracene thiosemicarbazone ligand.

    Science.gov (United States)

    Kate, Anup N; Kumbhar, Anupa A; Khan, Ayesha A; Joshi, Pranaya V; Puranik, Vedavati G

    2014-01-15

    The thiosemicarbazone derivative of anthracene (ATSC, anthracene thiosemicarbazone 1) and its copper(II) complex (CuATSC, 2) were synthesized and characterized by spectroscopic, electrochemical, and crystallographic techniques. Interaction of 1 and 2 with calf thymus (CT) DNA was explored using absorption and emission spectral methods, and viscosity measurements reveal a partial-intercalation binding mode. Their protein binding ability was monitored by the quenching of tryptophan emission using bovine serum albumin (BSA) as a model protein. Furthermore, their cellular uptake, in vitro cytotoxicity testing on the HeLa cell line, and flow cytometric analysis were carried out to ascertain the mode of cell death. Cell cycle analysis indicated that 1 and 2 cause cell cycle arrest in sub-G1 phase. PMID:24328322

  17. Synthesis and Structure-Activity Correlation Studies of Metal Complexes of α-N-heterocyclic Carboxaldehyde Thiosemicarbazones in Shewanella oneidensis

    Directory of Open Access Journals (Sweden)

    Quintell Tillison

    2005-04-01

    Full Text Available This investigation involved the synthesis of metal complexes to test the hypothesis that structural changes and metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced reactivity exhibited by metal complexes of heterocyclic thiosemicarbazones, synthesis and structural characterization of di-2-pyridylketone 4N-phenyl thiosemicarbazone and diphenyl tin (Sn and platinum (Pt complexes were undertaken. Shewanella oneidensis MR-1, a metal ion-reducing bacterium, was used as a model organism to explore the biological activity under aerobic conditions. A comparision of the cytotoxic potential of selected ligand and metal-complex thiosemicarbazones on cell growth in wild type MR-1 and mutant DSP-010 Shewanella oneidensis strains at various concentrations (0, 5, 10, 15, 20 or 25 ppm was performed. The wild type (MR-1 grown in the presence of increasing concentrations of Sn- thiosemicarbazone complexes was comparatively more sensitive (mean cell number = 4.8 X 108 + 4.3 X 107 SD than the DSP-010, a spontaneous rifampicillin derivative of the parent strain (mean cell number = 5.6 x 108 + 6.4 X 107 SD under comparable aerobic conditions (p=0.0004. No differences were observed in the sensitivity of the wild and mutant types when exposed to various concentrations of diphenyl Pt- thiosemicarbazone complex (p= 0.425 or the thiosemicarbazone ligand (p=0.313. Growth of MR-1 in the presence of diphenyl Sn- thiosemicarbazone was significantly different among treatment groups (p=0.012. MR-1 cell numbers were significantly higher at 5ppm than at 10 to 20ppm (p = 0.05. The mean number of DSP-010 variant strain cells also differed among diphenyl Sn

  18. Explorations of Crystalline Effects on 4-(Benzyloxy)Benzaldehyde Properties

    Science.gov (United States)

    Harismah, Kun; Ozkendir, O. Murat; Mirzaei, Mahmoud

    2015-12-01

    The properties of 4-(benzyloxy)benzaldehyde (BBA), as a pharmaceutically important compound, have been investigated through the density functional theory (DFT) calculations. The properties of original crystalline and optimised gaseous structures have been evaluated to recognise the crystalline effects. In addition to the structural properties, nuclear magnetic resonance (NMR) properties have also been evaluated for both investigated systems to better detect the effects in atomic levels. The results indicated that the structural shape of BBA is significantly changed in the optimised gaseous system, showing significant crystalline effects on the geometrical positions. Moreover, the magnitudes for energies and dipole moments indicate notable effects on the electronic properties. The evaluated NMR properties also show that the atoms of aromatic systems detect significant changes more than the atoms of aliphatic systems in the investigated BBA. And finally, the oxygen bridge atom plays a dominant role in combining two benzene rings of BBA.

  19. SYNTHESIS AND BIOEVALUATION OF KETOCONAZOLE THIOSEMICARBAZONE ANALOGUES

    OpenAIRE

    Y. Murti

    2011-01-01

    Ketoconazole (KTZ) is a synthetic antifungal drug used to prevent and treat fungal infections, especially in immunocompromised patients such as those with AIDS. Resistance to ketoconazole has been observed in a number of clinical fungal isolates, including C. albicans. Thus new effective agents with less toxicity against fungal infection are urgently required. With this view, ketoconazole thiosemicarbazone analogues (Compounds 1-10) were synthesized wherein condensation of different thiosemic...

  20. Investigation of the salicylaldehyde thiosemicarbazone scaffold for inhibition of influenza virus PA endonuclease.

    Science.gov (United States)

    Rogolino, Dominga; Bacchi, Alessia; De Luca, Laura; Rispoli, Gabriele; Sechi, Mario; Stevaert, Annelies; Naesens, Lieve; Carcelli, Mauro

    2015-10-01

    The influenza virus PA endonuclease is an attractive target for the development of novel anti-influenza virus therapeutics, which are urgently needed because of the emergence of drug-resistant viral strains. Reported PA inhibitors are assumed to chelate the divalent metal ion(s) (Mg²⁺ or Mn²⁺) in the enzyme's catalytic site, which is located in the N-terminal part of PA (PA-Nter). In the present work, a series of salicylaldehyde thiosemicarbazone derivatives have been synthesized and evaluated for their ability to inhibit the PA-Nter catalytic activity. Compounds 1-6 have been evaluated against influenza virus, both in enzymatic assays with influenza virus PA-Nter and in virus yield assays in MDCK cells. In order to establish a structure-activity relationship, the hydrazone analogue of the most active thiosemicarbazone has also been evaluated. Since chelation may represent a mode of action of such class of molecules, we studied the interaction of two of them, one with and one without biological activity versus the PA enzyme, towards Mg²⁺, the ion that is probably involved in the endonuclease activity of the heterotrimeric influenza polymerase complex. The crystal structure of the magnesium complex of the o-vanillin thiosemicarbazone ligand 1 is also described. Moreover, docking studies of PA endonuclease with compounds 1 and 2 were performed, to further analyse the possible mechanism of action of this class of inhibitors. PMID:26323352

  1. Half-sandwich ruthenium-arene complexes with thiosemicarbazones: Synthesis and biological evaluation of [(η6-p-cymene)Ru(piperonal thiosemicarbazones)Cl]Cl complexes

    OpenAIRE

    Beckford, Floyd; Dourth, Deidra; Shaloski, Michael; Didion, Jacob; Thessing, Jeffrey; Woods, Jason; Crowell, Vernon; Gerasimchuk, Nikolay; Gonzalez-Sarrías, Antonio; Seeram, Navindra P.

    2011-01-01

    The synthesis and characterization of a number of organometallic ruthenium(II) complexes containing a series of bidentate thiosemicarbazone ligands derived from piperonal is reported. The structure of compounds have been confirmed by spectroscopic analysis (IR and NMR) as well as X-ray crystallographic analysis of [(η6-p-cymene)Ru(pPhTSC)Cl]Cl (4) (pPhTSC is piperonal-N(4)-phenylthiosemicarbazone). The interaction of the complexes ([(η6-p-cymene)Ru(pEtTSC)Cl]Cl) (3) (pEtTSC is piperonal-N(4)-...

  2. Synthesis and Characterization of Some New Cu(II), Ni(II) and Zn(II) Complexes with Salicylidene Thiosemicarbazones: Antibacterial, Antifungal and in Vitro Antileukemia Activity

    OpenAIRE

    Pahontu, Elena; Fala, Valeriu; Aurelian GULEA; POIRIER, DONALD; Tapcov, Victor; Rosu, Tudor

    2013-01-01

    Thirty two new Cu(II), Ni(II) and Zn(II) complexes (1–32) with salicylidene thiosemicarbazones (H2L1–H2L10) were synthesized. Salicylidene thiosemicarbazones, of general formula (X)N-NH-C(S)-NH(Y), were prepared through the condensation reaction of 2-hydroxybenzaldehyde and its derivatives (X) with thiosemicarbazide or 4-phenylthiosemicarbazide (Y = H, C6H5). The characterization of the new formed compounds was done by 1H-NMR, 13C-NMR, IR spectroscopy, elemental analysis, magnetochemical, the...

  3. Synthesis, Spectroscopic and Toxicity Studies of Titanocene Chelates of Isatin-3-Thiosemicarbazones

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    Garima Vatsa

    2004-01-01

    Full Text Available The reactions of bis(cyclopentadienyltitanium(IV dichloride with a new class of thiosemicarbazone (LH2, derived by condensing isatin with different N(4-substituted thiosemicarbazides, have been studied and products of type [Cp2Ti(L] have been isolated. On the basis of various physico-chemical and spectral studies, five coordinate structures have been assigned to these derivatives. Toxicity studies of titanocene complexes at tbur different concentrations have been carried out against snail Lymnaea acuminata. The effect of most potent compounds on the activity of acetylcholinesterase enzyme, which inhibits the activity of enzyme, possibly by the formation of enzyme-inhibitor complex, was also studied.

  4. Benzaldehyde in cherry flavour as a precursor of benzene formation in beverages.

    Science.gov (United States)

    Loch, Christine; Reusch, Helmut; Ruge, Ingrid; Godelmann, Rolf; Pflaum, Tabea; Kuballa, Thomas; Schumacher, Sandra; Lachenmeier, Dirk W

    2016-09-01

    During sampling and analysis of alcohol-free beverages for food control purposes, a comparably high contamination of benzene (up to 4.6μg/L) has been detected in cherry-flavoured products, even when they were not preserved using benzoic acid (which is a known precursor of benzene formation). There has been some speculation in the literature that formation may occur from benzaldehyde, which is contained in natural and artificial cherry flavours. In this study, model experiments were able to confirm that benzaldehyde does indeed degrade to benzene under heating conditions, and especially in the presence of ascorbic acid. Analysis of a large collective of authentic beverages from the market (n=170) further confirmed that benzene content is significantly correlated to the presence of benzaldehyde (r=0.61, pcherry flavoured beverages, industrial best practices should include monitoring for benzene. Formulations containing either benzoic acid or benzaldehyde in combination with ascorbic acid should be avoided. PMID:27041300

  5. Potentiometric studies on complexation equilibria between some transition metal ions and 2-hydroxy-1-naphthaldehyde thiosemicarbazone in dioxane-water medium

    International Nuclear Information System (INIS)

    In continuation of our study on the metal complexes of biologically active o-hydroxynaphthaldehyde and its derivatives, potentiometric studies on the chelation behaviour of bivalent metal complexes of 2-hydroxy-1-naphthaldehyde thiosemicarbazone are described. (author). 11 refs., 2 tabs

  6. Solubilities of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures

    International Nuclear Information System (INIS)

    Highlights: • Solubilities of benzoic acid in (benzyl alcohol + benzaldehyde) mixtures were measured at 1 atm. • The experimental temperature ranges at (298.35 to 355.65) K. • Effects of benzyl alcohol mass concentration at (0.00 to 1.00) on the solubilities of benzoic acid were studied. • The experimental data were correlated with NRTL model. • Thermodynamic functions of dissolution of benzoic acid in (benzyl alcohol + benzaldehyde) mixtures were discussed. - Abstract: The solubility of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures was measured at temperature from (298.35 to 355.65) K and atmospheric pressure. The measured solubility increases with the increasing temperature at constant solvent composition. The effects of mass fraction benzaldehyde in the solvent mixtures at (0.0 to 1.00) on the solubility were studied. The measured solubility decreases with the increasing mass fraction of benzaldehyde. The experimental results were correlated with the non-random two-liquid (NRTL) equations, and good agreement between the correlated and the experimental values was obtained. Thermodynamic functions for the solution of benzoic acid in binary (benzyl alcohol + benzaldehyde) solvent mixtures were calculated with the van’t Hoff plot. The apparent dissolution Gibbs free energy change was also calculated

  7. Metal chelates of 2-acetylbenzimidazole thiosemicarbazones

    International Nuclear Information System (INIS)

    Earlier unknown complexes of ML' and ML2 compositions were prepared on the basis of thiosemicarbazones of 2-acetylbenzimidazole (L'H2) and 2-acetyl-1-methylbenzimidazole (LH) and metal (M=Cu2+, VO2+, Co2+, Ni2+) acetates in ethanol medium. Data of IR and ESR spectra and magnetochemical measurements, as well as correlation of experimental and calculated values of the polar magnetic susceptibility in 80-300K range enabled to assign polymeric structure to complexes of ML' composition and monomeric structure - to complexes of ML2 composition

  8. Trypanotoxic activity of thiosemicarbazone iron chelators

    OpenAIRE

    Ellis, Samuel; Sexton, Darren; Steverding, Dietmar

    2015-01-01

    Only a few drugs are available for treating sleeping sickness and nagana disease; parasitic infections caused by protozoans of the genus Trypanosoma in sub-Saharan Africa. There is an urgent need for the development of new medicines for chemotherapy of these devastating diseases. In this study, three newly designed thiosemicarbazone iron chelators, TSC24, Dp44mT and 3-AP, were tested for in vitro activity against bloodstream forms of T. brucei and human leukaemia HL-60 cells. In addition to t...

  9. Management of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone-induced methemoglobinemia

    Science.gov (United States)

    Kunos, Charles A; Radivoyevitch, Tomas; Ingalls, Stephen T; Hoppel, Charles L

    2012-01-01

    The anticancer agent 3-aminopyridine-2-carboxaldehyde thiosemicarbazone is a ribonucleotide reductase inhibitor. It inactivates ribonucleotide reductase by disrupting an iron-stabilized radical in ribonucleotide reductase's small subunits, M2 and M2b (p53R2). Unfortunately, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone also alters iron II (Fe2+) in hemoglobin. This creates Fe3+ methemoglobin that does not deliver oxygen. Fe2+ in hemoglobin normally auto-oxidizes to inactive Fe3+ methemoglobin at a rate of nearly 3% per day and this is counterbalanced by a reductase system that normally limits methemoglobin concentrations to less than 1% of hemoglobin. This balance may be perturbed by symptomatic toxicity levels during 3-aminopyridine-2-carboxaldehyde thiosemicarbazone therapy. Indications of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone sequelae attributable to methemoglobinemia include resting dyspnea, headaches and altered cognition. Management of methemoglobinemia includes supplemental oxygen, ascorbate and, most importantly, intravenously administered methylene blue as a therapeutic antidote. PMID:22335579

  10. Study of complexes of isonitrosoacetophenone thiosemicarbazone (Preprint No. CT-32)

    International Nuclear Information System (INIS)

    Uranyl complexes of isonitrosoacetophenone thiosemicarbazone (INAPT) have been synthesized and characterized with the aid of analytical, conductance and spectral (IR, electronic, 1H NMR and TG) studies. (author). 6 refs

  11. Ferromagnetism in Cu 3-thiosemicarbazone- 2,3-dioxoindole complexes

    Science.gov (United States)

    Zentková, M.; Kováč, J.; Zentko, A.; Košturiak, A.

    1991-12-01

    We report evidence for ferromagnetic ordering in Cu-chelates of 3-thiosemicarbazone-2,3-dioxoindole (isatine). It has been found that the Curie temperature is 16.8 K and is independent of the Cu content.

  12. Management of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone-induced methemoglobinemia

    OpenAIRE

    Kunos, Charles A.; Radivoyevitch, Tomas; Ingalls, Stephen T.; Hoppel, Charles L.

    2012-01-01

    The anticancer agent 3-aminopyridine-2-carboxaldehyde thiosemicarbazone is a ribonucleotide reductase inhibitor. It inactivates ribonucleotide reductase by disrupting an iron-stabilized radical in ribonucleotide reductase's small subunits, M2 and M2b (p53R2). Unfortunately, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone also alters iron II (Fe2+) in hemoglobin. This creates Fe3+ methemoglobin that does not deliver oxygen. Fe2+ in hemoglobin normally auto-oxidizes to inactive Fe3+ methemog...

  13. Synthesis, characterization and biological activity of uranyl thiosemicarbazone complexes

    International Nuclear Information System (INIS)

    A new thiosemicarbazone namely phenacyl thioacetic acid thiosemicarbazone was synthesized and its UO22+ complexes were prepared. The synthesized ligand and complexes were characterized by elemental analyses, spectral (IR, 1H NMR and Mass) studies. In all complexes the ligand coordinates through carboxylic oxygen, azomethine nitrogen and thiolate sulfur. Antimicrobial screening of the free ligand and its complexes showed that, the free ligand and metal complexes possess antimicrobial activities towards two types of bacteria and two types of fungi. (author)

  14. Complexes of 3dn Metal Ions with Thiosemicarbazones: Synthesis and Antimicrobial Activity

    OpenAIRE

    Tudor Rosu; Aurelian Gulea; Anca Nicolae; Rodica Georgescu

    2007-01-01

    The chelating behavior of the thiosemicarbazone derivatives of 2-hydroxy-8-R-tricyclo[7.3.1.0.2,7]tridecane-13-one (where R = H, CH3, C6H5) towards Co(II), Ni(II) and Cu(II) has been investigated by elemental analysis, molar conductivity measurements, UV-VIS, IR, ESR spectroscopy and thermal studies. It was deduced from the experiments performed that the ligands coordinate to metal ions in different ways – neutral bidentate or mononegative bidentate – depending on the nature of R. A...

  15. Synthesis, structure and electrochemical properties of some thiosemicarbazone complexes of ruthenium

    OpenAIRE

    Datta, S.; Drew, Michael G B; Bhattacharya, S.

    2011-01-01

    Reaction of salicylaldehyde thiosemicarbazone (L-1), 2-hydroxyacetophenone thiosemicarbazone (L-2) and 2-hydroxynapthaldehyde thiosemicarbazone (L-3) with [Ru(dmso)(4)Cl-2] affords a family of three dimeric complexes (1), (2) and (3) respectively. Crystal structure of the complex (3) has been determined. In these complexes, each monomeric unit consists of one ruthenium center and two thiosemicarbazone ligands, one of which is coordinated to ruthenium as O,N,S-donor and the other as N,S-donor ...

  16. CHARACTERIZATION AND ANTIPARASITIC ACTIVITY OF BENZOPHENONE THIOSEMICARBAZONES ON Trypanosoma brucei brucei

    OpenAIRE

    Georges C. Accrombessi; Jacques Poupaert; Raymond H. Fatondji; Salomé D. S. Kpoviessi; Gbaguidi, Fernand A.; Bienvenu Glinma

    2011-01-01

    The structure of four synthesized thiosemicarbazones, substituted or not, of benzophenone has been confirmed by spectrometrical analysis IR, NMR 1H and 13C. Their anti-trypanosomal activities were evaluated on Trypanosoma brucei brucei. Among these compounds, benzophenone 4 phenyl-3-thiosemicarbazone 4 has the highest activity with the half-inhibitory concentration (IC50) = 8.48 micromolar (µM). Benzophenone 4-methyl-3-thiosemicarbazone 3 and benzophenone thiosemicarbazone 1 showed moderate a...

  17. 3-Hydroxy-4-methoxybenzaldehyde thiosemicarbazone hemihydrate

    Directory of Open Access Journals (Sweden)

    S. M. Dharmaprakash

    2008-12-01

    Full Text Available The asymmetric unit of the title compound, C9H11N3O2S·0.5H2O, comprises two crystallograpically independent thiosemicarbazone molecules (A and B and a water molecule of crystallization. In each of the thiosemicarbazone molecules, intramolecular O—H...O and N—H...N hydrogen bonds form five-membered rings, producing S(5 ring motifs. Intermolecular O—H...S and N—H...O interactions between molecule B and the water molecule form a six-membered ring, producing an R22(6 ring motif. Intermolecular N—H...S hydrogen bonds form dimers involving pairs of both A and B molecules, which form R22(8 ring motifs. The angles between the aromatic ring and thiourea unit in the two molecules are 0.80 (6 and 3.28 (5°, which proves that each molecule is fairly planar. The crystal structure is stabilized by intermolecular O—H...S (×2, O—H...O, N—H...S (×2 and N—H...O (×2 hydrogen bonds and C—H...O (×2 contacts to form a three-dimensional network.

  18. Synthesis and evaluation of copper radiopharmaceuticals with mixed bis(thiosemicarbazone) ligands

    International Nuclear Information System (INIS)

    Four 'mixed' bis(thiosemicarbazone) derivatives of pyruvaldehyde were synthesized that incorporate two dissimilar thiosemicarbazone functions. The corresponding [67Cu]copper(II) complexes were prepared and evaluated as possible copper radiopharmaceuticals. The pyruvaldehyde-based mixed bis(thiosemicarbazone) ligands, CH3C[=NNHC(S)NHMe]CH[=NNHC(S)NHEt] (1), CH3C[=NNHC(S)NHMe]CH[=NNHC(S)NEt2] (2), CH3C[=NNHC(S)NHMe]CH[=NNHC(S)-cyclo-N(CH2)5] (3), and CH3C[=NNHC(S)NHMe]CH[=NNHC(S)-cyclo-N(CH2)6] (4), were obtained by reaction of the appropriate thiosemicarbazide derivative with pyruvaldehyde-2-N4-methylthiosemicarbazone (CH3C[=NNHC(S)NHMe]CHO). The 67Cu-labeled copper(II) complexes of ligands 1-4 were prepared and screened in a rat model to assess the potential of each chelate as a 62Cu-radiopharmaceutical for imaging with positron emission tomography. The 67Cu-complexes of ligands 1-4 exhibit significant uptake into the brain and heart 1 min following intravenous administration to rats. For the 67Cu-complexes of ligands 2, 3, and 4, the cerebral and myocardial uptake of 67Cu is two-to-threefold lower at 2 h than at 1 min postinjection, due to significant biological clearance of these 67Cu-chelates. However, the 67Cu-complex of 1 affords cerebral and myocardial uptake and retention comparable to that of [67Cu]Cu-PTSM in this model. Although the kinetics of this new agent appear attractive, ultrafiltration studies using solutions of dog and human serum albumin reveal that the 67Cu-complex of ligand 1, like Cu-PTSM, interacts more strongly with human albumin than dog albumin. Thus, this new agent would appear to offer no advantage over Cu-PTSM as a 62Cu-labeled tracer for evaluation of regional tissue perfusion

  19. Nickel(ii) radical complexes of thiosemicarbazone ligands appended by salicylidene, aminophenol and aminothiophenol moieties.

    Science.gov (United States)

    Kochem, Amélie; Gellon, Gisèle; Jarjayes, Olivier; Philouze, Christian; du Moulinet d'Hardemare, Amaury; van Gastel, Maurice; Thomas, Fabrice

    2015-07-28

    The nickel(ii) complexes of three unsymmetrical thiosemicarbazone-based ligands featuring a sterically hindered salicylidene (1), aminophenol (2) or thiophenol (3) moiety were synthesized and structurally characterized. The metal ion lies in an almost square planar geometry in all the complexes. The cyclic voltammetry (CV) curve of 1 shows an irreversible oxidation wave at E = 0.49 V, which is assigned to the phenoxyl/phenolate redox couple. The CV curves of 2 and 3 display a reversible one-electron oxidation wave (E1/2 = 0.26 and 0.22 V vs. Fc(+)/Fc, respectively) and an one-electron reduction wave (E1/2 = -1.55 and -1.46 V, respectively). The cations 2(+) and 3(+) as well as the anions 2(-) and 3(-) were generated. The EPR spectra of the cations in THF show a rhombic signal at g1 = 2.034, g2 = 2.010 and g3 = 1.992 (2(+)) and g1 = 2.069, g2 = 2.018, g3 = 1.986 (3(+)) that is consistent with a main radical character of the complexes. The difference in anisotropy is assigned to the different nature of the radical, iminosemiquinonate vs. iminothiosemiquinonate. The anions display an isotropic EPR signal at giso = 2.003 (2(+)) and 2.006 (3(+)), which is indicative of a main α-diimine radical character of the compounds. Both the anions and cations exhibit charge transfer transitions of low to moderate intensity in their visible spectrum. Quantum chemical calculations (B3LYP) reproduce both the g-values and Vis-NIR spectra of the complexes. The radical anions readily react with dioxygen to give the radical cations. 2(+) catalyzes the aerobic oxidation of benzyl alcohol into benzaldehyde. PMID:26086684

  20. A novel series of thiosemicarbazone drugs: From synthesis to structure

    Science.gov (United States)

    Ebrahimi, Hossein Pasha; Hadi, Jabbar S.; Alsalim, Tahseen A.; Ghali, Thaer S.; Bolandnazar, Zeinab

    2015-02-01

    A new series of thiosemicarbazones (TSCs) and their 1,3,4-thiadiazolines (TDZs) containing acetamide group have been synthesized from thiosemicarbazide compounds by the reaction of TSCs with cyclic ketones as well as aromatic aldehydes. The structures of newly synthesized 1,3,4-thiadiazole derivatives obtained by heterocyclization of the TSCs with acetic anhydride were experimentally characterized by spectral methods using IR, 1H NMR, 13C NMR and mass spectroscopic methods. Furthermore, the structural, thermodynamic, and electronic properties of the studied compounds were also studied theoretically by performing Density Functional Theory (DFT) to access reliable results to the experimental values. The molecular geometry, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and Mulliken atomic charges of the studied compounds have been calculated at the B3LYP method and standard 6-31+G(d,p) basis set starting from optimized geometry. The theoretical 13C chemical shift results were also calculated using the gauge independent atomic orbital (GIAO) approach and their respective linear correlations were obtained.

  1. Manganese(II) complexes with thiosemicarbazones as potential anti-Mycobacterium tuberculosis agents.

    Science.gov (United States)

    Oliveira, Carolina G; da S Maia, Pedro Ivo; Souza, Paula C; Pavan, Fernando R; Leite, Clarice Q F; Viana, Rommel B; Batista, Alzir A; Nascimento, Otaciro R; Deflon, Victor M

    2014-03-01

    Through a systematic variation on the structure of a series of manganese complexes derived from 2-acetylpyridine-N(4)-R-thiosemicarbazones (Hatc-R), structural features have been investigated with the aim of obtaining complexes with potent anti-Mycobacterium tuberculosis activity. The analytical methods used for characterization included FTIR, EPR, UV-visible, elemental analysis, cyclic voltammetry, magnetic susceptibility measurement and single crystal X-ray diffractometry. Density functional theory (DFT) calculations were performed in order to evaluate the contribution of the thiosemicarbazonate ligands on the charge distribution of the complexes by changing the peripheral groups as well as to verify the Mn-donor atoms bond dissociation predisposition. The results obtained are consistent with the monoanionic N,N,S-tridentate coordination of the thiosemicarbazone ligands, resulting in octahedral complexes of the type [Mn(atc-R)2], paramagnetic in the extension of 5 unpaired electrons, whose EPR spectra are consistent for manganese(II). The electrochemical analyses show two nearly reversible processes, which are influenced by the peripheral substituent groups at the N4 position of the atc-R(1-) ligands. The minimal inhibitory concentration (MIC) of these compounds against M. tuberculosis as well as their in vitro cytotoxicity on VERO and J774A.1 cells (IC50) was determined in order to find their selectivity index (SI) (SI=IC50/MIC). The results evidenced that the compounds described here can be considered as promising anti-M. tuberculosis agents, with SI values comparable or better than some commercial drugs available for the tuberculosis treatment. PMID:24188534

  2. SYNTHESIS AND BIOEVALUATION OF KETOCONAZOLE THIOSEMICARBAZONE ANALOGUES

    Directory of Open Access Journals (Sweden)

    Y. Murti

    2011-12-01

    Full Text Available Ketoconazole (KTZ is a synthetic antifungal drug used to prevent and treat fungal infections, especially in immunocompromised patients such as those with AIDS. Resistance to ketoconazole has been observed in a number of clinical fungal isolates, including C. albicans. Thus new effective agents with less toxicity against fungal infection are urgently required. With this view, ketoconazole thiosemicarbazone analogues (Compounds 1-10 were synthesized wherein condensation of different thiosemicarbazides substituted by different cyclic and aromatic amines with the KTZ was done. Investigation of in-vitro antifungal activity of compounds was done by broth microdilution assay method against five pathogenic fungi Aspergillus niger, Candida albicans, Candida krusei, Candida glabrata and Candida tropicalis. Ketoconazole was used as reference for inhibitory activity against fungi. All the compounds were found potent antifungal agents, while compounds 8, 9 and 10 exhibited excellent in-vitro antifungal activity showing importance of halogenated compounds.

  3. A kinetic model for toluene oxidation comprising benzylperoxy benzoate ester as reactive intermediate in the formation of benzaldehyde

    NARCIS (Netherlands)

    Hoorn, J.A.A.; Alsters, P. L.; Versteeg, G. F.

    2005-01-01

    During the oxidation of toluene under semibatch conditions, the formation of benzyl alcohol is initially equal to the rate of formation of benzaldehyde. As the overall conversion increases the benzyl alcohol concentration at first decreases much faster than benzaldehyde, but this decrease slows down

  4. Synergism and antagonism in Iron base metallic glass corrosion inhibition by Thiosemicarbazone Compounds and Bromide Ions

    International Nuclear Information System (INIS)

    The synergistic and antagonism action caused by Br ions on the corrosion inhibition of fe78B13Si19 glassy alloy in 0.2 M Na2SO4 in absence and presence 10 (to power-4) M of some thiosemicarbazone derivatives have been investigated using potentiodynamic polarization, a.c. impedance techniques and morphological study. Results show that the addition of Br ions to sulphate solution inhibit the corrosion process by acting as an electron transfer barrier due to direct adsorption of these ions on alloy surface. A synergistic effect exists when fixed concentration of studied thiosemicarbazone derivatives and low concentration Br ions are used together to prevent glassy alloy corrosion in Na2SO4. The increase in surface coverage values in the presence at low concentrations Br ions indicates that an insoluble complex formed by undergoing a joint adsorption. The synergism parameter (S) is defined and calculated by the surface coverage values. The parameter in the case of small amount of Br found to be more than unity, indicating that the enhanced inhibition efficiency caused by the addition of Br ions is only due to synergism and there is a definite contribution from the inhibitor molecule. (author)

  5. GRAFTED STYRENE-DIVINYLBENZENE COPOLYMERS CONTAINING BENZALDEHYDES AND THEIR WITTIG REACTIONS WITH VARIOUS PHOSPHONIUM SALTS

    Institute of Scientific and Technical Information of China (English)

    Adriana Popa; Gheorghe Ilia; Aurelia Pascariu; Smaranda Iliescu; Nicoleta Plesu

    2005-01-01

    A chloromethylated styrene-divinylbenzene copolymer support system functionalized with 4-benzaldehyde and 2-benzaldehyde was prepared. The degree of functionalization with aldehyde groups is well suited for the subsequent use of the products as Wittig reagents. The polymer bound aldehyde was reacted with Wittig reagents to give olefin groups grafted on styrene-divinylbenzene copolymers. The reactions were carried out in phase transfer catalysis conditions. A simple procedure for the calculation of the degree of functionalization and the statistical modeling of the structural repetitive unit of the copolymer are reported.

  6. Antifungal activity of redox-active benzaldehydes that target cellular antioxidation

    Directory of Open Access Journals (Sweden)

    Mahoney Noreen

    2011-05-01

    Full Text Available Abstract Background Disruption of cellular antioxidation systems should be an effective method for control of fungal pathogens. Such disruption can be achieved with redox-active compounds. Natural phenolic compounds can serve as potent redox cyclers that inhibit microbial growth through destabilization of cellular redox homeostasis and/or antioxidation systems. The aim of this study was to identify benzaldehydes that disrupt the fungal antioxidation system. These compounds could then function as chemosensitizing agents in concert with conventional drugs or fungicides to improve antifungal efficacy. Methods Benzaldehydes were tested as natural antifungal agents against strains of Aspergillus fumigatus, A. flavus, A. terreus and Penicillium expansum, fungi that are causative agents of human invasive aspergillosis and/or are mycotoxigenic. The yeast Saccharomyces cerevisiae was also used as a model system for identifying gene targets of benzaldehydes. The efficacy of screened compounds as effective chemosensitizers or as antifungal agents in formulations was tested with methods outlined by the Clinical Laboratory Standards Institute (CLSI. Results Several benzaldehydes are identified having potent antifungal activity. Structure-activity analysis reveals that antifungal activity increases by the presence of an ortho-hydroxyl group in the aromatic ring. Use of deletion mutants in the oxidative stress-response pathway of S. cerevisiae (sod1Δ, sod2Δ, glr1Δ and two mitogen-activated protein kinase (MAPK mutants of A. fumigatus (sakAΔ, mpkCΔ, indicates antifungal activity of the benzaldehydes is through disruption of cellular antioxidation. Certain benzaldehydes, in combination with phenylpyrroles, overcome tolerance of A. fumigatus MAPK mutants to this agent and/or increase sensitivity of fungal pathogens to mitochondrial respiration inhibitory agents. Synergistic chemosensitization greatly lowers minimum inhibitory (MIC or fungicidal (MFC

  7. Trypanotoxic activity of thiosemicarbazone iron chelators.

    Science.gov (United States)

    Ellis, Samuel; Sexton, Darren W; Steverding, Dietmar

    2015-03-01

    Only a few drugs are available for treating sleeping sickness and nagana disease; parasitic infections caused by protozoans of the genus Trypanosoma in sub-Saharan Africa. There is an urgent need for the development of new medicines for chemotherapy of these devastating diseases. In this study, three newly designed thiosemicarbazone iron chelators, TSC24, Dp44mT and 3-AP, were tested for in vitro activity against bloodstream forms of Trypanosoma brucei and human leukaemia HL-60 cells. In addition to their iron chelating properties, TSC24 and Dp44mT inhibit topoisomerase IIα while 3-AP inactivates ribonucleotide reductase. All three compounds exhibited anti-trypanosomal activity, with minimum inhibitory concentration (MIC) values ranging between 1 and 100 µM and 50% growth inhibition (GI50) values of around 250 nM. Although the compounds did not kill HL-60 cells (MIC values >100 µM), TSC24 and Dp44mT displayed considerable cytotoxicity based on their GI50 values. Iron supplementation partly reversed the trypanotoxic and cytotoxic activity of TSC24 and Dp44mT but not of 3-AP. This finding suggests possible synergy between the iron chelating and topoisomerase IIα inhibiting activity of the compounds. However, further investigation using separate agents, the iron chelator deferoxamine and the topoisomerase II inhibitor epirubicin, did not support any synergy for the interaction of iron chelation and topoisomerase II inhibition. Furthermore, TSC24 was shown to induce DNA degradation in bloodstream forms of T. brucei indicating that the mechanism of trypanotoxic activity of the compound is topoisomerase II independent. In conclusion, the data support further investigation of thiosemicarbazone iron chelators with dual activity as lead compounds for anti-trypanosomal drug development. PMID:25595343

  8. Kinetic studies on the oxidation of oxyhemoglobin by biologically active iron thiosemicarbazone complexes: relevance to iron-chelator-induced methemoglobinemia.

    Science.gov (United States)

    Basha, Maram T; Rodríguez, Carlos; Richardson, Des R; Martínez, Manuel; Bernhardt, Paul V

    2014-03-01

    The oxidation of oxyhemoglobin to methemoglobin has been found to be facilitated by low molecular weight iron(III) thiosemicarbazone complexes. This deleterious reaction, which produces hemoglobin protein units unable to bind dioxygen and occurs during the administration of iron chelators such as the well-known 3-aminopyridine-2-pyridinecarbaldehyde thiosemicarbazone (3-AP; Triapine), has been observed in the reaction with Fe(III) complexes of some members of the 3-AP structurally-related thiosemicarbazone ligands derived from di-2-pyridyl ketone (HDpxxT series). We have studied the kinetics of this oxidation reaction in vitro using human hemoglobin and found that the reaction proceeds with two distinct time-resolved steps. These have been associated with sequential oxidation of the two different oxyheme cofactors in the α and β protein chains. Unexpected steric and hydrogen-bonding effects on the Fe(III) complexes appear to be the responsible for the observed differences in the reaction rate across the series of HDpxxT ligand complexes used in this study. PMID:24317633

  9. Methemoglobin formation by triapine, di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone (Dp44mT), and other anticancer thiosemicarbazones: identification of novel thiosemicarbazones and therapeutics that prevent this effect.

    Science.gov (United States)

    Quach, Patricia; Gutierrez, Elaine; Basha, Maram Talal; Kalinowski, Danuta S; Sharpe, Philip C; Lovejoy, David B; Bernhardt, Paul V; Jansson, Patric J; Richardson, Des R

    2012-07-01

    Thiosemicarbazones are a group of compounds that have received comprehensive investigation as anticancer agents. The antitumor activity of the thiosemicarbazone, 3-amino-2-pyridinecarboxaldehyde thiosemicarbazone (3-AP; triapine), has been extensively assessed in more than 20 phase I and II clinical trials. These studies have demonstrated that 3-AP induces methemoglobin (metHb) formation and hypoxia in patients, limiting its usefulness. Considering this problem, we assessed the mechanism of metHb formation by 3-AP compared with that of more recently developed thiosemicarbazones, including di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone (Dp44mT). This was investigated using intact red blood cells (RBCs), RBC lysates, purified oxyhemoglobin, and a mouse model. The chelation of cellular labile iron with the formation of a redox-active thiosemicarbazone-iron complex was found to be crucial for oxyhemoglobin oxidation. This observation was substantiated using a thiosemicarbazone that cannot ligate iron and also by using the chelator, desferrioxamine, that forms a redox-inactive iron complex. Of significance, cellular copper chelation was not important for metHb generation in contrast to its role in preventing tumor cell proliferation. Administration of Dp44mT to mice catalyzed metHb and cardiac metmyoglobin formation. However, ascorbic acid administered together with the drug in vivo significantly decreased metHb levels, providing a potential therapeutic intervention. Moreover, we demonstrated that the structure of the thiosemicarbazone is of importance in terms of metHb generation, because the DpT analog, di-2-pyridylketone-4-cyclohexyl-4-methyl-3-thiosemicarbazone (DpC), does not induce metHb generation in vivo. Hence, DpC represents a next-generation thiosemicarbazone that possesses markedly superior properties. This investigation is important for developing more effective thiosemicarbazone treatment regimens. PMID:22508546

  10. Synthesis, spectral characterization and eukaryotic DNA degradation of thiosemicarbazones and their platinum(IV) complexes

    Science.gov (United States)

    Al-Hazmi, G. A.; El-Metwally, N. M.; El-Gammal, O. A.; El-Asmy, A. A.

    2008-01-01

    The condensation products of acetophenone (or its derivatives), salicylaldehyde and o-hydroxy- p-methoxybenzophenone with thiosemicarbazide and ethyl- or phenyl-thiosemicarbazide are the investigated thiosemicarbazones. Their reactions with H 2PtCl 6 produced Pt(IV) complexes characterized by elemental, thermal, mass, IR and electronic spectral studies. The coordination modes were found mononegative bidentate in the acetophenone derivatives and binegative tridentate in the salicylaldehyde derivatives. The complexes were analyzed thermogravimetrically and found highly stable. Some ligands and their complexes were screened against Sarcina sp. and E. coli using the cup-diffusion technique. [Pt( oHAT)(OH)Cl] shows higher activity against E. coli than the other compounds. The degradation power of the tested compounds on the calf thymus DNA supports their selectivity against bacteria and not against the human or related eukaryotic organisms.

  11. Serotonin Mediates a Learned Increase in Attraction to High Concentrations of Benzaldehyde in Aged "C. elegans"

    Science.gov (United States)

    Tsui, David; van der Kooy, Derek

    2008-01-01

    We utilized olfactory-mediated chemotaxis in "Caenorhabditis elegans" to examine the effect of aging on information processing and animal behavior. Wild-type (N2) young adults (day 4) initially approach and eventually avoid a point source of benzaldehyde. Aged adult animals (day 7) showed a stronger initial approach and a delayed avoidance to…

  12. Preparation of 6,6'-Bisperfluoroalkylated BINOLs and Their Application in Asymmetric Alkylation of Benzaldehyde

    Institute of Scientific and Technical Information of China (English)

    YIN,Yue-Yan(尹月燕); ZHAO,Gang(赵刚); YANG,Gao-Sheng(杨高升); YIN,Wei-Xing(殷卫星)

    2002-01-01

    6,6'-Bis(1H,1H,2H,2H-perfluorooctyl)-BINOL and 6,6'-bis(1H ,1H , 2 H , 2 H- perfluorodecyl ) -BINOL were synthesized through Suzuki coupling reaction and used in fluorous biphase asymmetric alkylation of benzaldehyde. Good enantioselectivity was obtained and the catalysts could be recovered by liquid-liquid extraction.

  13. 4-Methyl­benzaldehyde thio­semi­carbazone

    OpenAIRE

    Zhang, Jian; Geng, Hao; Zhuang, Ling-hua; Wang, Guo-wei

    2009-01-01

    The title compound, C9H11N3S, was prepared by reacting 4-methyl­benzaldehyde with thio­semicarbazide. An intra­molecular N—H⋯N hydrogen bond helps to establish the observed mol­ecular conformation. The crystal packing is realized by inter­molecular N—H⋯S hydrogen bonds.

  14. Synthesis, experimental and theoretical studies on its crystal structure and FT-IR spectrum of new thiosemicarbazone compound E-2-(4-isopropylbenzylidene)thiosemicarbazone

    Science.gov (United States)

    Khalaji, Aliakbar Dehno; Mehrani, Sepideh; Eigner, Vaclav; Dusek, Michal

    2013-09-01

    The title compound E-2-(4-isopropylbenzylidene)thiosemicarbazone (1) derived from the reaction of 4-isopropylbenzaldehyde and thiosemicarbazide in ethanol solution has been synthesized and characterized by elemental analyses, FT-IR and 1H NMR spectroscopy and single-crystal X-ray diffraction. Its optimized geometry together with the theoretical assignment of the vibrational frequencies of the title compound has been computed by using density functional theory (DFT) method. In the gas phase the four conformers of the title compound were found and it was found that the conformer Sn1 is the most stable one. The title compound crystallizes in the monoclinic space group P21/c with unit cell parameters: a = 14.4054(4), b = 5.6832(10), c = 14.4337(3) Å, β = 93.306(2)°, V = 1179.70(5) Å3 and Z = 4.

  15. Lanthanum(III) and praseodymium(III) complexes with isatin thiosemicarbazones

    Science.gov (United States)

    Rai, Anita; Sengupta, Soumitra K.; Pandey, Om P.

    2005-09-01

    Ten new lanthanum(III) and praseodymium(III) complexes of the general formula Na[La(L) 2H 2O] (Ln = La(III) or Pr(III); LH 2 = thiosemicarbazones) derived from the condensation of isatin with 4-phenyl thiosemicarbazide, 4-(4-chlorophenyl) thiosemicarbazide, 4-(2-nitrophenyl) thiosemicarbazide, 4-(2-bromophenyl) thiosemicarbazide and 4-(2-methylphenyl) thiosemicarbazide, have been synthesized in methanol in presence of sodium hydroxide. The XRD spectra of the complexes were monitored to verify complex formation. The complexes have also been characterized by elemental analysis, molar conductance, electronic absorption and fluorescence, infrared, far infrared, 1H and 13C NMR spectral studies. Thermal studies of these complexes have been carried out in the temperature range 25-800 °C using TG, DTG and DTA techniques. All these complexes decompose gradually with the formation of Ln 2O 3 as the end product. The Judd-ofelt intensity parameter, oscillator strength, transition probability, stimulated emission cross section for different transitions of Pr 3+ for 4-phenyl thiosemicarbazones have been calculated.

  16. Vanadium Complexes with Hydrazone or Thiosemicarbazone Ligands as Potential Anti-Mycobacterium tuberculosis Agents.

    Science.gov (United States)

    de Souza, Paula C; Maia, Pedro I S; de Barros, Heloisa B; Leite, Clarice Q F; Deflon, Victor M; Pavan, Fernando R

    2015-01-01

    Tuberculosis (TB) is an infectious disease caused mainly by Mycobacterium tuberculosis (MTB) and still an important public health problem worldwide. Some factors like the emergence of multidrug resistant (MDR) and extensively drug-resistant (XDR) strains make urgent the research of new active compounds. Searching for new inorganic compounds against TB, three new dioxovanadium(V) complexes were obtained upon reaction of [VO(acac)2] with hydrazone and thiosemicarbazone ligands derived from di-2-pyridyl ketone. Spectroscopic studies and X-ray crystallography revealed asymmetrically oxo bridged binuclear complexes of the type [{VO(L(1,2))}2(μ-O)2], involving the hydrazone ligands, while a mononuclear square pyramidal complex of the type [VO2(L(3))] was formed with the thiosemicarbazone ligand. The compounds were tested against M. tuberculosis and three of them, with MICs values between 2.00 and 3.76 μM were considered promising for TB treatment. Such MIC values are comparable or better than those found for some drugs currently used in TB treatment. PMID:24433444

  17. Organometallic ruthenium complexes with thiosemicarbazone ligands: Synthesis, structure and cytotoxicity of [(η6-p-cymene)Ru(NS)Cl]+ (NS = 9-anthraldehyde thiosemicarbazones)

    OpenAIRE

    Beckford, Floyd A.; LeBlanc, Gabriel; Thessing, Jeffrey; Shaloski, Michael; Frost, Brian J.; LI, LIYA; Seeram, Navindra P.

    2009-01-01

    A series of half-sandwich arene-ruthenium complexes of the type [(η6-p-cymene) Ru(thiosemicarbazone)Cl]+ have been synthesized and their biological activity investigated. The first structurally characterized arene-ruthenium half-sandwich complex with a thiosemicarbazone ligand is reported.

  18. Organometallic ruthenium complexes with thiosemicarbazone ligands: Synthesis, structure and cytotoxicity of [(η6-p-cymene)Ru(NS)Cl]+ (NS = 9-anthraldehyde thiosemicarbazones)

    Science.gov (United States)

    Beckford, Floyd A.; Leblanc, Gabriel; Thessing, Jeffrey; Shaloski, Michael; Frost, Brian J.; Li, Liya; Seeram, Navindra P.

    2009-01-01

    A series of half-sandwich arene-ruthenium complexes of the type [(η6-p-cymene) Ru(thiosemicarbazone)Cl]+ have been synthesized and their biological activity investigated. The first structurally characterized arene-ruthenium half-sandwich complex with a thiosemicarbazone ligand is reported. PMID:20160909

  19. Synthesis and biochemical evaluation of benzoylbenzophenone thiosemicarbazone analogues as potent and selective inhibitors of cathepsin L.

    Science.gov (United States)

    Parker, Erica N; Song, Jiangli; Kishore Kumar, G D; Odutola, Samuel O; Chavarria, Gustavo E; Charlton-Sevcik, Amanda K; Strecker, Tracy E; Barnes, Ashleigh L; Sudhan, Dhivya R; Wittenborn, Thomas R; Siemann, Dietmar W; Horsman, Michael R; Chaplin, David J; Trawick, Mary Lynn; Pinney, Kevin G

    2015-11-01

    Upregulation of cathepsin L in a variety of tumors and its ability to promote cancer cell invasion and migration through degradation of the extracellular matrix suggest that cathepsin L is a promising biological target for the development of anti-metastatic agents. Based on encouraging results from studies on benzophenone thiosemicarbazone cathepsin inhibitors, a series of fourteen benzoylbenzophenone thiosemicarbazone analogues were designed, synthesized, and evaluated for their inhibitory activity against cathepsins L and B. Thiosemicarbazone inhibitors 3-benzoylbenzophenone thiosemicarbazone 1, 1,3-bis(4-fluorobenzoyl)benzene thiosemicarbazone 8, and 1,3-bis(2-fluorobenzoyl)-5-bromobenzene thiosemicarbazone 32 displayed the greatest potency against cathepsin L with low IC50 values of 9.9 nM, 14.4 nM, and 8.1 nM, respectively. The benzoylbenzophenone thiosemicarbazone analogues evaluated were selective in their inhibition of cathepsin L compared to cathepsin B. Thiosemicarbazone analogue 32 inhibited invasion through Matrigel of MDA-MB-231 breast cancer cells by 70% at 10 μM. Thiosemicarbazone analogue 8 significantly inhibited the invasive potential of PC-3ML prostate cancer cells by 92% at 5 μM. The most active cathepsin L inhibitors from this benzoylbenzophenone thiosemicarbazone series (1, 8, and 32) displayed low cytotoxicity toward normal primary cells [in this case human umbilical vein endothelial cells (HUVECs)]. In an initial in vivo study, 3-benzoylbenzophenone thiosemicarbazone (1) was well-tolerated in a CDF1 mouse model bearing an implanted C3H mammary carcinoma, and showed efficacy in tumor growth delay. Low cytotoxicity, inhibition of cell invasion, and in vivo tolerability are desirable characteristics for anti-metastatic agents functioning through an inhibition of cathepsin L. Active members of this structurally diverse group of benzoylbenzophenone thiosemicarbazone cathepsin L inhibitors show promise as potential anti-metastatic, pre

  20. Synthesis, characterization and spectral studies of some lanthanide complexes with p-(methoxy or chloro) phenylglyoxal thiosemicarbazone

    International Nuclear Information System (INIS)

    The present work deals with the synthesis of trivalent Pr, Nd, Sm, Eu, Gd, Tb, Dy and Yb complexes of p-methoxyphenylglyoxal thiosemicarbazone (PMPGT) and p-chlorophenylglyoxal thiosemicarbazone (PCPGT). 15 refs., 2 tabs

  1. Synthesis of complex compounds in the system [ReOG5]2--thiosemicarbazone acetone-Hg-acetone

    International Nuclear Information System (INIS)

    Present article is devoted to synthesis of complex compounds in the system [ReOG5]2--thiosemicarbazone acetone-Hg-acetone. The literature data on complex compounds of various metals with thiosemicarbazone was summarized. The synthesis of complex compounds in the system [ReOG5]2--thiosemicarbazone acetone-Hg-acetone was conducted. The complex compounds of rhenium with methyl ident thiosemicarbazone were synthesized.

  2. Effect of Triethanolamine and Benzaldehyde on the Storage Stability of Polystyrene- Ammonium Perchlorate Propellant

    Directory of Open Access Journals (Sweden)

    K. Kishore

    1986-10-01

    Full Text Available The effect of triethanolamine and benzaldehyde on the stability of polystyrene has been studied by dynamic thermogravimetry (TG. Slower decomposition of polymer in the presence of these compounds indicates their inhibiting ability on the oxidation of the polymer. The burning rate measurements of polystyrene (PS/ammonium perchlorate (AP propellants at ambient temperature and pressure shows an increase with the storage time. The percentage change in the burning rate of the propellants containing aldehyde and amine is less during the ageing which indicates the increased stability of the propellants. The safe-life time of the propellants for the ballistic stability has been calculated from the activation energy for the ageing process using an Arrhenius type equation. The safe-life of the propellants containing triethanolamine and benzaldehyde is more than the neat propellant.

  3. Kinetics of the Benzaldehyde-Inhibited Oxidation of Sulfite by Chlorine Dioxide.

    Science.gov (United States)

    Pan, Changwei; Gao, Qingyu; Stanbury, David M

    2016-01-01

    There has been steady interest in the aqueous reaction of ClO2• with sulfur(IV) since the 1950s, and a wide variety of rate laws and mechanisms have been proposed. In neutral-to-alkaline media, the reaction is challenging to study because of its great rate. Here it is shown that benzaldehyde can be used as an additive to slow the reaction and make its rates more amenable to study. The rates can be quantitatively modeled by a mechanism that includes reversible binding of sulfur(IV) by benzaldehyde and a rate-limiting mixed second-order reaction of ClO2• with SO3(2-). The latter reaction occurs through parallel electron transfer from SO3(2-) to ClO2• and oxygen-atom transfer from ClO2• to SO3(2-). PMID:26678913

  4. Synthesis and evaluation of copper radiopharmaceuticals with mixed bis(thiosemicarbazone) ligands

    Energy Technology Data Exchange (ETDEWEB)

    Ackerman, Lily J.; West, Douglas X.; Mathias, Carla J.; Green, Mark A. E-mail: magreen@pharmacy.purdue.edu

    1999-07-01

    Four 'mixed' bis(thiosemicarbazone) derivatives of pyruvaldehyde were synthesized that incorporate two dissimilar thiosemicarbazone functions. The corresponding [{sup 67}Cu]copper(II) complexes were prepared and evaluated as possible copper radiopharmaceuticals. The pyruvaldehyde-based mixed bis(thiosemicarbazone) ligands, CH{sub 3}C[=NNHC(S)NHMe]CH[=NNHC(S)NHEt] (1), CH{sub 3}C[=NNHC(S)NHMe]CH[=NNHC(S)NEt{sub 2}] (2), CH{sub 3}C[=NNHC(S)NHMe]CH[=NNHC(S)-cyclo-N(CH{sub 2}){sub 5}] (3), and CH{sub 3}C[=NNHC(S)NHMe]CH[=NNHC(S)-cyclo-N(CH{sub 2}){sub 6}] (4), were obtained by reaction of the appropriate thiosemicarbazide derivative with pyruvaldehyde-2-N{sup 4}-methylthiosemicarbazone (CH{sub 3}C[=NNHC(S)NHMe]CHO). The {sup 67}Cu-labeled copper(II) complexes of ligands 1-4 were prepared and screened in a rat model to assess the potential of each chelate as a {sup 62}Cu-radiopharmaceutical for imaging with positron emission tomography. The {sup 67}Cu-complexes of ligands 1-4 exhibit significant uptake into the brain and heart 1 min following intravenous administration to rats. For the {sup 67}Cu-complexes of ligands 2, 3, and 4, the cerebral and myocardial uptake of {sup 67}Cu is two-to-threefold lower at 2 h than at 1 min postinjection, due to significant biological clearance of these {sup 67}Cu-chelates. However, the {sup 67}Cu-complex of 1 affords cerebral and myocardial uptake and retention comparable to that of [{sup 67}Cu]Cu-PTSM in this model. Although the kinetics of this new agent appear attractive, ultrafiltration studies using solutions of dog and human serum albumin reveal that the {sup 67}Cu-complex of ligand 1, like Cu-PTSM, interacts more strongly with human albumin than dog albumin. Thus, this new agent would appear to offer no advantage over Cu-PTSM as a {sup 62}Cu-labeled tracer for evaluation of regional tissue perfusion.

  5. Study of Thiosemicarbazone Derivative of Essential Fatty Acid

    OpenAIRE

    Borhade, Shobha

    2014-01-01

    Essential fatty acids results in numerous health benefits. Only two fatty acids are known to be essential for human alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid).The importance of omega-3 fatty acids for physical well-being has been recognised for several decades . Omega-3 fatty acids have anti-inflammatory, antithrombotic, antiarrhythmic and hypolipidaemic effects. Cannabis sativa (Hemp) is an angiosperm belonging to the cannabaceae family and cannabi...

  6. STRUCTURE CHARACTERIZATION AND APPLICATION OF NI HYDROTALCITE AS ENVIRONMENTALLY FRIENDLY CATALYSTS FOR REDUCTIVE AMINATION OF BENZALDEHYDE

    OpenAIRE

    Ateeq Rahman

    2013-01-01

    Ni/hydrotalcite catalysts with ratios 2:1, 2.5 and 3:1 exhibit catalytic activity for reductive amination of benzaldehyde to amine. Ni HTLC is prepared by co-precipitation method, which is characterized by XRD, IR and TPR instruments. Carbonate present in the brucite layer of hydrotalcite and calcined hydrotalcite produce mixed oxides, exhibits catalytic activity for variety of organic transformations ex: selective aldol, nitro aldol, wittig, knoevenegal oxidation, reduction reactions. Hydrot...

  7. Synthesis and Characterization of Some New Cu(II, Ni(II and Zn(II Complexes with Salicylidene Thiosemicarbazones: Antibacterial, Antifungal and in Vitro Antileukemia Activity

    Directory of Open Access Journals (Sweden)

    Tudor Rosu

    2013-07-01

    Full Text Available Thirty two new Cu(II, Ni(II and Zn(II complexes (1–32 with salicylidene thiosemicarbazones (H2L1–H2L10 were synthesized. Salicylidene thiosemicarbazones, of general formula (XN-NH-C(S-NH(Y, were prepared through the condensation reaction of 2-hydroxybenzaldehyde and its derivatives (X with thiosemicarbazide or 4-phenylthiosemicarbazide (Y = H, C6H5. The characterization of the new formed compounds was done by 1H-NMR, 13C-NMR, IR spectroscopy, elemental analysis, magnetochemical, thermoanalytical and molar conductance measurements. In addition, the structure of the complex 5 has been determined by X-ray diffraction method. All ligands and metal complexes were tested as inhibitors of human leukemia (HL-60 cells growth and antibacterial and antifungal activities.

  8. Copper complexes of bis(thiosemicarbazones): from chemotherapeutics to diagnostic and therapeutic radiopharmaceuticals.

    Science.gov (United States)

    Paterson, Brett M; Donnelly, Paul S

    2011-05-01

    The molecules known as bis(thiosemicarbazones) derived from 1,2-diones can act as tetradentate ligands for Cu(II), forming stable, neutral complexes. As a family, these complexes possess fascinating biological activity. This critical review presents an historical perspective of their progression from potential chemotherapeutics through to more recent applications in nuclear medicine. Methods of synthesis are presented followed by studies focusing on their potential application as anti-cancer agents and more recent investigations into their potential as therapeutics for Alzheimer's disease. The Cu(II) complexes are of sufficient stability to be used to coordinate copper radioisotopes for application in diagnostic and therapeutic radiopharmaceuticals. Detailed understanding of the coordination chemistry has allowed careful manipulation of the metal based properties to engineer specific biological activities. Perhaps the most promising complex radiolabelled with copper radioisotopes to date is Cu(II)(atsm), which has progressed to clinical trials in humans (162 references). PMID:21409228

  9. Nickel(II) complexes containing thiosemicarbazone and triphenylphosphine: Synthesis, spectroscopy, crystallography and catalytic activity

    Science.gov (United States)

    Priyarega, S.; Kalaivani, P.; Prabhakaran, R.; Hashimoto, T.; Endo, A.; Natarajan, K.

    2011-09-01

    Four new Ni(II) complexes of the general formula [Ni(PPh 3)(L)] (L = dibasic tridentate ligand derived from 4-diethylamino-salicylaldehyde and thiosemicarbazide or 4-N-substituted thiosemicarbazide) have been reported. The new complexes have been synthesized and characterized by analytical and spectroscopic (IR, electronic, 1H NMR and 31P NMR) techniques. Molecular structure of one of the complexes has been determined by X-ray crystallography. The complex, [Ni(PPh 3)(L4)] (H 2L4 = thiosemicarbazone prepared from 4-diethylamino-salicylaldehyde and 4-phenylthiosemicarbazide) crystallized in monoclinic space group with two molecules per unit cell and has the dimensions of a = 13.232(6) Å, b = 10.181(5) Å, c = 13.574(7) Å, α = 90°, β = 98.483(2)° and γ = 90°. Catalytic activity of the complexes has been explored for aryl-aryl coupling reaction.

  10. Vibrational spectroscopic studies and computational study of ethyl methyl ketone thiosemicarbazone

    Science.gov (United States)

    Anoop, M. R.; Binil, P. S.; Suma, S.; Sudarsanakumar, M. R.; Y, Sheena Mary.; Varghese, Hema Tresa; Panicker, C. Yohannan

    2010-04-01

    FT-IR and FT-Raman spectra of ethyl methyl ketone thiosemicarbazone were recorded and analyzed. The crystal structure is also described. The vibrational wavenumbers were computed using HF/6-31G(d) and B3LYP/6-31G(d) basis sets and are assigned with the aid of MOLEKEL program. The first hyperpolarizability, infrared intensities and Raman activities are also reported. The calculated first hyperpolarizability is comparable with the reported values of similar derivatives and is an attractive molecule for future applications in non-linear optics. The geometrical parameters of the title compound obtained from XRD studies are in agreement with the calculated values. The red shift of the NH stretching wavenumber in the infrared spectrum compared to the computed wavenumber indicates the weakening of the N-H bond resulting in proton transfer to the neighbouring sulfur atom.

  11. Synthesis and Biochemical Evaluation of Thiochromanone Thiosemicarbazone Analogues as Inhibitors of Cathepsin L

    Science.gov (United States)

    2012-01-01

    A series of 36 thiosemicarbazone analogues containing the thiochromanone molecular scaffold functionalized primarily at the C-6 position were prepared by chemical synthesis and evaluated as inhibitors of cathepsins L and B. The most promising inhibitors from this group are selective for cathepsin L and demonstrate IC50 values in the low nanomolar range. In nearly all cases, the thiochromanone sulfide analogues show superior inhibition of cathepsin L as compared to their corresponding thiochromanone sulfone derivatives. Without exception, the compounds evaluated were inactive (IC50 > 10000 nM) against cathepsin B. The most potent inhibitor (IC50 = 46 nM) of cathepsin L proved to be the 6,7-difluoro analogue 4. This small library of compounds significantly expands the structure–activity relationship known for small molecule, nonpeptidic inhibitors of cathepsin L. PMID:24900494

  12. Comparative analysis of the cytotoxicity of substituted (phenylglyoxal bis(4-methyl-3-thiosemicarbazone)) copper (II) chelates.

    Science.gov (United States)

    Coats, E A; Milstein, S R; Holbein, G; McDonald, J; Reed, R; Petering, H G

    1976-01-01

    Seven para-substituted [phenylglyoxal bis(4-methyl-3-thiosemicarbazone)]copper (II) chelates (12-18) have been designed, synthesized, and tested for their ability to inhibit the respiration of rat liver slices as a normal cell model and Ehrlich ascites cells as a tumor cell model. Relationships between chemical structure and respiratory inhibition are described on a quantitative basis using substituent contants (pi, Es, and sigmap) by computerized multiparameter regression analyses. The correlations indicate that changes in Es have the largest effect on liver slice toxicity of chelates while pi and sigmap account for most of the variation in toxicity to ascites cells. A comparative analysis strongly suggests that electron-donating substituents with greater water solubility should increase cytotoxicity to ascites cells at the expense of cytotoxicity to the rat liver cells. The predictions of the equations were checked by synthesizing and testing an additional derivative. The results strengthen the initial predictions. PMID:1246035

  13. Novel ruthenium(II) cyclopentadienyl thiosemicarbazone compounds with antiproliferative activity on pathogenic trypanosomatid parasites.

    Science.gov (United States)

    Fernández, Mariana; Arce, Esteban Rodríguez; Sarniguet, Cynthia; Morais, Tânia S; Tomaz, Ana Isabel; Azar, Claudio Olea; Figueroa, Roberto; Diego Maya, J; Medeiros, Andrea; Comini, Marcelo; Helena Garcia, M; Otero, Lucía; Gambino, Dinorah

    2015-12-01

    Searching for new prospective antitrypanosomal agents, three novel Ru(II)-cyclopentadienyl compounds, [Ru(η(5)-C5H5)(PPh3)L], with HL=bioactive 5-nitrofuryl containing thiosemicarbazones were synthesized and characterized in the solid state and in solution. The compounds were evaluated in vitro on the blood circulating trypomastigote form of Trypanosoma cruzi (Dm28c strain), the infective form of Trypanosoma brucei brucei (strain 427) and on J774 murine macrophages and human-derived EA.hy926 endothelial cells. The compounds were active against both parasites with IC50 values in the micromolar or submicromolar range. Interestingly, they are much more active on T. cruzi than previously developed Ru(II) classical and organometallic compounds with the same bioactive ligands. The new compounds showed moderate to very good selectivity towards the parasites in respect to mammalian cells. The global results point at [RuCp(PPh3)L2] (L2=N-methyl derivative of 5-nitrofuryl containing thiosemicarbazone and Cp=cyclopentadienyl) as the most promising compound for further developments (IC50T. cruzi=0.41μM; IC50T. brucei brucei=3.5μM). Moreover, this compound shows excellent selectivity towards T. cruzi (SI>49) and good selectivity towards T. brucei brucei (SI>6). In order to get insight into the mechanism of antiparasitic action, the intracellular free radical production capacity of the new compounds was assessed by ESR. DMPO (5,5-dimethyl-1-pirroline-N-oxide) spin adducts related to the bioreduction of the complexes and to redox cycling processes were characterized. In addition, DNA competitive binding studies with ethidium bromide by fluorescence measurements showed that the compounds interact with this biomolecule. PMID:26275470

  14. Improved cytotoxicity of pyridyl-substituted thiosemicarbazones against MCF-7 when used as metal ionophores.

    Science.gov (United States)

    Akladios, Fady N; Andrew, Scott D; Parkinson, Christopher J

    2016-02-01

    Zinc is the second most abundant transition metal in the human body, between 3 and 10% of human genes encoding for zinc binding proteins. We have investigated the interplay of reactive oxygen species and zinc homeostasis on the cytotoxicity of the thiosemicarbazone chelators against the MCF-7 cell line. The cytotoxicity of thiosemicarbazone chelators against MCF-7 can be improved through supplementation of ionic zinc provided the zinc ion is at a level exceeding the thiosemicarbazone concentration. Elimination of the entire cell population can be accomplished with this regime, unlike the plateau of cytotoxicity observed on thiosemicarbazone monotherapy. The cytotoxic effects of copper complexes of the thiosemicarbazone are not enhanced by zinc supplementation, displacement of copper from the complex being disfavoured. Treatment of MCF-7 with uncomplexed thiosemicarbazone initiates post G1 blockade alongside the induction of apoptosis, cell death being abrogated through subsequent supplementation with zinc ion after drug removal. This would implicate a metal depletion mechanism in the cytotoxic effect of the un-coordinated thiosemicarbazone. The metal complexes of the species, however, fail to initiate similar G1 blockade and apparently exert their cytotoxic effect through generation of reactive oxygen species, suggesting that multiple mechanisms of cytotoxicity can be associated with the thiosemicarbazones dependant on the level of metal ion association. PMID:26683314

  15. Synthesis and biochemical evaluation of benzoylbenzophenone thiosemicarbazone analogues as potent and selective inhibitors of cathepsin L

    DEFF Research Database (Denmark)

    Parker, Erica N; Song, Jiangli; Kishore Kumar, G D;

    2015-01-01

    selective in their inhibition of cathepsin L compared to cathepsin B. Thiosemicarbazone analogue 32 inhibited invasion through Matrigel of MDA-MB-231 breast cancer cells by 70% at 10μM. Thiosemicarbazone analogue 8 significantly inhibited the invasive potential of PC-3ML prostate cancer cells by 92% at 5μ...

  16. A 119Sn Moessbauer Study of Tin(IV) Complexes of 2- and 4-Benzoylpyridine Thiosemicarbazone and 4-Benzoylpyridine Semicarbazone

    International Nuclear Information System (INIS)

    A 119Sn Moessbauer study was carried out of tin(IV) complexes with 2-benzoylpyridine thiosemicarbazone (H2Bz4DH) and its N(4)-methyl (H2Bz4M) and N(4)-phenyl (H2Bz4Ph) derivatives: [Sn(2Bz4DH)Cl3] (1), [Sn(2Bz4DH)PhCl2] (2), [Sn(2Bz4M)Cl3] (3), [H22Bz4M]2[Ph2SnCl4] (4), [Sn(2Bz4Ph)PhCl2] (5), [Sn(2Bz4Ph)Ph2Cl] (6), in which H2Bz4R stands for the neutral ligand and 2Bz4R stands for the anionic thiosemicarbazone. In addition, 119Sn Moessbauer studies of the tin(IV) complexes [Sn(H4Bz4DH)2Cl4H2O] (7), [Sn(H4BzPS)2Cl4H2O] (8) with 4-benzoylpyridine thiosemicarbazone (H4Bz4DH) and the correspondent semicarbazone (H4BzPS) were performed. The isomer shifts decrease upon coordination due to the variation in the percentage of s character as tin changes from approximately sp3 hybridization in the tin salts to sp3d2 in the octahedral or sp3d3 in the heptahedral complexes. The Moessbauer parameters of compound (4) showed the existence of two tin(IV) sites, which have been attributed to the presence of the cis and trans isomers.

  17. Vibrational spectra of palladium 5-nitrofuryl thiosemicarbazone complexes: Experimental and theoretical study

    Science.gov (United States)

    Gambino, Dinorah; Otero, Lucía; Vieites, Marisol; Boiani, Mariana; González, Mercedes; Baran, Enrique J.; Cerecetto, Hugo

    2007-10-01

    The vibrational spectroscopic behavior of a series of 16 palladium(II) complexes with 8 bioactive nitrofuran containing thiosemicarbazones as ligands has been studied in the solid state. The IR and Raman spectra of these complexes and the free nitrofuran thiosemicarbazone ligands were recorded and analyzed. Experimental spectra were satisfactorily described by density functional theory (DFT) calculations. The combination of experimental and theoretical methods allowed us to perform the characterization of the main vibrations that show the mode of coordination of the thiosemicarbazone moiety to palladium even though these vibration bands are located in spectral regions showing a complicated pattern due to the presence of vibrations of the nitrofuran moiety and combination modes involving furan vibrations. A characteristic vibrational spectroscopic pattern has been defined for Pd(II) 5-nitrofuryl thiosemicarbazone complexes. This systematic knowledge may be useful for the analysis of the spectroscopic behavior of other coordination compounds holding the 5-nitrofuran thiosemicarbazone moiety.

  18. CHARACTERIZATION AND ANTIPARASITIC ACTIVITY OF BENZOPHENONE THIOSEMICARBAZONES ON Trypanosoma brucei brucei

    Directory of Open Access Journals (Sweden)

    Georges C. Accrombessi

    2011-02-01

    Full Text Available The structure of four synthesized thiosemicarbazones, substituted or not, of benzophenone has been confirmed by spectrometrical analysis IR, NMR 1H and 13C. Their anti-trypanosomal activities were evaluated on Trypanosoma brucei brucei. Among these compounds, benzophenone 4 phenyl-3-thiosemicarbazone 4 has the highest activity with the half-inhibitory concentration (IC50 = 8.48 micromolar (µM. Benzophenone 4-methyl-3-thiosemicarbazone 3 and benzophenone thiosemicarbazone 1 showed moderate anti-trypanosomal activity with IC50 values equal to 23.27 µM and 67.17 µM respectively. Benzophenone 2 methyl-3-thiosemicarbazone 2 showed no activity up to IC50 = 371.74 µM.

  19. Titanium zirconium and hafnium coordination compounds with vanillin thiosemicarbazone

    International Nuclear Information System (INIS)

    Coordination compounds of titanium zirconium and hafnium tetrachlorides with vanillin thiosemicarbazone of MCl4 x nLig composition, where n=1.5, 4 for titanium and 1, 2, 4 for zirconium and hafnium, are synthesized. Molar conductivity of ethanol solutions is measured; IR spectroscopic and thermochemical investigation are carried out. The supposition about ligand coordination via sulfur and azomethine nitrogen atoms is made. In all cases hafnium forms stable compounds than zirconium

  20. Thiosemicarbazones: preparation methods, synthetic applications and biological importance

    International Nuclear Information System (INIS)

    Thiosemicarbazones are a class of compounds known by their chemical and biological properties, such as antitumor, antibacterial, antiviral and antiprotozoal activity. Their ability to form chelates with metals has great importance in their biological activities. Their synthesis is very simple, versatile and clean, usually giving high yields. They are largely employed as intermediates, in the synthesis of others compounds. This article is a survey of some of these characteristics showing their great importance to organic and medicinal chemistry. (author)

  1. Synthesis of a sugar-based thiosemicarbazone series and structure-activity relationship versus the parasite cysteine proteases rhodesain, cruzain, and Schistosoma mansoni cathepsin B1.

    Science.gov (United States)

    Fonseca, Nayara Cristina; da Cruz, Luana Faria; da Silva Villela, Filipe; do Nascimento Pereira, Glaécia Aparecida; de Siqueira-Neto, Jair Lage; Kellar, Danielle; Suzuki, Brian M; Ray, Debalina; de Souza, Thiago Belarmino; Alves, Ricardo José; Sales Júnior, Policarpo Ademar; Romanha, Alvaro José; Murta, Silvane Maria Fonseca; McKerrow, James H; Caffrey, Conor R; de Oliveira, Renata Barbosa; Ferreira, Rafaela Salgado

    2015-05-01

    The pressing need for better drugs against Chagas disease, African sleeping sickness, and schistosomiasis motivates the search for inhibitors of cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1), the major cysteine proteases from Trypanosoma cruzi, Trypanosoma brucei, and S. mansoni, respectively. Thiosemicarbazones and heterocyclic analogues have been shown to be both antitrypanocidal and inhibitory against parasite cysteine proteases. A series of compounds was synthesized and evaluated against cruzain, rhodesain, and SmCB1 through biochemical assays to determine their potency and structure-activity relationships (SAR). This approach led to the discovery of 6 rhodesain, 4 cruzain, and 5 SmCB1 inhibitors with 50% inhibitory concentrations (IC50s) of ≤ 10 μM. Among the compounds tested, the thiosemicarbazone derivative of peracetylated galactoside (compound 4i) was discovered to be a potent rhodesain inhibitor (IC50 = 1.2 ± 1.0 μM). The impact of a range of modifications was determined; removal of thiosemicarbazone or its replacement by semicarbazone resulted in virtually inactive compounds, and modifications in the sugar also diminished potency. Compounds were also evaluated in vitro against the parasites T. cruzi, T. brucei, and S. mansoni, revealing active compounds among this series. PMID:25712353

  2. Synthesis and characterization of mixed-ligand diimine-piperonal thiosemicarbazone complexes of ruthenium(II): Biophysical investigations and biological evaluation as anticancer and antibacterial agents

    Science.gov (United States)

    Beckford, Floyd A.; Thessing, Jeffrey; Shaloski, Michael, Jr.; Canisius Mbarushimana, P.; Brock, Alyssa; Didion, Jacob; Woods, Jason; Gonzalez-Sarrías, Antonio; Seeram, Navindra P.

    2011-04-01

    We have used a novel microwave-assisted method developed in our laboratories to synthesize a series of ruthenium-thiosemicarbazone complexes. The new thiosemicarbazone ligands are derived from benzo[ d][1,3]dioxole-5-carbaldehyde (piperonal) and the complexes are formulated as [(diimine) 2Ru(TSC)](PF 6) 2 (where the TSC is the bidentate thiosemicarbazone ligand). The diimine in the complexes is either 2,2'-bipyridine or 1,10-phenanthroline. The complexes have been characterized by spectroscopic means (NMR, IR and UV-Vis) as well as by elemental analysis. We have studied the biophysical characteristics of the complexes by investigating their anti-oxidant ability as well as their ability to disrupt the function of the human topoisomerase II enzyme. The complexes are moderately strong binders of DNA with binding constants of 10 4 M -1. They are also strong binders of human serum albumin having binding constants on the order of 10 4 M -1. The complexes show good in vitro anticancer activity against human colon cancer cells, Caco-2 and HCT-116 and indeed show some cytotoxic selectivity for cancer cells. The IC 50 values range from 7 to 159 μM (after 72 h drug incubation). They also have antibacterial activity against Gram-positive strains of pathogenic bacteria with IC 50 values as low as 10 μM; little activity was seen against Gram-negative strains. It has been established that all the compounds are catalytic inhibitors of human topoisomerase II.

  3. Crystal structures of copper(II) complexes of 2-formylpyridine substituted thiosemicarbazones; the first example of a coordinated thiosemicarbazone with a thiol function

    Science.gov (United States)

    West, D. X.; Swearingen, J. K.; Romack, T. J.; Billeh, I. S.; Jasinski, J. P.; Li, Y.; Staples, R. J.

    2001-08-01

    The crystal structures of two 5-coordinate copper(II) complexes containing neutral, tridentate 2-formylpyridine N(4)-substituted thiosemicarbazones have been determined. 2-Formylpyridine N(4)-cyclohexylthiosemicarbazone, HFo4CHex coordinates via the pyridine nitrogen, imine nitrogen and thione sulfur with two chloro ligands to produce [Cu(HFo4CHex)Cl 2]. Similarly, 2-formylpyridine 3-(4-methylpiperazine)thiosemicarbazone, HFoppz4M, produces [Cu(HFoppz4M)Cl 2] with one major difference; rather than the expected thione form of the thiosemicarbazone moiety, it coordinates as the thiol isomer. Both complexes are close to a square pyramid structure with axial and equatorial chloro ligands and the thiosemicarbazone moieties of both ligands nearly planar. Also included is the crystal structure of N-cyclohexylthiosemicarbazide, CHextsc.

  4. 3-Methoxy­benzaldehyde thio­semi­carbazone

    OpenAIRE

    Zhang, Jian; Wu, Lin-Ping; Zhuang, Ling-hua; Wang, Guo-wei

    2009-01-01

    The title compound, C9H11N3OS, was prepared by the reaction of 3-methoxy­benzaldehyde and thio­semicarbazide. The benzyl­idene ring and the thio­semicarbazone fragment are slightly twisted, making a dihedral angle of 14.1 (1)°. A weak intra­molecular N—H⋯N hydrogen bond may influence the conformation of the mol­ecule. Inter­molecular N—H⋯S hydrogen bonds build up a three-dimensional network.

  5. Indole-7-carbaldehyde thiosemicarbazone as a flexidentate ligand toward ZnII, CdII, PdII and PtII ions: cytotoxic and apoptosis-inducing properties of the PtII complex.

    Science.gov (United States)

    Ibrahim, Abeer A; Khaledi, Hamid; Hassandarvish, Pouya; Mohd Ali, Hapipah; Karimian, Hamed

    2014-03-14

    A new thiosemicarbazone (LH2) derived from indole-7-carbaldehyde was synthesized and reacted with Zn(II), Cd(II), Pd(II) and Pt(II) salts. The reactions with zinc and cadmium salts in 2 : 1 (ligand-metal) molar ratio afforded complexes of the type MX2(LH2)2, (X = Cl, Br or OAc), in which the thiosemicarbazone acts as a neutral S-monodentate ligand. In the presence of potassium hydroxide, the reaction of LH2 with ZnBr2 resulted in deprotonation of the thiosemicarbazone at the hydrazine and indole nitrogens to form Zn(L)(CH3OH). The reaction of LH2 with K2PdCl4 in the presence of triethylamine, afforded Pd(L)(LH2) which contains two thiosemicarbazone ligands: one being dianionic N,N,S-tridentate while the other one is neutral S-monodentate. When PdCl2(PPh3)2 was used as the Pd(II) ion source, Pd(L)(PPh3) was obtained. In a similar manner, the analogous platinum complex, Pt(L)(PPh3), was synthesized. The thiosemicarbazone in the latter two complexes behaves in a dianionic N,N,S-tridentate fashion. The platinum complex was found to have significant cytotoxicity toward four cancer cells lines, namely MDA-MB-231, MCF-7, HT-29, and HCT-116 but not toward the normal liver WRL-68 cell line. The apoptosis-inducing properties of the Pt complex was explored through fluorescence microscopy visualization, DNA fragmentation analysis and propidium iodide flow cytometry. PMID:24442181

  6. Copper(II) bis(thiosemicarbazone) complexes as potential tracers for evaluation of cerebral and myocardial blood flow with PET

    International Nuclear Information System (INIS)

    Wider application of positron emission tomography would be facilitated by the availability of positron-emitting radiopharmaceuticals labeled with nuclides, like 62Cu, that are available from parent/daughter generator systems. Using a longer-lived copper isotope (67Cu) we have examined three derivatives of copper(II) pyruvaldehyde bis(thiosemicarbazone) as potential tracers for evaluation of cerebral and myocardial blood flow: Cu(PTS), Cu(PTSM), and Cu(PTSM2) (where PTS = pyruvaldehyde bis(thiosemicarbazone), PTSM = pyruvaldehyde bis(N4-methylthiosemicarbazone), and PTSM2 = pyruvaldehyde bis(N4-dimethylthiosemicarbazone). All three lipophilic radiocopper complexes were obtained in high yield via a procedure that could be adapted to a ''kit'' formulation. In animal model systems Cu(PTSM) and Cu(PTSM2) show excellent uptake in the brain and heart following i.v. injection. These tracers differ in that Cu(PTSM) exhibits microsphere-like retention in the brain and heart, whereas Cu(PTSM2) substantially clears from these organs. The relative cerebral pharmacokinetics of [67Cu]Cu(PTSM) and [67Cu]Cu(PTSM2) are consistent with their known reactivity towards intracellular sulfhydryl groups

  7. Experimental and theoretical evaluation of two pyridinecarboxaldehyde thiosemicarbazone compounds as corrosion inhibitors for mild steel in hydrochloric acid solution

    International Nuclear Information System (INIS)

    Highlights: •The studied inhibitors contain both pyridine ring and Schiff’s base structure. •The inhibitors show good inhibitive properties for mild steel in HCl. •The inhibitors adsorb on mild steel surface both physically and chemically. •The PZC measurements show the mild steel surface was positively charged. -- Abstract: The inhibition effect of two Schiff’s base derivatives on the corrosion of mild steel in 1.0 M HCl solution was studied by electrochemical techniques, SEM and theoretical calculation methods. The experimental results show that the inhibition efficiency of 2-pyridinecarboxaldehyde thiosemicarbazone (2-PCT) is higher than that of 4-pyridinecarboxaldehyde thiosemicarbazone (4-PCT), and both the two compounds are good inhibitors for mild steel in 1.0 M HCl. Potentiodynamic polarization curves show that the two inhibitors act as mixed type inhibitors. The adsorption of inhibitors obeys the Langmuir adsorption isotherm, and the thermodynamic parameters (Ea, Kads, ΔGads0) were calculated and discussed. The mechanism of inhibition was determined by PZC measurements and theoretical calculation methods

  8. Copper(II) bis(thiosemicarbazone) complexes as potential tracers for evaluation of cerebral and myocardial blood flow with PET

    Energy Technology Data Exchange (ETDEWEB)

    Green, M.A.; Klippenstein, D.L.; Tennison, J.R.

    1988-09-01

    Wider application of positron emission tomography would be facilitated by the availability of positron-emitting radiopharmaceuticals labeled with nuclides, like /sup 62/Cu, that are available from parent/daughter generator systems. Using a longer-lived copper isotope (/sup 67/Cu) we have examined three derivatives of copper(II) pyruvaldehyde bis(thiosemicarbazone) as potential tracers for evaluation of cerebral and myocardial blood flow: Cu(PTS), Cu(PTSM), and Cu(PTSM2) (where PTS = pyruvaldehyde bis(thiosemicarbazone), PTSM = pyruvaldehyde bis(N4-methylthiosemicarbazone), and PTSM2 = pyruvaldehyde bis(N4-dimethylthiosemicarbazone). All three lipophilic radiocopper complexes were obtained in high yield via a procedure that could be adapted to a ''kit'' formulation. In animal model systems Cu(PTSM) and Cu(PTSM2) show excellent uptake in the brain and heart following i.v. injection. These tracers differ in that Cu(PTSM) exhibits microsphere-like retention in the brain and heart, whereas Cu(PTSM2) substantially clears from these organs. The relative cerebral pharmacokinetics of (/sup 67/Cu)Cu(PTSM) and (/sup 67/Cu)Cu(PTSM2) are consistent with their known reactivity towards intracellular sulfhydryl groups.

  9. Synthesis, characterization and biological evaluation of paeonol thiosemicarbazone analogues as mushroom tyrosinase inhibitors.

    Science.gov (United States)

    Zhu, Tian-Hua; Cao, Shu-Wen; Yu, Yan-Ying

    2013-11-01

    A series of hydroxy- and methoxy-substituted paeonol thiosemicarbazone analogues were synthesized as potential tyrosinase inhibitors and their inhibitory effects on mushroom tyrosinase and inhibitory mechanism were evaluated. Paeonol thiosemicarbazone analogues have been found exhibiting more remarkable inhibition than their indexcompounds on mushroom tyrosinase. Among them, compound 2,4-dihydroxy acetophenone-4-phenyl-3-thiosemicarbazone (d1) had the most potent inhibition activity with the IC50 value of 0.006 ± 0.001 mM, displayed as a reversible competitive inhibitor. The inhibitory ability of o- or p-substituted acetophenone thiosemicarbazones was: di-substituted acetophenone thiosemicarbazones>mono-substituted acetophenone thiosemicarbazones>non-substituted acetophenone thiosemicarbazones. Copper ions chelation assay explained that compound d1 exhibited competitive inhibition by forming a chelate with the copper ions at the catalytic domain of tyrosinase as well as indicate a 1.5:1 binding ratio of compound d1 with copper ions. In the fluorescence spectrum study, compound d1 behaved stronger fluorescence quenching on tyrosinase towards d1-Cu(2+) complex, inhibiting tyrosinase mainly by means of chelating the two copper ions in the active site. The newly synthesized compounds may serve as structural templates for designing and developing novel tyrosinase inhibitors. PMID:24120880

  10. The effect of solvent on the kinetics of the oxidation of benzaldehydes by quinolinium chlorochromate in aqueous organic solvent media

    Directory of Open Access Journals (Sweden)

    G. FATIMA JEYANTHI

    2002-12-01

    Full Text Available The kinetics of the oxidation of benzaldehyde and para-substituted benzaldehydes by quinolinium chlorochromate in water-dimethylformamide mixtures has been studied under pseudo-first-order conditions at 25±0.2°C. The operation of non-specific and specific solvent-solute interactions was explored by correlating the rate data with solvent parameters through a correlation analysis technique. Both electron-releasing and electron-withdrawing substitutents enhance the rate of oxidation and the Hammett plot shows a break in the reactivity order indicating the applicability of a dual mechanism.

  11. Two photon dissociation of benzene, phenylacetylene, and benzaldehyde at 243 nm: translational energy releases in the H atom channel

    International Nuclear Information System (INIS)

    Hydrogen atom production channels from photodissociation of benzene, phenylacetylene, and benzaldehyde at 243 nm have been investigated by detecting H atoms using two photon absorption at 243.2 nm and induced fluorescence at 121.6 nm. Translational energies of the H atoms were measured by Doppler broadened H atom spectra. By absorption of two photons at 243 nm, the H atoms are statistically produced from benzene and phenylacetylene whereas the H atoms from the aldehyde group in benzaldehyde are produced from different pathways. The possible dissociation mechanisms are discussed from the measured translational energy releases

  12. Enhancement of reaction rates for catalytic benzaldehyde hydrogenation and sorbitol dehydration in water solvent by addition of carbon dioxide

    Indian Academy of Sciences (India)

    Masayuki Shirai; Osamu Sato; Norihito Hiyoshi; Aritomo Yamaguchi

    2014-03-01

    The effect of pressured carbon dioxide on heterogeneous hydrogenation of benzaldehyde and homogeneous dehydration of sorbitol in water solvent was studied. Initial hydrogenation rates of benzaldehyde over a charcoal-supported palladium catalyst in water at 313 K were enhanced by the addition of carbon dioxide. The initial rate increased with an increase in carbon dioxide pressure and became a maximum at 5 MPa. Dehydration of sorbitol proceeded in water phase at 500 K and initial dehydration rates were enhanced by addition of 30 MPa of carbon dioxide.

  13. Aldol condensation of acyclic ketones with benzaldehyde and subsequent cyclodehydration to form indenes over halide cluster catalysts

    OpenAIRE

    黒川, 秀樹; 千原, 貞次

    2006-01-01

    When a molecular halide cluster [(Ta6Cl12)C-12(H2O)(4)]-4H(2)O (1)/SiO2 was treated in a helium stream above 200 degrees C, it catalyzed the aldol condensation of acetone with benzaldehyde to yield E-4-phenyl-3-buten-2-one. The bromide cluster of Ta and chloride clusters of Nb, Mo, and W of the same octahedral metal framework also catalyzed the reaction. 3,3-Dimethyl-2-butanone combined with benzaldehyde similarly yielded the corresponding aldol condensation product over 1/SiO2 at 400 degrees...

  14. Effect of benzaldehyde on the electrodeposition and corrosion properties of Ni–W alloys

    Institute of Scientific and Technical Information of China (English)

    U. Pramod Kumar; C. Joseph Kennady

    2015-01-01

    The effect of different concentrations of benzaldehyde on the electrodeposition of Ni–W alloy coatings on a mild steel substrate from a citrate electrolyte was investigated in this study. The electrolytic alkaline bath (pH 8.0) contained stoichiometric amounts of nickel sulfate, sodium tungstate, and trisodium citrate as precursors. The corrosion resistance of the Ni–W-alloy-coated specimens in 0.2 mol/L H2SO4 was studied using various electrochemical techniques. Tafel polarization studies reveal that the alloy coatings obtained from the bath containing 50 ppm benzaldehyde exhibit a protection efficiency of 95.33%. The corrosion rate also decreases by 21.5 times compared with that of the blank. A higher charge-transfer resistance of 1159.40?·cm2 and a lower double-layer capacitance of 29.4 μF·cm?2 further confirm the better corrosion resistance of the alloy coating. X-ray diffraction studies reveal that the deposits on the mild steel surface are consisted of nanocrystals. A lower surface roughness value (Rmax) of the deposits is confirmed by atomic force microscopy.

  15. Effect of benzaldehyde on the electrodeposition and corrosion properties of Ni-W alloys

    Science.gov (United States)

    Pramod Kumar, U.; Kennady, C. Joseph

    2015-10-01

    The effect of different concentrations of benzaldehyde on the electrodeposition of Ni-W alloy coatings on a mild steel substrate from a citrate electrolyte was investigated in this study. The electrolytic alkaline bath (pH 8.0) contained stoichiometric amounts of nickel sulfate, sodium tungstate, and trisodium citrate as precursors. The corrosion resistance of the Ni-W-alloy-coated specimens in 0.2 mol/L H2SO4 was studied using various electrochemical techniques. Tafel polarization studies reveal that the alloy coatings obtained from the bath containing 50 ppm benzaldehyde exhibit a protection efficiency of 95.33%. The corrosion rate also decreases by 21.5 times compared with that of the blank. A higher charge-transfer resistance of 1159.40 Ω·cm2 and a lower double-layer capacitance of 29.4 μF·cm-2 further confirm the better corrosion resistance of the alloy coating. X-ray diffraction studies reveal that the deposits on the mild steel surface are consisted of nanocrystals. A lower surface roughness value ( R max) of the deposits is confirmed by atomic force microscopy.

  16. SYNTHESIS AND BIOLOGICAL ACTIVITY OF BUTANONE THIOSEMICARBAZONE AND THEIR METALLIC COMPLEXES

    OpenAIRE

    Sandeep Kumar; Nitin Kumar

    2013-01-01

    In present work, Ligand butanone thiosemicarbazone and their 11 complexes of the type ML2X2, ML2X’, where M = Cu(II), Cd(II), Co(II), Zn(II), Hg(II); L = butanone thiosemicarbazone; X = Cl, NO3 or CH3COO; X’ = SO4 have been synthesized and characterized with the help of infra-red and ultra-violet spectroscopy. The spectral data revealed that the thiosemicarbazone act as bidentate ligand, making use of thionic sulphur and the azomethine nitrogen atom for co-ordination to the central metal a...

  17. Eco-Friendly Synthesis of Some Thiosemicarbazones and Their Applications as Intermediates for 5-Arylazothiazole Disperse Dyes

    Directory of Open Access Journals (Sweden)

    Hatem E. Gaffer

    2015-12-01

    Full Text Available The solid-solid reactions of thiosemicarbazide with 4-formylantipyrine, 2-acetylpyrrole and camphor were performed to afford the thiosemicarbazones 1–3 which underwent hetero-cyclization with phenacyl bromide to furnish the corresponding thiazole derivatives 4–6. The yields of the reactions are quantitative in all cases and the products do not require further purification. A series of 5-arylazo-2-(substituted ylidene-hydrazinyl-thiazole dyes 7–9 was then prepared by diazo coupling of thiazole derivatives 4–6 with several diazonium chlorides. The synthesized dyes were applied as disperse dyes for dyeing polyester fabric. The dyed fabrics exhibit good washing, perspiration, sublimation and light fastness properties, with little variation in their moderate to good rubbing fastness.

  18. 4-(3-Fluorophenyl)-1-(propan-2-ylidene)thiosemicarbazone

    OpenAIRE

    Barbara Miroslaw; Daniel Szulczyk; Anna E. Koziol; Marta Struga

    2011-01-01

    The title compound, C10H12FN3S, crystallizes in the same space group (P21/c) as two polymorphic forms of 4-phenyl-1-(propan-2-ylidene)thiosemicarbazone [Jian et al. (2005). Acta Cryst. E61, o653–o654; Venkatraman et al. (2005). Acta Cryst. E61, o3914–o3916]. The arrangement of molecules relative to the twofold screw axes is similar to that in the crystal structure of the lower density polymorph. In the solid state, the molecular conformation is stabilized by an intramolecu...

  19. Antimicrobial activity of some isatin-3--thiosemicarbazone complexes

    OpenAIRE

    SANDRA S. KONSTANTINOVIC; Radovanovic, Blaga C.; Sovilj, Sofija P.; SVETLANA STANOJEVIC

    2008-01-01

    Isatin-3-thiosemicarbazone complexes with Co(II), Ni(II), Cu(II), Zn(II), Hg(II) and Pd(II) were synthesized and evaluated for their antimicrobial activity against 7 pathogenic bacteria and 4 fungi. The complexes have an enhanced activity compared to the ligand due to transition metal involved in coordination. The anti-amoebic activity in vitro was evaluated against the HM1:IMSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. The preliminar...

  20. Reinvestigation of growth of urea thiosemicarbazone monohydrate crystal

    Science.gov (United States)

    Srinivasan, Bikshandarkoil R.; Raghavaiah, Pallepogu; Nadkarni, V. S.

    2013-08-01

    The reaction of urea with thiosemicarbazide in 1:1 mole ratio in aqueous solution does not result in the formation of urea thiosemicarbazone monohydrate crystal, as reported by Hanumantharao, Kalainathan and Bhagavannarayana [Spectrochim. Acta A91 (2012) 345-351]. A reinvestigation of the reported reaction reveals that the crystal obtained is the starting material namely thiosemicarbazide, which has been unambiguously confirmed with the aid of infrared and 1H NMR spectra and single crystal X-ray structure determination. Analysis of 1H NMR spectrum reveals that thiosemicarbazide exhibits thione-thiol tautomerism in solution. In contrast, thiosemicarbazide exists as the thione tautomer in the solid state.

  1. A spectral study of 2-formylimidazole 4N-substituted thiosemicarbazones and their copper(II) complexes

    Science.gov (United States)

    West, Douglas X.; Lockwood, Mark A.; Albert, Julyan N.; Liberta, Anthony E.

    1993-11-01

    Copper(II) complexes of 2-formylimidazole 4N-methyl-, 4N-dimethyl- 4N-ethyl- and 3-hexa-methyleneiminylthiosemicarbazone, along with two nickel(II) complexes of the latter thiosemicarbazone, have been synthesized. Infrared, electronic, NMR and ESR spectra have been used to characterize the complexes and the uncomplexed thiosemicarbazones. None of the complexes or thiosemicarbazones possess growth inhibitory activity against Aspergillus niger and Paecilomyces variotii.

  2. Structural studies of six and four coordinate zinc(II), nickel(II) and dioxovanadium(V) complexes with thiosemicarbazones

    Science.gov (United States)

    Sreekanth, A.; Sivakumar, S.; Prathapachandra Kurup, M. R.

    2003-07-01

    Three Zn(II) complexes of di-2-pyridyl ketone thiosemicarbazone, an octahedral Ni(II) complex of 2-acetylpyridine hexamethyleneiminyl-3-thiosemicarbazone, and a V(V) complex of 2-acetylpyridine morpholyl-3-thiosemicarbazone were prepared and characterized. Crystal structure of Ni(II) and V(V) complexes are reported. The ligand in the nickel complex is found to coordinate in the thione form with a pseudo octahedral geometry and the vanadium(V) complex has trigonal bipyramidal geometry.

  3. Preparation and Biodistribution Studies of a Radiogallium-Acetylacetonate Bis (Thiosemicarbazone) Complex in Tumor-Bearing Rodents

    OpenAIRE

    Jalilian, Amir Reza; Yousefnia, Hassan; SHAFAII, KAMALEDDIN; Novinrouz, Aytak; Rajamand, Amir Abbas

    2012-01-01

    Various radiometal complexes have been developed for tumor imaging, especially Ga-68 tracer. In the present study, the development of a radiogallium bis-thiosemicarbazone complex has been reported. [67Ga] acetylacetonate bis(thiosemicarbazone) complex ([67Ga] AATS) was prepared starting [67Ga]Gallium acetate and freshly prepared acetylacetonate bis (thiosemicarbazone) (AATS) in 30 min at 90°C. The partition co-efficient and the stability of the tracer were determined in final solution (25°C) ...

  4. Quantification of brown dog tick repellents, 2-hexanone and benzaldehyde, and release from tick-resistant beagles, Canis lupus familiaris

    Science.gov (United States)

    We have recently shown that repellency of the tick Rhipicephalus sanguineus sensu lato by the tick resistant dog breed Beagle is mediated by volatile organic compounds 2-hexanone and benzaldehyde present in Beagle dog odour. Ectoparasite location on animal hosts is affected by variation in odour com...

  5. Quantification of brown dog tick repellent, 2-hexanone and benzaldehyde, release from tick-resistant Beagle dogs, Canis lupus familiaris

    Science.gov (United States)

    We have recently shown that repellency of the tick Rhipicephalus sanguineus sensu lato by the tick resistant dog breed Beagle is mediated by volatile organic compounds 2-hexanone and benzaldehyde present in Beagle dog odour. Ectoparasite location on animal hosts is affected by variation in odour com...

  6. Enzymatic reduction of 4-(dimethylamino)benzaldehyde with carrot bits (Daucus carota): a simple experiment for understanding biocatalysis

    International Nuclear Information System (INIS)

    The present paper describes a simple, low-costly and environmentally friendly procedure for reduction of 4-(dimethylamino)benzaldehyde using carrot bits in water. This interdisciplinary experiment can be used to introduce the concepts of biocatalysis and green chemistry to undergraduate students. (author)

  7. SPECTROSCOPIC AND BIOLOGICAL STUDIES ON NEWLY SYNTHESIZED COPPER (II AND NICKEL (II COMPLEXES WITH p -DIMETHYLAMINOBANZALDEHYDE SEMICARBAZONE AND p -DIMETHYLAMINOBANZALDEHYDE THIOSEMICARBAZONE

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2012-08-01

    Full Text Available Cu (II and Ni (II complexes of general composition [ML2]X2(M = Cu(II, Ni(II; X = Cl-, NO3- weresynthesized by the condensation of metal salts with semicarbazone / thiosemicarbazone derived from p-dimethylaminobanzaldehyde. The metal complexes were characterized by elemental analysis, molar conductance, magneticsusceptibility measurements, IR and atomic absorption spectral studies. On the basis of electronic and infrared spectralstudies, the metal complexes were found to have tetrahedral geometry. The Schiff bases and their metal complexeswere tested for their antibacterial and antioxidant activities

  8. Spectroscopic and Biological Studies on Newly Synthesized Cobalt (II and Nickel (II Complexes with 2-Acetyl Coumarone Semicarbazone and 2-Acetyl Coumarone Thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Sanjay Goel

    2013-01-01

    Full Text Available Co(II and Ni(II complexes of general composition ML2X2 (M = Co(II, Ni(II; X = Cl−, NO3 − were synthesized by the condensation of metal salts with semicarbazone/thiosemicarbazone derived from 2-acetyl coumarone. The ligands and metal complexes were characterized by NMR, elemental analysis, molar conductance, magnetic susceptibility measurements, IR, and atomic absorption spectral studies. On the basis of electronic, molar conductance and infrared spectral studies, the complexes were found to have square planar geometry. The Schiff bases and their metal complexes were tested for their antibacterial and antioxidant activities.

  9. (E)-4-(Benz­yloxy)benzaldehyde thio­semicarbazone

    OpenAIRE

    Tarafder, M. T. H.; Islam, M. A. A. A. A.; Crouse, K. A.; Chantrapromma, Suchada; Fun, Hoong-Kun

    2008-01-01

    In the title compound, C15H15N3OS, the thio­semicarbazone group adopts an E configuration with respect to the C=N bond. The benzaldehyde thio­semicarbazone fragment is almost planar [maximum deviation = 0.012 (1) Å], while the dihedral angle between the benz­yloxy and phenyl rings is 72.48 (5)°. In the crystal structure, mol­ecules are inter­connected by N—H⋯N and N—H⋯S hydrogen bonds, forming a two-dimensional network parallel to the bc plane and are further stacked along the a axis by π–π i...

  10. Transition metal quinone-thiosemicarbazone complexes 3: Spectroscopic characterizations of spin-mixed iron (III) of naphthoquinone-thiosemicarbazones

    Science.gov (United States)

    Chikate, Rajeev C.; Padhye, Subhash B.

    2007-04-01

    An interesting series of iron (III) complexes with naphthoquinone-thiosemicarbazones are synthesized and physico-chemically characterized by elemental analysis, UV-vis, IR, EPR and magnetic susceptibility measurements. They possess a cationic octahedral [FeL 2] + species and a tetrahedral [FeCl 4] - anion and exhibit unusual spin-mixed states involving high-spin and low-spin ferric centers as revealed from magnetic behavior with significant amount of exchange interactions mediated by intermolecular associations. The magnetic susceptibility data is fitted with S=5/2 and S=1/2 Heisengberg's exchange coupled model; Hˆ=-2JSS and the magnetic exchange interactions are found to be of the order of -13.6 cm -1 indicating the moderate coupling between two paramagnetic centers present in different chemical and structural environment. The presence of spin-paired iron (III) cation having dxz2dxz2dxz1 ground state is revealed from the EPR spectra with three prominent peaks while the high-spin tetrahedral iron (III) anion exhibits characteristics g = 4 signal whose intensity increases with lowering the temperature suggesting its influence on the magnetic properties of the complex molecule. FTIR measurements indicate tridentate ONS donor systems involving quinone/hydroxyl oxygen, imine/hydrazinic nitrogen and thione/thiol sulfur atoms as binding sites for naphthoquinone-thiosemicarbazones.

  11. Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes.

    Science.gov (United States)

    Babahan, İlknur; Özmen, Ali; Orhan, Nil; Kazar, Didem; Değirmenci, Esin Hafize

    2014-04-01

    Two novel vicinal dioxime ligands containing thiosemicarbazone units, (2E)-2-[4-(diethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazine carbothioamide (L(1)H2) and (2E)-2-[4-(dimethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazinecarbothioamide (L(2)H2), were synthesized. Using the HL-60 human leukemia cell line, the in vitro anti-neoplastic activity of these thiosemicarbazone-oxime derivatives was evaluated. Mononuclear nickel(II), copper(II), and cobalt(II) complexes with a metal:ligand ratio of 1:2 for both the L(1)H2 and L(2)H2 ligands were also synthesized. To characterize these compounds, Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), magnetic susceptibility measurements, (1)H and (13)C nuclear magnetic resonance (NMR), ultraviolet-visible (UV-Vis) absorption spectroscopy, heteronuclear multiple-bond correlation (HMQC), and elemental analysis were performed. For L(1)H2, L(2)H2, and each of their derivatives, antiproliferative effects against HL-60 cells were exhibited and the associated IpC50 values ranged from 5μM to 20μM. Furthermore, L(1)H2 and its derivatives inhibited the proliferation of HL-60 cells more effectively than L(2)H2, and 5μM [Cu(L(1)H)2] exhibited the strongest antiproliferative activity. PMID:24651042

  12. A {sup 119}Sn Moessbauer Study of Tin(IV) Complexes of 2- and 4-Benzoylpyridine Thiosemicarbazone and 4-Benzoylpyridine Semicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Perez-Rebolledo, Anayive [Universidade Federal de Minas Gerais, Departamento de Quimica (Brazil); Ardisson, Jose D., E-mail: jdr@cdtn.br [Centro de Desenvolvimento da Tecnologia Nuclear, Laboratorio de Fisica Aplicada (LFA/CDTN) (Brazil); Lima, Geraldo M. de [Universidade Federal de Minas Gerais, Departamento de Quimica (Brazil); Macedo, Waldemar A. A. [Centro de Desenvolvimento da Tecnologia Nuclear, Laboratorio de Fisica Aplicada (LFA/CDTN) (Brazil); Beraldo, Heloisa, E-mail: hberaldo@ufmg.br [Universidade Federal de Minas Gerais, Departamento de Quimica (Brazil)

    2005-06-15

    A {sup 119}Sn Moessbauer study was carried out of tin(IV) complexes with 2-benzoylpyridine thiosemicarbazone (H2Bz4DH) and its N(4)-methyl (H2Bz4M) and N(4)-phenyl (H2Bz4Ph) derivatives: [Sn(2Bz4DH)Cl{sub 3}] (1), [Sn(2Bz4DH)PhCl{sub 2}] (2), [Sn(2Bz4M)Cl{sub 3}] (3), [H{sub 2}2Bz4M]{sub 2}[Ph{sub 2}SnCl{sub 4}] (4), [Sn(2Bz4Ph)PhCl{sub 2}] (5), [Sn(2Bz4Ph)Ph{sub 2}Cl] (6), in which H2Bz4R stands for the neutral ligand and 2Bz4R stands for the anionic thiosemicarbazone. In addition, {sup 119}Sn Moessbauer studies of the tin(IV) complexes [Sn(H4Bz4DH){sub 2}Cl{sub 4}H{sub 2}O] (7), [Sn(H4BzPS){sub 2}Cl{sub 4}H{sub 2}O] (8) with 4-benzoylpyridine thiosemicarbazone (H4Bz4DH) and the correspondent semicarbazone (H4BzPS) were performed. The isomer shifts decrease upon coordination due to the variation in the percentage of s character as tin changes from approximately sp{sup 3} hybridization in the tin salts to sp{sup 3}d{sup 2} in the octahedral or sp{sup 3}d{sup 3} in the heptahedral complexes. The Moessbauer parameters of compound (4) showed the existence of two tin(IV) sites, which have been attributed to the presence of the cis and trans isomers.

  13. A 119Sn Mössbauer Study of Tin(IV) Complexes of 2- and 4-Benzoylpyridine Thiosemicarbazone and 4-Benzoylpyridine Semicarbazone

    Science.gov (United States)

    Pérez-Rebolledo, Anayive; Ardisson, José D.; de Lima, Geraldo M.; Macedo, Waldemar A. A.; Beraldo, Heloisa

    2005-06-01

    A 119Sn Mössbauer study was carried out of tin(IV) complexes with 2-benzoylpyridine thiosemicarbazone (H2Bz4DH) and its N(4)-methyl (H2Bz4M) and N(4)-phenyl (H2Bz4Ph) derivatives: [Sn(2Bz4DH)Cl3] (1), [Sn(2Bz4DH)PhCl2] (2), [Sn(2Bz4M)Cl3] (3), [H22Bz4M]2[Ph2SnCl4] (4), [Sn(2Bz4Ph)PhCl2] (5), [Sn(2Bz4Ph)Ph2Cl] (6), in which H2Bz4R stands for the neutral ligand and 2Bz4R stands for the anionic thiosemicarbazone. In addition, 119Sn Mössbauer studies of the tin(IV) complexes [Sn(H4Bz4DH)2Cl4H2O] (7), [Sn(H4BzPS)2Cl4H2O] (8) with 4-benzoylpyridine thiosemicarbazone (H4Bz4DH) and the correspondent semicarbazone (H4BzPS) were performed. The isomer shifts decrease upon coordination due to the variation in the percentage of s character as tin changes from approximately sp3 hybridization in the tin salts to sp3d2 in the octahedral or sp3d3 in the heptahedral complexes. The Mössbauer parameters of compound (4) showed the existence of two tin(IV) sites, which have been attributed to the presence of the cis and trans isomers.

  14. Antimicrobial activity of some isatin-3--thiosemicarbazone complexes

    Directory of Open Access Journals (Sweden)

    SANDRA S. KONSTANTINOVIC

    2008-01-01

    Full Text Available Isatin-3-thiosemicarbazone complexes with Co(II, Ni(II, Cu(II, Zn(II, Hg(II and Pd(II were synthesized and evaluated for their antimicrobial activity against 7 pathogenic bacteria and 4 fungi. The complexes have an enhanced activity compared to the ligand due to transition metal involved in coordination. The anti-amoebic activity in vitro was evaluated against the HM1:IMSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. The preliminary test results showed that the complexes had better anti-amoebic activity than their respective ligands. Moreover, the complexes showed better inhibition of the test organism.

  15. Quantification of brown dog tick repellents, 2-hexanone and benzaldehyde, and release from tick-resistant beagles, Canis lupus familiaris.

    Science.gov (United States)

    de Oliveira Filho, Jaires Gomes; Sarria, André Lucio Franceschini; Ferreira, Lorena Lopes; Caulfield, John C; Powers, Stephen J; Pickett, John A; de León, Adalberto A Pérez; Birkett, Michael A; Borges, Lígia Miranda Ferreira

    2016-06-01

    We have recently shown that repellency of the tick Rhipicephalus sanguineus sensu lato by the tick resistant dog breed, the beagle, is mediated by volatile organic compounds (VOCs) 2-hexanone and benzaldehyde present in beagle odour. Ectoparasite location of animal hosts is affected by variation in these odour components and their ratios. The aim of this study was to quantify the release rate, and the ratio, of 2-hexanone and benzaldehyde from beagles. The odour of three beagles was collected, for four days, over one week (day 0, day 1, day 4 and day 7). The compounds were identified using coupled high-resolution gas chromatography-mass spectrometry (GC-MS), and authentic standards of compounds were used to generate external calibration curves for quantification. Both compounds were found in all dogs on all days. The amount of benzaldehyde was always higher than that of 2-hexanone and so their ratio varied from unity, on average (over time) being 3.128±0.365, 1.902±0.390, 1.670±0.671ngmL(-1) for beagle 1, 2 and 3, respectively. There was no significant (p<0.05, F-test) effect of time. The overall mean was 2.233±0.387ngmL(-1). These results further previous findings by documenting the presence of 2-hexanone and benzaldehyde in beagle odour samples covering a 7-day period. This knowledge enables development of repellents to protect dogs from R. sanguineus s. l. infestation. PMID:27085013

  16. Benzaldehyde is a precursor of phenylpropylamino alkaloids as revealed by targeted metabolic profiling and comparative biochemical analyses in Ephedra spp.

    Science.gov (United States)

    Krizevski, Raz; Bar, Einat; Shalit, O R; Levy, Asaf; Hagel, Jillian M; Kilpatrick, Korey; Marsolais, Frédéric; Facchini, Peter J; Ben-Shabat, Shimon; Sitrit, Yaron; Lewinsohn, Efraim

    2012-09-01

    Ephedrine and pseudoephedrine are phenylpropylamino alkaloids widely used in modern medicine. Some Ephedra species such as E. sinica Stapf (Ephedraceae), a widely used Chinese medicinal plant (Chinese name: Ma Huang), accumulate ephedrine alkaloids as active constituents. Other Ephedra species, such as E. foeminea Forssk. (syn. E. campylopoda C.A. Mey) lack ephedrine alkaloids and their postulated metabolic precursors 1-phenylpropane-1,2-dione and (S)-cathinone. Solid-phase microextraction analysis of freshly picked young E. sinica and E. foeminea stems revealed the presence of increased benzaldehyde levels in E. foeminea, whereas 1-phenylpropane-1,2-dione was detected only in E. sinica. Soluble protein preparations from E. sinica and E. foeminea stems catalyzed the conversion of benzaldehyde and pyruvate to (R)-phenylacetylcarbinol, (S)-phenylacetylcarbinol, (R)-2-hydroxypropiophenone (S)-2-hydroxypropiophenone and 1-phenylpropane-1,2-dione. The activity, termed benzaldehyde carboxyligase (BCL) required the presence of magnesium and thiamine pyrophosphate and was 40 times higher in E. sinica as compared to E. foeminea. The distribution patterns of BCL activity in E. sinica tissues correlates well with the distribution pattern of the ephedrine alkaloids. (S)-Cathinone reductase enzymatic activities generating (1R,2S)-norephedrine and (1S,1R)-norephedrine were significantly higher in E. sinica relative to the levels displayed by E. foeminea. Surprisingly, (1R,2S)-norephedrine N-methyltransferase activity which is a downstream enzyme in ephedrine biosynthesis was significantly higher in E. foeminea than in E. sinica. Our studies further support that benzaldehyde is the metabolic precursor to phenylpropylamino alkaloids in E. sinica. PMID:22727117

  17. Highly selective luminescence sensing of nitrite and benzaldehyde based on 3d-4f heterometallic metal-organic frameworks.

    Science.gov (United States)

    Du, Pei-Yao; Gu, Wen; Liu, Xin

    2016-06-01

    Framework-isomeric three-dimensional (3D) Zn-Ln heterometallic metal-organic frameworks, {[Ln2Zn(abtc)2(H2O)4]·2H2O}∞ {Ln = Sm(1), Tb(2)}, were synthesized using a convenient solvothermal reaction. They can serve as excellent sensors for the specific identification of benzaldehyde and NO2(-) through a fluorescence quenching process. PMID:27117937

  18. The Production of Benzaldehyde by Rhizopus oligosporus USM R1 in a Solid State Fermentation (SSF System of Soy Bean Meal: Rice Husks

    Directory of Open Access Journals (Sweden)

    Norliza, A. W.

    2005-01-01

    Full Text Available The cultivation of Rhizopus oligosporus USM R1 for the production of benzaldehyde, a bitter cherry almond flavour was performed using soya bean meal and rice husks as the substrates. The identification of R. oligosporus USM R1 was performed based on the observation made under light microscope and scanning electron microscope (SEM. The optimum conditions for the SSF in a 250-ml Erlenmeyer flask system were 40% (v/w water content, substrate particle size of 0.7 mm; inoculum size of 1 x 10^5 spores/g substrate; incubation temperature of 30C; substrate amount of 7 g and the ratio of soy bean meal: rice husks of 50:50%. A maximum benzaldehyde production was obtained when the substrate was agitated after 48 hour for a 96 hour fermentation time. The highest benzaldehyde production obtained after 96 hour cultivation was 5.47 mg g-1 substrate. The supplementation of carbon and nitrogen sources in the substrate mixture revealed an enhancement in the growth and benzyldehyde production. A maximum production of benzaldehyde was obtained with the supplementation of L-phenylalanine, a precursor for benzaldehyde biosynthesis which gave 38.69 mg benzaldehyde/g substrate. This is approximately 6-folds higher compared to the substrates without the supplementation of L-phenylalanine.

  19. Large-scale synthesis of ultrathin tungsten oxide nanowire networks: an efficient catalyst for aerobic oxidation of toluene to benzaldehyde under visible light

    Science.gov (United States)

    Bai, Hua; Yi, Wencai; Liu, Jingyao; Lv, Qing; Zhang, Qing; Ma, Qiang; Yang, Haifeng; Xi, Guangcheng

    2016-07-01

    As a very important chemical raw material, the selective formation of benzaldehyde from toluene at preparative or industrial levels requires the use of highly corrosive chlorine and high reaction temperatures, which severely corrodes equipment, pollutes the environment, and consumes a lot of energy. Herein, we report a robust and highly active catalyst for the benzaldehyde evolution reaction that is constructed by the surfactant-free growth of oxygen vacancy-rich W18O49 ultrathin nanowire networks. Under atmospheric pressure and visible-light irradiation, the new catalyst can selectively (92% selectivity) catalyze the aerobic oxidation of toluene to benzaldehyde with yields of above 95%.As a very important chemical raw material, the selective formation of benzaldehyde from toluene at preparative or industrial levels requires the use of highly corrosive chlorine and high reaction temperatures, which severely corrodes equipment, pollutes the environment, and consumes a lot of energy. Herein, we report a robust and highly active catalyst for the benzaldehyde evolution reaction that is constructed by the surfactant-free growth of oxygen vacancy-rich W18O49 ultrathin nanowire networks. Under atmospheric pressure and visible-light irradiation, the new catalyst can selectively (92% selectivity) catalyze the aerobic oxidation of toluene to benzaldehyde with yields of above 95%. Electronic supplementary information (ESI) available: Experimental procedure, XRD patterns, TEM and HRTEM images, energy-dispersive X-ray spectra, UV-vis spectra, X-ray photoelectron spectroscopy (XPS), and EDS. See DOI: 10.1039/c6nr02949c

  20. A nanoporous 3D zinc(II) metal–organic framework for selective absorption of benzaldehyde and formaldehyde

    International Nuclear Information System (INIS)

    A new 3D nanoporous metal–organic framework (MOF), [[Zn4O(C24H15N6O6)2(H2O)2]·6H2O·DMF]n (1) based on 4,4′,4″-s-triazine-1,3,5-triyltri-p-aminobenzoate (TATAB) ligand was solvothermally synthesized and characterized by single–crystal X-ray diffraction, Powder X-ray diffraction (PXRD), infrared spectroscopy (IR) and Brunauer–Emmett–Teller (BET) analyses. X-ray single crystal diffraction analysis reveals that 1 exhibits a 3D network with new kvh1 topology. Semi-empirical (AM1) calculations were carried out to obtain stable conformers for TATAB ligand. In addition, the absorption of two typical aldehydes (benzaldehyde and formaldehyde) in the presence of 1 was investigated and the effect of the aldehyde concentration, exposure time and temperature was studied. It was found that compound 1 has a potential for the absorption of aldehydes under mild conditions. - Graphical abstract: Absorption of two typical aldehydes (formaldehyde and benzaldehyde) by solvothermally synthesized of a 3D nano-porous MOF based on TATAB tricarboxylate ligand and Zn (NO3)2·6H2O. - Highlights: • We present a 3D Zn(II)-MOF with TATAB linker by solvothermal method. • The framework possesses a new kvh1 topology. • The framework displays formaldehyde and benzaldehyde absorption property. • Conformational analysis was performed to determine the stable linker geometry

  1. Spectral, thermal, electrochemical and analytical studies on Cd(II) and Hg(II) thiosemicarbazone complexes

    Science.gov (United States)

    El-Asmy, A. A.; El-Gammal, O. A.; Saleh, H. S.

    2008-11-01

    The coordination characteristic of the investigated thiosemicarbazones towards hazard pollutants, Cd(II) and Hg(II), becomes the first goal. Their complexes have been studied by microanalysis, thermal, electrochemical and spectral (electronic, IR and MS) studies. The substitutent (salicylaldehyde, acetophenone, benzophenone, o-hydroxy- p-methoxybenzophenone or diacetylmonoxime) plays an important role in the complex formation. The coordination sites were the S for thiosemicarbazide (HTS); NN for benzophenone thiosemicarbazone (HBTS); NS for acetophenone thiosemicarbazone (HATS) and salicylaldehyde thiosemicarbazone (H 2STS); NNS or NSO for diacetylmonoxime thiosemicarbazone (H 2DMTS). The stability constants of Hg(II) complexes were higher than Cd(II). The kinetic and thermodynamic parameters for the different thermal decomposition steps in the complexes have been evaluated. The activation energy values of the first step ordered the complexes as: [Cd(H 2STS)Cl 2]H 2O > [Cd(H 2DAMTS)Cl 2] > [Cd(HBTS) 2Cl 2]2H 2O > [Cd(HATS) 2Cl 2]. The CV of [Cd(H 2STS)Cl 2]H 2O and [Hg(HBTS)Cl 2] were recorded. The use of H 2DMTS as a new reagent for the separation and determination of Cd(II) ions from water and some synthetic samples using flotation technique is aimed to be discussed.

  2. Amorphous metal-aluminophosphate catalysts for aldol condensation of n-heptanal and benzaldehyde to jasminaldehyde

    Institute of Scientific and Technical Information of China (English)

    A. Hamza; N. Nagaraju

    2015-01-01

    Amorphous aluminophosphate (AlP) and metal‐aluminophosphates (MAlPs, where M=2.5 mol%Cu, Zn, Cr, Fe, Ce, or Zr) were prepared by coprecipitation method. Their surface properties and catalytic activity for the synthesis of jasminaldehyde through the aldol condensation of n‐heptanal and benzaldehyde were investigated. The nitrogen adsorption‐desorption isotherms showed that the microporosity exhibited by the aluminophosphate was changed to a mesoporous and macroporous structure which depended on the metal incorporated, with a concomitant change in the surface area. Temperature‐programmed desorption of NH3 and CO2 revealed that the materials possessed both acidic and basic sites. The acidic strength of the material was either increased or decreased depending on the nature of the metal. The basicity was increased compared to AlP. All the materials were X‐ray amorphous and powder X‐ray diffraction studies indicated the absence of metal oxide phases. The Fourier transform infrared analysis confirmed the presence of phosphate groups and also the absence of any M‐O moieties in the materials. The selected organic reaction occurred only in the presence of the AlP and MAlPs. The selectivity for the jasminaldehyde product was up to 75%with a yield of 65%. The best conversion of n‐heptanal with a high selectivity to jasminaldehyde was obtained with FeAlP as the catalyst, and this material was characterized to have less weak acid sites and more basic sites.

  3. Polyoxometalate coordinated transition metal complexes as catalysts: Oxidation of styrene to benzaldehyde/benzoic acid

    Indian Academy of Sciences (India)

    Srinivasa Rao Amanchi; Anjali Patel; Samar K Das

    2014-11-01

    Oxidation of styrene is carried out by using heptamolybdate coordinated transition metal (Co2+, Zn2+) complexes, [2-ampH]4[{Co(H2O)5}Mo7O24]·9H2O (1), [3-ampH]4[{Co(H2O)5}Mo7O24]·9H2O (2), [2-ampH]4[{Zn(H2O)5}Mo7O24]·4H2O (3) and [3-ampH]4[{Zn(3-ampy)(H2O)4}Mo7O24]·4H2O (4) as catalysts and H2O2 as an oxidant at 80°C. The leaching study has been carried out to check the quality of catalyst and it has been reused for three times with good percentage of conversion. For the first two catalysts (compounds 1 and 2), the major product obtained is benzaldehyde, and benzoic acid is the major product for next two catalysts (compounds 3 and 4). Stability of the catalysts has been analyzed by IR, UV-spectroscopy and powder X-ray crystallography.

  4. Crystal Structures of Two Calix[4]arene Isomers with Benzaldehyde Moiety and Their Photophysical Properties with Terbium(Ⅲ) Ions

    Institute of Scientific and Technical Information of China (English)

    王浩; 张衡益; 刘育

    2005-01-01

    Two calix[4]arene isomers with benzaldehyde moieties, i.e., 5,11,17,23-tetra-tert-butyl-25,27-bis[2-(o-formyl-phenoxy)ethoxy]-26,28-dihydroxycalix[4]arene (3) and 5,11,17,23-tetra-tert-butyl-25,27-bis[2-(p-formylphenoxy)-ethoxy]-26,28-dihydroxycalix[4]arene (4), were synthesized according to a newly designed route in high yields, and their crystal structures have been determined by X-ray crystallographic study. The photophysical behavior on complexation of calix[4]arene derivatives 3 and 4 with terbium(Ⅲ) nitrate was investigated in anhydrous acetonitrile at 25℃ by UV-Vis and fluorescence spectroscopies. The crystallographic structure of 3 indicated that the eight oxygen atoms formed a preorganized ionophoric cavity due to intramolecular π-π stacking, which could encapsulate lanthanide ions tightly. In sharp contrast, the compound 4 formed a linear array by intermolecular π-π stacking, hence the oxygen atoms of pendant arms could not coordinate with metal ions, giving a poor binding ability to Tb3+. The absorption spectra of 3 with Tb3+ showed clearly a new broad intense absorption at 385nm. Interestingly, the narrow emission line spectrum has also been observed for compound 3 with Tb3+, and the results obtained were discussed from the viewpoint of energy transfer mechanism between host structures and the properties of lanthanide ions.

  5. Spectral studies of copper(II) complexes of 6-(3-thienyl) pyridine-2-thiosemicarbazone

    International Nuclear Information System (INIS)

    Two novel copper(II) complexes [Cu(HL)Cl]Cl.H2O (1) and [Cu(L)NO3]Ðœ‡H2O (2) of the three NNS donor thiosemicarbazone ligand 6-(3-thienyl) pyridine-2-thiosemicarbazone have been synthesized. The ligand and its copper(II) complexes were characterized by elemental analysis (C, H, N, and S), FT-IR, UV-visible, magnetic susceptibility and molar conductance. The thiosemicarbazone is present either as the thione form in complex 1 or as thiol form in complex 2 and is coordinated to copper(II) atom via the pyridine nitrogen atom, the azomethine nitrogen atom and the sulfur atom. The physicochemical and spectral data suggest square planar geometry for copper(II) atoms

  6. Spectral studies of copper(II) complexes of 6-(3-thienyl) pyridine-2-thiosemicarbazone

    Science.gov (United States)

    Mahjoub, Omima Abdalla; Farina, Yang

    2014-09-01

    Two novel copper(II) complexes [Cu(HL)Cl]Cl˙H2O (1) and [Cu(L)NO3]˙H2O (2) of the three NNS donor thiosemicarbazone ligand 6-(3-thienyl) pyridine-2-thiosemicarbazone have been synthesized. The ligand and its copper(II) complexes were characterized by elemental analysis (C, H, N, and S), FT-IR, UV-visible, magnetic susceptibility and molar conductance. The thiosemicarbazone is present either as the thione form in complex 1 or as thiol form in complex 2 and is coordinated to copper(II) atom via the pyridine nitrogen atom, the azomethine nitrogen atom and the sulfur atom. The physicochemical and spectral data suggest square planar geometry for copper(II) atoms.

  7. SYNTHESIS AND BIOLOGICAL ACTIVITY OF BUTANONE THIOSEMICARBAZONE AND THEIR METALLIC COMPLEXES

    Directory of Open Access Journals (Sweden)

    Sandeep Kumar

    2013-01-01

    Full Text Available In present work, Ligand butanone thiosemicarbazone and their 11 complexes of the type ML2X2, ML2X’, where M = Cu(II, Cd(II, Co(II, Zn(II, Hg(II; L = butanone thiosemicarbazone; X = Cl, NO3 or CH3COO; X’ = SO4 have been synthesized and characterized with the help of infra-red and ultra-violet spectroscopy. The spectral data revealed that the thiosemicarbazone act as bidentate ligand, making use of thionic sulphur and the azomethine nitrogen atom for co-ordination to the central metal atom. All the compounds have been screened for their antibacterial activity against Gram positive bacteria Staphylococcus aureus, Staphylococcus epidermidis and Gram negative bacteria Escherichia coli and Pseudomonas aeruginosa. Some of complexes exhibited appreciable activity.

  8. Spectral studies of copper(II) complexes of 6-(3-thienyl) pyridine-2-thiosemicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Mahjoub, Omima Abdalla; Farina, Yang [School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor (Malaysia)

    2014-09-03

    Two novel copper(II) complexes [Cu(HL)Cl]Cl.H{sub 2}O (1) and [Cu(L)NO{sub 3}]Ðœ‡H{sub 2}O (2) of the three NNS donor thiosemicarbazone ligand 6-(3-thienyl) pyridine-2-thiosemicarbazone have been synthesized. The ligand and its copper(II) complexes were characterized by elemental analysis (C, H, N, and S), FT-IR, UV-visible, magnetic susceptibility and molar conductance. The thiosemicarbazone is present either as the thione form in complex 1 or as thiol form in complex 2 and is coordinated to copper(II) atom via the pyridine nitrogen atom, the azomethine nitrogen atom and the sulfur atom. The physicochemical and spectral data suggest square planar geometry for copper(II) atoms.

  9. EPR, mass, IR, electronic, and magnetic studies on copper(II) complexes of semicarbazones and thiosemicarbazones

    Science.gov (United States)

    Chandra, Sulekh; Gupta, Lokesh Kumar

    2005-01-01

    Copper(II) complexes having the general composition Cu(L) 2X 2 [where L = isopropyl methyl ketone semicarbazone (LLA), isopropyl methyl ketone thiosemicarbazone (LLB), 4-aminoacetophenone semicarbazone (LLC), and 4-aminoacetophenone thiosemicarbazone (LLD) and X = Cl -, 1/2SO 42-] have been synthesized. All the Cu(II) complexes reported here have been characterized by elemental analyses, molar conductance, magnetic moment susceptibility, EI mass, 1H NMR, IR, EPR, and electronic spectral studies. All the complexes were found to have magnetic moments corresponding to one unpaired electrons. The possible geometries of the complexes were assigned on the basis of EPR, electronic, and infrared spectral studies.

  10. Synthesis, EPR, Electronic and Magnetic Studies on Cobalt (II) Complexes of Semicarbazone and Thiosemicarbazone

    International Nuclear Information System (INIS)

    Cobalt (II) complexes having the general composition Co(L2) X2 [where Lisopropyl methyl ketone semicarbazone (LLA), isopropyl methyl ketone thiosemicarbazone (LLB), 4-aminoacetophenone semicarbazone (LLC) and4-aminoacetophenone thiosemicarbazone (LLD) and X=Cl] have been synthesized. All the Co(II) complexes reported here have been characterized by elemental analyses, magnetic moments, IR, electronic and EPR spectral studies. All the complexes were found to have magnetic moments corresponding to three unpaired electrons. The possible geometries of the complexes were assigned on the basis of electronic infrared and EPR spectral studies. (author) = = = = = = = = = = = = = = =

  11. 2-Hydroxy-4-n-butoxy-5-bromoacetophenone thiosemicarbazone as an extractive spectrophotometric reagent for nickel

    OpenAIRE

    K N Patel; K. S. Parikh; Rashmin Manubhai Patel

    2011-01-01

    2-hydroxy-4-n-butoxy-5-bromoacetophenone thiosemicarbazone (HBBrAT) is spectrophotometric reagent for nickel (II) in chloroform. The metal ion reacts with 2-hydroxy-4-n-butoxy-5-bromoacetophenone thiosemicarbazone (HBBrAT) forming a dark brown coloured complex in the pH range 7.0-11.0. The complex shows maximum absorption at 440 nm. Beer’s law is obeyed in the range 2.74-6.86 µg/mL. The molar absorptivity and Sandell’s sensitivity are found to be 5229 Lmol-1cm-1 and 0.0105 &...

  12. Synthesis and thermal study of rhenium(V) coordination compounds with pyroracemic acid and phenylglyoxylic acid thiosemicarbazones

    International Nuclear Information System (INIS)

    One synthesized rhenium (V) coordination compounds with pyroracemic acid and phenylglyoxylic acid thiosemicarbazones at metal:ligand various ratios within 1-7 mole/l concentration hydrohalic acid media. On the basis of the package of the physical and chemical procedures one studied the synthesized composition and structure. By means of the thermogravimetry one studied the thermal stability of rhenium (V) coordination compounds with pyroracemic acid and phenylglyoxylic acid thiosemicarbazones, as well as that of rhenium (V) solvatocomplexes with pyroacemic acid thiosemicarbazone. One determined thermal decomposition mechanism of the coordination compounds: separation of the second sphere water, decarboxylizing and dehalogenation

  13. Quinoline-2-carboxaldehyde thiosemicarbazones and their Cu(II) and Ni(II) complexes as topoisomerase IIa inhibitors.

    Science.gov (United States)

    Bisceglie, Franco; Musiari, Anastasia; Pinelli, Silvana; Alinovi, Rossella; Menozzi, Ilaria; Polverini, Eugenia; Tarasconi, Pieralberto; Tavone, Matteo; Pelosi, Giorgio

    2015-11-01

    A series of quinoline-2-carboxaldehyde thiosemicarbazones and their copper(II) and nickel(II) complexes were synthesized and characterized. In all complexes the ligands are in the E configuration with respect to the imino bond and behave as terdentate. The copper(II) complexes form square planar derivatives with one molecule of terdentate ligand and chloride ion. A further non-coordinated chloride ion compensates the overall charge. Nickel(II) ions form instead octahedral complexes with two ligands for each metal ion, independently from the stoichiometric metal:ligand ratio used in the synthesis. Ligands and complexes were tested for their antiproliferative properties on histiocytic lymphoma cell line U937. Copper(II) derivatives are systematically more active than the ligands and the nickel complexes. All copper derivatives result in inhibiting topoisomerase IIa in vitro. Computational methods were used to propose a model to explain the different extent of inhibition presented by these compounds. The positive charge of the dissociated form of the copper complexes may play a key role in their action. PMID:26335598

  14. Synthesis, characterization and X-ray structures of new antiproliferative and proapoptotic natural aldehyde thiosemicarbazones and their nickel(II) and copper(II) complexes.

    Science.gov (United States)

    Belicchi Ferrari, Marisa; Bisceglie, Franco; Pelosi, Giorgio; Sassi, Monica; Tarasconi, Pieralberto; Cornia, Mara; Capacchi, Silvia; Albertini, Roberto; Pinelli, Silvana

    2002-06-01

    Synthesis and characterization of new thiosemicarbazones derived from natural aldehydes (1-9) have been investigated in order to develop a research program aimed at the development of compounds with antiviral, antibacterial, and antitumor properties. These substances contain both a chain with N and S nucleophilic centers with tuberculostatic activity, and an alkyl or terpenic moiety. In addition, a few nickel(II) and copper(II) complexes (10-18), derived also from the previously studied ligands, were synthesized and characterized by means of NMR and IR techniques. The trans-2-octenal N(1)-phenylthiosemicarbazone and its nickel complex were also characterized by X-ray diffractometry. Biological studies, performed with some of these compounds, have involved both inhibition of cell proliferation and apoptosis tests in vitro on human leukemia cell line U937 to deepen our knowledge on the way these substances interfere with biological processes in leukemic cells. PMID:12031803

  15. A nanoporous 3D zinc(II) metal–organic framework for selective absorption of benzaldehyde and formaldehyde

    Energy Technology Data Exchange (ETDEWEB)

    Moradpour, Tahereh [School of Chemistry, College of Science, University of Tehran, Tehran (Iran, Islamic Republic of); Abbasi, Alireza, E-mail: aabbassi@khayam.ut.ac.ir [School of Chemistry, College of Science, University of Tehran, Tehran (Iran, Islamic Republic of); Van Hecke, Kristof [XStruct, Department of Inorganic and Physical Chemistry, Ghent University, Krigslaan 281-S3, Ghent B-9000 (Belgium)

    2015-08-15

    A new 3D nanoporous metal–organic framework (MOF), [[Zn{sub 4}O(C{sub 24}H{sub 15}N{sub 6}O{sub 6}){sub 2}(H{sub 2}O){sub 2}]·6H{sub 2}O·DMF]{sub n} (1) based on 4,4′,4″-s-triazine-1,3,5-triyltri-p-aminobenzoate (TATAB) ligand was solvothermally synthesized and characterized by single–crystal X-ray diffraction, Powder X-ray diffraction (PXRD), infrared spectroscopy (IR) and Brunauer–Emmett–Teller (BET) analyses. X-ray single crystal diffraction analysis reveals that 1 exhibits a 3D network with new kvh1 topology. Semi-empirical (AM1) calculations were carried out to obtain stable conformers for TATAB ligand. In addition, the absorption of two typical aldehydes (benzaldehyde and formaldehyde) in the presence of 1 was investigated and the effect of the aldehyde concentration, exposure time and temperature was studied. It was found that compound 1 has a potential for the absorption of aldehydes under mild conditions. - Graphical abstract: Absorption of two typical aldehydes (formaldehyde and benzaldehyde) by solvothermally synthesized of a 3D nano-porous MOF based on TATAB tricarboxylate ligand and Zn (NO{sub 3}){sub 2}·6H{sub 2}O. - Highlights: • We present a 3D Zn(II)-MOF with TATAB linker by solvothermal method. • The framework possesses a new kvh1 topology. • The framework displays formaldehyde and benzaldehyde absorption property. • Conformational analysis was performed to determine the stable linker geometry.

  16. Synthesis of diverse dihydropyrimidine-related scaffolds by fluorous benzaldehyde-based Biginelli reaction and post-condensation modifications

    Directory of Open Access Journals (Sweden)

    Bruno Piqani

    2011-09-01

    Full Text Available Dihydropyrimidinones and dihydropyrimidinethiones generated from the Biginelli reactions of perfluorooctanesulfonyl-attached benzaldehydes are used as common intermediates for post-condensation modifications such as cycloaddition, Liebeskind–Srogl reaction and Suzuki coupling to form biaryl-substituted dihydropyrimidinone, dihydropyrimidine, and thiazolopyrimidine compounds. The high efficiency of the diversity-oriented synthesis is achieved by conducting a multicomponent reaction for improved atom economy, under microwave heating for fast reaction, and with fluorous solid-phase extractions (F-SPE for ease of purification.

  17. Isolation of liver aldehyde oxidase containing fractions from different animals and determination of kinetic parameters for benzaldehyde

    Directory of Open Access Journals (Sweden)

    Kadam R

    2008-01-01

    Full Text Available Aldehyde oxidase activity containing fractions from rabbit, guinea pig, rat and mouse livers were obtained by heat treatment and ammonium sulfate precipitation. Aldehyde oxidase activity was observed in rabbit and guinea pig livers, while aldehyde oxidase activity was absent in rat and mouse liver fractions. Enzyme kinetic parameters, K m and V max , were determined for the oxidation of benzaldehyde to benzoic acid by rabbit and guinea pig liver fractions, by spectrophotometric method, with potassium ferricyanide as the electron acceptor. The K m values obtained for both animal liver fractions were in the range of 10.3-19.1 µM.

  18. Semicarbazonas e tiossemicarbazonas: o amplo perfil farmacológico e usos clínicos Semicarbazones and thiosemicarbazones: their wide pharmacological profile and clinical applications

    OpenAIRE

    Heloisa Beraldo

    2004-01-01

    This article shows that thiosemicarbazones, semicarbazones and their metal complexes can exhibit target selectivity along with a wide pharmacological profile. Complexes of thiosemicarbazones with cytotoxic or antitumoral activity are presented, some of which show activity against cisplatinum-resistant cells. The inhibition mechanism of the enzyme ribonucleoside diphosphate reductase (RDR), involved in DNA syntheses, by alpha(N)-heterocyclic thiosemicarbazones is discussed. The encouraging res...

  19. Synthesis and Structure-Activity Correlation Studies of Metal Complexes of α-N-heterocyclic Carboxaldehyde Thiosemicarbazones in Shewanella oneidensis

    OpenAIRE

    Quintell Tillison; Cedrick Whitaker; Ramaiyer Venkatraman; Wilson, Barbara A

    2005-01-01

    This investigation involved the synthesis of metal complexes to test the hypothesis that structural changes and metal coordination in pyridine thiosemicarbazones affect cell growth and cell proliferation in vitro. Thiosemicarbazones are well known to possess antitumor, antiviral, antibacterial, antimalarial, and other activities. Extensive research has been carried out on aliphatic, aromatic, heterocyclic and other types of thiosemicarbazones and their metal complexes. Due to the pronounced r...

  20. An Expedient Method for the Synthesis of Thiosemicarbazones under Microwave Irradiation in Solvent-free Medium

    Institute of Scientific and Technical Information of China (English)

    LI, Jian-Ping; ZHENG, Peng-Zhi; ZHU, Jun-Ge; LIU, Rui-Jie; QU, Gui-Rong

    2006-01-01

    A simple, efficient and eco-friendly method for the synthesis of thiosemicarbazones from thiosemicarbazides and aldehyde under microwave irradiation has been reported, and no solvent and catalyst were used. And the technique of microwave irradiation coupled with solvent-free condition proved to be a quite valuable method in the organic synthesis.

  1. Synthesis, Cytotoxic and Antimalarial Activities of Benzoyl Thiosemicarbazone Analogs of Isoquinoline and Related Compounds

    Directory of Open Access Journals (Sweden)

    Somsak Ruchirawat

    2010-02-01

    Full Text Available Thiosemicarbazone analogs of papaveraldine and related compounds 1–6 were synthesized and evaluated for cytotoxic and antimalarial activities. The cytotoxic activity was tested against HuCCA-1, HepG2, A549 and MOLT-3 human cancer cell lines. Thiosemicarbazones 1–5 displayed cytotoxicity toward all the tested cell lines, while compounds 2–5 selectively showed potent activity against the MOLT-3 cell lines. Significantly, N(4-phenyl-2-benzoylpyridine thiosemicarbazone 4 exhibited the most potent activity against HuCCA-1, HepG2, A549 and MOLT-3 cell lines with IC50 values of 0.03, 4.75, 0.04 and 0.004 µg/mL, respectively. In addition, 2-benzoylpyridine thio-semicarbazones 3 and 4 showed antimalarial activity against Plasmodium falciparum with IC50 of 10-7 to < 10-6 M. The study demonstrates the quite promising activity of analog 4 as a lead molecule for further development.

  2. Preparation of [61Cu]-2-acetylpyridine thiosemicarbazone complex as a possible PET tracer for malignancies

    International Nuclear Information System (INIS)

    Due to the interesting anti-proliferative properties of copper-thiosemicarbazone complexes, the production of a 61Cu-labeled thiosemicarbazone, i.e. 2-acetylpyridine thiosemicarbazone (APTS) was investigated. Copper-61 (T1/2=3.33h) was produced via the 64Zn(p,α)61Cu nuclear reaction using a natural zinc target irradiated with 22MeV protons for 500μAh. The 61Cu was separated from the irradiated target material by a two-step method and converted to acetate; this yielded a final activity of 222GBq (6.0Ci), with a radiochemical yield of >95%. The 61Cu-acetate was mixed with 2-acetylpyridine thiosemicarbazone for 30min at room temperature to yield [61Cu]APTS with a radiochemical yield of more than 80%. Colorimetric methods showed that residual chemical impurities in the product were below the accepted limits. Radio thin layer chromatography (RTLC) showed a radiochemical purity of more than 99% after C18 column chromatography. A specific activity of about 370-740MBq/mmol (10-20Ci/mmol) was obtained. The stability of the final product was checked in the absence and presence of human serum at 37oC for up to 3h. The partition coefficient of the final complex was also determined

  3. Coordination compounds of succinate some 3d-metals with thiosemicarbazone furfurol

    International Nuclear Information System (INIS)

    In article the results of synthesis and investigations of the Ni (II), Co (II), Cu (II) and Zn succinates with thiosemicarbazone furfurol complexes were shown. The consistence, individuality, the pattern of coordination of apical ligand and the thermal behavior of obtained complexes were established. (author)

  4. Preparation of [{sup 61}Cu]-2-acetylpyridine thiosemicarbazone complex as a possible PET tracer for malignancies

    Energy Technology Data Exchange (ETDEWEB)

    Jalilian, A.R. [Cyclotron and Nuclear Medicine Department, Nuclear Research Center for Agriculture and Medicine (NRCAM), Atomic Energy Organization of Iran, Moazzen Boulevard, Rajaeeshahr, P.O. Box 31485-498 Karaj (Iran, Islamic Republic of)]. E-mail: ajalilian@nrcam.org; Rowshanfarzad, P. [Cyclotron and Nuclear Medicine Department, Nuclear Research Center for Agriculture and Medicine (NRCAM), Atomic Energy Organization of Iran, Moazzen Boulevard, Rajaeeshahr, P.O. Box 31485-498 Karaj (Iran, Islamic Republic of); Sabet, M. [SSDL and Health Physics Department, Nuclear Research Center for Agriculture and Medicine (NRCAM), Atomic Energy Organization of Iran, Moazzen Boulevard, Rajaeeshahr, P.O. Box 31485-498 Karaj, Iran. (Iran); Shafiee, A. [Faculty of Pharmacy and Pharmaceutical Sciences Research center, Tehran University of Medical Sciences, P.O. Box 14155-6451 Tehran (Iran, Islamic Republic of)

    2006-03-15

    Due to the interesting anti-proliferative properties of copper-thiosemicarbazone complexes, the production of a {sup 61}Cu-labeled thiosemicarbazone, i.e. 2-acetylpyridine thiosemicarbazone (APTS) was investigated. Copper-61 (T{sub 1/2}=3.33h) was produced via the {sup 64}Zn(p,{alpha}){sup 61}Cu nuclear reaction using a natural zinc target irradiated with 22MeV protons for 500{mu}Ah. The {sup 61}Cu was separated from the irradiated target material by a two-step method and converted to acetate; this yielded a final activity of 222GBq (6.0Ci), with a radiochemical yield of >95%. The {sup 61}Cu-acetate was mixed with 2-acetylpyridine thiosemicarbazone for 30min at room temperature to yield [{sup 61}Cu]APTS with a radiochemical yield of more than 80%. Colorimetric methods showed that residual chemical impurities in the product were below the accepted limits. Radio thin layer chromatography (RTLC) showed a radiochemical purity of more than 99% after C{sub 18} column chromatography. A specific activity of about 370-740MBq/mmol (10-20Ci/mmol) was obtained. The stability of the final product was checked in the absence and presence of human serum at 37{sup o}C for up to 3h. The partition coefficient of the final complex was also determined.

  5. The wide pharmacological versatility of semicarbazones, thiosemicarba-zones and their metal complexes.

    Science.gov (United States)

    Beraldo, Heloisa; Gambino, Dinorah

    2004-01-01

    The more significant bioactivities of a variety of semicarbazones (anti-protozoa, anticonvulsant) and thiosemicarbazones (antibacterial, antifungal, antitumoral, antiviral) and their metal complexes are reviewed together with proposed mechanisms of action and structure-activity relationships. Clinical or potential pharmacological applications of these versatile compounds are discussed. PMID:14754441

  6. Coordination compounds of manganese(2) and cadmium(2) with α-ketoacid thiosemicarbazones

    International Nuclear Information System (INIS)

    Manganese (2) and cadmium (2) coordination compounds with gluoxalic, pyroacemic and benzoyl formic acid thiosemicarbazones are synthesized. ESR spectra of polycrystalline samples of manganese compounds and cadmium compounds activated with manganese at T=113 295 deg K allow to suppose that Mn2+ takes the position of Cd2+ ion which is in a weakly distorted octahedron crystal field

  7. Synthesis and Spectral Investigations of Some Platinum Metals Ions Coordination Compounds of 4[N-(Furan-2'-carboxalidene)Amino]Antipyrine Thiosemicarbazone and 4[N-(3',4',5'-Trimethoxybenzalidene)Amino]Antipyrine Thiosemicarbazone

    OpenAIRE

    Ram K. Agarwal; PRASAD, Surendra

    2005-01-01

    The present work describes the synthesis and spectral properties of some platinum metals chlorides coordination compounds of 4[N-(-(furan-2'-carboxalidene)amino]antipyrine thiosemicarbazone (FFAAPTS) and 4[N-(3',4',5'-trimethoxybenzalidene)amino]antipyrine thiosemicarbazone (TMBAAPTS). All the compounds have the general composition MCl2(L) (M = Pd2+ or Pt2+ ; L = FFAAPTS or TMBAAPTS) or MCl3(L) (M = Ru3+ , Rh3+ or Ir3+ ; L = FFAAPTS or TMBAAPTS). All the complexes...

  8. Synthesis and structure-activity relationship study of a new series of antiparasitic aryloxyl thiosemicarbazones inhibiting Trypanosoma cruzi cruzain.

    Science.gov (United States)

    Espíndola, José Wanderlan Pontes; Cardoso, Marcos Veríssimo de Oliveira; Filho, Gevanio Bezerra de Oliveira; Oliveira E Silva, Dayane Albuquerque; Moreira, Diogo Rodrigo Magalhaes; Bastos, Tanira Matutino; Simone, Carlos Alberto de; Soares, Milena Botelho Pereira; Villela, Filipe Silva; Ferreira, Rafaela Salgado; Castro, Maria Carolina Accioly Brelaz de; Pereira, Valéria Rego Alves; Murta, Silvane Maria Fonseca; Sales Junior, Policarpo Ademar; Romanha, Alvaro José; Leite, Ana Cristina Lima

    2015-08-28

    The discovery of new antiparasitic compounds against Trypanosoma cruzi, the etiological agent of Chagas disease, is necessary. Novel aryloxy/aryl thiosemicarbazone-based conformationally constrained analogs of thiosemicarbazones (1) and (2) were developed as potential inhibitors of the T. cruzi protease cruzain, using a rigidification strategy of the iminic bond of (1) and (2). A structure-activity relationship analysis was performed in substituents attached in both aryl and aryloxy rings. This study indicated that apolar substituents or halogen atom substitution at the aryl position improved cruzain inhibition and antiparasitic activity in comparison to unsubstituted thiosemicarbazone. Two of these compounds displayed potent inhibitory antiparasitic activity by inhibiting cruzain and consequently were able to reduce the parasite burden in infected cells and cause parasite cell death through necrosis. In conclusion, we demonstrated that conformational restriction is a valuable strategy in the development of antiparasitic thiosemicarbazones. PMID:26231082

  9. Electrical Wiring of the Aldehyde Oxidoreductase PaoABC with a Polymer Containing Osmium Redox Centers: Biosensors for Benzaldehyde and GABA

    Directory of Open Access Journals (Sweden)

    Artavazd Badalyan

    2014-11-01

    Full Text Available Biosensors for the detection of benzaldehyde and g-aminobutyric acid (GABA are reported using aldehyde oxidoreductase PaoABC from Escherichia coli immobilized in a polymer containing bound low potential osmium redox complexes. The electrically connected enzyme already electrooxidizes benzaldehyde at potentials below −0.15 V (vs. Ag|AgCl, 1 M KCl. The pH-dependence of benzaldehyde oxidation can be strongly influenced by the ionic strength. The effect is similar with the soluble osmium redox complex and therefore indicates a clear electrostatic effect on the bioelectrocatalytic efficiency of PaoABC in the osmium containing redox polymer. At lower ionic strength, the pH-optimum is high and can be switched to low pH-values at high ionic strength. This offers biosensing at high and low pH-values. A “reagentless” biosensor has been formed with enzyme wired onto a screen-printed electrode in a flow cell device. The response time to addition of benzaldehyde is 30 s, and the measuring range is between 10–150 µM and the detection limit of 5 µM (signal to noise ratio 3:1 of benzaldehyde. The relative standard deviation in a series (n = 13 for 200 µM benzaldehyde is 1.9%. For the biosensor, a response to succinic semialdehyde was also identified. Based on this response and the ability to work at high pH a biosensor for GABA is proposed by coimmobilizing GABA-aminotransferase (GABA-T and PaoABC in the osmium containing redox polymer.

  10. Ribonucleotide reductase inhibition by metal complexes of Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone): A combined experimental and theoretical study

    OpenAIRE

    Popović-Bijelić, Ana; Kowol, Christian R.; Lind, Maria E S; Luo, Jinghui; Himo, Fahmi; Enyedy, Éva A.; Arion, Vladimir B.; Gräslund, Astrid

    2011-01-01

    Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone, 3-AP) is currently the most promising chemotherapeutic compound among the class of α-N-heterocyclic thiosemicarbazones. Here we report further insights into the mechanism(s) of anticancer drug activity and inhibition of mouse ribonucleotide reductase (RNR) by Triapine. In addition to the metal-free ligand, its iron(III), gallium(III), zinc(II) and copper (II) complexes were studied, aiming to correlate their cytotoxic activities wi...

  11. SPECTROSCOPIC AND BIOLOGICAL STUDIES OF SOME NEW COORDINATION COMPOUNDS OF TIN (II) AND (IV) WITH SEMICARBAZONES AND THIOSEMICARBAZONES.

    OpenAIRE

    JITENDRA KUMAR RAWAT; HARI SHANKAR YADAV; A.K. VARSHNEY; Varshney, S.

    2012-01-01

    The present paper is a report on the synthesis of some new tin (II) and tin (IV) complexes by the reaction of stannous chloride and dimethyltin dichloride with semicarbazones and thiosemicarbazones using tetrahydrofuran(THF) as reaction medium. Semicarbazones and thiosemicarbazones used in these studies are synthesized by the condensation of 1-acetyl-2-naphthol, 2-acetyl-1-naphathol, 2-acetyl-5-methyl furan, 2-acetyl-4-methyl thiophene and 2-acetyl-naphthalene with ...

  12. G2/M Cell Cycle Arrest and Tumor Selective Apoptosis of Acute Leukemia Cells by a Promising Benzophenone Thiosemicarbazone Compound

    OpenAIRE

    Cabrera, Maia; Gomez, Natalia; Remes Lenicov, Federico; Echeverría, Emiliana; Shayo, Carina; Moglioni, Albertina; Fernández, Natalia; Davio, Carlos

    2015-01-01

    Anti-mitotic therapies have been considered a hallmark in strategies against abnormally proliferating cells. Focusing on the extensively studied family of thiosemicarbazone (TSC) compounds, we have previously identified 4,4’-dimethoxybenzophenone thiosemicarbazone (T44Bf) as a promising pharmacological compound in a panel of human leukemia cell lines (HL60, U937, KG1a and Jurkat). Present findings indicate that T44Bf-mediated antiproliferative effects are associated with a reversible chronic ...

  13. Evaluation of benzaldehyde derivatives from Morinda officinalis as anti-mite agents with dual function as acaricide and mite indicator

    OpenAIRE

    Ji-Yeon Yang; Min-Gi Kim; Jun-Hwan Park; Seong-Tshool Hong; Hoi-Seon Lee

    2014-01-01

    Severe fever with thrombocytopenia syndrome (SFTS) is an emerging infectious disease caused by SFTS virus with 12–30% fatality rate. Despite severity of the disease, any medication or treatment for SFTS has not developed yet. One approach to prevent SFTS spreading is to control the arthropod vector carrying SFTS virus. We report that 2–methylbenzaldehyde analogues from M. officinalis have a dual function as acaricide against Dermatophagoides spp. and Haemaphysalis longicornis and indicator (c...

  14. Evaluation of benzaldehyde derivatives from Morinda officinalis as anti-mite agents with dual function as acaricide and mite indicator.

    Science.gov (United States)

    Yang, Ji-Yeon; Kim, Min-Gi; Park, Jun-Hwan; Hong, Seong-Tshool; Lee, Hoi-Seon

    2014-01-01

    Severe fever with thrombocytopenia syndrome (SFTS) is an emerging infectious disease caused by SFTS virus with 12-30% fatality rate. Despite severity of the disease, any medication or treatment for SFTS has not developed yet. One approach to prevent SFTS spreading is to control the arthropod vector carrying SFTS virus. We report that 2-methylbenzaldehyde analogues from M. officinalis have a dual function as acaricide against Dermatophagoides spp. and Haemaphysalis longicornis and indicator (color change) against Dermatophagoides spp. Based on the LD50 values, 2,4,5-trimethylbenzaldehyde (0.21, 0.19, and 0.68 μg/cm(3)) had the highest fumigant activity against D. farinae, D. pteronyssinus, and H. longicornis, followed by 2,3-dimethylbenzaldehyde (0.46, 0.44, and 0.79 μg/cm(3)), 2,4-dimethylbenzaldehyde (0.66, 0.59, and 0.95 μg/cm(3)), 2,5-dimethylbenzaldehyde (0.65, 0.68, and 0.88 μg/cm(3)), 2-methylbenzaldehyde (0.95, 0.87, and 1.28 μg/cm(3)), 3-methylbenzaldehyde (0.99, 0.93, and 1.38 μg/cm(3)), 4-methylbenzaldehyde (1.17, 1.15, and 3.67 μg/cm(3)), and M. officinalis oil (7.05, 7.00, and 19.70 μg/cm(3)). Furthermore, color alteration of Dermatophagoides spp. was shown to be induced, from colorless to dark brown, by the treatment of 2,3-dihydroxybenzaldehyde. These finding indicated that 2-methylbenzaldehyde analogues could be developed as functional agent associated with the arthropod vector of SFTS virus and allergen. PMID:25434408

  15. Microwave Synthesis and Antimicrobial Activity of some Copper (II, Cobalt (II, Nickel (II and Chromium (III Complexes with Schiff Base 2, 6-Pyridinedi carboxaldehyde-Thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Dr.Mohammed.Fakruddin Ali Ahmed

    2014-03-01

    Full Text Available Some novel Schiff base metal complexes of Cr(III, Co(II, Ni(II andCu(II derived from 2, 6-pyridinedicarboxaldehyde-Thiosemicarbazone(PDCTC was synthesized by conventional as well as microwavemethods. This compound wascharacterized by elemental analysis, FT-IR, Mass, molar conductanceand magneticsusceptibilitymeasurements analyses. Analytical data revealed that all the complexesexhibited 1:1 (metal: ligand ratio with a coordination number of six.The IR data showed that the ligand coordinates with the metal ions in ahexa-dentate manner. The solid state electricalconductivity of the metal complexes was also measured. Solid state electricalconductivity studies reflected a semi-conducting nature of the complexes. The Schiff base and metal complexes displayed good activity againstthe Gram-positive bacteria Staphylococcus aureus, the Gram-negative bacteriaEscherichia coli and the fungi AspergillusnigerandCandida albicans. The antimicrobialresults also indicated that the metal complexes displayed betterantimicrobial activity as compared to the Schiff bases.

  16. Spectral, IR and magnetic studies of Mn(II), Co(II), Ni(II) and Cu(II) complexes with pyrrole-2-carboxyaldehyde thiosemicarbazone (L)

    Science.gov (United States)

    Chandra, Sulekh; Kumar, Anil

    2007-11-01

    Mn(II), Co(II), Ni(II) and Cu(II) complexes are synthesized with thiosemicarbazone (L) derived from pyrrole-2-carboxyaldehyde. These complexes are characterized by elemental analysis, molar conductance, magnetic susceptibility measurement, mass, IR, electronic and EPR spectral studies. The molar conductance measurement of the complexes in DMSO indicates that the complexes are non-electrolyte except Co(L) 2(NO 3) 2 and Ni(L) 2(NO 3) 2 complexes which are 1:2 electrolyte. All the complexes are of high-spin type. On the basis of spectral studies an octahedral geometry may be assigned for Mn(II), Co(II) and Ni(II) complexes except Co(L) 2(NO 3) 2 and Ni(L) 2(NO 3) 2 which are of tetrahedral geometry. A tetragonal geometry may be suggested for Cu(II) complexes.

  17. Flow Injection Analysis of Mercury Using 4-(Dimethylamino Benzaldehyde-4-Ethylthiosemicarbazone as the Ionophore of a Coated Wire Electrode

    Directory of Open Access Journals (Sweden)

    Sulaiman Ab Ghani

    2012-11-01

    Full Text Available A flow injection analysis (FIA incorporating a thiosemicarbazone-based coated wire electrode (CWE was developed method for the determination of mercury(II. A 0.1 M KNO3 carrier stream with pH between 1 and 5 and flow rate of 1 mL·min−1 were used as optimum parameters. A linear plot within the concentration range of 5 × 10−6–0.1 M Hg(II, slope of 27.8 ± 1 mV per decade and correlation coefficient (R2 of 0.984 were obtained. The system was successfully applied for the determination of mercury(II in dental amalgam solutions and spiked environmental water samples. Highly reproducible measurements with relative standard deviation (RSD < 1% (n = 3 were obtained, giving a typical throughput of 30 samples·h−1.

  18. Single-crystal growth of 4-hydroxy-3-methoxy benzaldehyde by the Bridgman technique and its characterization

    Science.gov (United States)

    Kannan, V.; Jayaprakasan, M.; Bairava Ganesh, R.; Ramasamy, P.

    2006-08-01

    Single-crystal growth of 4-hydroxy-3-methoxy benzaldehyde (vanillin), an excellent molecular nonlinear optical (NLO) material, from the melt using the Bridgman technique is reported for the first time. Differential thermal analysis experiments indicated that the substance melts congruently at 81 °C. A precise temperature profile plot of the resistive furnace used was measured using a simple PC-based time-temperature data logging system. Powder X-ray diffraction analysis of the grown crystal revealed the crystal belongs to the monoclinic system. Fourier transform infrared spectra were used to assign various modes and identify the functional groups. The crystal exhibited a wide window of transmission unlike other organic NLO crystals. The optical second harmonic generation conversion efficiency of vanillin was determined using the Kurtz powder technique.

  19. Synthesis, Crystal Structural Investigations, and DFT Calculations of Novel Thiosemicarbazones

    Directory of Open Access Journals (Sweden)

    Brian J. Anderson

    2016-02-01

    Full Text Available The crystal and molecular structures of three new thiosemicarbazones, 2-[1-(2-hydroxy-5-methoxyphenylethylidene]-N-methyl-hydrazinecarbothioamide monohydrate (1, 2-[1-(2-hydroxy-5-methoxyphenylethylidene]-N-ethyl-hydrazinecarbothioamide (2 and 2-[1-(2-hydroxy-4-methoxyphenylethylidene]-N-ethyl-hydrazinecarbothioamide acetonitrile solvate (3, are reported and confirmed by single crystal X-ray diffraction, NMR and UV-vis spectroscopic data. Compound (1, C11H15N3O2S·H2O, crystallizes in the monoclinic with space group P21/c, with cell parameters a = 8.2304(3 Å, b = 16.2787(6 Å, c = 9.9708(4 Å, and β = 103.355(4°. Compound (2, C12H17N3O2S, crystallizes in the C2/c space group with cell parameters a = 23.3083(6 Å, b = 8.2956(2 Å, c = 13.5312(3 Å, β = 91.077(2°. Compound (3, C11H15N3O2S·C2H3N, crystallizes in the triclinic P-1 space group with cell constants a = 8.9384(7 Å, b = 9.5167(8 Å, c = 10.0574(8 Å, α = 110.773(7°, β = 92.413(6°, and γ = 90.654(7°. DFT B3LYP/6-31(G geometry optimized molecular orbital calculations were also performed and frontier molecular orbitals of each compound are displayed. The correlations between the calculated molecular orbital energies (eV for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound have been proposed. Additionally, similar correlations observed among three closely related compounds, (4, 2-[1-(2-hydroxy-4-methoxyphenylethylidene]-N-methyl-hydrazinecarbothioamide, (5, 2-[1-(2-hydroxy-6-methoxyphenylethylidene]-N-methyl-hydrazinecarbothioamide acetonitrile monosolvate and (6, 2-[1-(2-hydroxy-6-methoxyphenylethylidene]-N-ethyl-hydrazinecarbothioamide, examining structural differences from the substitution of the methoxy group from the phenyl ring (4, 5, or 6 position and the substitution of the terminal amine (methyl or ethyl to their frontier molecular orbital surfaces and from their Density Functional

  20. Spectroscopic and biological studies on newly synthesized nickel(II) complexes of semicarbazones and thiosemicarbazones

    Science.gov (United States)

    Chandra, Sulekh; Gupta, Lokesh Kumar

    2005-12-01

    Nickel(II) complexes, having the general composition Ni(L) 2X 2, have been synthesized [where L: isopropyl methyl ketone semicarbazone (LLA), isopropyl methyl ketone thiosemicarbazone (LLB), 4-aminoacetophenone semicarbazone (LLC) and 4-aminoacetophenone thiosemicarbazone (LLD) and X = Cl -, 1/2SO 42-]. All the Ni(II) complexes reported here have been characterized by elemental analyses, magnetic moments, IR, electronic and mass spectral studies. All the complexes were found to have magnetic moments corresponding to two unpaired electrons. The possible geometries of the complexes were assigned on the basis of electronic and infrared spectral studies. Newly synthesized ligand and its nickel(II) complexes have been screened against different bacterial and fungal growth.

  1. Synthesis and Antiproliferative Activity of Steroidal Thiosemicarbazone Platinum (Pt(II)) Complexes.

    Science.gov (United States)

    Huang, Yanmin; Kong, Erbin; Gan, Chunfang; Liu, Zhiping; Lin, Qifu; Cui, Jianguo

    2015-01-01

    Steroidal compounds exhibit particular physiological activities. In this paper, some steroidal thiosemicarbazones platinum (Pt(II)) complexes were synthesized by the condensation of steroidal ketones with thiosemicarbazide using estrone, chenodeoxycholic acid, and 7-deoxycholic acid as starting materials and complexation of steroidal thiosesemicarbazones with Pt(II). The complexes were characterized by IR, NMR, and MS, and their antiproliferative activities were evaluated. The results showed that some steroidal thiosemicarbazones platinum (Pt(II)) complexes displayed moderate cytotoxicity to HeLa and Bel-7404 cells. Thereinto, complex 6 showed an excellent inhibited selectivity to HeLa cells with an IC50 value of 9.2 μM and SI value of 21.7. At the same time, all compounds were almost inactive to HEK293T (normal kidney epithelial cells). The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. PMID:26635511

  2. Synthesis and Antiproliferative Activity of Steroidal Thiosemicarbazone Platinum (Pt(II Complexes

    Directory of Open Access Journals (Sweden)

    Yanmin Huang

    2015-01-01

    Full Text Available Steroidal compounds exhibit particular physiological activities. In this paper, some steroidal thiosemicarbazones platinum (Pt(II complexes were synthesized by the condensation of steroidal ketones with thiosemicarbazide using estrone, chenodeoxycholic acid, and 7-deoxycholic acid as starting materials and complexation of steroidal thiosesemicarbazones with Pt(II. The complexes were characterized by IR, NMR, and MS, and their antiproliferative activities were evaluated. The results showed that some steroidal thiosemicarbazones platinum (Pt(II complexes displayed moderate cytotoxicity to HeLa and Bel-7404 cells. Thereinto, complex 6 showed an excellent inhibited selectivity to HeLa cells with an IC50 value of 9.2 μM and SI value of 21.7. At the same time, all compounds were almost inactive to HEK293T (normal kidney epithelial cells. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.

  3. Synergistic extraction of uranium(VI) by 2-hydroxy-1-naphthaldehyde thiosemicarbazone and several neutral donors

    International Nuclear Information System (INIS)

    The extraction behaviour of U (VI) from an aqueous nitric acid medium employing a 2-hydroxy-1-naphthaldehyde thiosemicarbazone in ethyl acetate has been studied in presence of different neutral donors like trioctyl phosphine oxide (TOPO), dimethyl sulphoxide (DMSO) and trioctyl amine (TOA). The extraction constant (log kex) for the binary organic phases UO2.A.X (where A = ligand, X = NO3-1) was found to be 1.976 which is by far the largest value amongst known values for the thiosemicarbazone. The overall equilibrium constant (log K) for the ternary complexes UO2A(NO3).TOPO, UO2A(NO3).TOA and UO2A(NO3).DMSO were estimated to be 6.06, 6.77 and 4.95, respectively. The effect of different diluents on the extraction behaviour has also been studied. (orig.)

  4. Deposition of rod-shaped antimony sulfide thin films from single-source antimony thiosemicarbazone precursors

    Energy Technology Data Exchange (ETDEWEB)

    Biswal, Jasmine B.; Sawant, Narayan V. [Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (East), Mumbai - 400 098 (India); Garje, Shivram S., E-mail: ssgarje@chem.mu.ac.i [Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (East), Mumbai - 400 098 (India)

    2010-04-02

    Antimony sulfide thin films were deposited on glass substrates by aerosol assisted chemical vapour deposition technique using single source precursors, namely, antimony(III) thiosemicarbazones, SbCl{sub 3}(L) (L = thiosemicarbazones of thiophene-2-carboxaldehyde (1) and cinnamaldehyde (2)). The deposited films were characterized by X-ray diffraction, scanning electron microscopy, energy dispersive X-ray analysis and UV-visible spectroscopy in order to identify their phases, morphologies, compositions and optical properties respectively. These characterizations revealed that the films were comprised of rod-shaped particles of orthorhombic stibnite (Sb{sub 2}S{sub 3}) with a Sb:S stoichiometry of {approx} 1:1.3. The calculated optical band gap from UV-vis absorption spectrum is found to be 3.48 eV.

  5. Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates.

    Science.gov (United States)

    Blau, Lorena; Menegon, Renato Farina; Trossini, Gustavo H G; Molino, João Vitor Dutra; Vital, Drielli Gomes; Cicarelli, Regina Maria Barretto; Passerini, Gabriela Duó; Bosquesi, Priscila Longhin; Chin, Chung Man

    2013-09-01

    The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Trypanosoma cruzi in in vitro assays (IC50 < 57 μM), and no mutagenic profile was observed in micronucleous tests. Although the in vitro inhibition test showed that 10-μM doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. PMID:23851115

  6. Synergistic extraction of uranium(VI) by 2-hydroxy-1-naphthaldehyde thiosemicarbazone and several neutral donors

    Energy Technology Data Exchange (ETDEWEB)

    Banerjee, S.; Bhar, M.; Basu, S. [Dept. of Chemistry, The Univ. of Burdwan, Golapbag, Burdwan (India)

    2003-07-01

    The extraction behaviour of U (VI) from an aqueous nitric acid medium employing a 2-hydroxy-1-naphthaldehyde thiosemicarbazone in ethyl acetate has been studied in presence of different neutral donors like trioctyl phosphine oxide (TOPO), dimethyl sulphoxide (DMSO) and trioctyl amine (TOA). The extraction constant (log k{sub ex}) for the binary organic phases UO{sub 2}.A.X (where A = ligand, X = NO{sub 3}{sup -1}) was found to be 1.976 which is by far the largest value amongst known values for the thiosemicarbazone. The overall equilibrium constant (log K) for the ternary complexes UO{sub 2}A(NO{sub 3}).TOPO, UO{sub 2}A(NO{sub 3}).TOA and UO{sub 2}A(NO{sub 3}).DMSO were estimated to be 6.06, 6.77 and 4.95, respectively. The effect of different diluents on the extraction behaviour has also been studied. (orig.)

  7. Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors.

    Science.gov (United States)

    Hameed, Abdul; Khan, Khalid Mohammed; Zehra, Syeda Tazeen; Ahmed, Ramasa; Shafiq, Zahid; Bakht, Syeda Mahwish; Yaqub, Muhammad; Hussain, Mazhar; de la Vega de León, Antonio; Furtmann, Norbert; Bajorath, Jürgen; Shad, Hazoor Ahmad; Tahir, Muhammad Nawaz; Iqbal, Jamshed

    2015-08-01

    Urease is an important enzyme which breaks urea into ammonia and carbon dioxide during metabolic processes. However, an elevated activity of urease causes various complications of clinical importance. The inhibition of urease activity with small molecules as inhibitors is an effective strategy for therapeutic intervention. Herein, we have synthesized a series of 19 benzofurane linked N-phenyl semithiocarbazones (3a-3s). All the compounds were screened for enzyme inhibitor activity against Jack bean urease. The synthesized N-phenyl thiosemicarbazones had varying activity levels with IC50 values between 0.077 ± 0.001 and 24.04 ± 0.14 μM compared to standard inhibitor, thiourea (IC50 = 21 ± 0.11 μM). The activities of these compounds may be due to their close resemblance of thiourea. A docking study with Jack bean urease (PDB ID: 4H9M) revealed possible binding modes of N-phenyl thiosemicarbazones. PMID:26119990

  8. Microwave-Assisted Synthesis of New N1,N4-Substituted Thiosemicarbazones

    Directory of Open Access Journals (Sweden)

    Aurea Echevarria

    2011-12-01

    Full Text Available We present an efficient procedure for the synthesis of thirty-six N1,N4-substituted thiosemicarbazones, including twenty-five ones that are reported for the first time, using a microwave-assisted methodology for the reaction of thiosemicarbazide intermediates with aldehydes in the presence of glacial acetic acid in ethanol and under solvent free conditions. Overall reaction times (20–40 min when ethanol as solvent, and 3 min under solvent free conditions were much shorter than with the traditional procedure (480 min; satisfactory yields and high-purity compounds were obtained. The thiosemicarbazide intermediates were obtained from alkyl or aryl isothiocyanates and hydrazine hydrate or phenyl hydrazine by stirring at room temperature for 60 min or by microwave irradiation for 30 min, with lower yields for the latter. The preliminary in vitro antifungal activity of thiosemicarbazones was evaluated against Aspergillus parasiticus and Candida albicans.

  9. Avaliação do potencial anticorrosivo de tiossemicarbazonas solubilizadas em microemulsão Evaluation of anticorrosive effectiveness of thiosemicarbazones solubilized in a microemulsion system

    Directory of Open Access Journals (Sweden)

    Elaine Cristina M. de Moura

    2013-01-01

    Full Text Available In this paper, thiosemicarbazones 4-N-cinnamoyl-thiosemicarbazone (CTSC, 4-N-(2'-methoxycinnamoyl-thiosemicarbazone (MCTSC, and 4-N-(4'-hydroxy-3'-methoxybenzoyl- thiosemicarbazone (HMBTSC were solubilized in an oil-in-water (O/W microemulsion system (ME_OCS, forming systems CTSC_ME_OCS, MCTSC_ME_OCS and HMBTSC_ME_OCS. The effectiveness of these systems in the process of inhibiting AISI 1020 carbon steel corrosion was evaluated in a saline solution (NaCl 0.5%, using a galvanostatic method. The tested thiosemicarbazones showed higher inhibitory effects (85.7% for CTSC_ME_OCS, 84.0% for MCTSC_ME_OCS, and 83.3% for HMBTSC_ME_OCS. The surfactant OCS (dissolved in H2O and the ME_OCS system showed lower efficacies, with 71.0% for OCS and 74.0% for ME_OCS system.

  10. Spectroscopic, Thermal and Biological Studies on Some Trivalent Ruthenium and Rhodium NS Chelating Thiosemicarbazone Complexes

    OpenAIRE

    Vinod K Sharma; Shipra Srivastava; Ankita Srivastava

    2007-01-01

    The synthetic, spectroscopic, and biological studies of sixteen ring-substituted 4-phenylthiosemicarbazones and 4-nitrophenyl-thiosemicarbazones of anisaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde, and vanillin with ruthenium(III) and rhodium(III) chlorides are reported here. Their structures were determined on the basis of the elemental analyses, spectroscopic data (IR, electronic, 1H and 13C NMR) along with magnetic susceptibility measurements, molar conductivity and thermogravimetr...

  11. The Hypolipidemic Activity of Heterocyclic Thiosemicarbazones, Thioureas and Their Metal Complexes in Sprague Dawley Male Rats

    OpenAIRE

    Hall, Iris H.; Chen, S. Y.; Barnes, Betsy Jo; West, Douglas X.

    1999-01-01

    Heterocyclic thiosemicarbazones, thioureas and their copper, nickel, and cobalt complexes were shown to be potent hypolipidemic agents in male Sprague Dawley rats at 8 mg/kg/day, orally. These agents lowered the activity of rat hepatic rate limiting enzymes for the synthesis of cholesterol and triglycerides. The effects of these agnets on cytoplasmic ATP-dependent citrate lyase, acetyl CoA synthetase and HMG-CoA reductase activities were reduced by a magnitude to explain the reduction of seru...

  12. Antineoplastic and Cytotoxic Activities of Nickel(II) Complexes of Thiosemicarbazones

    OpenAIRE

    Hall, Iris H.; Miller, Merrill C.III; West, Douglas X.

    1997-01-01

    Nickel(II) complexes of thiosemicarbazons were observed to be potent cytotoxic agents in human and rodent tissue cultured tumor cells. Each compound demonstrated a slightly different profile in the various histological types of tumors. The nickel complex of Appip demonstrated the most potent in vivo activity in the Ehrlich ascites carcinoma. This agent selectively inhibited L1210 DNA and purine syntheses, and DNA polymerase α, PRPP-amido transferase, IMP-dehydrogenase, dihydrofolate reductase...

  13. Synthesis and Antiproliferative Activity of Steroidal Thiosemicarbazone Platinum (Pt(II)) Complexes

    OpenAIRE

    Yanmin Huang; Erbin Kong; Chunfang Gan; Zhiping Liu; Qifu Lin; Jianguo Cui

    2015-01-01

    Steroidal compounds exhibit particular physiological activities. In this paper, some steroidal thiosemicarbazones platinum (Pt(II)) complexes were synthesized by the condensation of steroidal ketones with thiosemicarbazide using estrone, chenodeoxycholic acid, and 7-deoxycholic acid as starting materials and complexation of steroidal thiosesemicarbazones with Pt(II). The complexes were characterized by IR, NMR, and MS, and their antiproliferative activities were evaluated. The results showed ...

  14. New organoruthenium complexes with bioactive thiosemicarbazones as co-ligands: potential anti-trypanosomal agents†

    OpenAIRE

    Demoro, Bruno; Sarniguet, Cynthia; Sánchez-Delgado, Roberto; Rossi, Miriam; Liebowitz, Daniel; Caruso, Francesco; Olea-Azar, Claudio; Moreno, Virtudes; Medeiros, Andrea; Comini, Marcelo A.; Otero, Lucía; Gambino, Dinorah

    2011-01-01

    In the search for new therapeutic tools against neglected diseases produced by trypanosomatid parasites, and particularly against African Trypanosomiasis, whose etiological agent is Trypanosoma brucei, organoruthenium compounds with bioactive nitrofuran containing thiosemicarbazones (L) as co-ligands were obtained. Four ruthenium(ii) complexes with the formula [Ru2(p-cymene)2(L)2]X2, where X = Cl or PF6, were synthesized and the crystal structures of two of them were solved by X-ray diffracti...

  15. Complexes of nickel-, copper-, zinc-, cadmium- and mercury (II) with salicyaldehyde-4, 4-dimethyl-3-thiosemicarbazone

    International Nuclear Information System (INIS)

    Complexes of salicylaldehyde-4, 4-dimethyl-3-thiosemicarbazone (H2 saldmtsc) with bivalent metal ions of composition [M(saldmtsc).nH2O] (M NiII, CuII, ZnII, CdII or HgII and n=0 or 1), [M(saldmtsc)py] (M=NiII, CuII or ZnII) and [Ni(saldmtsc)B] (B = α-, β- or γ-picoline) have been prepared and characterised. (author)

  16. Intracellular reduction/activation of a disulfide switch in thiosemicarbazone iron chelators

    OpenAIRE

    Akam, Eman A.; Chang, Tsuhen M.; Astashkin, Andrei V.; Tomat, Elisa

    2014-01-01

    Iron scavengers (chelators) offer therapeutic opportunities in anticancer drug design by targeting the increased demand for iron in cancer cells as compared to normal cells. Prochelation approaches are expected to avoid systemic iron depletion as chelators are liberated under specific intracellular conditions. In the strategy described herein, a disulfide linkage is employed as a redox-directed switch within the binding unit of an antiproliferative thiosemicarbazone prochelator, which is acti...

  17. Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB

    OpenAIRE

    Mallari, Jeremy P.; Shelat, Anang; Kosinski, Aaron; Conor R Caffrey; Connelly, Michele; Zhu, Fangyi; McKerrow, James H.; Guy, R. Kiplin

    2008-01-01

    Human African trypanosomiasis (HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T.brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T.bruc...

  18. Solvent extraction of cobalt(II) with 2,4-dihydroxyacetophenone thiosemicarbazone

    International Nuclear Information System (INIS)

    The extraction of cobalt(II) from ammonium chloride-ammonium hydroxide buffer solutions of pH 6.5 by 2,4-dihydroxyacetophenone thiosemicarbazone (DATS) in n-butanol has been studied. Cobalt(II) forms 1:1 complex (metal:reagent) with DATS. Addition to pyridine enhances the extraction. The influence of metal concentration and the effect of diverse ions on the extraction of cobalt(II) have been investigated. (author)

  19. Investigation of some novel ligands of pyruvaldehyde bis(thiosemicarbazone) as pet radiopharmaceuticals

    International Nuclear Information System (INIS)

    Three novel ligands of pyruvaldehyde bis (thiosemicarbazone) have been synthesized. These ligands are labelled with 64Cu. The factors that affect labelling yield are also investigated. The biodistribution of three 64Cu ligand complexes in mice are determined. The higher brain uptake with a prolonged retention time is found in case of 64Cu-PTSP. The results suggested that 62Cu-PTSP may be used as a PET tracer for cerebral perfusion and it needs more research

  20. Solvent extraction of cobalt(II) with 2,4-dihydroxyacetophenone thiosemicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Reddy, A.V.; Reddy, M.L.P.; Reddy, Y.K. (Sri Venkateswara Univ., Tirupati (India). Dept. of Chemistry)

    1984-07-19

    The extraction of cobalt(II) from ammonium chloride-ammonium hydroxide buffer solutions of pH 6.5 by 2,4-dihydroxyacetophenone thiosemicarbazone (DATS) in n-butanol has been studied. Cobalt(II) forms 1:1 complex (metal:reagent) with DATS. Addition to pyridine enhances the extraction. The influence of metal concentration and the effect of diverse ions on the extraction of cobalt(II) have been investigated.

  1. Spectroscopic characterization of copper(II) complexes of indoxyl N(4)-methyl thiosemicarbazone

    Science.gov (United States)

    Chandra, Sulekh; Kumar, Umendra

    2004-10-01

    New copper(II) complexes of indoxyl thiosemicarbazone (ITSC) of general composition CuL 2X 2 (where L: ITSC; X: Cl -, NO 3-, ClO 4-, NCS -) have been synthesized and characterized by elemental analysis, molar conductance, magnetic susceptibility measurements and spectral (electronic, IR, EPR, 1H NMR , Mass) studies. Cyclic voltammetry measurements show quasi-reversible Cu 2+/Cu 1+ couple. Various physico-chemical techniques suggest a tetragonal structure for these copper(II) complexes.

  2. Coordination Chemistry of Polyaromatic Thiosemicarbazones 2: Synthesis and Biological Activity of Zinc, Cobalt, and Copper Complexes of 1-(Naphthalene-2-yl)ethanone Thiosemicarbazone

    OpenAIRE

    Marc-Andre LeBlanc; Antonio Gonzalez-Sarrías; Beckford, Floyd A.; P. Canisius Mbarushimana; Seeram, Navindra P.

    2011-01-01

    A novel thiosemicarbazone from 2-acetonaphthone (represented as acnTSC) has been synthesized and its basic coordination chemistry with zinc(II), cobalt(II), and copper(II) explored. The complexes were characterized by elemental analysis and various spectroscopic techniques and are best formulated as [M(acnTSC)2Cl2] with the metal likely in an octahedral environment. The anticancer activity of the complexes was determined against a panel of human colon cancer cells (HCT-116 and Caco-2). The co...

  3. Synthesis and Evaluation of Some New Aza-B-homocholestane Derivatives as Anticancer Agents

    OpenAIRE

    Yanmin Huang; Jianguo Cui; Sijing Chen; Qifu Lin; Huacan Song; Chunfang Gan; Bin Su; Aimin Zhou

    2014-01-01

    Using analogues of some marine steroidal oximes as precursors, a series of aza-B-homocholestane derivatives possessing different substituted groups at the 3-position of the steroidal nucleus were synthesized. Their biological activity against cancer cell proliferation was determined with multiple cancer cell lines. Aza-B-homocholestane derivatives possessing 3-hydroxyl, 3-hydroximino and 3-thiosemicarbazone groups displayed remarkable cytotoxicity to cancer cells via apoptosis inducing mecha...

  4. Synthesis, structures, spectroscopy and antimicrobial properties of complexes of copper(II) with salicylaldehyde N-substituted thiosemicarbazones and 2,2'-bipyridine or 1,10-phenanthroline.

    Science.gov (United States)

    Lobana, Tarlok S; Indoria, Shikha; Jassal, Amanpreet Kaur; Kaur, Harpreet; Arora, Daljit S; Jasinski, Jerry P

    2014-04-01

    Among the biometals (Cu, Co, Ni-cofactors in many enzymes), copper derivatives of O, N, S-donor salicylaldehyde thiosemicarbazones have received considerable attention owing to their potential biological applications. Eight new complexes of salicylaldehyde-N-substituted thiosemicarbazones [5-MeO-2-HO-C₆H₄-C(2)(H)N(3)-N(2)H-C(1)(S)-N(1)HR; R = Me, H2L(1); Et, H₂L(1), Ph, H₂L(3), H, H₂L(4)] with copper(II), namely, [Cu(κ(3)-O,N,S-L)( κ(2)-N,N-L')] {(L)(2-) = (L(1))(2-), L' = bipy, 1, phen, 2; (L)(2-) = (L(2))(2-), L' = bipy, 3, phen, 4; (L)(2-) = (L(3))(2-), L' = bipy, 5, phen, 6; (L)(2-) = (L(4))(2-), L' = bipy, 7, phen, 8} have been isolated. Complexes have slightly distorted square pyramidal geometry around the metal center (τ parameter = 0.243-0.357) and display weak to intense fluorescence in the region, 375-475 nm. These copper complexes have shown significant growth inhibitory activity (antimicrobial activity) against Staphylococcus aureus (MTCC740), methicillin resistant Staphylococcus aureus (MRSA), Klebsiella pneumoniae 1 (MTCC109), Shigella flexneri (MTCC1457), Pseudomonas aeruginosa (MTCC741) and Candida albicans (MTCC227). The activity against MRSA is an interesting observation as the commercially available gentamycin is found to be inactive against this bacterial strain. Specifically complex 5 formed by 5-methoxysalicylaldehyde-N-phenylthiosemicatbazone has shown novel antimicrobial activity against various bacteria and yeast investigated. PMID:24583354

  5. In vivo anticancer activity of vanillin, benzophenone and acetophenone thiosemicarbazones on Swiss albino mice

    Institute of Scientific and Technical Information of China (English)

    Sha Md. Shahan Shahriar; Shaikh M Mohsin Ali; Mele Jesmin; Md. Khairul Islam; Sarozit Mondal

    2014-01-01

    Objective: To study the anticancer activities of three schiff bases viz. vanillin thiosemicarbazone, benzophenone thiosemicarbazone and acetophenone thiosemicarbazone against Ehrlich ascites carcinoma (EAC) cells in Swiss albino mice. Methods: Synthesized compounds have administrated into the intraperitoneal cavity of the EAC inoculated mice at two doses. The anticancer activities have studied by monitoring the parameters such as cell growth inhibition, tumor weight measurement, survival time of EAC bearing mice as well as the changes in depleted hematological parameters due to tumorgenesis. All such data have been compared with those of a known standard drug bleomycin at the dose of 0.3 mg/kg (i.p.).Results:It has been found that these bases enhanced life span, reduced average tumor weight and inhibited tumor cell growth of EAC cell bearing mice remarkably. The results were similar in potency to those obtained with bleomycin. It was also found that the depleted hematological parameters (red blood count, white blood count and haemoglobin content) were found to be restored gradually towards normal within few weeks after ceasing the treatment.Conclusions:The compounds can be primarily considered more or less as potent anticancer agents.

  6. Palladium complexes of pyrrole-2-aldehyde thiosemicarbazone: Synthesis, structure and spectral properties

    Indian Academy of Sciences (India)

    Piyali Paul; Samaresh Bhattacharya

    2014-09-01

    Reaction of pyrrole-2-aldehyde thiosemicarbazone (abbreviated as H2L, where H2 stands for the two potentially dissociable protons) with [Pd(PPh3)2Cl2] in ethanol in the presence of NEt3 afforded two complexes, [Pd(PPh3)(HLNS)Cl] and [Pd(PPh3)(LNNS)], where the thiosemicarbazone ligand is coordinated to the metal centre respectively as monoanionic N,S-donor (depicted by HLNS) and dianionic N,N,S-donor (depicted by LNNS). Similar reaction with Na2[PdCl4] afforded a bis-complex, [Pd(HLNS)2]. Crystal structures of all the three complexes have been determined.With reference to the structure of the uncoordinated thiosemicarbazone (H2L), the N,S-coordinationmode observed in [Pd(PPh3)(HLNS)Cl] and [Pd(HLNS)2] is associated with a geometrical change around the imine bond.While the N,N,S-mode of binding observed in [Pd(PPh3)(LNNS)] takes place without any such geometrical change. All three complexes display intense absorptions in the visible and ultraviolet regions, which have been analyzed by TDDFT method.

  7. Palladium(II) complexes with thiosemicarbazones: syntheses, characterization and cytotoxicity against breast cancer cells and Anti-Mycobacterium tuberculosis activity

    Energy Technology Data Exchange (ETDEWEB)

    Maia, Pedro I. da S.; Deflon, Victor M., E-mail: deflon@iqsc.usp.b [Universidade de Sao Paulo (USP), Sao Carlos, SP (Brazil). Inst. de Quimica; Graminha, Angelica; Batista, Alzir A. [Universidade Federal de Sao Carlos (UFSCar), SP (Brazil). Dept. de Quimica; Pavan, Fernando R.; Leite, Clarice Q.F. [UNESP, Araraquara, SP (Brazil). Faculdade de Ciencias Farmaceuticas; Back, Davi F.; Lang, Ernesto S. [Universidade Federal de Santa Maria (UFSM), RS (Brazil). Dept. de Quimica; Ellena, Javier [Universidade de Sao Paulo (USP), Sao Carlos, SP (Brazil). Inst. de Fisica; Lemos, Sebastiao de S. [Universidade de Brasilia (UnB), DF (Brazil). Inst. de Quimica; Salistre-de-Araujo, Heloisa S. [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Ciencias Fisiologicas

    2010-07-01

    Three Pd{sup II} complexes were prepared from N(4)-substituted thiosemicarbazones: [Pd(aptsc)(PPh{sub 3})](NO{sub 3}) centre dot H{sub 2}O, 1, [Pd(apmtsc)(PPh{sub 3})](NO{sub 3}), 2, and [Pd(apptsc)(PPh{sub 3})](NO{sub 3}) centre dot H{sub 2}O, 3, where PPh{sub 3} = triphenylphosphine; Haptsc 2-acetylpyridine-thiosemicarbazone; Hapmtsc 2-acetylpyridine-N(4)-methyl-thiosemicarbazone and Happtsc 2-acetylpyridine-N(4)-phenyl-thiosemicarbazone. All complexes were characterized by elemental analysis, IR, UV-Vis, {sup 1}H and {sup 31}P{l_brace}{sup 1}H{r_brace} NMR spectroscopies, and had their crystalline structures determined by X-ray diffractometry from single crystals. The monoanionic thiosemicarbazonate ligands act in a tridentate mode, binding to the metal through the pyridine nitrogen, the azomethine nitrogen and the sulfur atoms. The cytotoxic activity against the breast cancer cell line MDA-MB231 and the anti-Mycobacterium tuberculosis H{sub 37}Rv ATCC 27294 activity were evaluated for the compounds. All Pd{sup II} complexes were highly active against the studied cell line, presenting similar values of IC{sub 50}, around 5 mumol L{sup -1}, while the clinically applied antitumor agent cisplatin was inactive. The compounds show remarkable anti-M. tuberculosis activities, presenting MIC values comparable or better than some commercial anti-M tuberculosis drugs. (author)

  8. Palladium(II) complexes with thiosemicarbazones: syntheses, characterization and cytotoxicity against breast cancer cells and Anti-Mycobacterium tuberculosis activity

    International Nuclear Information System (INIS)

    Three PdII complexes were prepared from N(4)-substituted thiosemicarbazones: [Pd(aptsc)(PPh3)](NO3) · H2O, 1, [Pd(apmtsc)(PPh3)](NO3), 2, and [Pd(apptsc)(PPh3)](NO3) · H2O, 3, where PPh3 = triphenylphosphine; Haptsc 2-acetylpyridine-thiosemicarbazone; Hapmtsc 2-acetylpyridine-N(4)-methyl-thiosemicarbazone and Happtsc 2-acetylpyridine-N(4)-phenyl-thiosemicarbazone. All complexes were characterized by elemental analysis, IR, UV-Vis, 1H and 31P{1H} NMR spectroscopies, and had their crystalline structures determined by X-ray diffractometry from single crystals. The monoanionic thiosemicarbazonate ligands act in a tridentate mode, binding to the metal through the pyridine nitrogen, the azomethine nitrogen and the sulfur atoms. The cytotoxic activity against the breast cancer cell line MDA-MB231 and the anti-Mycobacterium tuberculosis H37Rv ATCC 27294 activity were evaluated for the compounds. All PdII complexes were highly active against the studied cell line, presenting similar values of IC50, around 5 μmol L-1, while the clinically applied antitumor agent cisplatin was inactive. The compounds show remarkable anti-M. tuberculosis activities, presenting MIC values comparable or better than some commercial anti-M tuberculosis drugs. (author)

  9. Zinc(II)-Thiosemicarbazone Complexes Are Localized to the Lysosomal Compartment Where They Transmetallate with Copper Ions to Induce Cytotoxicity.

    Science.gov (United States)

    Stacy, Alexandra E; Palanimuthu, Duraippandi; Bernhardt, Paul V; Kalinowski, Danuta S; Jansson, Patric J; Richardson, Des R

    2016-05-26

    As the di-2-pyridylketone thiosemicarbazone (DpT) and 2-acetylpyridine thiosemicarbazone (ApT) series show potent antitumor activity in vitro and in vivo, we synthesized their fluorescent zinc(II) complexes to assess their intracellular distribution. The Zn(II) complexes generally showed significantly greater cytotoxicity than the thiosemicarbazones alone in several tumor cell-types. Notably, specific structure-activity relationships demonstrated the importance of the di-2-pyridyl pharmacophore in their activity. Confocal fluorescence imaging and live cell microscopy showed that the Zn(II) complex of our lead compound, di-2-pyridylketone 4-cyclohexyl-4-methyl-3-thiosemicarbazone (DpC), which is scheduled to enter clinical trials, was localized to lysosomes. Under lysosomal conditions, the Zn(II) complexes were shown to transmetallate with copper ions, leading to redox-active copper complexes that induced lysosomal membrane permeabilization (LMP) and cytotoxicity. This is the first study to demonstrate direct lysosomal targeting of our novel Zn(II)-thiosemicarbazone complexes that mediate their activity via transmetalation with copper ions and LMP. PMID:27023111

  10. Synthesis of some novel fluoro isoxazolidine and isoxazoline derivatives using -benzyl fluoro nitrone via cycloaddition reaction in ionic liquid

    Indian Academy of Sciences (India)

    Bhaskar Chakraborty; Govinda Prasad Luitel

    2013-09-01

    1-Butyl-3-methylimidazolium-based ionic liquids are found to accelerate significantly the intermolecular 1,3-dipolar cycloaddition of -benzyl-fluoro nitrone derived in situ from 2,6-difluoro benzaldehyde and -benzylhydroxylamine, with activated alkenes and electron deficient alkynes to afford enhanced rates and improved yields of novel isoxazolidines and isoxazolines.

  11. Synthesis of naphthoxazinone derivatives using silica-bonded -sulfonic acid as catalyst under solvent-free conditions

    Indian Academy of Sciences (India)

    Khodabakhsh Niknam; Parisa Abolpour

    2015-07-01

    Silica-bonded -sulfonic acid is employed as a recyclable catalyst for the synthesis of naphthoxazinone derivatives from the reaction of -naphthol, aromatic aldehydes and urea at 150°C under solvent-free conditions. The heterogeneous catalyst was recycled for five runs after the reaction of -naphthol, benzaldehyde and urea without losing its catalytic activity.

  12. Synthesis, characterization and binding affinities of rhenium(I) thiosemicarbazone complexes for the estrogen receptor (α/β).

    Science.gov (United States)

    Núñez-Montenegro, Ara; Carballo, Rosa; Vázquez-López, Ezequiel M

    2014-11-01

    The binding affinities towards estrogen receptors (ERs) α and β of a set of thiosemicarbazone ligands (HL(n)) and their rhenium(I) carbonyl complexes [ReX(HL(n))(CO)3] (X=Cl, Br) were determined by a competitive standard radiometric assay with [(3)H]-estradiol. The ability of the coordinated thiosemicarbazone ligands to undergo deprotonation and the lability of the ReX bond were used as a synthetic strategy to obtain [Re(hpy)(L(n))(CO)3] (hpy=3- or 4-hydroxypyridine). The inclusion of the additional hpy ligand endows the new thiosemicarbazonate complexes with an improved affinity towards the estrogen receptors and, consequently, the values of the inhibition constant (Ki) could be determined for some of them. In general, the values of Ki for both ER subtypes suggest an appreciable selectivity towards ERα. PMID:25061691

  13. On the verification of binding modes of p-dimethylaminobenzaldehyde thiosemicarbazone with mercury(II). The solid state studies

    Science.gov (United States)

    Trzesowska-Kruszynska, Agata

    2014-08-01

    Two coordination compounds of p-dimethylaminobenzaldehyde thiosemicarbazone, fluorescent chemosensor, have been synthesised from the mercury(II) nitrate and mercury(II) chloride, and subsequently characterised by IR spectroscopy, thermal analysis, as well as single crystal X-ray diffraction technique. The inorganic anion has a distinct influence on binding mode of thiosemicarbazone ligand to Hg(II) ion. In both compounds the metal to ligand stoichiometry is 1:2 and the organic ligands coordinate to Hg ion in the neutral thione form, but they differ in a ligand binding mode and the conformation of the ligand. The crystal packing of mercury(II) nitrate complex with thiosemicarbazone is controlled by the mercury chelate ring-phenylene ring π···π stacking interactions.

  14. Inactivation of lambda phage infectivity and lambda deoxyribonucleic acid transfection by N-methyl-isatin beta-thiosemicarbazone-copper complexes.

    Science.gov (United States)

    Levinson, W; Helling, R

    1976-01-01

    The infectivity of intact lambda phage and transfection by lambda deoxyribonucleic acid were inactivated by exposure to the copper complexes of N-methyl-isatin beta-thiosemicarbazone, thiosemicarbazide, and semicarbazide, but not methyl-isatin. No inactivation was observed when these compounds were used in the absence of copper sulfate. This confirms our previous observation that the activity of N-methyl-isatin beta-thiosemicarbazone is mediated by its thiosemicarbazone moiety and that the presence of copper is required for action. This represents the first time, to our knowledge, that semicarbazide has been found to possess antiviral activity. It is clear that these compounds act directly on deoxyribonucleic acid; whether the compounds also act on proteins has not been determined. PMID:769669

  15. Deriving Derivatives

    OpenAIRE

    Soklakov, Andrei N.

    2013-01-01

    Quantitative Structuring is a rigorous framework for the design of financial products. We show how it incorporates traditional investment ideas while supporting a more accurate expression of clients' views on the market. We briefly touch upon adjacent topics regarding the safety of financial derivatives and the role of pricing models in product design.

  16. Ligational behavior of thiosemicarbazone, semicarbazone and thiocarbohydrazone ligands towards VO(IV), Ce(III), Th(IV) and UO 2(VI) ions: Synthesis, structural characterization and biological studies

    Science.gov (United States)

    Shebl, M.; Seleem, H. S.; El-Shetary, B. A.

    2010-01-01

    Mono- and binuclear VO(IV), Ce(III), Th(IV) and UO 2(VI) complexes of thiosemicarbazone, semicarbazone and thiocarbohydrazone ligands derived from 4,6-diacetylresorcinol were synthesized. The structures of these complexes were elucidated by elemental analyses, IR, UV-vis, ESR, 1H NMR and mass spectra as well as conductivity and magnetic susceptibility measurements and thermal analyses. The thiosemicarbazone (H 4L 1) and the semicarbazone (H 4L 2) ligands behave as dibasic pentadentate ligands in case of VO(IV) and UO 2(VI) complexes, tribasic pentadentate in case of Ce(III) complexes and monobasic pentadentate in case of Th(IV) complexes. However, the thiocarbohydrazone ligand (H 3L 3) acts as a monobasic tridentate ligand in all complexes except the VO(IV) complex in which it acts as a dibasic tridentate ligand. The antibacterial and antifungal activities were also tested against Rhizobium bacteria and Fusarium-Oxysporium fungus. The metal complexes of H 4L 1 ligand showed a higher antibacterial effect than the free ligand while the other ligands (H 4L 2 and H 3L 3) showed a higher effect than their metal complexes. The antifungal effect of all metal complexes is lower than the free ligands.

  17. Comparative study of Palladium (II using 4-Hydroxy 3, 5 dimethoxy benzaldehyde 4-hydroxy benzoyl hydrazone and Cinnamaldehyde 4-hydroxy benzoylhydrazone in presence of micellar medium by Spectrophotometry

    Directory of Open Access Journals (Sweden)

    D.Gopala Krishna,

    2010-09-01

    Full Text Available Two simple, sensitive, rapid and selective spectrophotometric methods have been developed for the determination of Palladium (II using newly synthesized reagents 4-Hdroxy3,5dimethoxy benzaldehyde-4-hydroxybenzoylhydrazone (HDMBHBH and Cinnamaldehyde 4-hydroxy benzoylhydrazone (CMHBH in presence of neutral surfactant TritonX-100-5% (micellar medium. Palladium (II forms a brown coluored water-soluble complex with HDMBHBH and CMHBH-in the pH range 1.0-6.0. The Pd (II-HDMBHBH complex shows maximum absorbance at max 373 nm in the pH range 3.0-4.0 and Pd (II-CMHBH shows at max 375 nm in thepH range 4.0-5.0. At these wavelengths (max, the complex shows maximum absorbance while the reagent blanks shows negligible absorbance. Hence, analytical studies were carried out at max 373 nm at pH 3.0 for HDMBHBH and 375 nm at pH 4.0 for CMHBH against reagent blanks. Beer's law is obeyed in the range 0.106-1.064 μg ml-1 and the optimum concentration range from ringbom plot is 0.212-0.957 g/ml of Palladium (II for both reagents. The molar absorptivity and Sandell's sensitivity for the coloured solution were found to be 7.5 x 104 L mol-1 cm-1 and 0.0015-μg. cm-2 for HDMBHBH, 6.0x104L mol-1 cm-1 , and 0.0017 -μg. cm-2 for CMHBH respectively. The interference effects of various diverse ions have been studied. Palladium (II forms 1:1 complex with HDMBHBH and CMHBH stoichiometry with stability constant 7.29 x 106 for HDMBHBH and 3.55 x 106 for CMHBH. The standard deviation in the determination of 0.638-μg ml-1 of Palladium (II is 0.003 for HDMBHBH and 0.008 for CMHBH. The Relative standard deviation is 0.71% for HDMBHBH and 2.5% for CMHBH. First and second order derivative spectroscopic methods were developed at max 422 nm and 444 nm for HDMBHBH and at 402 nm and438 nm for CMHBH respectively, for the determination of Palladium (II, which is more sensitive than the zero order method. The developed method has been employed for the determination of

  18. Strong effect of copper(II) coordination on antiproliferative activity of thiosemicarbazone-piperazine and thiosemicarbazone-morpholine hybrids.

    Science.gov (United States)

    Bacher, Felix; Dömötör, Orsolya; Chugunova, Anastasia; Nagy, Nóra V; Filipović, Lana; Radulović, Siniša; Enyedy, Éva A; Arion, Vladimir B

    2015-05-21

    In this study, 2-formylpyridine thiosemicarbazones and three different heterocyclic pharmacophores were combined to prepare thiosemicarbazone–piperazine mPip-FTSC (HL1) and mPip-dm-FTSC (HL2), thiosemicarbazone–morpholine Morph-FTSC (HL3) and Morph-dm-FTSC (HL4), thiosemicarbazone–methylpyrrole-2-carboxylate hybrids mPyrr-FTSC (HL5) and mPyrr-dm-FTSC (HL6) as well as their copper(II) complexes [CuCl(mPipH-FTSC-H)]Cl (1 + H)Cl, [CuCl(mPipH-dm-FTSC-H)]Cl (2 + H)Cl, [CuCl(Morph-FTSC-H)] (3), [CuCl(Morph-dm-FTSC-H)] (4), [CuCl(mPyrr-FTSC-H)(H2O)] (5) and [CuCl(mPyrr-dm-FTSC-H)(H2O)] (6). The substances were characterized by elemental analysis, one- and two-dimensional NMR spectroscopy (HL1–HL6), ESI mass spectrometry, IR and UV–vis spectroscopy and single crystal X-ray diffraction (1–5). All compounds were prepared in an effort to generate potential antitumor agents with an improved therapeutic index. In addition, the effect of structural alterations with organic hybrids on aqueous solubility and copper(II) coordination ability was investigated. Complexation of ligands HL2 and HL4 with copper(II) was studied in aqueous solution by pH-potentiometry, UV–vis spectrophotometry and EPR spectroscopy. Proton dissociation processes of HL2 and HL4 were also characterized in detail and microscopic constants for the Z/E isomers were determined. While the hybrids HL5, HL6 and their copper(II) complexes 5 and 6 proved to be insoluble in aqueous solution, precluding antiproliferative activity studies, the thiosemicarbazone–piperazine and thiosemicarbazone–morpholine hybrids HL1–HL4, as well as copper(II) complexes 1–4 were soluble in water enabling cytotoxicity assays. Interestingly, the metal-free hybrids showed very low or even a lack of cytotoxicity (IC50 values > 300 μM) in two human cancer cell lines HeLa (cervical carcinoma) and A549 (alveolar basal adenocarcinoma), whereas their copper(II) complexes were cytotoxic showing IC50 values from 25.5 to 65.1

  19. Synthesis of 5-,6-, and 7-membered heterocycles from barbituric acid derivatives

    OpenAIRE

    Guyader, David

    2011-01-01

    SUMMARY A new procedure has been developed for the synthesis of barbituric acid derivatives. The reactions were performed under solvent free conditions without any catalyst. Employing this synthetic route, a large number of chalconoids and 5-,6-, and 7-membered heterocycles have been successfully synthesized in a very short time. The chalconoids have been synthesized from a barbituric derivative and substituted benzaldehydes. The effect of different substituents on the yield of the re...

  20. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONE DERIVATIVES AND THEIR COPPERCOMPLEXES

    OpenAIRE

    P. M. Rachmale

    2012-01-01

    In the present investigation, 4-chloro acetophenone on condensation with 2-nitro benzaldehydes in methanolic NaOH solution yielded the corresponding chalcone. These chalcone were further reacted with Isonicotyl hydrazide and semicarbazide in ethanol which led to the formation of chalcone Isonicotyl hydrazone and chalcone semicarbazone derivatives respectively. The newly synthesized derivatives and there copper complexes were characterized on the basis of their chemical properties and spect...

  1. Gas Phase Selective Catalytic Oxidation of Toluene to Benzaldehyde on V2O5-Ag2O/η-Al2O3 Catalyst

    Institute of Scientific and Technical Information of China (English)

    Tonglai Zhang; Liqiu Mao; Weihua Liu

    2004-01-01

    Gas phase selective catalytic oxidation of toluene to benzaldehyde was studied on V2O5-Ag2O/η-Al2O3 catalyst prepared by impregnation. The catalyst was characterized by XRD, XPS, TEM,and FT-IR. The catalytic results showed that toluene conversion and selectivity for benzaldehyde on catalyst sample No.4 (V/(V+Ag)=0.68) was higher than other catalysts with different V/Ag ratios. This was attributed to the higher surface area, larger pore volume and pore diameter of the catalyst sample No.4 than the other catalysts. The XRD patterns recorded from the catalyst before and after the oxidation reaction revealed that the new phases were developed, and this suggested that silver had entered the vanadium lattice. XPS results showed that the vanadium on the surface of No.4 and No.5 sample was more than that in the bulk, thus forming a vanadium rich layer on the surface. It was noted that when the catalyst was doped by potassium promoter, the toluene conversion and selectivity for benzaldehyde were higher than those on the undoped catalyst. This was attributed to the disordered structure of V2O5 lattice of the K-doped catalyst and a better interfacial contact between the particles.

  2. A nanoporous 3D zinc(II) metal-organic framework for selective absorption of benzaldehyde and formaldehyde

    Science.gov (United States)

    Moradpour, Tahereh; Abbasi, Alireza; Van Hecke, Kristof

    2015-08-01

    A new 3D nanoporous metal-organic framework (MOF), [[Zn4O(C24H15N6O6)2(H2O)2]·6H2O·DMF]n (1) based on 4,4‧,4″-s-triazine-1,3,5-triyltri-p-aminobenzoate (TATAB) ligand was solvothermally synthesized and characterized by single-crystal X-ray diffraction, Powder X-ray diffraction (PXRD), infrared spectroscopy (IR) and Brunauer-Emmett-Teller (BET) analyses. X-ray single crystal diffraction analysis reveals that 1 exhibits a 3D network with new kvh1 topology. Semi-empirical (AM1) calculations were carried out to obtain stable conformers for TATAB ligand. In addition, the absorption of two typical aldehydes (benzaldehyde and formaldehyde) in the presence of 1 was investigated and the effect of the aldehyde concentration, exposure time and temperature was studied. It was found that compound 1 has a potential for the absorption of aldehydes under mild conditions.

  3. Growth and characterization of benzaldehyde 4-nitro phenyl hydrazone (BPH) single crystal: A proficient second order nonlinear optical material

    Science.gov (United States)

    Saravanan, M.; Abraham Rajasekar, S.

    2016-04-01

    The crystals (benzaldehyde 4-nitro phenyl hydrazone (BPH)) appropriate for NLO appliance were grown by the slow cooling method. The solubility and metastable zone width measurement of BPH specimen was studied. The material crystallizes in the monoclinic crystal system with noncentrosymmetric space group of Cc. The optical precision in the whole visible region was found to be excellent for non-linear optical claim. Excellence of the grown crystal is ascertained by the HRXRD and etching studies. Laser Damage Threshold and Photoluminescence studies designate that the grown crystal contains less imperfection. The mechanical behaviour of BPH sample at different temperatures was investigated to determine the hardness stability of the grown specimen. The piezoelectric temperament and the relative Second Harmonic Generation (for diverse particle sizes) of the material were also studied. The dielectric studies were executed at varied temperatures and frequencies to investigate the electrical properties. Photoconductivity measurement enumerates consummate of inducing dipoles due to strong incident radiation and also divulge the nonlinear behaviour of the material. The third order nonlinear optical properties of BPH crystals were deliberate by Z-scan method.

  4. Synthesis molecular modeling and anticonvulsant activity of some hydrazone, semicarbazone, and thiosemicarbazone derivatives of benzylidene camphor

    OpenAIRE

    Agrawal, Saurabh

    2014-01-01

    Saurabh Agrawal,1 Jainendra Jain,2 Ankit Kumar,3 Pratibha Gupta,4 Vikas Garg5 1Meerut Institute of Engineering and Technology, Meerut, Uttar Pradesh, India; 2Ram–Eesh Institute of Vocational and Technical Education, Greater Noida, Uttar Pradesh, India; 3Kharvel Subharti College of Pharmacy, Swami Vivekanand Subharti University, Meerut, Uttar Pradesh, India; 4Atarra Degree College, Atarra, Banda, India; 5Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, Karnata...

  5. Synthesis and Crystal Structural Characterization of a Thiosemicarbazone Derived from 4-Acylpyrazolone

    Institute of Scientific and Technical Information of China (English)

    LIU Guang-Fei; LIU Lang; HU Xin; JIA Dian-Zeng; YU Kai-Bei

    2006-01-01

    The reaction of 4-(p-fluobenzoyl)-2,5-dihydro-3-methyl-1-phenyl pyrazol-5-one with thiosemicarbazide in MeOH followed by recrystallization in EtOH gave rise to yellowish lamellar crystals of 4(p-fluo-α-aminothiocarbonyl hydrazonobenzal)-2,5-dihydro-3-methyl- 1 -phenyl pyrazol-5-one 1. It crystallizes in orthorhombic, space group Pbca with a = 18.445(4), b = 11.987(2),c = 19.249(4) (A), V= 4256.1(18) (A)3, Z = 8, Mr = 415.49, Dc= 1.297 g/cm3, T= 296(2) K, F(000) =1744, μ(MoKα) = 0.186 cm-1, R = 0.0521 and wR = 0.1211 for 1661 observed reflections with I >2σ(I). The compound was structurally characterized by elemental analyses, IR and 1H NMR. The intermolecular hydrogen bonds are present and a two-dimensional framework is formed by two intermolecular hydrogen bonds in the (001) plane.

  6. New Thiosemicarbazone and Talinum triangulare Vegetal Extract Formulations with Potential Anti-corrosion Activity [Novas Formulações de Tiossemicarbazonas e Extrato Vegetal de Talinum triangulare com Potencial Atividade Anticorrosão

    Directory of Open Access Journals (Sweden)

    Mariana A . de Albuquerque

    2013-06-01

    Full Text Available Corrosion is a process arising out of a chemical action of the environment on a particular material, causing its deterioration. It may occur in metals, concrete, organic polymers, and others. A promising alternative to prevent corrosion is the use of organic inhibitors. The search for new agents or formulations that enable the diminishing of corrosion effects is evidently necessary; therefore, this work evaluated 3 new formulations which contained thiosemicarbazones 4-hydroxy,3-methoxybenzaldehyde-thiosemicarbazone, 4-ethoxybenzaldehyde-thiosemicarbazone and 4-hydroxybenzaldehyde-thiosemicarbazone with the crude extract of Talinum triangulareleaves in ethyl acetate, aiming at the Fe2+ ion chelation for an anticorrosive action. UV-Vis spectroscopy was used to evaluate the formation of Fe2+ ion complexes; also, to determine the respective coordination numbers with the thiosemicarbazones. Results indicated the increase of the thiosemicarbazone anticorrosive action, which had been evaluated by molecular modeling and potentiodynamic polarization, when there were crude extract of T. triangulareleaves in the formulation.

  7. 1-Pyrenecarboxaldehyde thiosemicarbazone:A novel fluorescent molecular sensor towards mercury(Ⅱ)ion

    Institute of Scientific and Technical Information of China (English)

    Xue Mei Wang; Hua Yan; Xin Lu Feng; Yong Chen

    2010-01-01

    A novel and simple fluorescent molecular sensor,1-pyrenecarboxaldehyde thiosemicarbazone(Hpytsc),was synthesized.Its higher sensitivity and selectivity to mercury(Ⅱ)ion were studied through absorption and emission channels.The UV-vis spectra show that the increasing mercury(Ⅱ)ion concentrations result in the decreasing absorption intensity.The fluorescence monomer emission of Hpytsc is enhanced upon binding mercury(Ⅱ)ion,which should be due to the 1:1 complex formation between Hpytsc and metal ion.

  8. Novel rhenium(V) complexes with thiosemicarbazones of pyruvic or phenylglyoxylic acids

    International Nuclear Information System (INIS)

    New rhenium(V) complexes with thiosemicarbazones of pyruvic (L') or phenylglyoxylic (L'') acids were synthesized and isolated in solid state in aqueous solutions of concentrated hydrohalic acids. By the method of elementary analysis formation of complexes, featuring the following composition [ReOL'Cl3]·2H2O, [ReOL''2Br]Br2·2H2O, [ReOL'Br2(OH)]·2H2O, [ReOL''2(OH)]Cl·2H2O, [Re2O3L'2Cl4]·2H2O, was ascertained. Solubility of the complexes in organic solvents was determined

  9. Solvent extraction of silver(I) from dilute cyanide solutions with 2,4-dihydroxyacetophenone thiosemicarbazone

    International Nuclear Information System (INIS)

    The solvent extraction of silver(I) was carried out in 0.5M nitric acid in the presence of cyanide by 2,4-dihydroxyacetophenone thiosemicarbazone (DATS). Ethyl acetate was used as a solvent and quantitative recovery was possible with 12.5-fold excess of the reagent in a single extraction. In this medium silver(I) forms a 2:2 complex (metal:ligand) with DATS. The effect of diverse ions on the extraction of silver(I) was investigated. (author)

  10. Coordination compounds of titanium(4), zirconium and hafnium(4) with acetone thiosemicarbazone

    International Nuclear Information System (INIS)

    Adducts of titanium, zirconium and hafnium tetrachlorides with acetone thiosemicarbazone of 1:1 composition are synthesized from ethyl acetate solutions. It is shown on the base of studying infrared spectra that the ligand is coordinated to titanium, zirconium and hafnium bidentately via atoms of sulphur and azomething nitrogen. Heats of ligands and adducts dissolution in 4N- muriatic acid at 298 K are determined by calorimetry. Heats of gaseous ligand addition to the mole of tetrachloride calculated according to Haber cycle on the base of the conducted measurements are localized in the series Ti > Hf > Zr

  11. Spectrophotometric Determination of Arsenic in Water Samples by Thiophene-2-Carboxaldehyde Thiosemicarbazone impregnated with alumina

    OpenAIRE

    Md. Faridur Rahman; Aniruddha Chakraborty; Tanmoy Das

    2015-01-01

    Thiophene-2-carboxaldehyde thiosemicarbazone has been successfully applied as an analytical reagent for micro level solid phase spectrophotometric determination of As (III) at pH 3.5. Here it can be seen that arsenic reacts with the new chelating ligand in acidic medium to form the As (III)-tctsc complex. The complex showed maximum absorbance at λ max 281 nm for As (III) ions. The Beer’s law range was 0.1-1.0 mg/L. Job’s method and Mole-ratio method showed that As (III)-ligand ratio in the co...

  12. Study on the Interaction between Isatin-β-Thiosemicarbazone and Calf Thymus DNA by Spectroscopic Techniques

    OpenAIRE

    Pakravan, Parvaneh; Masoudian, Shahla

    2015-01-01

    The interaction between isatin-β-thiosemicarbazone (IBT) and calf thymus DNA (CT-DNA) was investigated in physiological buffer (pH 7.4) using Neutral Red (NR) dye as a spectral probe by UV–Vis absorption and fluorescence spectroscopy, as well as viscosity measurements. The IBT is stabilized by intercalation in the DNA (K [IBT –DNA] = 1.03×105 M−1), and displaces the NR dye from the NR–DNA complex. The binding constants Kf and number of binding sites (n≈1) of IBT with DNA were obtained by fluor...

  13. Discovery of trypanocidal thiosemicarbazone inhibitors of rhodesain and TbcatB

    Science.gov (United States)

    Mallari, Jeremy P.; Shelat, Anang; Kosinski, Aaron; Caffrey, Conor R.; Connelly, Michele; Zhu, Fangyi; McKerrow, James H.; Guy, R. Kiplin

    2008-01-01

    Human African trypanosomiasis (HAT) is caused by the protozoan parasite Trypanosoma brucei. The cysteine proteases of T.brucei have been shown to be crucial for parasite replication and represent an attractive point for therapeutic intervention. Herein we describe the synthesis of a series of thiosemicarbazones and their activity against the trypanosomal cathepsins TbcatB and rhodesain, as well as human cathepsins L and B. The activity of these compounds was determined against cultured T.brucei, and specificity was assessed with a panel of four mammalian cell lines. PMID:18420405

  14. Solvent extraction of silver(I) with 2,4-dihydroxy-acetophenone thiosemicarbazone

    International Nuclear Information System (INIS)

    The solvent extraction of silver(I) is carried out in acetic acid-sodium acetate buffer solution at pH 5.0 by 2,4-dihydroxyacetophenone thiosemicarbazone (DATS). Ethyl acetate was used as a solvent. It is found that single extraction is sufficient to remove silver(I) completely from the aqueous phase. Silver(I) forms 1:1 complex (metal:reagent) with DATS. The effect of diverse ions on the extraction of silver(I) was investigated. (author)

  15. Bis(pyridine-2-carbaldehyde thiosemicarbazone)zinc(II) dinitrate dihydrate

    OpenAIRE

    Jian-Quan Wang; Li-Min Zhang; Lin Cheng

    2010-01-01

    The asymmetric unit of the title compound, [Zn(C7H8N4S)2](NO3)2·2H2O, contains two Zn(pht)2 cations (pht is pyridine-2-carbaldehyde thiosemicarbazone), four nitrate anions and four water molecules. In the cations, each ZnII ion adopts a distorted octahedral coordination geometry, being chelated by two tridentate pht ligands. In the crystal, the cations, anions and water molecules are connected via O—H...O and N—H...O hydrogen bonds into a three-dimensional network.

  16. Crystal structures of crotonaldehyde semicarbazone and crotonaldehyde thiosemicarbazone from X-ray powder diffraction data

    OpenAIRE

    Atef Arfan; Mwaffak Rukiah

    2015-01-01

    Crotonaldehyde semicarbazone {systematic name: (E)-2-[(E)-but-2-en-1-ylidene]hydrazinecarboxamide}, C5H9N3O, (I), and crotonaldehyde thiosemicarbazone {systematic name: (E)-2-[(E)-but-2-en-1-yldene]hydrazinecarbothioamide}, C5H9N3S, (II), show the same E conformation around the imine C=N bond. Compounds (I) and (II) were obtained by the condensation of crotonaldehyde with semicarbazide hydrochloride and thiosemicarbazide, respectively. Each molecule has an intramolecular N—H...N hydrogen bond...

  17. EXTRACTIVE SPECTROPHOTOMETRIC STUDIES OF ACETOPHENONE 2’, 4’-DIHYDROXY THIOSEMICARBAZONE WITH IRON

    OpenAIRE

    P. K. Rana; R. S. Lokhande; S. M. Pitale; S.P. Janwadkar; P. S. Navarkar; D K Yadav

    2012-01-01

    Acetophenone 2’, 4’-Dihydroxy thiosemicarbazone (APDHTS) as a reagent for the extractive spectrophotometric determination of Iron. The reagent APDHTS gave instantaneous and stable violet colour with Iron at pH 5.0. A linear calibration graph over the concentration range 1 ppm to 10 ppm with a 3σ limit of detection of 0.66 ppm was obtained by applying the spectrophotometric method at wavelength 370 nm. The stoichiometry of the complex is established as 1:1 (M: L) by Job’s method of continuous ...

  18. Synthesis, Spectroscopic, and Antimicrobial Studies on Bivalent Zinc and Mercury Complexes of 2-Formylpyridine Thiosemicarbazone

    OpenAIRE

    Yatendra Kumar; Shikha Parmar; Sulekh Chandra

    2009-01-01

    A series of metal complexes of Zn(II) and Hg(II) having the general composition [ M ( L ) 2 ] X 2 [where L = 2-formylpyridine thiosemicarbazone; M = Zn(II) and Hg(II); X = C l − , N O − 3 and 1 / 2 S O 4 2 − ] have been prepared and characterized by elemental chemical analysis, molar conductance, and spectral (IR and mass) studies. The IR spectral data suggests the involvement of sulphur and azomethane nitrogen in coordination to the central metal ion. On the basis of spectral studies, a tetr...

  19. Metal complexes with paramagnetic thiosemicarbazone. [Complexes of Ni,Fe,Zn,Cd,Pd,Pt

    Energy Technology Data Exchange (ETDEWEB)

    Ovcharenko, V.I.; Larionov, S.V. (AN SSSR, Novosibirsk. Inst. Neorganicheskoj Khimii)

    1981-10-01

    The complexes of Ni(2), Fe(2), Zn(2), Cd(2), Pd(2) and Pt(2) with the stable nitroxyl radical of thiosemicarbazone 4-formyl- 2, 2, 5, 5-tetramethyl-3-imidazoline-1-oxyl of the composition ML/sub 2/ are synthesized. In the basis of the data of physical methods (IR, EPR, electron spectroscopy) a conclusion is made on the way of the ligand coordination. The study of the magnetic properties of the complexes has shown that in the compounds prepared a weak exchange interaction between unpaired electrons of paramagnetic centres takes place.

  20. Solvent extraction of silver(I) with 2,4-dihydroxy-acetophenone thiosemicarbazone

    Energy Technology Data Exchange (ETDEWEB)

    Reddy, A.V.; Reddy, Y.K. (Sri Venkateswara Univ., Tirupati (India). Dept. of Chemistry); Reddy, G.S. (Sri Venkateswara Univ. Post-Graduate Centre, Cuddapah (India). Dept. of Chemistry)

    1985-03-01

    The solvent extraction of silver(I) is carried out in acetic acid-sodium acetate buffer solution at pH 5.0 by 2,4-dihydroxyacetophenone thiosemicarbazone (DATS). Ethyl acetate was used as a solvent. It is found that single extraction is sufficient to remove silver(I) completely from the aqueous phase. Silver(I) forms 1:1 complex (metal:reagent) with DATS. The effect of diverse ions on the extraction of silver(I) was investigated.

  1. Coordination Chemistry of Polyaromatic Thiosemicarbazones 2: Synthesis and Biological Activity of Zinc, Cobalt, and Copper Complexes of 1-(Naphthalene-2-ylethanone Thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Marc-Andre LeBlanc

    2011-01-01

    Full Text Available A novel thiosemicarbazone from 2-acetonaphthone (represented as acnTSC has been synthesized and its basic coordination chemistry with zinc(II, cobalt(II, and copper(II explored. The complexes were characterized by elemental analysis and various spectroscopic techniques and are best formulated as [M(acnTSC2Cl2] with the metal likely in an octahedral environment. The anticancer activity of the complexes was determined against a panel of human colon cancer cells (HCT-116 and Caco-2. The compounds bind to DNA via an intercalative mode with binding constants of 9.7×104 M-1, 1.8×105 M-1, and 9.5×104 M-1 for the zinc, cobalt, and copper complexes, respectively.

  2. Coordination Chemistry of Polyaromatic Thiosemicarbazones 2: Synthesis and Biological Activity of Zinc, Cobalt, and Copper Complexes of 1-(Naphthalene-2-yl)ethanone Thiosemicarbazone

    Science.gov (United States)

    LeBlanc, Marc-Andre; Gonzalez-Sarrías, Antonio; Beckford, Floyd A.; Mbarushimana, P. Canisius; Seeram, Navindra P.

    2012-01-01

    A novel thiosemicarbazone from 2-acetonaphthone (represented as acnTSC) has been synthesized and its basic coordination chemistry with zinc(II), cobalt(II), and copper(II) explored. The complexes were characterized by elemental analysis and various spectroscopic techniques and are best formulated as [M(acnTSC)2Cl2] with the metal likely in an octahedral environment. The anticancer activity of the complexes was determined against a panel of human colon cancer cells (HCT-116 and Caco-2). The compounds bind to DNA via an intercalative mode with binding constants of 9.7 × 104 M−1, 1.8 × 105 M−1, and 9.5 × 104 M−1 for the zinc, cobalt, and copper complexes, respectively. PMID:22303515

  3. Redox activation of Fe(III)-thiosemicarbazones and Fe(III)-bleomycin by thioredoxin reductase: specificity of enzymatic redox centers and analysis of reactive species formation by ESR spin trapping

    OpenAIRE

    Myers, Judith M.; Cheng, Qing; Antholine, William E.; Kalyanaraman, Balaraman; Filipovska, Aleksandra; Arnér, ArnerElias S.J.; Myers, Charles R.

    2013-01-01

    Thiosemicarbazones such as triapine (Tp) and Dp44mT are tridentate iron (Fe) chelators that have well-documented anti-neoplastic activity. While Fe-thiosemicarbazones can undergo redox-cycling to generate reactive species that may have important roles in their cytotoxicity, there is only limited insight into specific cellular agents that can rapidly reduce Fe(III)-thiosemicarbazones and thereby promote their redox activity. Here we report that thioredoxin reductase-1 (TrxR1) and glutathione r...

  4. Syntheses and spectroscopic studies on zinc(II) and mercury(II) complexes of isatin-3-thiosemicarbazone

    Science.gov (United States)

    Akinchan, N. T.; Drożdżewski, P. M.; Holzer, W.

    2002-10-01

    Zinc(II) and mercury(II) complexes were prepared by reacting isatin-3-thiosemicarbazone (ISTSCH) with zinc(II) acetate or mercury(II) bromide. The complexes were characterized by IR, Raman, diffuse reflectance, 1H and 13C NMR spectra and elemental analysis. Tetrahedral structures for Zn(ISTSC) 2 and Hg(ISTSCH)Br 2 are suggested.

  5. Microwave-assisted synthesis of new N4-[bi-(4-fluorophenyl)-methyl]-piperazine thiosemicarbazones under solvent-free conditions

    Institute of Scientific and Technical Information of China (English)

    Qing Han Li; Zhi Gang Zhao

    2008-01-01

    Six new N4-[bi-(4-fluorophenyl)-methyl]-piperazine thiosemicarbazones 3a-f have been prepared starting from [bi-(4-fluor-ophenyl)-methyl]-piperazine in solvent-free condition under microwave irradiation with excellent yields. Their structures have been determined by elemental analysis, IR, MS and 1H NMR data.

  6. Crystal structure of copper(I) thiosemicarbazone complex [CuI(PPh.sub.3./sub.)(catsc)

    Czech Academy of Sciences Publication Activity Database

    Shahsavani, E.; Feizi, N.; Eigner, Václav; Dušek, Michal; Khalaji, A.D.

    2015-01-01

    Roč. 56, č. 5 (2015), s. 1003-1007. ISSN 0022-4766 R&D Projects: GA ČR GA15-12653S Institutional support: RVO:68378271 Keywords : copper (I) * thiosemicarbazone * crystal structure * single crystal Subject RIV: BM - Solid Matter Physics ; Magnetism Impact factor: 0.508, year: 2014

  7. Increased generation of intracellular reactive oxygen species initiates selective cytotoxicity against the MCF-7 cell line resultant from redox active combination therapy using copper-thiosemicarbazone complexes.

    Science.gov (United States)

    Akladios, Fady N; Andrew, Scott D; Parkinson, Christopher J

    2016-06-01

    The combination of cytotoxic copper-thiosemicarbazone complexes with phenoxazines results in an up to 50-fold enhancement in the cytotoxic potential of the thiosemicarbazone against the MCF-7 human breast adenocarcinoma cell line over the effect attributable to drug additivity-allowing minimization of the more toxic copper-thiosemicarbazone component of the therapy. The combination of a benzophenoxazine with all classes of copper complex examined in this study proved more effective than combinations of the copper complexes with related isoelectronic azines. The combination approach results in rapid elevation of intracellular reactive oxygen levels followed by apoptotic cell death. Normal fibroblasts representative of non-cancerous cells (MRC-5) did not display a similar elevation of reactive oxygen levels when exposed to similar drug levels. The minimization of the copper-thiosemicarbazone component of the therapy results in an enhanced safety profile against normal fibroblasts. PMID:26951232

  8. Anti-Plasmodial Activity of Aroylhydrazone and Thiosemicarbazone Iron Chelators: Effect on Erythrocyte Membrane Integrity, Parasite Development and the Intracellular Labile Iron Pool

    OpenAIRE

    Walcourt, Asikiya; Kurantsin-Mills, Joseph; Kwagyan, John; Adenuga, Babafemi B.; Kalinowski, Danuta S.; Lovejoy, David B.; Lane, Darius J.R.; Richardson, Des R.

    2013-01-01

    Iron chelators inhibit the growth of the malaria parasite, Plasmodium falciparum, in culture and in animal and human studies. We previously reported the anti-plasmodial activity of the chelators, 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone (311), 2-hydroxy-1-naphthylaldehyde 4-methyl-3-thiosemicarbazone (N4mT), and 2-hydroxy-1-naphthylaldehyde 4-phenyl-3-thiosemicarbazone (N4pT). In fact, these ligands showed greater growth inhibition of chloroquine-sensitive (3D7) and chloroquine-re...

  9. Examination of the Impact of Copper(II) α-(N)-Heterocyclic Thiosemicarbazone Complexes on DNA Topoisomerase IIα.

    Science.gov (United States)

    Wilson, James T; Jiang, Xiaohua; McGill, Bradley C; Lisic, Edward C; Deweese, Joseph E

    2016-04-18

    Type II DNA topoisomerases resolve topological knots and tangles in DNA that result from routine cellular processes and are effective targets for anticancer therapeutics. To this end, thiosemicarbazones have been identified as having the ability to kill cancer cells from several cell lines. Literature evidence suggests that at least some thiosemicarbazones have an impact on topoisomerase II activity. However, the mechanism is not as clearly defined. Therefore, we set out to analyze the activity of four α-(N)-heterocyclic thiosemicarbazone compounds against topoisomerase IIα. The ligands, acetylpyridine-ethylthiosemicarbazone (APY-ETSC) and acetylpyrazine-methylthiosemicarbazone (APZ-MTSC), and their copper(II) [Cu(II)] complexes [Cu(APY-ETSC)Cl] and [Cu(APZ-MTSC)Cl] were examined for the ability to impact the catalytic cycle of human topoisomerase IIα. Both [Cu(APY-ETSC)Cl] and [Cu(APZ-MTSC)Cl] were more effective at inhibiting DNA relaxation compared with the ligands alone. Further, both [Cu(APY-ETSC)Cl] and [Cu(APZ-MTSC)Cl] increased double-stranded DNA cleavage levels without inhibiting topoisomerase IIα-mediated DNA ligation. The Cu(II) complexes inactivate enzyme activity over time suggesting a critical interaction with the enzyme. Additionally, we found that the Cu(II)-thiosemicarbazone complexes do not significantly impact DNA cleavage by the catalytic core of the enzyme. This evidence is supported by the fact that both [Cu(APY-ETSC)Cl] and [Cu(APZ-MTSC)Cl], and to a lesser extent the ligands, inhibit topoisomerase IIα-mediated ATP hydrolysis. Based upon kinetic analysis, the Cu(II) complexes appear to be noncompetitive inhibitors of the ATPase domain of topoisomerase IIα. Taken together, our results provide evidence that Cu(II) complexes of α-(N)-heterocyclic thiosemicarbazones catalytically inhibit the enzyme through the ATPase domain but also promote double-stranded DNA cleavage by the enzyme. PMID:26982206

  10. Identification of differential anti-neoplastic activity of copper bis(thiosemicarbazones) that is mediated by intracellular reactive oxygen species generation and lysosomal membrane permeabilization.

    Science.gov (United States)

    Stefani, Christian; Al-Eisawi, Zaynab; Jansson, Patric J; Kalinowski, Danuta S; Richardson, Des R

    2015-11-01

    Bis(thiosemicarbazones) and their copper (Cu) complexes possess unique anti-neoplastic properties. However, their mechanism of action remains unclear. We examined the structure-activity relationships of twelve bis(thiosemicarbazones) to elucidate factors regarding their anti-cancer efficacy. Importantly, the alkyl substitutions at the diimine position of the ligand backbone resulted in two distinct groups, namely, unsubstituted/monosubstituted and disubstituted bis(thiosemicarbazones). This alkyl substitution pattern governed their: (1) Cu(II/I) redox potentials; (2) ability to induce cellular (64)Cu release; (3) lipophilicity; and (4) anti-proliferative activity. The potent anti-cancer Cu complex of the unsubstituted bis(thiosemicarbazone) analog, glyoxal bis(4-methyl-3-thiosemicarbazone) (GTSM), generated intracellular reactive oxygen species (ROS), which was attenuated by Cu sequestration by a non-toxic Cu chelator, tetrathiomolybdate, and the anti-oxidant, N-acetyl-l-cysteine. Fluorescence microscopy suggested that the anti-cancer activity of Cu(GTSM) was due, in part, to lysosomal membrane permeabilization (LMP). For the first time, this investigation highlights the role of ROS and LMP in the anti-cancer activity of bis(thiosemicarbazones). PMID:26335599

  11. Mononuclear ruthenium(III) complexes containing chelating thiosemicarbazones: Synthesis, characterization and catalytic property

    Science.gov (United States)

    Raja, N.; Ramesh, R.

    2010-02-01

    Mononuclear ruthenium(III) complexes of the type [RuX(EPh 3) 2(L)] (E = P or As; X = Cl or Br; L = dibasic terdentate dehydroacetic acid thiosemicarbazones) have been synthesized from the reaction of thiosemicarbazone ligands with ruthenium(III) precursors, [RuX 3(EPh 3) 3] (where E = P, X = Cl; E = As, X = Cl or Br) and [RuBr 3(PPh 3) 2(CH 3OH)] in benzene. The compositions of the complexes have been established by elemental analysis, magnetic susceptibility measurement, FT-IR, UV-vis and EPR spectral data. These complexes are paramagnetic and show intense d-d and charge transfer transitions in dichloromethane. The complexes show rhombic EPR spectra at LNT which are typical of low-spin distorted octahedral ruthenium(III) species. All the complexes are redox active and display an irreversible metal centered redox processes. Complex [RuCl(PPh 3) 2(DHA-PTSC)] ( 5) was used as catalyst for transfer hydrogenation of ketones in the presence of isopropanol/KOH and was found to be the active species.

  12. Spectral characterization of iron(III) complexes of 2-benzoylpyridine N(4)-substituted thiosemicarbazones

    Science.gov (United States)

    Joseph, Marthakutty; Sreekanth, Anandaram; Suni, V.; Kurup, M. R. Prathapachandra

    2006-06-01

    Three iron(III) complexes (1-3) of 2-benzoylpyridine N(4)-phenyl thiosemicarbazone (HL 1) and one iron(III) complex (4) of 2-benzoylpyridine N(4)-cyclohexyl thiosemicarbazone (HL 2) were synthesized and characterized by means of different physicochemical techniques viz., molar conductivity measurements, magnetic susceptibility studies and electronic, infrared and EPR spectral studies. The analytical data and the molar conductance measurements of the complexes reveal that two molecules of the ligand and the anion are coordinated to the metal atom in all the four complexes. The magnetic moments of the complexes suggest that they are of low spin. From the infrared spectra of the ligands and the complexes it is confirmed that the ligands coordinate to iron(III) as an anion coordinating via the azomethine nitrogen, pyridyl nitrogen, and the thiolate sulphur. The EPR spectra of the complexes in the polycrystalline state at 298 and 110 K and in DMF solution at 110 K were recorded and all the spectra show three g values indicating that these complexes have rhombic distortion. All the iron(III) complexes in DMF solution at 110 K have similar anisotropic spectra with almost the same gav values, indicating that the bonding in all the complexes is similar and is unaffected by the coordination of the anion.

  13. Vanadium(IV/V) complexes of Triapine and related thiosemicarbazones: Synthesis, solution equilibrium and bioactivity.

    Science.gov (United States)

    Kowol, Christian R; Nagy, Nóra V; Jakusch, Tamás; Roller, Alexander; Heffeter, Petra; Keppler, Bernhard K; Enyedy, Éva A

    2015-11-01

    The stoichiometry and thermodynamic stability of vanadium(IV/V) complexes of Triapine and two related α(N)-heterocyclic thiosemicarbazones (TSCs) with potential antitumor activity have been determined by pH-potentiometry, EPR and (51)V NMR spectroscopy in 30% (w/w) dimethyl sulfoxide/water solvent mixtures. In all cases, mono-ligand complexes in different protonation states were identified. Dimethylation of the terminal amino group resulted in the formation of vanadium(IV/V) complexes with considerably higher stability. Three of the most stable complexes were also synthesized in solid state and comprehensively characterized. The biological evaluation of the synthesized vanadium complexes in comparison to the metal-free ligands in different human cancer cell lines revealed only minimal influence of the metal ion. Thus, in addition the coordination ability of salicylaldehyde thiosemicarbazone (STSC) to vanadium(IV/V) ions was investigated. The exchange of the pyridine nitrogen of the α(N)-heterocyclic TSCs to a phenolate oxygen in STSC significantly increased the stability of the complexes in solution. Finally, this also resulted in increased cytotoxicity activity of a vanadium(V) complex of STSC compared to the metal-free ligand. PMID:26349014

  14. Synthesis and biological evaluation of some new N4-aryl substituted 5-chloroisatin-3-thiosemicarbazones.

    Science.gov (United States)

    Pervez, Humayun; Ramzan, Muhammad; Yaqub, Muhammad; Nasim, Faiz-ul-Hassan; Khan, Khalid Mohammed

    2012-05-01

    A new series of sixteen N4-aryl substituted 5-chloroisatin-3-thiosemicarbazones 2a-2p has been synthesized, characterized and tested for selected biological activities i.e. cytotoxicity, phytotoxicity and urease inhibition. In the brine shrimp bioassay, all the synthesized compounds gave LD50 values>2.30x10(-4) M-2.79x10(-4) M and were, therefore, found to be almost inactive, whereas in phytotoxicity assay, regardless of the nature of aryl substituents, they displayed weak to moderate (5-40%) phytotoxic activity at the highest tested concentrations (500 or 1000 μg/mL). In urease inhibition bioassay, compounds 2a, 2c, 2e, 2f, 2k and 2m exhibited relatively a higher degree of urease inhibition with IC50 values ranging from 38.91 μM to 76.65 μM and thus proved to be potent inhibitors of the enzyme. Of these, 2f and 2m displayed pronounced inhibition with IC50 values 38.91 μM and 39.50 μM, respectively, and may act as lead compounds for further studies. Structure-activity relationship (SAR) studies revealed that electronic effects of the substituents about the phenyl ring at N4 of the thiosemicarbazone moiety played an important role in enhancing the urease inhibitory potential of some of the synthesized compounds. PMID:22530899

  15. The development of radiogallium-acetylacetonate bis(thiosemicarbazone) complex for tumour imaging

    International Nuclear Information System (INIS)

    Background: Various radiometal complexes have been developed for tumour imaging, especially Ga-68 tracer. In this work, the development of a radiogallium bis(thiosemicarbazone) complex has been reported. Material and method: [67Ga]acetylacetonate bis(thio-semicarbazone) complex ([67Ga]AATS) was prepared starting with [67Ga]Gallium acetate and freshly prepared acetylacetonate bis(thiosemicarbazone) (AATS) for 30 min at 90oC. The partition co-efficient and stability of the tracer was determined in final solution (25oC) and the presence of human serum (37oC) for up to 24 hours. The biodistribution of the labelled compound in wild-type and fibrosarcoma-bearing rodents were determined for up to 72 hours. Results: The radiolabelled Ga complex was prepared to a high radiochemical purity (> 97%, HPLC) followed by initial biodistribution data with the significant tumour accumulation of the tracer at two hours, which is far higher than free Ga-67 cation, while the compound wash-out is significantly faster. Conclusion: The above-mentioned pharmacokinetic properties suggest an interesting radiogallium complex prepared by the PET Ga radioisotope, 68Ga, in accordance with the physical half life, for use in fibrosarcoma tumours and possibly in other malignancies. (authors)

  16. Preparation and evaluation of 61Cu-thiophene-2-aldehyde thiosemicarbazone for PET studies

    International Nuclear Information System (INIS)

    Background: [61Cu]Thiophene-2-aldehyde thiosemicarbazone (61CuTATS) was prepared according to an analogy of carrier copper compound with antitumor activity, for eventual use in PET. Material and Methods: [61Cu]TATS was prepared using copper-61 acetate and in-house made ligand (TATS) in one step. 61Cu was produced via the natZn(p,x)61Cu nuclear reaction (180 eA, 22 MeV, 3.2 h) followed by a two-step chromatography method (222 GBq of 61Cu2+). 61Cu TATS preparation was optimized for reaction conditions (buffer concentration and temperature). The tracer was finally administered to normal rats for biodistribution studies. Results: Total radiolabelling of the tracer took 30 minutes with a radiochemical purity of more than 90% (using HPLC and RTLC) and specific activity of about 250-300 Ci/mmol. The complex was stable in the presence of human serum for an hour. The biodistribution of copper cation and the tracer was checked in wild-type rats for up to 2 hours with significant spleen and lung uptake of the tracer. Preparation and evaluation of 61Cu-thiophene-2-aldehyde thiosemicarbazone for PET studies. Conclusion: The production of 61Cu via the natZn(p,x)61Cu is an efficient and reproducible method with high specific activity leading to the production and preliminary evaluation of 61Cu TATS, a potential PET tracer, was reported. (authors)

  17. 2-Hydroxy-4-n-butoxy-5-bromoacetophenone thiosemicarbazone as an extractive spectrophotometric reagent for nickel

    Directory of Open Access Journals (Sweden)

    K. N. Patel

    2011-05-01

    Full Text Available 2-hydroxy-4-n-butoxy-5-bromoacetophenone thiosemicarbazone (HBBrAT is spectrophotometric reagent for nickel (II in chloroform. The metal ion reacts with 2-hydroxy-4-n-butoxy-5-bromoacetophenone thiosemicarbazone (HBBrAT forming a dark brown coloured complex in the pH range 7.0-11.0. The complex shows maximum absorption at 440 nm. Beer’s law is obeyed in the range 2.74-6.86 µg/mL. The molar absorptivity and Sandell’s sensitivity are found to be 5229 Lmol-1cm-1 and 0.0105 µgcm-2, respectively. The solid complex have been isolated and characterized on the basis of elemental analysis, UV, IR, NMR and Mass spectra. HBBrAT is found to be a selective and strong chelating agent for nickel. The results deduced from Job’s method of continuous variation, the mole ratio and the slope ratio method showed that metal: ligand ratio in the complex to be 1:2. The stability constant of the complex found to be 1.92 X 107. The free energy change for the complex formation reaction is found to be -10.158 K cal/mole at 32 0C. The complex is fairly stable for about 24 h and up to 55 oC.

  18. A novel zinc bis(thiosemicarbazone) complex for live cell imaging.

    Science.gov (United States)

    Dayal, Disha; Palanimuthu, Duraippandi; Shinde, Sridevi Vijay; Somasundaram, Kumaravel; Samuelson, Ashoka G

    2011-04-01

    Fluorescent zinc complexes have recently attracted a lot of interest owing to their vast applications in cellular imaging. We report the synthesis as well as physical, chemical and biological studies of a novel zinc glyoxalbis(4-methyl-4-phenyl-3-thiosemicarbazone), [Zn(GTSC)]₃, complex. As compared with the well-studied zinc biacetylbis(4-methyl-3-thiosemicarbazone), Zn(ATSM), complex, which was used as a reference, [Zn(GTSC)]₃ had 2.5-fold higher fluorescence. When cellular fluorescence was measured using flow cytometry, we observed that [Zn(GTSC)]₃ had 3.4-fold to 12-fold higher fluorescence than Zn(ATSM) in various cell lines (n = 9) of different tissue origin. Confocal fluorescence microscopy results showed that [Zn(GTSC)]₃ appeared to have a nuclear localization within 30 min of addition to MCF7 cells. Moreover, [Zn(GTSC)]₃ showed minimal cytotoxicity compared with Zn(ATSM), suggesting that [Zn(GTSC)]₃ may be less deleterious to cells when used as an imaging agent. Our data suggest that the novel [Zn(GTSC)]₃ complex can potentially serve as a biocompatible fluorescent imaging agent for live cells. PMID:21384247

  19. Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity

    OpenAIRE

    Mistry, Rakesh N.; K. R. Desai

    2005-01-01

    1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl) - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid g...

  20. Study on the Synthesis Process of Dibenzylidene Sorbitol and Derivative

    Institute of Scientific and Technical Information of China (English)

    Li JiChun

    2001-01-01

    @@ Dibenzylidene Sorbitol (DBS) and Di(P-methylbenzylidene) Sorbitol (P-MeDBS) derivatives, used as crystallinity Polyolefine kind resin transparency nucleating agent, can reduce to a large extent the product's haze, improve its transparency, validly resin's rigidity, heat resistant temperature and modulus of bending. Its good transparency and glossiness are as good as transparent material. It has become polyolefine processing auxiliary that develop most quickly and consume most massively in the world. It is used widely in the processing of transparent plastic package vessel, equipment's parts, file folder and transperene material. The nucleating agent of DBS analog is made from one mole Sorbitol and two mole benzaldehyde dehydration condensation reaction, which associates with by-reaction. Sorbitol containing six hydroxyl group ring condensates with benzaldehyde and yield three acetal compounds-monobenzylidene Sorbitol(hereafier briefly referred to as "MBS”), DBS and Tridibenzylidene Sorbitol(hereafter briefly referred to as "TBS”). MBS and TBS are by-products. The experiment is carried out under the condition of temperature 75'C, reaction time 4 hours and agitation velocity 370 r/min. We conducted intensive research on the effects of Sorbitol/benzaldehyde(S/B) and Sorbitol/P-Me-DBS feeding molar ratios. When B/S is 2, the target product's yield can even be improved to 98.5% and 97.17% respectively, whereas feeding molar ratio are increased or reduced, the product's yield reduces definitely. The reason is that DBS and Derivative are produced by the process that one mole Sorbitol and two mole benzaldehyde condense. Sorbitol can't react validly with the molar ratio being lower than 2 .While B/S is in excess of 2.1, the excess benzaldehyde condenses some yielded DBS and produces TBS. Research data show that feeding molar ratio ought to range from 1.9 to 2.1 in order to acquire high yield and selectivity's target product. The result of synthesizing P

  1. Study on the Synthesis Process of Dibenzylidene Sorbitol and Derivative

    Institute of Scientific and Technical Information of China (English)

    Li; JiChun

    2001-01-01

    Dibenzylidene Sorbitol (DBS) and Di(P-methylbenzylidene) Sorbitol (P-MeDBS) derivatives, used as crystallinity Polyolefine kind resin transparency nucleating agent, can reduce to a large extent the product's haze, improve its transparency, validly resin's rigidity, heat resistant temperature and modulus of bending. Its good transparency and glossiness are as good as transparent material. It has become polyolefine processing auxiliary that develop most quickly and consume most massively in the world. It is used widely in the processing of transparent plastic package vessel, equipment's parts, file folder and transperene material. The nucleating agent of DBS analog is made from one mole Sorbitol and two mole benzaldehyde dehydration condensation reaction, which associates with by-reaction. Sorbitol containing six hydroxyl group ring condensates with benzaldehyde and yield three acetal compounds-monobenzylidene Sorbitol(hereafier briefly referred to as "MBS”), DBS and Tridibenzylidene Sorbitol(hereafter briefly referred to as "TBS”). MBS and TBS are by-products. The experiment is carried out under the condition of temperature 75'C, reaction time 4 hours and agitation velocity 370 r/min. We conducted intensive research on the effects of Sorbitol/benzaldehyde(S/B) and Sorbitol/P-Me-DBS feeding molar ratios. When B/S is 2, the target product's yield can even be improved to 98.5% and 97.17% respectively, whereas feeding molar ratio are increased or reduced, the product's yield reduces definitely. The reason is that DBS and Derivative are produced by the process that one mole Sorbitol and two mole benzaldehyde condense. Sorbitol can't react validly with the molar ratio being lower than 2 .While B/S is in excess of 2.1, the excess benzaldehyde condenses some yielded DBS and produces TBS. Research data show that feeding molar ratio ought to range from 1.9 to 2.1 in order to acquire high yield and selectivity's target product. The result of synthesizing P-Me-DBS homologue

  2. Synthesis and Conformational Assignment of N-(E-Stilbenyloxymethylenecarbonyl-Substituted Hydrazones of Acetone and o-(m- and p- Chloro- (nitro- benzaldehydes by Means of and NMR Spectroscopy

    Directory of Open Access Journals (Sweden)

    Przemysław Patorski

    2013-01-01

    Full Text Available Eighteen new N-(E-stilbenyloxyalkylcarbonyl-substituted hydrazones of ortho- (meta- and para- chloro- (nitro- benzaldehydes 1–18 and two analogous hydrazones of acetone 19-20 were prepared. The stereochemical behavior of 1–18 in dimethyl-d6 sulfoxide solution has been studied by NMR and NMR techniques, using spectral data of 19 and 20 as supporting material. The E-geometrical isomers and cis-/trans-amide conformers have been found for these hydrazones. Energy barriers of isomers are reported.

  3. Density, Viscosity, Sound Speed, and Thermoacoustical Parameters of Benzaldehyde with Chlorobenzene or Nitrobenzene at 303.15 K, 308.15 K, and 313.15 K

    Science.gov (United States)

    Lavanya, T. G.; Saravanakumar, K.; Baskaran, R.; Kubendran, T. R.

    2013-07-01

    The values of the density, viscosity, and speed of sound for binary liquid mixtures of benzaldehyde with chlorobenzene or nitrobenzene have been measured over the entire range of composition at (303.15, 308.15, and 313.15) K. These values have been used to calculate the excess molar volume (), and excess free volume (). McAllister's three-body interaction model is used for correlating the kinematic viscosity of binary mixtures. The thermophysical properties (density, viscosity, and ultrasonic velocity) under study were fit to the Jouyban-Acree model.

  4. Novel Steroidal (6R)-Spiro-1,3,4-thiadiazoline Derivatives as Anti-bacterial Agents

    Institute of Scientific and Technical Information of China (English)

    Khan Salman A.; Asiri, Abdullah M.

    2012-01-01

    Novel steroidal (6R)-spiro-1,3,4-thiadiazoline derivatives have been synthesized by the cyclization of steroidal thiosemiearbazones. Thiosemicarbazones have been synthesized by the reaction of steroidal ketones with thiosemi- carbazide. All the compounds have been characterized by IR, 1H NMR, mass and elemental analyses. The antibacterial activities of these compounds have been first tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC) values have been determined with the reference of standard drug amoxicillin. The results showed that steroidal thiadiazoline de- rivatives exhibited better antibacterial activity than the steroidal thiosemicarbazone derivatives. Chloro and acetoxy substituents on the 3β-position of the steroidal thiadiazoline ring increased the anti-bacterial activity. Among all the compounds, compounds 7 and 8 were found better inhibitors as compared to the respective drug amoxicillin.

  5. An Efficient One-Pot Multicomponent Synthesis of 4-Aza-Podophyllotoxin Derivatives in Ionic Liquid

    Directory of Open Access Journals (Sweden)

    Hossein Naeimi

    2013-01-01

    Full Text Available A simple, green, and efficient procedure for the synthesis of 4-aza-podophyllotoxin derivatives by using a one-pot three-component reaction of benzaldehydes, 1,3-cyclohexanediones, and anilinolactones in the presence of catalytic amount of alum in 1-butyl-3-methylimidazolium triflate as green media is described. This reaction proceeded under mild conditions with the use of an inexpensive and readily available catalyst, high to excellent yields, and simple workup procedure.

  6. Synthesis of 4-aryl-3,4-dihydrocoumarin derivatives catalyzed by NbCl{sub 5}; Sintese de derivados 4-aril-3,4-di-hidrocuraminicos catalisada por NbCl{sub 5}

    Energy Technology Data Exchange (ETDEWEB)

    Santos, Willian Henrique dos; Siqueira, Mayara de Souza; Silva-Filho, Luiz Carlos da, E-mail: lcsilva@fc.unesp.br [Universidade Estadual Paulista Julio de Mesquita Filho (UNESP), Bauru, SP (Brazil). Faculdade de Ciencias

    2013-11-01

    Multicomponent reactions between phenols, {beta}-diesters and benzaldehydes for the synthesis of 4-aryl-3,4-dihydrocoumarin derivatives were carried out under mild conditions (room temperature) and presented moderate yields (38-88%) and reasonable reaction times (2-4 days), using niobium pentachloride as a catalyst. (author)

  7. Simultaneous quantitation of trace level hydrazine and acetohydrazide in pharmaceuticals by benzaldehyde derivatization with sample 'matrix matching' followed by liquid chromatography-mass spectrometry.

    Science.gov (United States)

    Cui, Li; Jiang, Kaina; Liu, David Q; Facchine, Kevin L

    2016-09-01

    Hydrazine and acetohydrazide are potential genotoxins and therefore need to be controlled in APIs and drug products to ppm levels for patient safety in cases where there is a reasonable probability of either of them being present. They are structurally related and could both be formed in the same chemical process under certain circumstances. However, no previous studies have reported simultaneous trace level quantification of these two compounds. Herein, a chemical derivatization scheme using benzaldehyde followed by LC-MS analysis is presented to address that need. During method development, unexpectedly high recoveries were encountered and presented a major challenge. A systematic investigation was undertaken to understand the benzaldehyde derivatization reaction and determine the underlying causes of the unacceptable recovery. It was found that this was due to the presence of the counter ion of the API in the sample matrix. Employing a 'matrix matching' sample preparation strategy, which involved acidifying the derivatization reaction medium with benzoic acid, gave similar reaction rates for the chemical derivatization in the presence and absence of the API salt and accordingly more consistent recoveries. Resultantly, a robust method for simultaneous quantification of hydrazine and acetohydrazide (1-100ppm) was successfully developed and validated. PMID:27495371

  8. Iron Chelators of the Di-2-pyridylketone Thiosemicarbazone and 2-Benzoylpyridine Thiosemicarbazone Series Inhibit HIV-1 Transcription: Identification of Novel Cellular Targets—Iron, Cyclin-Dependent Kinase (CDK) 2, and CDK9S⃞

    Science.gov (United States)

    Debebe, Zufan; Ammosova, Tatyana; Breuer, Denitra; Lovejoy, David B.; Kalinowski, Danuta S.; Karla, Pradeep K.; Kumar, Krishna; Jerebtsova, Marina; Ray, Patricio; Kashanchi, Fatah; Gordeuk, Victor R.; Richardson, Des R.

    2011-01-01

    HIV-1 transcription is activated by HIV-1 Tat protein, which recruits cyclin-dependent kinase 9 (CDK9)/cyclin T1 and other host transcriptional coactivators to the HIV-1 promoter. Tat itself is phosphorylated by CDK2, and inhibition of CDK2 by small interfering RNA, the iron chelator 2-hydroxy-1-naphthylaldehyde isonicotinoyl hydrazone (311), and the iron chelator deferasirox (ICL670) inhibits HIV-1 transcription. Here we have analyzed a group of novel di-2-pyridylketone thiosemicarbazone- and 2-benzoylpyridine thiosemicarbazone-based iron chelators that exhibit marked anticancer activity in vitro and in vivo (Proc Natl Acad Sci USA 103:7670–7675, 2006; J Med Chem 50:3716–3729, 2007). Several of these iron chelators, in particular 2-benzoylpyridine 4-allyl-3-thiosemicarbazone (Bp4aT) and 2-benzoylpyridine 4-ethyl-3-thiosemicarbazone (Bp4eT), inhibited HIV-1 transcription and replication at much lower concentrations than did 311 and ICL670. Neither Bp4aT nor Bp4eT were toxic after a 24-h incubation. However, longer incubations for 48 h or 72 h resulted in cytotoxicity. Analysis of the molecular mechanism of HIV-1 inhibition showed that the novel iron chelators inhibited basal HIV-1 transcription, but not the nuclear factor-κB-dependent transcription or transcription from an HIV-1 promoter with inactivated SP1 sites. The chelators inhibited the activities of CDK2 and CDK9/cyclin T1, suggesting that inhibition of CDK9 may contribute to the inhibition of HIV-1 transcription. Our study suggests the potential usefulness of Bp4aT or Bp4eT in antiretroviral regimens, particularly where resistance to standard treatment occurs. PMID:20956357

  9. Dynamic Combinatorial Chemistry and Organocatalysis with Thiosemicarbazones and Organocatalysts for Hydrazone and Oxime Bioconjugations

    DEFF Research Database (Denmark)

    Larsen, Dennis

    The first part of this thesis describes the use of thiosemicarbazones for dynamic combinatorial chemistry. Building blocks incorporating thiosemicarbazides and acetalprotected aldehydes were synthesised and conditions where these building blocks formed dynamic combinatorial libraries under...... of this thesis describes the development of new bifunctional organocatalysts for the formation of hydrazones and oximes at neutral pH. New effective variants of the previously known anthranilic acid-based catalysts were discovered, and via a virtual breakdown of the structure of already identified...... catalysts, two new types of catalysts were discovered: The 2-aminophenols and the 2-(aminomethyl)benzimidazoles. With aldehyde substrates none of the newly discovered catalysts were as effective as a previously discovered benzenephosphonic acid, but with aromatic ketones, an otherwise challenging class of...

  10. Spectroscopic, Thermal and Biological Studies on Some Trivalent Ruthenium and Rhodium NS Chelating Thiosemicarbazone Complexes

    Directory of Open Access Journals (Sweden)

    Vinod K. Sharma

    2007-03-01

    Full Text Available The synthetic, spectroscopic, and biological studies of sixteen ring-substituted 4-phenylthiosemicarbazones and 4-nitrophenyl-thiosemicarbazones of anisaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde, and vanillin with ruthenium(III and rhodium(III chlorides are reported here. Their structures were determined on the basis of the elemental analyses, spectroscopic data (IR, electronic, H1 and C13 NMR along with magnetic susceptibility measurements, molar conductivity and thermogravimetric analyses. Electrical conductance measurement revealed a 1:3 electrolytic nature of the complexes. The resulting colored products are monomeric in nature. On the basis of the above studies, three ligands were suggested to be coordinated to each metal atom by thione sulphur and azomethine nitrogen to form low-spin octahedral complexes with ruthenium(III while forming diamagnetic complexes with rhodium(III. Both ligands and their complexes have been screened for their bactericidal activities and the results indicate that they exhibit a significant activity.

  11. Antibacterial, antifungal and in vitro antileukaemia activity of metal complexes with thiosemicarbazones

    OpenAIRE

    Pahontu, Elena; Julea, Felicia; Rosu, Tudor; Purcarea, Victor; Chumakov, Yurie; Petrenco, Petru; Aurelian GULEA

    2015-01-01

    1-phenyl-3-methyl-4-benzoyl-5-pyrazolone 4-ethyl-thiosemicarbazone (HL) and its copper(II), vanadium(V) and nickel(II) complexes: [Cu(L)(Cl)]·C2H5OH·(1), [Cu(L)2]·H2O (2), [Cu(L)(Br)]·H2O·CH3OH (3), [Cu(L)(NO3)]·2C2H5OH (4), [VO2(L)]·2H2O (5), [Ni(L)2]·H2O (6), were synthesized and characterized. The ligand has been characterized by elemental analyses, IR, 1H NMR and 13C NMR spectroscopy. The tridentate nature of the ligand is evident from the IR spectra. The copper(II), vanadium(V) and nicke...

  12. Syntheses and Supramolecular Structures of Two Nickel(Ⅱ) Compounds Based on Two Thiosemicarbazone Ligands

    Institute of Scientific and Technical Information of China (English)

    LI Cheng-juan; FENG Ze-jing; ZHAO Xiao-juan; WANG Su-na; DOU Jian-min

    2013-01-01

    Two new compounds,[Ni2(L1)(Py)6]Py·CH3OH(1) and [Ni3(L2)2(Py)4]·2DMF(2)(H4L1=N,N'-bisalicylbisthiocarbamide; H3L2=3-hydroxyl-2-naphthalene thiosemicarbazide; Py=pyridine; DMF=dimethyl fumarate),based upon two thiosemicarbazone ligands have been obtained and characterized by elemental analysis,Fourier transform infrared(FTIR) and X-ray diffraction(XRD).Compound 1 possesses a binuclear cluster,in which the bisalicylbisthiocarbamide acts as a hexadentate bridge.Compound 2 exhibits a linear trinuclear cluster with the triply-deprotonated ligand acting as pentadentate bridge.C—H…O,C—H…π and C—H…S weak interactions further link these molecules to form interesting supramolecular networks.

  13. Synthesis and physicochemical study of rhenium(V) complexes with phenylglyoxylic acid thiosemicarbazone

    International Nuclear Information System (INIS)

    With high yield (75-93 %) rhenium(V) complexes were prepared with thiosemicarbazone of phenylglyoxylic acid (L) of the composition [ReOLX3]·2H2O, [ReOL2X]X2·2H2O, [ReOLX2(OH)]·2H2O, [ReOL2(OH)]X2 (X = Cl, Br). The compounds prepared were characterized by the methods of elementary and thermal analyses, IR spectroscopy and conductometry. It was ascertained that depending on synthesis conditions, initial concentration of hydrohalic acid first of all, rhenium(V) complexes are formed with different number of ligands in the inner sphere. In all the complexes studied ligand L is coordinated by rhenium atom in bidentate way via sulfur and nitrogen atoms of hydrazine fragment, forming a five-member chelate node

  14. Synthesis, Spectroscopic, and Antimicrobial Studies on Bivalent Zinc and Mercury Complexes of 2-Formylpyridine Thiosemicarbazone

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2009-01-01

    Full Text Available A series of metal complexes of Zn(II and Hg(II having the general composition [M(L2]X2 [where L = 2-formylpyridine thiosemicarbazone; M = Zn(II and Hg(II; X = Cl−, NO−3 and 1/2SO42−] have been prepared and characterized by elemental chemical analysis, molar conductance, and spectral (IR and mass studies. The IR spectral data suggests the involvement of sulphur and azomethane nitrogen in coordination to the central metal ion. On the basis of spectral studies, a tetrahedral geometry has been assigned for Zn(II and Hg(II complexes. The free ligand and its metal complexes have been tested in vitro against a number of microorganisms in order to assess their antimicrobial properties.

  15. Coordination compounds of titanium(4), zirconium(4) and hafnium(4) with cyclohexanone thiosemicarbazone

    International Nuclear Information System (INIS)

    Adducts of titanium, zirconium and hafnium tetrachlorides with cyclohexanone thiosemicarbazone of 1:1, 1:2, 1:4 composition for zirconium and hafnium, 1:1.5 and 1:4 for titanium were synthesized. Infrared spectra of prepared compounds were studied and an assumption was made concerning the bidentate ligand coordination through sulfur atoms and amino group nitrogen. Solution heats of synthesized adducts in hydrochloric acid were determined and formation heats of adducts and heats of gaseous ligand addition to metal tetrachloride were calculated. It was shown that hafnium formed more stable compounds as compared to zirconium. Ways of coordination of the first, the second, the third and the fourth ligand (L) molecules in MCl4 X 4L compounds were discussed on the basis of infrared spectroscopic and thermochemical investigation

  16. Synthesis, Spectroscopic, and Antimicrobial Studies on Bivalent Zinc and Mercury Complexes of 2-Formylpyridine Thiosemicarbazone

    Science.gov (United States)

    Chandra, Sulekh; Parmar, Shikha; Kumar, Yatendra

    2009-01-01

    A series of metal complexes of Zn(II) and Hg(II) having the general composition [M(L)2]X2 [where L = 2-formylpyridine thiosemicarbazone; M = Zn(II) and Hg(II); X = Cl−, NO3− and 1/2SO42−] have been prepared and characterized by elemental chemical analysis, molar conductance, and spectral (IR and mass) studies. The IR spectral data suggests the involvement of sulphur and azomethane nitrogen in coordination to the central metal ion. On the basis of spectral studies, a tetrahedral geometry has been assigned for Zn(II) and Hg(II) complexes. The free ligand and its metal complexes have been tested in vitro against a number of microorganisms in order to assess their antimicrobial properties. PMID:19421419

  17. Tin(II) Selective PVC Membrane Electrode Based on Salicylaldehyde Thiosemicarbazone as an Ionophore

    OpenAIRE

    Sulekh Chandra; Kusum Sharma; Adarsh Kumar

    2013-01-01

    A polymeric membrane-based tin selective electrode was developed by using salicylaldehyde thiosemicarbazone (STSC). The best performance was recorded with a membrane composition of PVC : TBP : ionophore : NaTPB as 28 : 59 : 8 : 5 (w/w%). The Nernstian slope calculated from the calibration curve for Sn2+ sensor was 28.8 ± 0.4 mV/decade. The detection limit of the sensor was 2.10 × 10−8 M, in the linear concentration range of 1.0 × 10−2−1.1 × 10−7 M. It was relatively fast response time (...

  18. Synthesis and spectral studies of platinum metal complexes of benzoin thiosemicarbazone

    Science.gov (United States)

    Offiong, Offiong E.

    1994-11-01

    The platinum metal chelates of benzoin thiosemicarbazone obtained with Ru(III), Rh(III), Ir(III), Pd(II) and Pt(II) were prepared from their corresponding halide salts. The complexes were characterized by elemental analysis, conductance measurement, IR, Raman, 1H-NMR, 13C-NMR and UV-visible spectra studies. Various ligand field parameters and nephelauxetic parameters were also calculated. The mode of bonding and the geometry of the ligand environment around the metal ion have been discussed in the light of the available data obtained. Complexes of Ru(III), Rh(III) and Ir(III) are six-coordinate octahedral, while Pd(II) and Pt(II) halide complexes are four-coordinated with halides bridging.

  19. Ruthenium (II) complexes of thiosemicarbazone: Synthesis, biosensor applications and evaluation as antimicrobial agents

    Energy Technology Data Exchange (ETDEWEB)

    Yildirim, Hatice [Dokuz Eylul University, The Graduate School of Natural and Applied Sciences, Department of Chemistry, 35160 Buca, Izmir (Turkey); Guler, Emine [Ege University, Faculty of Science, Department of Biochemistry, 35100 Bornova, Izmir (Turkey); Yavuz, Murat, E-mail: myavuz@dicle.edu.tr [Ege University, Faculty of Science, Department of Biochemistry, 35100 Bornova, Izmir (Turkey); Dicle University, Faculty of Science, Department of Chemistry, 21280 Diyarbakir (Turkey); Ozturk, Nurdan; Kose Yaman, Pelin [Dokuz Eylul University, The Graduate School of Natural and Applied Sciences, Department of Chemistry, 35160 Buca, Izmir (Turkey); Subasi, Elif; Sahin, Elif [Dokuz Eylul University, Faculty of Science, Department of Chemistry, 35160 Buca, Izmir (Turkey); Timur, Suna [Ege University, Faculty of Science, Department of Biochemistry, 35100 Bornova, Izmir (Turkey); Ege University, Institute on Drug Abuse, Toxicology and Pharmaceutical Science (BATI), 35100 Bornova, Izmir (Turkey)

    2014-11-01

    A conformationally rigid half-sandwich organoruthenium (II) complex [(η{sup 6}-p-cymene)RuClTSC{sup N–S}]Cl, (1) and carbonyl complex [Ru(CO)Cl(PPh{sub 3}){sub 2}TSC{sup N–S}] (2) have been synthesized from the reaction of [{(η"6-p-cymene)RuCl}{sub 2}(μ-Cl){sub 2}] and [Ru(H)(Cl)(CO)(PPh{sub 3}){sub 3}] with thiophene-2-carboxaldehyde thiosemicarbazon (TSC) respectively and both novel ruthenium (II) complexes have been characterized by elemental analysis, FT-IR and NMR spectroscopy. The peripheral TSC in the complexes acts as an electrochemical coupling unit providing the ability to carry out electrochemical deposition (ED) and to form an electro-deposited film on a graphite electrode surface. The biosensing applicability of complexes 1 and 2 was investigated by using glucose oxidase (GOx) as a model enzyme. Electrochemical measurements at − 0.9 V versus Ag/AgCl electrode by following the ED Ru(II) reduction/oxidation due to from the enzyme activity, in the presence of glucose substrate. The designed biosensor showed a very good linearity for 0.01–0.5 mM glucose. The in vitro antimicrobial activities of complexes 1 and 2 were also investigated against nine bacterial strains and one fungus by the disc diffusion test method. No activity was observed against the Gram-negative strains and fungus, whereas complex 1 showed moderate antibacterial activities against Gram-positive bacterial strains. - Highlights: • Novel Ru (II) thiosemicarbazone complexes were synthesized and characterized. • Electrochemical depositions were performed. • Rigid half-sandwich Ru (II) complex showed enhanced antibacterial activity.

  20. Synthesis and crystal structure of [chlorobis(triphenylphospino) (p-chlorobenzaldehyde thiosemicarbazone)] copper(I) complex

    Indian Academy of Sciences (India)

    Ashiq Khan; Poonam Sharma; Rajnikant; Vivek K Gupta; Naresh Padha; Rekha Sharma

    2016-02-01

    Reactions of copper(I) halides with p-chlorobenzaldehyde thiosemicarbazone (H1L) and triphenylphosphine in 1 : 1 : 2 molar ratio yielded complexes of stoichiometry, [CuX(1-S- H1L)(Ph3P)2] (X = I, 1: Br, 2; Cl, 3). All the three complexes were characterized using analytical (CHNS) and spectroscopic (IR, 1H NMR) techniques. The structure of complex 3 was confirmed by X-ray crystallography. It has been found to crystallize in the triclinic system with space group P-1 and unit cell parameters: a = 10.207(5) Å, b = 13.027(5) Å, c = 16.269(5) Å, = 100.054(5)°, = 99.228(5)° and = 97.234(5)°. This complex has distorted tetrahedral geometry with two phosphorus atoms from two triphenylphosphine ligands, thione sulfur of thiosemicarbazone ligand and chloride ion occupying the four corners of the tetrahedron. The structure of complex 3 was in contrast to sulfur-bridged dinuclear complex of copper(I) chloride with benzaldehydethiosemicarbazone, [Cu2Cl2(2-S-Hbtsc)2(Ph3P)2]·2H2O. The intermolecular H-bonding, Cl· · ·HCph, 2.733 Å and interactions, {CHph · · · , 2.796; 2.776 Å} in this complex led to the formation of 1D chain. Two such 1D chains were cross-linked via, Cl· · ·HCph, 2.896 Å H-bonding to form a 2D network.

  1. Ruthenium (II) complexes of thiosemicarbazone: Synthesis, biosensor applications and evaluation as antimicrobial agents

    International Nuclear Information System (INIS)

    A conformationally rigid half-sandwich organoruthenium (II) complex [(η6-p-cymene)RuClTSCN–S]Cl, (1) and carbonyl complex [Ru(CO)Cl(PPh3)2TSCN–S] (2) have been synthesized from the reaction of [{(η6-p-cymene)RuCl}2(μ-Cl)2] and [Ru(H)(Cl)(CO)(PPh3)3] with thiophene-2-carboxaldehyde thiosemicarbazon (TSC) respectively and both novel ruthenium (II) complexes have been characterized by elemental analysis, FT-IR and NMR spectroscopy. The peripheral TSC in the complexes acts as an electrochemical coupling unit providing the ability to carry out electrochemical deposition (ED) and to form an electro-deposited film on a graphite electrode surface. The biosensing applicability of complexes 1 and 2 was investigated by using glucose oxidase (GOx) as a model enzyme. Electrochemical measurements at − 0.9 V versus Ag/AgCl electrode by following the ED Ru(II) reduction/oxidation due to from the enzyme activity, in the presence of glucose substrate. The designed biosensor showed a very good linearity for 0.01–0.5 mM glucose. The in vitro antimicrobial activities of complexes 1 and 2 were also investigated against nine bacterial strains and one fungus by the disc diffusion test method. No activity was observed against the Gram-negative strains and fungus, whereas complex 1 showed moderate antibacterial activities against Gram-positive bacterial strains. - Highlights: • Novel Ru (II) thiosemicarbazone complexes were synthesized and characterized. • Electrochemical depositions were performed. • Rigid half-sandwich Ru (II) complex showed enhanced antibacterial activity

  2. Synthesis of biological active thiosemicarbazone and characterization of the interaction with human serum albumin

    Energy Technology Data Exchange (ETDEWEB)

    Yu, Wangshu; Shi, Lei; Hui, Guangquan [College of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007 (China); Cui, Fengling, E-mail: fenglingcui@hotmail.com [College of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007 (China)

    2013-02-15

    The synthesis of a new biological active reagent, 2-((1,4-dihydroxy)-9,10-anthraquinone) aldehyde thiosemicarbazone (DHAQTS), was designed. The interaction between DHAQTS and HSA was studied by fluorescence spectroscopy in combination with molecular modeling under simulation of physiological conditions. According to the results of fluorescence measurements, the quenching mechanism was suggested to be static. The thermodynamic parameters are calculated by van't Hoff equation, which demonstrated that hydrophobic interactions are the predominant intermolecular forces stabilizing the complex. The number of binding sites (n) was calculated. Through the site marker competitive experiment, DHAQTS was confirmed to be located in site I of HSA. The binding distance r=2.83 nm between the donor HSA and acceptor DHAQTS was obtained according to Foerster's non-radiative energy transfer theory. The three-dimensional fluorescence spectral results showed the conformation and microenvironment of HSA changed in the presence of DHAQTS. The effects of common ions on the binding of DHAQTS to HSA were also evaluated. The experimental results were in agreement with the results obtained via a molecular docking study. - Highlights: Black-Right-Pointing-Pointer 2-((1,4-dihydroxy)-9,10-anthraquinone)aldehyde thiosemicarbazone (DHAQTS) was synthesized. Black-Right-Pointing-Pointer DHAQTS can quench the fluorescence of human serum albumin (HSA) by static quenching mechanism. Black-Right-Pointing-Pointer Hydrophobic interactions were the predominant intermolecular forces. Black-Right-Pointing-Pointer The competitive experiment was carried out to identify the DHAQTS binding site on HSA. Black-Right-Pointing-Pointer Three-dimensional spectra confirmed DHAQTS caused the conformational change of HSA.

  3. Synthesis of biological active thiosemicarbazone and characterization of the interaction with human serum albumin

    International Nuclear Information System (INIS)

    The synthesis of a new biological active reagent, 2-((1,4-dihydroxy)-9,10-anthraquinone) aldehyde thiosemicarbazone (DHAQTS), was designed. The interaction between DHAQTS and HSA was studied by fluorescence spectroscopy in combination with molecular modeling under simulation of physiological conditions. According to the results of fluorescence measurements, the quenching mechanism was suggested to be static. The thermodynamic parameters are calculated by van't Hoff equation, which demonstrated that hydrophobic interactions are the predominant intermolecular forces stabilizing the complex. The number of binding sites (n) was calculated. Through the site marker competitive experiment, DHAQTS was confirmed to be located in site I of HSA. The binding distance r=2.83 nm between the donor HSA and acceptor DHAQTS was obtained according to Förster's non-radiative energy transfer theory. The three-dimensional fluorescence spectral results showed the conformation and microenvironment of HSA changed in the presence of DHAQTS. The effects of common ions on the binding of DHAQTS to HSA were also evaluated. The experimental results were in agreement with the results obtained via a molecular docking study. - Highlights: ► 2-((1,4-dihydroxy)-9,10-anthraquinone)aldehyde thiosemicarbazone (DHAQTS) was synthesized. ► DHAQTS can quench the fluorescence of human serum albumin (HSA) by static quenching mechanism. ► Hydrophobic interactions were the predominant intermolecular forces. ► The competitive experiment was carried out to identify the DHAQTS binding site on HSA. ► Three-dimensional spectra confirmed DHAQTS caused the conformational change of HSA.

  4. Gold(III) complexes with ONS-Tridentate thiosemicarbazones: Toward selective trypanocidal drugs.

    Science.gov (United States)

    Rettondin, Andressa R; Carneiro, Zumira A; Gonçalves, Ana C R; Ferreira, Vanessa F; Oliveira, Carolina G; Lima, Angélica N; Oliveira, Ronaldo J; de Albuquerque, Sérgio; Deflon, Victor M; Maia, Pedro I S

    2016-09-14

    Tridentate thiosemicarbazone ligands with an ONS donor set, H2L(R) (R = Me and Et) were prepared by reactions of 1-phenyl-1,3-butanedione with 4-R-3-thiosemicarbazides. H2L(R) reacts with Na[AuCl4]·2H2O in MeOH in a 1:1 M ratio under formation of green gold(III) complexes of composition [AuCl(L(R))]. These compounds represent the first examples of gold(III) complexes with ONS chelate-bonded thiosemicarbazones. The in vitro anti-Trypanosoma cruzi activity against both trypomastigote and amastigote forms (IC50try/ama) of CL Brener strains as well as the cytotoxicity against LLC-MK2 cells of the free ligands and complexes was evaluated. The complex [AuCl(L(Me))] was found to be more active and more selective than its precursor ligand and the standard drug benznidazole with a SItry/ama value higher than 200, being considered as a lead candidate for Chagas disease treatment. Moreover the in vitro activity against the replicative amastigote form (IC50ama) of T. cruzi was additionally investigated revealing that [AuCl(L(Me))] was also more potent than benznidazole still with a similar selectivity index. Finally, docking studies showed that free ligands and complexes interact with the same residues of the parasite protease cruzain but with different intensities, suggesting that this protease could be a possible target for the trypanocidal action of the obtained compounds. PMID:27191616

  5. Synergistic extraction of Th(IV) by 2-hydroxy-1-naphthaldehyde thiosemicarbazone and neutral donors

    International Nuclear Information System (INIS)

    The extraction behaviour of Th(IV) from aqueous nitric acid medium employing 2-hydroxy-1-naphthaldehyde thiosemicarbazone has been studied in the presence of various donors, like trioctyl phosphine oxide (TOPO), calix[3]OH[3]OMe[6]arene, trioctyl amine (TOA), dimethyl sulphoxide (DMSO) in ethylacetate solvent. The constants (log kex) for the binary complex in organic phase [Th(A)(NO3)3], where A is the ligand, was found to be 3.99, which was by far the largest amongst the corresponding values known for the other thiosemicarbazones. The overall equilibrium constants (log K) for the ternary species [Th(A)TOPO(NO3)3], [Th(A)TOA(NO3)3], [Th(A)Calix[3]OH[3]OMe[6]arene(NO3)3], [Th(A)DMSO(NO3)3] were estimated to be 8.287, 8.862, 8.415, 6.921 respectively. The trend in equilibrium constants were in accordance with the substitution of the donor. The extraction of Th4+ by the ligand-donor combination was maximum at pH = 1 and extraction decreases with increase in pH. It has been found that the extent of extraction of Th4+ in the organic phase as the binary as well as ternary complex [Th(A)(NO3)3] and [Th(A)(NO3)3S], where S is the donor, increases with increase in the concentration of the ligand. Similar trend is obtained in the extraction by donors in absence of ligand. In case of ternary extraction, using different donors, amines are found to perform best compared to the other donors. The trend is as follows: TOA > calix[3]OH[3]OMe[6]arene > TOPO > DMSO. In addition, the effect of different diluents on extraction was also studied and the observed trend was methyl salicylate > ethyl acetate > methyl isobutyl ketone > ethyl benzoate. (orig.)

  6. Interaction of Triapine and related thiosemicarbazones with iron(III)/(II) and gallium(III): a comparative solution equilibrium study†

    OpenAIRE

    Enyedy, Éva A.; Primik, Michael F.; Kowol, Christian R.; Arion, Vladimir B.; Kiss, Tamás; Keppler, Bernhard K.

    2011-01-01

    Stoichiometry and stability of GaIII, FeIII, FeII complexes of Triapine and five related α-N heterocyclic thiosemicarbazones with potential antitumor activity have been determined by pH-potentiometry, UV-vis spectrophotometry, 1H NMR spectroscopy, and spectrofluorimetry in aqueous solution (with 30% DMSO), together with the characterization of the proton dissociation processes. Additionally, the redox properties of the iron complexes were studied by cyclic voltammetry at various pH values. Fo...

  7. Thiosemicarbazones: preparation methods, synthetic applications and biological importance; Tiossemicarbazonas: metodos de obtencao, aplicacoes sinteticas e importancia biologica

    Energy Technology Data Exchange (ETDEWEB)

    Tenorio, Romulo P.; Goes, Alexandre J.S. [Universidade Federal de Pernambuco, Recife, PE (Brazil). Dept. de Antibioticos]. E-mail: ajsg@ufpe.br; Lima, Jose G. de; Faria, Antonio R. de; Alves, Antonio J.; Aquino, Thiago M. de [Universidade Federal de Pernambuco, Recife, PE (Brazil). Dept. de Ciencias Farmaceuticas

    2005-11-15

    Thiosemicarbazones are a class of compounds known by their chemical and biological properties, such as antitumor, antibacterial, antiviral and antiprotozoal activity. Their ability to form chelates with metals has great importance in their biological activities. Their synthesis is very simple, versatile and clean, usually giving high yields. They are largely employed as intermediates, in the synthesis of others compounds. This article is a survey of some of these characteristics showing their great importance to organic and medicinal chemistry. (author)

  8. Spectroscopic, Viscositic and Molecular Modeling Studies on the Interaction of 3′-Azido-Daunorubicin Thiosemicarbazone with DNA

    OpenAIRE

    Cui, Fengling; Liu, Qingfeng; Luo, Hongxia; Zhang, Guisheng

    2013-01-01

    A new daunorubicin has been synthesized and structurally characterized. The interaction of native calf thymus DNA (ctDNA) with 3′-azido-daunorubicin thiosemicarbazone (ADNRT) was investigated under simulated physiological conditions by multi-spectroscopic techniques, viscometric measurements and molecular modeling study. It concluded that ADNRT could intercalate into the base pairs of ctDNA, and the fluorescence quenching by ctDNA was static quenching type. Thermodynamic parameters calculated...

  9. Bp44mT: an orally active iron chelator of the thiosemicarbazone class with potent anti-tumour efficacy

    Science.gov (United States)

    Yu, Y; Rahmanto, Y Suryo; Richardson, DR

    2012-01-01

    BACKGROUND AND PURPOSE Our previous studies demonstrated that a thiosemicarbazone iron chelator (di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone; Dp44mT) possesses potent and selective anti-cancer activity but led to cardiotoxicity at non-optimal doses. In this study, we examined the in vivo anti-tumour efficacy and tolerability of a new-generation 2-benzoylpyridine thiosemicarbazone iron chelator (2-benzoylpyridine-4,4-dimethyl-3-thiosemicarbazone; Bp44mT) administered via the oral or i.v. routes. EXPERIMENTAL APPROACH BpT chelators were tested in vitro against human lung cancer cells (DMS-53) and in vivo in DMS-53 tumour xenografts in mice. The toxicity of Bp44mT in vivo and its effects on the expression of iron-regulated molecules involved in growth and cell cycle control were investigated. KEY RESULTS Administration of Bp44mT by either route resulted in marked dose-dependent inhibition of tumour growth. When administered at 50 mg·kg−1 via oral gavage three times per week for 23 days, the net xenograft growth was inhibited by 75%, compared with vehicle-treated mice. Toxicological examination showed reversible alterations including slight reduction of RBC count, with a decrease of liver and splenic iron levels, which confirmed iron chelation in vivo. Importantly, in contrast to Dp44mT, the chelator-treated mice did not show cardiac histological abnormalities. There was also no significant weight loss in mice, suggesting oral administration of Bp44mT was well tolerated. CONCLUSIONS AND IMPLICATIONS This is the first study to show that Bp44mT can be given orally with potent anti-tumour efficacy. Oral administration of a novel and effective chemotherapeutic agent provides the benefits of convenience for chronic dosing regimens. PMID:21658021

  10. Preparation and Biodistribution Studies of a Radiogallium-Acetylacetonate Bis (Thiosemicarbazone) Complex in Tumor-Bearing Rodents

    Science.gov (United States)

    Jalilian, Amir Reza; Yousefnia, Hassan; Shafaii, Kamaleddin; Novinrouz, Aytak; Rajamand, Amir Abbas

    2012-01-01

    Various radiometal complexes have been developed for tumor imaging, especially Ga-68 tracer. In the present study, the development of a radiogallium bis-thiosemicarbazone complex has been reported. [67Ga] acetylacetonate bis(thiosemicarbazone) complex ([67Ga] AATS) was prepared starting [67Ga]Gallium acetate and freshly prepared acetylacetonate bis (thiosemicarbazone) (AATS) in 30 min at 90°C. The partition co-efficient and the stability of the tracer were determined in final solution (25°C) and the presence of human serum (37°C) up to 24 h. The biodistribution of the labeled compound in wild-type and fibrosarcoma-bearing rodents were determined up to 72 h. The radiolabled Ga complex was prepared in high radiochemical purity (> 97%, HPLC) followed by initial biodistribution data with the significant tumor accumulation of the tracer in 2 h which is far higher than free Ga-67 cation while the compound wash-out is significantly faster. Above-mentioned pharmacokinetic properties suggest an interesting radiogallium complex while prepared by the PET Ga radioisotope, 68Ga, in accordance with the physical half life, for use in fibrosarcoma tumors, and possibly other malignancies. PMID:24250475

  11. G2/M Cell Cycle Arrest and Tumor Selective Apoptosis of Acute Leukemia Cells by a Promising Benzophenone Thiosemicarbazone Compound.

    Science.gov (United States)

    Cabrera, Maia; Gomez, Natalia; Remes Lenicov, Federico; Echeverría, Emiliana; Shayo, Carina; Moglioni, Albertina; Fernández, Natalia; Davio, Carlos

    2015-01-01

    Anti-mitotic therapies have been considered a hallmark in strategies against abnormally proliferating cells. Focusing on the extensively studied family of thiosemicarbazone (TSC) compounds, we have previously identified 4,4'-dimethoxybenzophenone thiosemicarbazone (T44Bf) as a promising pharmacological compound in a panel of human leukemia cell lines (HL60, U937, KG1a and Jurkat). Present findings indicate that T44Bf-mediated antiproliferative effects are associated with a reversible chronic mitotic arrest caused by defects in chromosome alignment, followed by induced programmed cell death. Furthermore, T44Bf selectively induces apoptosis in leukemia cell lines when compared to normal peripheral blood mononuclear cells. The underlying mechanism of action involves the activation of the mitochondria signaling pathway, with loss of mitochondrial membrane potential and sustained phosphorylation of anti-apoptotic protein Bcl-xL as well as increased Bcl-2 (enhanced phosphorylated fraction) and pro-apoptotic protein Bad levels. In addition, ERK signaling pathway activation was found to be a requisite for T44Bf apoptotic activity. Our findings further describe a novel activity for a benzophenone thiosemicarbazone and propose T44Bf as a promising anti-mitotic prototype to develop chemotherapeutic agents to treat acute leukemia malignancies. PMID:26360247

  12. G2/M Cell Cycle Arrest and Tumor Selective Apoptosis of Acute Leukemia Cells by a Promising Benzophenone Thiosemicarbazone Compound.

    Directory of Open Access Journals (Sweden)

    Maia Cabrera

    Full Text Available Anti-mitotic therapies have been considered a hallmark in strategies against abnormally proliferating cells. Focusing on the extensively studied family of thiosemicarbazone (TSC compounds, we have previously identified 4,4'-dimethoxybenzophenone thiosemicarbazone (T44Bf as a promising pharmacological compound in a panel of human leukemia cell lines (HL60, U937, KG1a and Jurkat. Present findings indicate that T44Bf-mediated antiproliferative effects are associated with a reversible chronic mitotic arrest caused by defects in chromosome alignment, followed by induced programmed cell death. Furthermore, T44Bf selectively induces apoptosis in leukemia cell lines when compared to normal peripheral blood mononuclear cells. The underlying mechanism of action involves the activation of the mitochondria signaling pathway, with loss of mitochondrial membrane potential and sustained phosphorylation of anti-apoptotic protein Bcl-xL as well as increased Bcl-2 (enhanced phosphorylated fraction and pro-apoptotic protein Bad levels. In addition, ERK signaling pathway activation was found to be a requisite for T44Bf apoptotic activity. Our findings further describe a novel activity for a benzophenone thiosemicarbazone and propose T44Bf as a promising anti-mitotic prototype to develop chemotherapeutic agents to treat acute leukemia malignancies.

  13. Enzymatic reduction of 4-(dimethylamino)benzaldehyde with carrot bits (Daucus carota): a simple experiment for understanding biocatalysis; Reducao enzimatica do 4-(dimetilamino)benzaldeido com pedacos de cenoura (Daucus carota): um experimento simples na compreensao da biocatalise

    Energy Technology Data Exchange (ETDEWEB)

    Omori, Alvaro Takeo; Portas, Viviane Barbosa; Oliveira, Camila de Souza de, E-mail: alvaro.omori@ufabc.edu.br [Centro de Ciencias Naturais e Humanas, Universidade Federal do ABC, SP (Brazil)

    2012-07-01

    The present paper describes a simple, low-costly and environmentally friendly procedure for reduction of 4-(dimethylamino)benzaldehyde using carrot bits in water. This interdisciplinary experiment can be used to introduce the concepts of biocatalysis and green chemistry to undergraduate students. (author)

  14. Proline and benzylpenicillin derivatives grafted into mesoporous MCM-41: Novel organic–inorganic hybrid catalysts for direct aldol reaction

    OpenAIRE

    Dhar, Dwairath; Beadham, Ian; Chandrasekaran, Srinivasan

    2003-01-01

    New organic–inorganic hybrid catalysts were synthesized by covalent grafting of proline and benzylpenicillin derivatives into mesoporous MCM-41. These catalysts were extensively characterized using FT-IR, $^{13}CCP MAS$ solid state NMR, XRD and TEM techniques. These were used as catalysts for direct, asymmetric aldol reaction between acetone and activated aromatic aldehydes. In the reaction of 4-nitro and 4-fluoro benzaldehyde, the aldol products were obtained in 36% and 59% ee respective...

  15. Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

    Science.gov (United States)

    Ayoup, Mohammed Salah; Cordes, David B; Slawin, Alexandra M Z

    2015-01-01

    Summary Palladium catalysed carbonylation reactions using the meta- and para-iodo derivatives of all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane (4) are illustrated as the start point for a variety of functional group interconversions. The resultant benzaldehyde and benzoic acids offer novel building blocks for further derivatisation and facilitate the incorporation of the facially polarised all-cis-1,2,4,5-tetrafluorocyclohexane motif into more advanced molecular scaffolds. PMID:26877788

  16. Derivative couplings between TDDFT excited states obtained by direct differentiation in the Tamm-Dancoff approximation

    International Nuclear Information System (INIS)

    Working within the Tamm-Dancoff approximation, we calculate the derivative couplings between time-dependent density-functional theory excited states by assuming that the Kohn-Sham superposition of singly excited determinants represents a true electronic wavefunction. All Pulay terms are included in our derivative coupling expression. The reasonability of our approach can be established by noting that, for closely separated electronic states in the infinite basis limit, our final expression agrees exactly with the Chernyak-Mukamel expression (with transition densities from response theory). Finally, we also validate our approach empirically by analyzing the behavior of the derivative couplings around the T1/T2 conical intersection of benzaldehyde

  17. Synthesis, characterization, electrochemical studies, and in vitro antibacterial activity of novel thiosemicarbazone and its Cu(II), Ni(II), and Co(II) complexes.

    Science.gov (United States)

    Khan, Salman A; Asiri, Abdullah M; Al-Amry, Khalid; Malik, Maqsood Ahmad

    2014-01-01

    Metal complexes were prepared by the reaction of thiosemicarbazone with CuCl2, NiCl2, CoCl2, Cu(OAc)2, Ni(OAc)2, and Co(OAc)2. The thiosemicarbazone coordinates to metal through the thionic sulfur and the azomethine nitrogen. The thiosemicarbazone was obtained by the thiosemicarbazide with 3-acetyl-2,5-dimethylthiophene. The identities of these compounds were elucidated by IR, (1)H, (13)C-NMR, and GC-MS spectroscopic methods and elemental analyses. The antibacterial activity of these compounds was first tested in vitro by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC) was determined by using chloramphenicol as reference drug. The results showed that compound 1.1 is better inhibitor of both types of tested bacteria as compared to chloramphenicol. PMID:24523641

  18. Preparation and biodistribution studies of [67Ga]2-acetylpyridine 4,4-dimethyl thiosemicarbazone complex as a possible SPECT tracer for detection of malignancies

    International Nuclear Information System (INIS)

    Due to the interesting anti-proliferative properties of gallium-thiosemicarbazone complexes, the production of [67Ga]labeled 2-acetylpyridine 4,4- dimethyl thiosemicarbazone (APTSM2) was investigated. The freshly prepared [67Ga]GaCl3 was mixed with 2-acetylpyridine 4,4-dimethyl thiosemicarbazone for 60 minutes at 90 deg C to yield [67Ga]APTSM2 with a radiochemical yield of more than 98%. Radio-thin-layerchromatography (RTLC) showed a radiochemical purity of more than 99%. A specific activity of about 370-740 MBq/mmol (10-20 Ci/mmol) was obtained. The stability of the final product was checked in the absence and presence of human serum at 37 deg C. The partition coefficient of the final complex was also determined. The biodistribution of the labeled compound in normal rats was compared with that of free Ga3+ cation up to 22 hours. (author)

  19. Synthesis, Characterization, Electrochemical Studies, and In Vitro Antibacterial Activity of Novel Thiosemicarbazone and Its Cu(II, Ni(II, and Co(II Complexes

    Directory of Open Access Journals (Sweden)

    Salman A. Khan

    2014-01-01

    Full Text Available Metal complexes were prepared by the reaction of thiosemicarbazone with CuCl2, NiCl2, CoCl2, Cu(OAc2, Ni(OAc2, and Co(OAc2. The thiosemicarbazone coordinates to metal through the thionic sulfur and the azomethine nitrogen. The thiosemicarbazone was obtained by the thiosemicarbazide with 3-acetyl-2,5-dimethylthiophene. The identities of these compounds were elucidated by IR, 1H, 13C-NMR, and GC-MS spectroscopic methods and elemental analyses. The antibacterial activity of these compounds was first tested in vitro by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC was determined by using chloramphenicol as reference drug. The results showed that compound 1.1 is better inhibitor of both types of tested bacteria as compared to chloramphenicol.

  20. Promoting the Hydrosilylation of Benzaldehyde by Using a Dicationic Antimony-Based Lewis Acid: Evidence for the Double Electrophilic Activation of the Carbonyl Substrate.

    Science.gov (United States)

    Hirai, Masato; Cho, Junsang; Gabbaï, François P

    2016-05-01

    The concomitant activation of carbonyl substrates by two Lewis acids has been investigated by using [1,2-(Ph2 MeSb)2 C6 H4 ](2+) ([1](2+) ), an antimony-based bidentate Lewis acid obtained by methylation of the corresponding distibine. Unlike the simple stibonium cation [Ph3 MeSb](+) , dication [1](2+) efficiently catalyzes the hydrosilylation of benzaldehyde under mild conditions. The catalytic activity of this dication is correlated to its ability to doubly activate the carbonyl functionality of the organic substrate. This view is supported by the isolation of [1-μ2 -DMF][OTf]2 , an adduct, in which the DMF oxygen atom bridges the two antimony centers. PMID:26934491

  1. The synthesis and investigation of impurities found in Clandestine Laboratories: Baeyer-Villiger Route Part I; Synthesis of P2P from benzaldehyde and methyl ethyl ketone.

    Science.gov (United States)

    Doughty, David; Painter, Ben; Pigou, Paul E; Johnston, Martin R

    2016-06-01

    The synthesis of impurities detected in clandestinely manufactured Amphetamine Type Stimulants (ATS) has emerged as more desirable than simple "fingerprint" profiling. We have been investigating the impurities formed when phenyl-2-propanone (P2P) 5, a key ATS precursor, is synthesised in three steps; an aldol condensation of benzaldehyde and methyl ethyl ketone (MEK); a Baeyer-Villiger reaction; and ester hydrolysis. We have identified and selectively synthesised several impurities that may be used as route specific markers for this series of synthetic steps. Specifically these impurities are 3-methyl-4-phenyl-3-buten-2-one 3, 2-methyl-1,5-diphenylpenta-1,4-diene-3-one 9, 2-(methylamino)-3-methyl-4-phenyl-3-butene 16, 2-(Methylamino)-3-methyl-4-phenylbutane 17, and 1-(methylamino)-2-methyl-1,5-diphenylpenta-4-ene-3-one 22. PMID:27081790

  2. MCM-41 supported 12-tungstophosphoric acid mesoporous materials: Preparation, characterization, and catalytic activities for benzaldehyde oxidation with H2O2

    Science.gov (United States)

    Chen, Ya; Zhang, Xiao-Li; Chen, Xi; Dong, Bei-Bei; Zheng, Xiu-Cheng

    2013-10-01

    Mesoporous molecular sieves MCM-41 and bulk 12-tungstophosphoric acid (HPW) were synthesized and employed to prepare 5-45 wt.% HPW/MCM-41 mesoporous materials. Characterization results suggested the good dispersion of HPW within MCM-41 when the loading of HPW was less than 35 wt.% and HPW/MCM-41 retained the typical mesopore structure of the supports. The results of the catalytic oxidation of benzaldehyde to benzoic acid with 30% H2O2, in the absence of any organic solvent and co-catalysts, indicated that HPW/MCM-41 was an efficient catalyst and 30 wt.% HPW/MCM-41 sample exhibited the highest catalytic activity among these materials.

  3. High efficient photocatalytic selective oxidation of benzyl alcohol to benzaldehyde by solvothermal-synthesized ZnIn{sub 2}S{sub 4} microspheres under visible light irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Chen, Zhixin, E-mail: czx@fzu.edu.cn [State Key Laboratory Breeding Base of Photocatalysis, College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002 (China); Instrumental Measurement and Analysis Center, Fuzhou University, Fuzhou 350002 (China); Xu, Jingjing; Ren, Zhuyun [State Key Laboratory Breeding Base of Photocatalysis, College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002 (China); He, Yunhui; Xiao, Guangcan [State Key Laboratory Breeding Base of Photocatalysis, College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350002 (China); Instrumental Measurement and Analysis Center, Fuzhou University, Fuzhou 350002 (China)

    2013-09-15

    Hexagonal ZnIn{sub 2}S{sub 4} samples have been synthesized by a solvothermal method. Their properties have been determined by X-ray diffraction, ultraviolet–visible-light diffuse reflectance spectra, field emission scanning electron microscopy, nitrogen adsorption–desorption and X-ray photoelectron spectra. These results demonstrate that ethanol solvent has significant influence on the morphology, optical and electronic nature for such marigold-like ZnIn{sub 2}S{sub 4} microspheres. The visible light photocatalytic activities of the ZnIn{sub 2}S{sub 4} have been evaluated by selective oxidation of benzyl alcohol to benzaldehyde using molecular oxygen as oxidant. The results show that 100% conversion along with >99% selectivity are reached over ZnIn{sub 2}S{sub 4} prepared in ethanol solvent under visible light irradiation (λ>420 nm) of 2 h, but only 58% conversion and 57% yield are reached over ZnIn{sub 2}S{sub 4} prepared in aqueous solvent. A possible mechanism of the high photocatalytic activity for selective oxidation of benzyl alcohol over ZnIn{sub 2}S{sub 4} is proposed and discussed. - Graphical abstract: Marigold-like ZnIn{sub 2}S{sub 4} microspheres were synthesized by a solvothermal method. The high visible photocatalytic activities of ZnIn{sub 2}S{sub 4} were evaluated by selective oxidation of benzyl alcohol to benzaldehyde under mild conditions. Display Omitted - Highlights: • Marigold-like ZnIn{sub 2}S{sub 4} microspheres were synthesized by a solvothermal method. • The solvents have a remarkably influence on the morphology and properties of samples. • It is the first time to apply ZnIn{sub 2}S{sub 4} for selective oxidation of benzyl alcohol. • ZnIn{sub 2}S{sub 4} shows high photocatalytic activity for selective oxidation of benzyl alcohol.

  4. High efficient photocatalytic selective oxidation of benzyl alcohol to benzaldehyde by solvothermal-synthesized ZnIn2S4 microspheres under visible light irradiation

    International Nuclear Information System (INIS)

    Hexagonal ZnIn2S4 samples have been synthesized by a solvothermal method. Their properties have been determined by X-ray diffraction, ultraviolet–visible-light diffuse reflectance spectra, field emission scanning electron microscopy, nitrogen adsorption–desorption and X-ray photoelectron spectra. These results demonstrate that ethanol solvent has significant influence on the morphology, optical and electronic nature for such marigold-like ZnIn2S4 microspheres. The visible light photocatalytic activities of the ZnIn2S4 have been evaluated by selective oxidation of benzyl alcohol to benzaldehyde using molecular oxygen as oxidant. The results show that 100% conversion along with >99% selectivity are reached over ZnIn2S4 prepared in ethanol solvent under visible light irradiation (λ>420 nm) of 2 h, but only 58% conversion and 57% yield are reached over ZnIn2S4 prepared in aqueous solvent. A possible mechanism of the high photocatalytic activity for selective oxidation of benzyl alcohol over ZnIn2S4 is proposed and discussed. - Graphical abstract: Marigold-like ZnIn2S4 microspheres were synthesized by a solvothermal method. The high visible photocatalytic activities of ZnIn2S4 were evaluated by selective oxidation of benzyl alcohol to benzaldehyde under mild conditions. Display Omitted - Highlights: • Marigold-like ZnIn2S4 microspheres were synthesized by a solvothermal method. • The solvents have a remarkably influence on the morphology and properties of samples. • It is the first time to apply ZnIn2S4 for selective oxidation of benzyl alcohol. • ZnIn2S4 shows high photocatalytic activity for selective oxidation of benzyl alcohol

  5. Syntheses, structural and spectral studies of six-coordinate, [Ph 2SnCl(acpm)], and seven-coordinate, [ nBu 2Sn(dapm)], diorganotin(IV) complexes with N, N, S-tridentate and S, N, N, N, S-pentadentate N4-heterocyclic thiosemicarbazones

    Science.gov (United States)

    de Sousa, Gerimário F.; Manso, Luís Carlos C.; Lang, Ernesto S.; Gatto, Claudia C.; Mahieu, Bernard

    2007-01-01

    The reaction of the N, N, S-tridentate ligand 2-acetylpyridine ( N4-morpholyl thiosemicarbazones), Hacpm, with Ph 2SnCl 2 leads to the formation of the six-coordinate complex [Ph 2SnCl(acpm)] ( 1), whereas the reaction of the S, N, N, N, S-pentadentate ligand 2,6-diacetylpyridine bis( N4-morpholyl thiosemicarbazone), H 2dapm, with nBu 2SnCl 2 leads to the formation of the seven-coordinate complex [ nBu 2Sn(dapm)] ( 2). Both compounds were studied by microanalyses, IR, NMR ( 1H, 13C, 119Sn) and Mössbauer spectroscopy to investigate their structural properties. The organotin(IV) complexes were also studied by single crystal X-ray diffraction and the structure determination revealed that the phenyl derivative crystallizes in the triclinic space group (P1¯) as discrete neutral molecules, with the tin(IV) ion in a distorted octahedral geometry with the acpm 1- ligand in a meridional configuration and the phenyl groups in trans positions. X-ray analysis shows that the n-butyl complex crystallizes in the monoclinic space group ( P2 1/ c) as discrete neutral complexes, with the tin(IV) ion in a distorted pentagonal bipyramidal geometry. A correlation between Mössbauer and X-ray data based on the point-charge model is discussed.

  6. Synthesis, Spectroscopic and Physicochemical Characterization and Biological Activity of Co(II) and Ni(II) Coordination Compounds with 4-Aminoantipyrine Thiosemicarbazone

    OpenAIRE

    Ram K. Agarwal; Surendra Prasad

    2004-01-01

    We describe the synthesis and characterization of cobalt(II) and nickel(II) coordination compounds of 4[N-(furan-2’-aldimine)amino]antipyrine thiosemicarbazone (FFAAPTS) and 4[N-(4'-nitrobenzalidene) amino]antipyrine thiosemicarbazone (4'-NO2BAAPTS). All the isolated compounds have the general composition MX2(L)(H2O) (M = Co2+ or Ni2+; X = Cl, Br, NO3, NCS or CH3COO; L = FFAAPTS or 4'-NO2BAAPTS) and M(ClO4)2(L)2 (M = Co2+ or Ni2+; L = FFAAPTS or 4'-NO2BAAPTS). Infrared spectral studies i...

  7. The anticancer thiosemicarbazones Dp44mT and triapine lack inhibitory effects as catalytic inhibitors or poisons of DNA topoisomerase IIα

    OpenAIRE

    Yalowich, Jack C.; Wu, Xing; Zhang, Rui; Kanagasabai, Ragu; Hornbaker, Marissa; Hasinoff, Brian B

    2012-01-01

    The thiosemicarbazones Dp44mT (di-2-pyridylketone-4,4-dimethyl-3-thiosemicarbazone) and triapine have potent antiproliferative activity and have been evaluated as anticancer agents. While these compounds strongly bind iron and copper, their mechanism(s) of action are incompletely understood. A recent report (Rao et al., Cancer Research 69:948-957, 2009) suggested that Dp44mT may, in part, exert its cytotoxicity through poisoning of DNA topoisomerase IIα. In the present report, a variety of as...

  8. DNA-binding, catalytic oxidation, C—C coupling reactions and antibacterial activities of binuclear Ru(II) thiosemicarbazone complexes: Synthesis and spectral characterization

    OpenAIRE

    Arumugam Manimaran; Chinnasamy Jayabalakrishnan

    2012-01-01

    New hexa-coordinated binuclear Ru(II) thiosemicarbazone complexes of the type {[(B)(EPh3)(CO)ClRu]2L} (where, E = P or As; B = PPh3 or AsPh3 or pyridine; L = mononucleating NS donor of N-substituted thiosemicarbazones) have been synthesized and characterized by elemental analysis, FT-IR, UV–vis and 31P{1H} NMR cyclic voltammetric studies. The DNA-binding studies of Ru(II) complexes with calf thymus DNA (CT-DNA) were investigated by UV–vis, viscosity measurements, gel-electrophoresis and fluor...

  9. Novel and potent anti-tumor and anti-metastatic di-2-pyridylketone thiosemicarbazones demonstrate marked differences in pharmacology between the first and second generation lead agents

    OpenAIRE

    Sestak, Vit; Stariat, Jan; Cermanova, Jolana; Potuckova, Eliska; Chladek, Jaroslav; Roh, Jaroslav; Bures, Jan; Jansova, Hana; Prusa, Petr; Sterba, Martin; Micuda, Stanislav; Simunek, Tomas; Kalinowski, Danuta S.; Richardson, Des R.; Kovarikova, Petra

    2015-01-01

    Di(2-pyridyl)ketone 4,4-dimethyl-3-thiosemicarbazone (Dp44mT) and di(2-pyridyl)ketone 4-cyclohexyl-4-methyl-3-thiosemicarbazone (DpC) are novel, highly potent and selective anti-tumor and anti-metastatic drugs. Despite their structural similarity, these agents differ in their efficacy and toxicity in-vivo. Considering this, a comparison of their pharmacokinetic and pharmaco/toxico-dynamic properties was conducted to reveal if these factors are involved in their differential activity. Both com...

  10. Synthesis, characterization and antibacterial studies of ruthenium(III) complexes derived from chitosan schiff base.

    Science.gov (United States)

    Vadivel, T; Dhamodaran, M

    2016-09-01

    Chitosan can be modified chemically by condensation reaction of deacetylated chitosan with aldehyde in homogeneous phase. This condensation is carried by primary amine (NH2) with aldehyde (CHO) to form corresponding schiff base. The chitosan biopolymer schiff base derivatives are synthesized with substituted aldehydes namely 4-hydroxy-3-methoxy benzaldehyde, 2-hydroxy benzaldehyde, and 2-hydroxy-3-methoxy benzaldehyde, becomes a complexing agent or ligand. The Ruthenium(III) complexes were obtained by complexation of Ruthenium with schiff base ligands and this product exhibits as an excellent solubility and more biocompatibility. The novel series of schiff base Ruthenium(III) complexes are characterized by Elemental analysis, FT-IR spectroscopy, and Thermo-gravimetric analysis (TGA). The synthesized complexes have been subjected to antibacterial study. The antibacterial results indicated that the antibacterial activity of the complexes were more effective against Gram positive and Gram negative pathogenic bacteria. These findings are giving suitable support for developing new antibacterial agent and expand our scope for applications. PMID:26562551

  11. Cobalt substituted thiosemicarbazone metal complex induced apoptosis in cancer cells via activation of mitochondrial pathway

    International Nuclear Information System (INIS)

    Thiosemicarbazone (TSC) and their transition metal complexes are broad class of biologically active small molecules and present a great variety of biological activity ranging from antitumour, fungicide, bacteriocide, anti inflammatory and antiviral activities. These characteristics render the whole class of compounds very interesting. In the present study, we sought to examine cytotoxic activity of thiosemicarbazone cobalt complex on various cancer cell lines along with the possible mechanism through which the compound induce apoptosis in these cell lines. Cytotoxicity of TSC cobalt complex was studied by performing standard MTT drug sensitivity assay and determining its IC50 value on various leukemic and solid cancer cell lines like HL-60, MOLT-4, K-562 and COLO-205. Cellular damage upon the treatment of test molecule was analyzed by conducting LDH release assay. DNA fragmentation and morphology of apoptotic cells were assessed respectively by performing ladder assay and acridine orange/ethidium bromide staining. Role of mitochondria in the induction of cell death was studied by measuring mitochondrial membrane potential (ΔΨm) using JC-1 probe. The cytotoxicity studies confirms that TSC cobalt complex is having potent anticancer activity on HL-60, K-562, MOLT-4 and COLO-205 cell lines with the IC50 value in the range 0.225-29.00 μM. Dose dependent increase in the LDH release into the surrounding media depicts the cell membrane disintegrity. DNA fragmentation on treated cells revealed the cell death, which is commonly associated with apoptosis. Fluorescence microscopic imaging of treated cells confirms that the mode of cell death was through apoptosis. Loss of the ΔΨm in treated cells explicates the involvement of mitochondria in the cell death induction. Further increase in caspase-3 activity upon treatment corroborates that molecule induces apoptosis. Taken together, this exploratory study revealed that TSC cobalt complex possesses potent cytotoxic and

  12. 99mTc(CO)3 - nitrofuryl thiosemicarbazone a novel infection imaging agent

    International Nuclear Information System (INIS)

    Full text: To develop a potential Technetium labeled infection imaging agent 5-NTS prepared and labeled and its scintigraphic imaging done in rat model. Objective: Diagnosis of deep seated infection is a very challenging problem. Differentiation between bacterial infection and sterile inflammation is also difficult. As thiosemicarbazone compound show antibacterial activity, so a new infection imaging agent was prepared. Their in-vitro and in-vitro stability studies, through biological screening and scintigraphic imaging of the chelates labeled with 99mTc studied on infected thigh muscle tissues in rat model. Materials and Methods: Synthesis of 5-nitrofural thiosemicarbazone An equimolar mixture of 5 nitrofural and thiosemicarbazide was stirred with p-TsOH (catalytic amounts) in dry toluene. Synthesized compound characterized by 1H-NMR and ESI-MS. The synthesized compound labeled with 99mTc(CO)3 precursor and 99mTc-oxo(V) core using stannous chloride reduction method. Labeled compound was characterized by TLC in acetone, brine, and ethanol: water: acetic acid: pyridine (1:5:5:1) and also with reverse phase C-18 column. In-vitro stability study was tested in challenge assay with increasing concentration of DTPA (0, 102, 103, 104, 105 molar excess) for 4 hour. Serum stability was also done and its stability analyzed at 0, 2, 8, 18, 24 hour. Infection was induced in rats (Sprague Dawley, 200-220gm) by injecting 0.2 ml of freshly prepared harvested culture of S. aureus (2x108cfu) in left thigh muscle. One day after when the infection was apparent, radiopharmaceutical (185-259 kBq/0.1ml) was injected intravenously. For comparison sterile inflammation was induced by an intramuscular injection of 0.1ml of Terpentine oil I. P. to left thigh muscle. The infected animal with radiopharmaceuticals sacrificed at 1, 4, 8, 24 hour post injection, desired organ were collected and transferred to counting vials. Blood samples were obtained by puncture of the heart. Results: Expressed

  13. Bis(ethanol-κO)bis(pyridine-3-carbaldehyde-κN thiosemicarbazone)bis(thiocyanato-κN)iron(II)–pyridine-3-carbaldehyde thiosemicarbazone (1/2)

    OpenAIRE

    Shao-Mei Wang

    2009-01-01

    The crystal structure of the title FeII complex, [Fe(NCS)2(C7H8N4S)2(CH3CH2OH)2]·2C7H8N4S, based on the Schiff base ligand pyridine-3-carbaldehyde thiosemicarbazone (pct), results from the cocrystallization of an FeII coordination compound together with two of the pct ligands. The complex unit is mononuclear, with the central FeII ion located on a crystallographic centre of inversion and coordinated by four N atoms from two pct ligands and two thiocyanate anions. The slightly distort...

  14. Mesostructured SBA-15-Pr-SO3H: An efficient solid acid catalyst for one-pot and solvent-free synthesis of 3,4-dihydro-2-pyridone derivatives

    Indian Academy of Sciences (India)

    Ghodsi Mohammadi Ziarani; Somayeh Mousavi; Negar Lashgari; Alireza Badiei

    2013-11-01

    3,4-Dihydro-2-pyridone derivatives have been prepared efficiently via a one-pot four-component reaction of benzaldehyde derivatives, Meldrum’s acid, methyl acetoacetate and ammonium acetate in the presence of sulphonic acid-functionalized ordered nanoporous SBA-15 as a nano heterogeneous catalyst under solvent-free conditions. This process is a simple, environmentally friendly, rapid and high yielding reaction.

  15. Evidence for dual mode of action of a thiosemicarbazone, NSC73306: A potent substrate of the multidrug resistance-linked ABCG2 transporter

    Science.gov (United States)

    Wu, Chung-Pu; Shukla, Suneet; Calcagno, Anna Maria; Hall, Matthew D.; Gottesman, Michael M.; Ambudkar, Suresh V.

    2008-01-01

    Multidrug resistance due to reduced drug accumulation is a phenomenon predominantly caused by the overexpression of members of the ATP-binding cassette transporters, including ABCB1 (P-glycoprotein), ABCG2 and several ABCC family members (MRPs). We previously reported that a thiosemicarbazone derivative, NSC73306, is cytotoxic to carcinoma cells that overexpress functional P-glycoprotein and it re-sensitizes these cells to chemotherapeutics. In this study, we investigated the effect of NSC73306 on cells overexpressing other ABC drug transporters, including ABCG2, MRP1, MRP4 and MRP5. Our findings demonstrated that NSC73306 is not more toxic to cells that overexpress these transporters compared to their respective parental cells, and these transporters do not confer resistance to NSC73306 either. In spite of this, we observed that NSC73306 is a transport substrate for ABCG2 that can effectively inhibit ABCG2-mediated drug transport and reverse resistance to both mitoxantrone and topotecan in ABCG2-expressing cells. Interactions between NSC73306 and the ABCG2 drug-binding site(s) were confirmed by its stimulatory effect on ATPase activity (140–150 nM concentration required for 50% stimulation) and by inhibition of [125I]-Iodoarylazidoprazosin photolabeling (50% inhibition at 250–400 nM) of the substrate-binding site(s). Overall, NSC73306 appears to be a potent modulator of ABCG2 that does not interact with MRP1, MRP4 or MRP5. Collectively, these data suggest that NSC73306 can potentially be used, due to its dual mode of action, as an effective agent to overcome drug resistance by eliminating P-glycoprotein-overexpressing cells, and by acting as a potent modulator that re-sensitizes ABCG2-expressing cancer cells to chemotherapeutics. PMID:18089722

  16. Binuclear ruthenium(III) bis(thiosemicarbazone) complexes: Synthesis, spectral, electrochemical studies and catalytic oxidation of alcohol

    Science.gov (United States)

    Mohamed Subarkhan, M.; Ramesh, R.

    2015-03-01

    A new series of binuclear ruthenium(III) thiosemicarbazone complexes of general formula [(EPh3)2(X)2Ru-L-Ru(X)2(EPh3)2] (where E = P or As; X = Cl or Br; L = NS chelating bis(thiosemicarbazone ligands) has been synthesized and characterized by analytical and spectral (FT-IR, UV-Vis and EPR). IR spectra show that the thiosemicarbazones behave as monoanionic bidentate ligands coordinating through the azomethine nitrogen and thiolate sulphur. The electronic spectra of the complexes indicate that the presence of d-d and intense LMCT transitions in the visible region. The complexes are paramagnetic (low spin d5) in nature and all the complexes show rhombic distortion around the ruthenium ion with three different 'g' values (gx ≠ gy ≠ gz) at 77 K. All the complexes are redox active and exhibit an irreversible metal centered redox processes (RuIII-RuIII/RuIV-RuIV; RuIII-RuIII/RuII-RuII) within the potential range of 0.38-0.86 V and -0.39 to -0.66 V respectively, versus Ag/AgCl. Further, the catalytic efficiency of one of the complexes [Ru2Cl2(AsPh3)4(L1)] (4) has been investigated in the case of oxidation of primary and secondary alcohols into their corresponding aldehydes and ketones in the presence of N-methylmorpholine-N-oxide(NMO) as co-oxidant. The formation of high valent RuVdbnd O species is proposed as catalytic intermediate for the catalytic cycle.

  17. Identification of semicarbazones, thiosemicarbazones and triazine nitriles as inhibitors of Leishmania mexicana cysteine protease CPB.

    Directory of Open Access Journals (Sweden)

    Jörg Schröder

    Full Text Available Cysteine proteases of the papain superfamily are present in nearly all eukaryotes. They play pivotal roles in the biology of parasites and inhibition of cysteine proteases is emerging as an important strategy to combat parasitic diseases such as sleeping sickness, Chagas' disease and leishmaniasis. Homology modeling of the mature Leishmania mexicana cysteine protease CPB2.8 suggested that it differs significantly from bovine cathepsin B and thus could be a good drug target. High throughput screening of a compound library against this enzyme and bovine cathepsin B in a counter assay identified four novel inhibitors, containing the warhead-types semicarbazone, thiosemicarbazone and triazine nitrile, that can be used as leads for antiparasite drug design. Covalent docking experiments confirmed the SARs of these lead compounds in an effort to understand the structural elements required for specific inhibition of CPB2.8. This study has provided starting points for the design of selective and highly potent inhibitors of L. mexicana cysteine protease CPB that may also have useful efficacy against other important cysteine proteases.

  18. Synthesis, structure and biological activity of nickel(II) complexes of 5-methyl 2-furfural thiosemicarbazone.

    Science.gov (United States)

    Jouad, E M; Larcher, G; Allain, M; Riou, A; Bouet, G M; Khan, M A; Thanh, X D

    2001-09-01

    5-Methyl 2-furfuraldehyde thiosemicarbazone (M5HFTSC) with nickel(II) leads to three types of complexes: [Ni(M5HFTSC)(2)X(2)], [Ni(M5FTSC)(2)] and [Ni(M5FTSC)(2)] x 2DMF. In the first type the ligand remains in thione form, while in the two other, the anionic thiolato form is involved. The species [Ni(M5HFTSC)(2)X(2)] has been characterized spectroscopically. The structures of [Ni(M5FTSC)(2)] x 2DMF and [Ni(M5FTSC)(2)] have been solved using X-ray diffraction. Biological studies of [Ni(M5HFTSC)(2)Cl(2)] have been carried out in vitro for antifungal activity on human pathogenic fungi, Aspergillus fumigatus and Candida albicans, and in vivo for toxicity on mice. The results are compared to those of the ligand, the metal salt and a similar copper complex [Cu(M5HFTSC)Cl(2)]. PMID:11566328

  19. 2-Acetylpyridine N4-Phenyl- Thiosemicarbazone as a new tool for tumour diagnosis

    International Nuclear Information System (INIS)

    The aim of this work was to determine in vivo biodistribution of radiolabelled 2-acetylpyridine N4 phenyl thiosemicarbazone (Ph) and to evaluate its applicability for tumour diagnosis. Ph was labelled with 125I using lactoperoxidase method and radiochemical analysis was performed by chromatography. 125I-Ph production was successful with 86 ± 9.2% of radiochemical purity and high specific activity (17.6 TBq /mmol). 125I-Ph was used for biodistribution and pharmacokinetics studies on Swiss mice bearing Ehrlich solid tumour. 125I-Ph presented a rapid blood clearance (T1/2= 97.2 min.) and the kidneys were the main excretion pathway (CL0.01 mL/min). 125I-Ph uptake was significant in tumour (2.5%ID/g) and tumour-to-normal tissue uptake was more than 20-fold higher depending on the organ. The uptake by the organs like heart, lungs, stomach and liver followed the blood perfusion. Our results suggest that 125I-Ph possess indispensable characteristics for an efficient radiopharmaceutical for tumour diagnosis. The next step will be to evaluate the quality of tumour SPECT images provided by 131I-Ph. (author)

  20. Study on the Interaction between Isatin-β-Thiosemicarbazone and Calf Thymus DNA by Spectroscopic Techniques

    Science.gov (United States)

    Pakravan, Parvaneh; Masoudian, Shahla

    2015-01-01

    The interaction between isatin-β-thiosemicarbazone (IBT) and calf thymus DNA (CT-DNA) was investigated in physiological buffer (pH 7.4) using Neutral Red (NR) dye as a spectral probe by UV–Vis absorption and fluorescence spectroscopy, as well as viscosity measurements. The IBT is stabilized by intercalation in the DNA (K [IBT –DNA] = 1.03×105 M−1), and displaces the NR dye from the NR–DNA complex. The binding constants Kf and number of binding sites (n≈1) of IBT with DNA were obtained by fluorescence quenching method at different temperatures. Furthermore, the enthalpy and entropy of the reaction between IBT and CT-DNA showed that the reaction is enthalpy-favored and entropy-disfavored. The changes in the base stacking of CT-DNA upon the binding of IBT are reflected in the circular dichroic (CD) spectral studies. The viscosity increase of CT-DNA solution is another evidence to indicate that, IBT is able to be intercalated in the DNA base pairs. PMID:25561917

  1. Ruthenium (II) complexes of thiosemicarbazone: synthesis, biosensor applications and evaluation as antimicrobial agents.

    Science.gov (United States)

    Yildirim, Hatice; Guler, Emine; Yavuz, Murat; Ozturk, Nurdan; Kose Yaman, Pelin; Subasi, Elif; Sahin, Elif; Timur, Suna

    2014-11-01

    A conformationally rigid half-sandwich organoruthenium (II) complex [(η(6)-p-cymene)RuClTSC(N-S)]Cl, (1) and carbonyl complex [Ru(CO)Cl(PPh3)2TSC(N-S)] (2) have been synthesized from the reaction of [{(η(6)-p-cymene)RuCl}2(μ-Cl)2] and [Ru(H)(Cl)(CO)(PPh3)3] with thiophene-2-carboxaldehyde thiosemicarbazon (TSC) respectively and both novel ruthenium (II) complexes have been characterized by elemental analysis, FT-IR and NMR spectroscopy. The peripheral TSC in the complexes acts as an electrochemical coupling unit providing the ability to carry out electrochemical deposition (ED) and to form an electro-deposited film on a graphite electrode surface. The biosensing applicability of complexes 1 and 2 was investigated by using glucose oxidase (GOx) as a model enzyme. Electrochemical measurements at -0.9V versus Ag/AgCl electrode by following the ED Ru(II) reduction/oxidation due to from the enzyme activity, in the presence of glucose substrate. The designed biosensor showed a very good linearity for 0.01-0.5mM glucose. The in vitro antimicrobial activities of complexes 1 and 2 were also investigated against nine bacterial strains and one fungus by the disc diffusion test method. No activity was observed against the Gram-negative strains and fungus, whereas complex 1 showed moderate antibacterial activities against Gram-positive bacterial strains. PMID:25280673

  2. Synthesis and spectral investigations of Mn(II) complexes of pentadentate bis(thiosemicarbazones)

    Science.gov (United States)

    Krishnan, Suja; Laly, K.; Prathapachandra Kurup, M. R.

    2010-02-01

    Five Mn(II) complexes of bis(thiosemicarbazones) which are represented as [Mn(H 2Ac4Ph)Cl 2] ( 1), [Mn(Ac4Ph)H 2O] ( 2), [Mn(H 2Ac4Cy)Cl 2]·H 2O ( 3), [Mn(H 2Ac4Et)Cl 2]·3H 2O ( 4) and [Mn(H 2Ac4Et)(OAc) 2]·3H 2O ( 5) have been synthesized and characterized by elemental analyses, electronic, infrared and EPR spectral techniques. In all the complexes except [Mn(Ac4Ph)H 2O], the ligands act as pentadentate neutral molecules and coordinate to Mn(II) ion through two thione sulfur atoms, two azomethine nitrogens and the pyridine nitrogen, suggesting a heptacoordination. While in compound [Mn(Ac4Ph)H 2O], the dianionic ligand is coordinated to the metal suggesting six coordination in this case. Magnetic studies indicate the high spin state of Mn(II). Conductivity measurements reveal their non-electrolyte nature. EPR studies indicate five g values for [Mn(Ac4Ph)H 2O] showing zero field splitting.

  3. Intracellular reduction/activation of a disulfide switch in thiosemicarbazone iron chelators

    Science.gov (United States)

    Akam, Eman A.; Chang, Tsuhen M.; Astashkin, Andrei V.

    2014-01-01

    Iron scavengers (chelators) offer therapeutic opportunities in anticancer drug design by targeting the increased demand for iron in cancer cells as compared to normal cells. Prochelation approaches are expected to avoid systemic iron depletion as chelators are liberated under specific intracellular conditions. In the strategy described herein, a disulfide linkage is employed as a redox-directed switch within the binding unit of an antiproliferative thiosemicarbazone prochelator, which is activated for iron coordination following reduction to the thiolate chelator. In glutathione redox buffer, this reduction event occurs at physiological concentrations and half-cell potentials. Consistent with concurrent reduction and activation, higher intracellular thiol concentrations increase cell susceptibility to prochelator toxicity in cultured cancer cells. The reduction of the disulfide switch and intracellular iron chelation are confirmed in cell-based assays using calcein as a fluorescent probe for paramagnetic ions. The resulting low-spin Fe(III) complex is identified in intact Jurkat cells by EPR spectroscopy measurements, which also document a decreased concentration of active ribonucleotide reductase following exposure to the prochelator. Cell viability and fluorescence-based assays show that the iron complex presents low cytotoxicity and does not participate in intracellular redox chemistry, indicating that this antiproliferative chelation strategy does not rely on the generation of reactive oxygen species. PMID:25100578

  4. EXTRACTIVE SPECTROPHOTOMETRIC STUDIES OF ACETOPHENONE 2’, 4’-DIHYDROXY THIOSEMICARBAZONE WITH IRON

    Directory of Open Access Journals (Sweden)

    P. K. Rana

    2012-10-01

    Full Text Available Acetophenone 2’, 4’-Dihydroxy thiosemicarbazone (APDHTS as a reagent for the extractive spectrophotometric determination of Iron. The reagent APDHTS gave instantaneous and stable violet colour with Iron at pH 5.0. A linear calibration graph over the concentration range 1 ppm to 10 ppm with a 3σ limit of detection of 0.66 ppm was obtained by applying the spectrophotometric method at wavelength 370 nm. The stoichiometry of the complex is established as 1:1 (M: L by Job’s method of continuous variation and confirmed by mole ratio method. The standard deviation and the coefficient of variations are presented. The molar absorptivity and Sandal’s sensitivity of the complex is 0.4469 x 103 L mol-1cm –1 and 0.0125 µg cm-2 respectively. The results of the prescribed procedure applied for the determination of the micro amounts of Fe (III in various synthetic and standard steel samples are presented.

  5. Species Dependence of [64Cu]Cu-Bis(thiosemicarbazone) Radiopharmaceutical Binding to Serum Albumins

    Science.gov (United States)

    Basken, Nathan E.; Mathias, Carla J.; Lipka, Alexander E.; Green, Mark A.

    2008-01-01

    Introduction Interactions of three copper(II) bis(thiosemicarbazone) PET radiopharmaceuticals with human serum albumin, and the serum albumins of four additional mammalian species, were evaluated. Methods 64Cu-labeled diacetyl bis(N4-methylthiosemicarbazonato)copper(II) (Cu-ATSM), pyruvaldehyde bis(N4-methylthiosemicarbazonato)copper(II) (Cu-PTSM), and ethylglyoxal bis(thiosemicarbazonato)copper(II) (Cu-ETS) were synthesized and their binding to human, canine, rat, baboon, and porcine serum albumins quantified by ultrafiltration. Protein binding was also measured for each tracer in human, porcine, rat, and mouse serum. Results The interaction of these neutral, lipophilic copper chelates with serum albumin is highly compound- and species-dependent. Cu-PTSM and Cu-ATSM exhibit particularly high affinity for human serum albumin (HSA), while the albumin binding of Cu-ETS is relatively insensitive to species. At HSA concentrations of 40 mg/mL, “% Free” (non-albumin-bound) levels of radiopharmaceutical were 4.0 ± 0.1%; 5.3 ± 0.2%; and 38.6 ± 0.8% for Cu-PTSM; Cu-ATSM; and Cu-ETS, respectively. Conclusions Species-dependent variations in radiopharmaceutical binding to serum albumin may need to be considered when using animal models to predict the distribution and kinetics of these compounds in humans. PMID:18355683

  6. Crystal structures of crotonaldehyde semicarbazone and crotonaldehyde thiosemicarbazone from X-ray powder diffraction data.

    Science.gov (United States)

    Arfan, Atef; Rukiah, Mwaffak

    2015-02-01

    Crotonaldehyde semicarbazone {systematic name: (E)-2-[(E)-but-2-en-1-yl-idene]hydrazinecarboxamide}, C5H9N3O, (I), and crotonaldehyde thio-semi-carba-zone {systematic name: (E)-2-[(E)-but-2-en-1-yldene]hydra-zinecarbo--thio-amide}, C5H9N3S, (II), show the same E conformation around the imine C=N bond. Compounds (I) and (II) were obtained by the condensation of crotonaldehyde with semicarbazide hydro-chloride and thio-semicarbazide, respectively. Each mol-ecule has an intra-molecular N-H⋯N hydrogen bond, which generates an S(5) ring. In (I), the crotonaldehyde fragment is twisted by 2.59 (5)° from the semicarbazide mean plane, while in (II) the corresponding angle (with the thio-semicarbazide mean plane) is 9.12 (5)°. The crystal packing is different in the two compounds: in (I) inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane, while weak inter-molecular N-H⋯S hydrogen bonds in (II) link the mol-ecules into chains propagating in [110]. PMID:25878810

  7. Tin(II Selective PVC Membrane Electrode Based on Salicylaldehyde Thiosemicarbazone as an Ionophore

    Directory of Open Access Journals (Sweden)

    Sulekh Chandra

    2013-01-01

    Full Text Available A polymeric membrane-based tin selective electrode was developed by using salicylaldehyde thiosemicarbazone (STSC. The best performance was recorded with a membrane composition of PVC : TBP : ionophore : NaTPB as 28 : 59 : 8 : 5 (w/w%. The Nernstian slope calculated from the calibration curve for Sn2+ sensor was 28.8 ± 0.4 mV/decade. The detection limit of the sensor was 2.10 × 10−8 M, in the linear concentration range of 1.0 × 10−2−1.1 × 10−7 M. It was relatively fast response time (<8 s for concentration ≥1.0×10−4 and <12 s for concentration of ≥1.0×10−6 M and can be used for 9 months without any considerable divergence in potentials. The proposed sensor exhibit relatively good selectivity and high sensitivity for tin(II as other mono-, di-, and trivalent cations and can be used in a pH range of 2.0–8.5. The analytical usefulness of the proposed electrode has been evaluated by its application in the determination of stannous in artificially made samples.

  8. Species dependence of [64Cu]Cu-Bis(thiosemicarbazone) radiopharmaceutical binding to serum albumins

    International Nuclear Information System (INIS)

    Introduction: Interactions of three copper(II) bis(thiosemicarbazone) positron emission tomography radiopharmaceuticals with human serum albumin, and the serum albumins of four additional mammalian species, were evaluated. Methods: 64Cu-labeled diacetyl bis(N4-methylthiosemicarbazonato)copper(II) (Cu-ATSM), pyruvaldehyde bis(N4-methylthiosemicarbazonato)copper(II) (Cu-PTSM) and ethylglyoxal bis(thiosemicarbazonato)copper(II) (Cu-ETS) were synthesized and their binding to human, canine, rat, baboon and porcine serum albumins quantified by ultrafiltration. Protein binding was also measured for each tracer in human, porcine, rat and mouse serum. Results: The interaction of these neutral, lipophilic copper chelates with serum albumin is highly compound- and species-dependent. Cu-PTSM and Cu-ATSM exhibit particularly high affinity for human serum albumin (HSA), while the albumin binding of Cu-ETS is relatively insensitive to species. At HSA concentrations of 40 mg/ml, '% free' (non-albumin-bound) levels of radiopharmaceutical were 4.0±0.1%, 5.3±0.2% and 38.6±0.8% for Cu-PTSM, Cu-ATSM and Cu-ETS, respectively. Conclusions: Species-dependent variations in radiopharmaceutical binding to serum albumin may need to be considered when using animal models to predict the distribution and kinetics of these compounds in humans

  9. 2-Acetylpyridine N4-Phenyl- Thiosemicarbazone as a new tool for tumour diagnosis

    Energy Technology Data Exchange (ETDEWEB)

    Soares, Marcella Araugio; Pesquero, Jorge Luiz [Universidade Federal de Minas Gerais (UFMG), Belo Horizonte, MG (Brazil). Dept. de Fisiologia e Biofisica], e-mail: marcellaaraugio@yahoo.com.br; Costa, Pryscila R. da; Mendes, Isolda M.C.; Beraldo, Heloisa; Santos, Raquel Gouvea dos [Centro de Desenvolvimento da Tecnologia Nuclear (CDTN/CNEN-MG), Belo Horizonte, MG (Brazil)], e-mail: santosr@cdtn.br

    2009-07-01

    The aim of this work was to determine in vivo biodistribution of radiolabelled 2-acetylpyridine N4 phenyl thiosemicarbazone (Ph) and to evaluate its applicability for tumour diagnosis. Ph was labelled with {sup 125}I using lactoperoxidase method and radiochemical analysis was performed by chromatography. {sup 125}I-Ph production was successful with 86 {+-} 9.2% of radiochemical purity and high specific activity (17.6 TBq /mmol). {sup 125}I-Ph was used for biodistribution and pharmacokinetics studies on Swiss mice bearing Ehrlich solid tumour. {sup 125}I-Ph presented a rapid blood clearance (T{sub 1/2}= 97.2 min.) and the kidneys were the main excretion pathway (CL0.01 mL/min). {sup 125}I-Ph uptake was significant in tumour (2.5%ID/g) and tumour-to-normal tissue uptake was more than 20-fold higher depending on the organ. The uptake by the organs like heart, lungs, stomach and liver followed the blood perfusion. Our results suggest that {sup 125}I-Ph possess indispensable characteristics for an efficient radiopharmaceutical for tumour diagnosis. The next step will be to evaluate the quality of tumour SPECT images provided by {sup 131}I-Ph. (author)

  10. Species dependence of [{sup 64}Cu]Cu-Bis(thiosemicarbazone) radiopharmaceutical binding to serum albumins

    Energy Technology Data Exchange (ETDEWEB)

    Basken, Nathan E. [Division of Nuclear Pharmacy, Department of Industrial and Physical Pharmacy, Purdue University, West Lafayette, IN 47907 (United States)], E-mail: nbasken@purdue.edu; Mathias, Carla J. [Division of Nuclear Pharmacy, Department of Industrial and Physical Pharmacy, Purdue University, West Lafayette, IN 47907 (United States); Lipka, Alexander E. [Department of Statistics, Purdue University, West Lafayette, IN 47907 (United States); Green, Mark A. [Division of Nuclear Pharmacy, Department of Industrial and Physical Pharmacy, Purdue University, West Lafayette, IN 47907 (United States)], E-mail: magreen@purdue.edu

    2008-04-15

    Introduction: Interactions of three copper(II) bis(thiosemicarbazone) positron emission tomography radiopharmaceuticals with human serum albumin, and the serum albumins of four additional mammalian species, were evaluated. Methods: {sup 64}Cu-labeled diacetyl bis(N{sup 4}-methylthiosemicarbazonato)copper(II) (Cu-ATSM), pyruvaldehyde bis(N{sup 4}-methylthiosemicarbazonato)copper(II) (Cu-PTSM) and ethylglyoxal bis(thiosemicarbazonato)copper(II) (Cu-ETS) were synthesized and their binding to human, canine, rat, baboon and porcine serum albumins quantified by ultrafiltration. Protein binding was also measured for each tracer in human, porcine, rat and mouse serum. Results: The interaction of these neutral, lipophilic copper chelates with serum albumin is highly compound- and species-dependent. Cu-PTSM and Cu-ATSM exhibit particularly high affinity for human serum albumin (HSA), while the albumin binding of Cu-ETS is relatively insensitive to species. At HSA concentrations of 40 mg/ml, '% free' (non-albumin-bound) levels of radiopharmaceutical were 4.0{+-}0.1%, 5.3{+-}0.2% and 38.6{+-}0.8% for Cu-PTSM, Cu-ATSM and Cu-ETS, respectively. Conclusions: Species-dependent variations in radiopharmaceutical binding to serum albumin may need to be considered when using animal models to predict the distribution and kinetics of these compounds in humans.

  11. Study on the Interaction between Isatin-β-Thiosemicarbazone and Calf Thymus DNA by Spectroscopic Techniques.

    Science.gov (United States)

    Pakravan, Parvaneh; Masoudian, Shahla

    2015-01-01

    The interaction between isatin-β-thiosemicarbazone (IBT) and calf thymus DNA (CT-DNA) was investigated in physiological buffer (pH 7.4) using Neutral Red (NR) dye as a spectral probe by UV-Vis absorption and fluorescence spectroscopy, as well as viscosity measurements. The IBT is stabilized by intercalation in the DNA (K [IBT -DNA] = 1.03×10(5) M(-1)), and displaces the NR dye from the NR-DNA complex. The binding constants Kf and number of binding sites (n≈1) of IBT with DNA were obtained by fluorescence quenching method at different temperatures. Furthermore, the enthalpy and entropy of the reaction between IBT and CT-DNA showed that the reaction is enthalpy-favored and entropy-disfavored. The changes in the base stacking of CT-DNA upon the binding of IBT are reflected in the circular dichroic (CD) spectral studies. The viscosity increase of CT-DNA solution is another evidence to indicate that, IBT is able to be intercalated in the DNA base pairs. PMID:25561917

  12. Spectrophotometric Determination of Arsenic in Water Samples by Thiophene-2-Carboxaldehyde Thiosemicarbazone impregnated with alumina

    Directory of Open Access Journals (Sweden)

    Md. Faridur Rahman

    2015-12-01

    Full Text Available Thiophene-2-carboxaldehyde thiosemicarbazone has been successfully applied as an analytical reagent for micro level solid phase spectrophotometric determination of As (III at pH 3.5. Here it can be seen that arsenic reacts with the new chelating ligand in acidic medium to form the As (III-tctsc complex. The complex showed maximum absorbance at λ max 281 nm for As (III ions. The Beer’s law range was 0.1-1.0 mg/L. Job’s method and Mole-ratio method showed that As (III-ligand ratio in the complex is 1:2. The Molar absorptivity and Sandell’s sensitivity were 5.96 x 104 L mol-1 cm-1 and 0.01μg/cm2 respectively for As (III ions. The proposed method has been successfully applied to the determination of arsenic in drinking water samples of Kaliachak, in the district of Malda, West Bengal, India.

  13. 2-Butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids as potent inhibitors of Mycobacterium tuberculosis.

    Science.gov (United States)

    Jallapally, Anvesh; Addla, Dinesh; Yogeeswari, Perumal; Sriram, Dharmarajan; Kantevari, Srinivas

    2014-12-01

    Here a series of 2-butyl-4-chloroimidazole based substituted piperazine-thiosemicarbazone hybrids were designed by combining three different pharmacophoric fragments in single molecular architecture. 2-Butyl-4-chloro-1-(3-(4-substituted)piperazin-1-yl)propyl)-1H-imidazole-5-carbaldehydes (4a-p) prepared by reacting carboxaldehyde 2 with N-alkyl piperazines 3a-p which were condensed with thiosemicarbazine to give desired compounds 5a-p in very good yields. Among all sixteen compounds screened for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB), two compounds (E)-2-((2-butyl-4-chloro-1-(3-(4-(o-tolyl) piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene)hydrazinecarbothioamide 5e and (E)-2-((2-butyl-4-chloro-1-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-imidazol-5-yl)methylene) hydrazine carbothioamide 5f were found to be the most potent antitubercular agents (MIC: 3.13 μg/mL) with low toxicity profile. PMID:25451998

  14. Intracellular reduction/activation of a disulfide switch in thiosemicarbazone iron chelators.

    Science.gov (United States)

    Akam, Eman A; Chang, Tsuhen M; Astashkin, Andrei V; Tomat, Elisa

    2014-10-01

    Iron scavengers (chelators) offer therapeutic opportunities in anticancer drug design by targeting the increased demand for iron in cancer cells as compared to normal cells. Prochelation approaches are expected to avoid systemic iron depletion as chelators are liberated under specific intracellular conditions. In the strategy described herein, a disulfide linkage is employed as a redox-directed switch within the binding unit of an antiproliferative thiosemicarbazone prochelator, which is activated for iron coordination following reduction to the thiolate chelator. In glutathione redox buffer, this reduction event occurs at physiological concentrations and half-cell potentials. Consistent with concurrent reduction and activation, higher intracellular thiol concentrations increase cell susceptibility to prochelator toxicity in cultured cancer cells. The reduction of the disulfide switch and intracellular iron chelation are confirmed in cell-based assays using calcein as a fluorescent probe for paramagnetic ions. The resulting low-spin Fe(III) complex is identified in intact Jurkat cells by EPR spectroscopy measurements, which also document a decreased concentration of active ribonucleotide reductase following exposure to the prochelator. Cell viability and fluorescence-based assays show that the iron complex presents low cytotoxicity and does not participate in intracellular redox chemistry, indicating that this antiproliferative chelation strategy does not rely on the generation of reactive oxygen species. PMID:25100578

  15. Spectroscopic analysis, AIM, NLO and VCD investigations of acetaldehyde thiosemicarbazone using quantum mechanical simulations

    Science.gov (United States)

    Moorthy, N.; Prabakar, P. C. Jobe; Ramalingam, S.; Govindarajan, M.; Gnanamuthu, S. Joshua; Pandian, G. V.

    2016-08-01

    The prepared Acetaldehyde thiosemicarbazone (ATSC) have been investigated by both the experimental and theoretical methods; through this work, the essentiality of elucidation of molecular fragments source linear and non-linear optical properties was explored. The stability of the structure and entire calculations have been performed on HF and B3LYP methods with 6-311++G(d,p) level of basis set. The Mulliken charge profile, electronic, optical and hyper polarizability analyses have been carried out in order to evaluate nonlinear optical (NLO) performance of the present compound. The exact optical location of the ATSC was determined by executing UV-Visible calculations on TDSCF method. The existence of the molecular group for the inducement and tuning of NLO properties were thoroughly investigated by performing fundamental vibrational investigation. The optical energy transformation among frontier molecular levels has been described in UV-Visible region. The Gibbs energy coefficient of thermodynamic functions was monitored in different temperature and it was found constant irrespective of temperatures. The appearance of different chemical environment of H and C was monitored from the 1H and 13C NMR spectra. The vibrational optical polarization characteristics with respect to molecular composition in the compound have been studied by VCD spectrum. The bond critical point, Laplacian of electron density, electron kinetic energy density and total electron energy density have calculated and analysed using AIM study.

  16. Structural and biological evaluation of some metal complexes of vanillin-4N-(2-pyridyl) thiosemicarbazone

    Science.gov (United States)

    Yousef, T. A.; Abu El-Reash, G. M.; Al-Jahdali, M.; El-Rakhawy, El-Bastawesy R.

    2013-12-01

    The synthesis and characterization of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and U(VI)O2 complexes of vanillin-4N-(2-pyridyl) thiosemicarbazone (H2PVT) are reported. Theoretical calculations have been performed to obtain IR spectra of ligand and its complexes using AM1, Zindo/1, MM+ and PM3, methods. The Schiff base and its metal complexes have been screened for antibacterial Pseudomonas aeruginosa, Escherichia coli, Bacillus subtilis and Staphylococcus saprophyticus. H2VPT shows no apparent digestion effect on the egg albumin while Mn(II), Hg(II) and Cu(II) complexes exhibited a considerable digestion effect following the order Cu(II) > Mn(II) > Hg(II). Moreover, Ni(II) and Co(II) complexes revealed strong digestion effect. Fe(II), Mn(II), Cu(II), Zn(II) and Ni(II) acted as metal co- SOD enzyme factors, which are located in different compartments of the cell.

  17. Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones

    Directory of Open Access Journals (Sweden)

    Muhammad Yaqub

    2011-07-01

    Full Text Available A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%, containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN and spectral (IR, 1H-NMR, EIMS data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M. Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M. Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.

  18. Antiviral activity of platinum (II) and palladium (II) complexes of pyridine-2-carbaldehyde thiosemicarbazone.

    Science.gov (United States)

    Varadinova, T; Kovala-Demertzi, D; Rupelieva, M; Demertzis, M; Genova, P

    2001-04-01

    A heterocyclic compound, pyridine-2-carbaldehyde thiosemicarbazone (HFoTsc), and its six metal coordinated bound complexes, three with platinum (II) and three with palladium (II), were studied for their activity against herpes simplex virus 1 (HSV-1) infection in cultured cells. According to their cytotoxicity the compounds were divided into two groups. Group I (cytotoxic compounds) included all three palladium complexes and [Pt(HFoTsc)2] Cl2, with maximum non-toxic concentration (MNC) of 1-10 micromol/l and a 50% cytotoxic concentration (CC50) of 20-100 micromol/l. Group 2 (low cytotoxic compounds) with MNC of 100 micromol/l and CC50 of 548-5820 micromol/l included compounds in the following order: [Pt(HFoTsc)2] Cl2antiviral activity. IC50 and SI values of HFoTsc increased in parallel with the duration of action in HSV-1-infected cells. All three platinum complexes as well as [Pd(HFoTsc)2]Cl2 and [Pd(FoTsc)2] inhibited HSV- I infection following a structure-activity relationship but only [Pt(HFoTsc)2]Cl2 expressed a significant selectivity comparable to that of HFoTsc. However, [PdCl(FoTsc)] acting 48 hrs gave a higher infectious HSV-1 titer (170%) compared to control (100%, no compound). PMID:11719987

  19. Crystal structures of crotonaldehyde semicarbazone and crotonaldehyde thiosemicarbazone from X-ray powder diffraction data

    Directory of Open Access Journals (Sweden)

    Atef Arfan

    2015-02-01

    Full Text Available Crotonaldehyde semicarbazone {systematic name: (E-2-[(E-but-2-en-1-ylidene]hydrazinecarboxamide}, C5H9N3O, (I, and crotonaldehyde thiosemicarbazone {systematic name: (E-2-[(E-but-2-en-1-yldene]hydrazinecarbothioamide}, C5H9N3S, (II, show the same E conformation around the imine C=N bond. Compounds (I and (II were obtained by the condensation of crotonaldehyde with semicarbazide hydrochloride and thiosemicarbazide, respectively. Each molecule has an intramolecular N—H...N hydrogen bond, which generates an S(5 ring. In (I, the crotonaldehyde fragment is twisted by 2.59 (5° from the semicarbazide mean plane, while in (II the corresponding angle (with the thiosemicarbazide mean plane is 9.12 (5°. The crystal packing is different in the two compounds: in (I intermolecular N—H...O hydrogen bonds link the molecules into layers parallel to the bc plane, while weak intermolecular N—H...S hydrogen bonds in (II link the molecules into chains propagating in [110].

  20. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONE DERIVATIVES AND THEIR COPPERCOMPLEXES

    Directory of Open Access Journals (Sweden)

    P. M. Rachmale

    2012-03-01

    Full Text Available In the present investigation, 4-chloro acetophenone on condensation with 2-nitro benzaldehydes in methanolic NaOH solution yielded the corresponding chalcone. These chalcone were further reacted with Isonicotyl hydrazide and semicarbazide in ethanol which led to the formation of chalcone Isonicotyl hydrazone and chalcone semicarbazone derivatives respectively. The newly synthesized derivatives and there copper complexes were characterized on the basis of their chemical properties and spectroscopic data such as IR, NMR and UV. All newly synthesized compounds were evaluated for their antibacterial activities against E. coli and S. aureus also for antifungal activities against P. notatum.

  1. Technetium(I) tricarbonyl complexed with the N-heterocyclic aldehyde thiosemicarbazones: potential precursors of the radiopharmaceuticals

    International Nuclear Information System (INIS)

    Technetium(I) tricarbonyl complexes may form with the pyridine aldehyde thiosemicarbazones (TSCs), in which chelating ligand is bound tri- or bidentately. Intend of the presented work was to check, if labeling the N-heterocyclic TSCs with tricarbonyl [99mTc]-technetium(I) may lead to formation of the complexes suitable for the radiopharmaceutical purposes. Syntheses of the complexes were provided in the conditions analogous to those performed in the nuclear medicine laboratories. Main physicochemical properties of the complexes important in the medicinal chemistry were studied. Relevant results of the numerical calculations remain in fair agreement with these properties. (author)

  2. Targeting triple negative breast cancer cells by N3-substituted 9,10-Phenanthrenequinone thiosemicarbazones and their metal complexes

    Science.gov (United States)

    Afrasiabi, Zahra; Stovall, Preston; Finley, Kristen; Choudhury, Amitava; Barnes, Charles; Ahmad, Aamir; Sarkar, Fazlul; Vyas, Alok; Padhye, Subhash

    2013-10-01

    Novel N3-substituted 9,10-Phenanthrenequinone thiosemicarbazones and their copper, nickel and palladium complexes are structurally characterized and reported along with the single crystal X-ray structures of three ligands and one nickel complex. All compounds were evaluated for their antiproliferative potential against Triple Negative Breast Cancer (TNBC) cells which have poor prognosis and no effective drugs to treat with. All compounds exhibited antiproliferative activity against these cells. Among the metal complexes evaluated, redox active copper complexes were found to be more potent. The possible mechanism for such enhanced activity can be attributed to the generation of oxidative stress, which was amenable for targeting through metal complexation.

  3. Cytotoxic and Antitumour Studies of Acetoacetanilide N(4)-methyl(phenyl)thiosemicarbazone and its Transition Metal Complexes

    OpenAIRE

    Priya, N. P.; Firdous, A. P.; Jeevana, R.; Aravindakshan, K. K.

    2015-01-01

    Cytotoxic activities of acetoacetanilide N(4)-methyl(phenyl)thiosemicarbazone (L2H) and its seven different metal complexes were studied. Of these, IC50 value of the copper complex was found to be 46 μg/ml. Antitumour studies of this copper complex was carried out using Daltons Lymphoma Ascites cell-induced solid tumour model and Ehrlich's Ascites Carcinoma cell-induced ascites tumour model. Administration of the copper complex at different concentrations (10, 5 and 1 mg/kg b. wt) inhibited t...

  4. Effect of Diacetyl Monoxime Thiosemicarbazone on the Corrosion of Aged 18 Ni 250 Grade Maraging Steel in Sulphuric Acid Solution

    Directory of Open Access Journals (Sweden)

    T. Poornima

    2012-01-01

    Full Text Available The corrosion inhibition of the aged 18 Ni 250 grade maraging steel in 0.5 M sulphuric acid by diacetyl monoxime thiosemicarbazone (DAMTSC at 303–323 K has been investigated by potentiodynamic polarization, EIS, and SEM techniques. Good inhibition efficiency of DAMTSC was revealed even at low concentrations, which increased with the increase in DAMTSC concentration and decreased with the increase in temperature. The activation energies, , as well as other thermodynamic parameters (; ; , were evaluated and discussed. The adsorption of DAMTSC on the aged maraging steel surface was found to obey the Langmuir adsorption isotherm model and shows mixed type inhibition behavior.

  5. Synthesis, spectral and thermal studies of some lanthanide(III) complexes of 4-[N-(benzalidene) amino] antipyrine thiosemicarbazone

    International Nuclear Information System (INIS)

    A new series of sixteen lanthanide(III) complexes of 4[N-(benzalidene) amino] antipyrine thiosemicarbazone (BAAPTS) with the general composition LnX3.n(BAAPTS) (X =Cl-, n = 2; X = NO-3, n = 1; Ln = La, Pr, Nd, Sm, Gd, Tb, Dy and Ho) have been synthesized and characterized by chemical analysis, conductance, molar weight, magnetic moments measurements, infrared and electronic spectra. The ligand BAAPTS behaves as neutral tridentate (N, N, S) ligand. The probable coordination number is nine in these complexes. (author)

  6. Improved antiparasitic activity by incorporation of organosilane entities into half-sandwich ruthenium(II) and rhodium(III) thiosemicarbazone complexes.

    Science.gov (United States)

    Adams, Muneebah; de Kock, Carmen; Smith, Peter J; Land, Kirkwood M; Liu, Nicole; Hopper, Melissa; Hsiao, Allyson; Burgoyne, Andrew R; Stringer, Tameryn; Meyer, Mervin; Wiesner, Lubbe; Chibale, Kelly; Smith, Gregory S

    2015-02-01

    A series of ferrocenyl- and aryl-functionalised organosilane thiosemicarbazone compounds was obtained via a nucleophilic substitution reaction with an amine-terminated organosilane. The thiosemicarbazone (TSC) ligands were further reacted with either a ruthenium dimer [(η(6-i)PrC6H4Me)Ru(μ-Cl)Cl]2 or a rhodium dimer [(Cp*)Rh(μ-Cl)Cl]2 to yield a series of cationic mono- and binuclear complexes. The thiosemicarbazone ligands, as well as their metal complexes, were characterised using NMR and IR spectroscopy, and mass spectrometry. The molecular structure of the binuclear ruthenium(ii) complex was determined by single-crystal X-ray diffraction analysis. The thiosemicarbazones and their complexes were evaluated for their in vitro antiplasmodial activities against the chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) Plasmodium falciparum strains, displaying activities in the low micromolar range. Selected compounds were screened for potential β-haematin inhibition activity, and it was found that two Rh(iii) complexes exhibited moderate to good inhibition. Furthermore, the compounds were screened for their antitrichomonal activities against the G3 Trichomonas vaginalis strain, revealing a higher percentage of growth inhibition for the ruthenium and rhodium complexes over their corresponding ligand. PMID:25559246

  7. Synthesis and characterization of complexes of monoacetylferrocene-4-phenyl thiosemicarbazone with UO22+, Hg2+, Ni2+ or Zn2+ ions

    International Nuclear Information System (INIS)

    Complexes have been synthesized with monoacetylferrocene-4-phenyl thiosemicarbazone (L) combining with UO22+, Hg2+, Ni2+ or Zn2+ ions and characterized through elemental analysis, IR spectrum, UV spectrum and 1HNMR spectrum. The thermal stability and molar conductance have been studied. It shows that L coordinates to the metal ion in a Keto form and is a bidentate ligand

  8. Synthetic, structural and kinetic studies on the binding of cyclohexane-1,2-bis(4-methyl-3-thiosemicarbazone) to divalent metal ions (Co, Ni, Cu, Zn or Cd).

    Science.gov (United States)

    Al-Karawi, Ahmed Jasim M; Clegg, William; Harrington, Ross W; Henderson, Richard A

    2009-01-21

    The reactions of cyclohexane-1,2-bis(4-methyl-3-thiosemicarbazone) (CHMTSC) with MCl2 (M = Co, Ni, Cu or Zn) and Cd(NO3)2 have been shown to produce complexes in which the thiosemicarbazone has been doubly deprotonated [[M(CHMTSC - 2H+)] (M = Co, Ni or Ni)], analogous to those reported earlier with other Schiff base thiosemicarbazones. However, with ZnCl2 and Cd(NO3)2, the complexes isolated are [ZnCl(CHMTSC)]Cl and [Cd(NO3)(CHMTSC)]NO3, containing the protonated forms of the ligand, which have been characterised by X-ray crystallography, as has free CHMTSC. The kinetics of the reactions between CHMTSC and all the various metal salts have been determined by stopped-flow spectrophotometry. In all cases, the reactions are complete on the seconds timescale. The reactions exhibit a first-order dependence on the concentration of metal salt and a first-order dependence on the concentration of CHMTSC. The thermodynamic and kinetic factors influencing the protonation state of the coordinated thiosemicarbazone are discussed. PMID:19122915

  9. PPA-SiO2 Catalyzed Multi-component Synthesis of N-[α-(β-Hydroxy-α-naphthyl)(benzyl)]O-Alkyl Carbamate Derivatives

    Institute of Scientific and Technical Information of China (English)

    SHATERIAN,Hamid Reza; HOSSEINIAN,Asghar; GHASHANG,Majid

    2009-01-01

    Silica-supported polyphosphoric acid (PPA-SiO2) was found to be an efficient catalyst for the multi-component condensation reaction of benzaldehydes,2-naphthol,and methyl/benzyl carbamate to afford the corresponding N-[α-(β-hydroxy-α-naphthyl)(benzyl)]O-alkyl carbamate derivatives in good to excellent yields.This new approach consistently has the advantage of short reaction time,high conversions,clean reaction profiles,and simple experimental and work-up procedures.

  10. Synthesis and Some Reactions of 1-aryl-4-acetyl-5-methyl-1,2,3-triazole Derivatives with Anticonvulsant Activity.

    Science.gov (United States)

    Nassar, Ekhlass M; Abdelrazek, Fathy M; Ayyad, Rezk R; El-Farargy, Ahmed F

    2016-01-01

    The triazoles 3a-d underwent condensation reactions with 4-(piperidin-1-yl)-benzaldehyde to afford the chalcones 5a-d. Chalcone derivatives 5a-d were reacted with 2,3-diaminomaleonitrile, thiourea and hydrazine hydrate to afford the novel diazepine-dicarbonitrile derivatives 7a-d, the pyrimidine-2-thiol derivatives 9a-d and hydrazino-pyrimidines 10a-d respectively. Structures of the prepared compounds were elucidated by physical and spectral data like FT-IR, (1)H NMR, (13)C NMR, and mass spectroscopy. Some of the synthesized compounds were screened for their anticonvulsant activity and SAR. PMID:26776225

  11. One-step Synthesis of Benzaldehyde from Styrene by Ozonolysis Reaction%苯乙烯臭氧化一步法合成苯甲醛

    Institute of Scientific and Technical Information of China (English)

    刘慧; 梁政勇; 章亚东

    2012-01-01

    Carbonyl oxides ( zwitterions) are the most reactive intermediates in ozonolysis reaction. This paper describes the trapping of carbonyl oxides by amines or H2 O, and the subsequent direct ozonolytic conversion of styrene into benzaldehyde without the intermediacy of 1,2,4-trioxolanes( ozonides) and the traditional reduction decomposition. The effects of the type of solvent, amount of solvent, reaction temperature, the flow of ozone and the kind of additive were investigated. The results show that H2O gives better reactivity than amines, and that the reactivity of different amines descends in the order; Et3N > Bu3N > ( C8H17 )3N, tertiary amine > secondary amine. The appropriate reaction conditions are as follows(based on 0. 05 mol styrene) :25. 0 mL acetone as solvent,reaction temperature 0~5℃ ,the flow of ozone 200 mL/min, n ( H2O ) /n ( styrene) = 3. Under the above conditions, the average yield of benzaldehyde is about 96. 5% .%采用水或有机胺捕获苯乙烯臭氧化生成的两性离子,不经臭氧化物中间体及传统的还原分解反应一步法合成苯甲醛.考察了溶剂种类、溶剂用量、反应温度、臭氧流量和添加剂种类对反应的影响.结果表明,水捕获两性离子的活性大于有机胺,不同有机胺的反应活性不同,其活性大小顺序为:三乙胺>三正丁胺>三正辛胺,叔胺>仲胺.较佳的反应条件(以0.05 mol苯乙烯计)为:溶剂丙酮25.0 mL,反应温度0~5℃,臭氧流量200mL/min,n(水)/n(苯乙烯)=3.在该条件下,重复实验3次,所得苯甲醛的平均收率为96.5%.

  12. Effects of terminal dimethylation and metal coordination of proline-2-formylpyridine thiosemicarbazone hybrids on lipophilicity, antiproliferative activity, and hR2 RNR inhibition.

    Science.gov (United States)

    Bacher, Felix; Dömötör, Orsolya; Kaltenbrunner, Maria; Mojović, Miloš; Popović-Bijelić, Ana; Gräslund, Astrid; Ozarowski, Andrew; Filipovic, Lana; Radulović, Sinisa; Enyedy, Éva A; Arion, Vladimir B

    2014-12-01

    The nickel(II), copper(II), and zinc(II) complexes of the proline-thiosemicarbazone hybrids 3-methyl-(S)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazone (L-Pro-FTSC or (S)-H2L(1)) and 3-methyl-(R)-pyrrolidine-2-carboxylate-2-formylpyridine thiosemicarbazone (D-Pro-FTSC or (R)-H2L(1)), as well as 3-methyl-(S)-pyrrolidine-2-carboxylate-2-formylpyridine 4,4-dimethyl-thiosemicarbazone (dm-L-Pro-FTSC or (S)-H2L(2)), namely, [Ni(L-Pro-FTSC-2H)]2 (1), [Ni(D-Pro-FTSC-2H)]2 (2), [Ni(dm-L-Pro-FTSC-2H)]2 (3), [Cu(dm-L-Pro-FTSC-2H)] (6), [Zn(L-Pro-FTSC-2H)] (7), and [Zn(D-Pro-FTSC-2H)] (8), in addition to two previously reported, [Cu(L-Pro-FTSC-2H)] (4), [Cu(D-Pro-FTSC-2H)] (5), were synthesized and characterized by elemental analysis, one- and two-dimensional (1)H and (13)C NMR spectroscopy, circular dichroism, UV-vis, and electrospray ionization mass spectrometry. Compounds 1-3, 6, and 7 were also studied by single-crystal X-ray diffraction. Magnetic properties and solid-state high-field electron paramagnetic resonance spectra of 2 over the range of 50-420 GHz were investigated. The complex formation processes of L-Pro-FTSC with nickel(II) and zinc(II) were studied in aqueous solution due to the excellent water solubility of the complexes via pH potentiometry, UV-vis, and (1)H NMR spectroscopy. The results of the antiproliferative activity in vitro showed that dimethylation improves the cytotoxicity and hR2 RNR inhibition. Therefore, introduction of more lipophilic groups into thiosemicarbazone-proline backbone becomes an option for the synthesis of more efficient cytotoxic agents of this family of compounds. PMID:25391085

  13. Gas chromatography-flame ionization determination of benzaldehyde in non-steroidal anti-inflammatory drug injectable formulations using new ultrasound-assisted dispersive liquid-liquid micro extraction

    International Nuclear Information System (INIS)

    Summary: In this study, simple and efficient ultrasound-assisted dispersive liquid-liquid micro extraction combined with gas chromatography (GC) was developed for the preconcentration and determination of benzaldehyde in injectable formulations of the non-steroidal anti-inflammatory drugs, diclofenac, Vitamin B-complex and Voltaren injection solutions. Fourteen microliters of toluene was injected slowly into 10 mL home-designed centrifuge glass vial containing an aqueous sample without salt addition that was located inside the ultrasonic water bath. The formed emulsion was centrifuged and 2 macro L of separated toluene was injected into a gas chromatographic system equipped with a flame ionization detector (GC-FID) for analysis. Several factors influencing the extraction efficiency as the nature and volume of organic solvent, extraction temperature, ionic strength and centrifugation time were investigated and optimized. Using optimum extraction conditions a detection limit of 0.3 macro g L/sup -1/ and a good linearity in a calibration range of 2.0-1000 macro g L/sup -1/ were achieved for analyte. This proposed method was successfully applied to the analysis of benzaldehyde in three injection formulations and relative standard deviation (RSD) of analysis (n=3), before spiking with standard benzaldehyde were 3.3, 2.0 and 1.3% for Na-diclofenac, vitamin B-complex and voltaren, respectively and after spiking of standard benzaldehyde (0.3 mg L/sup -1/), the RSD were 6.5, 3.6 and 2.8% for Na-diclofenac, vitamin B-complex and voltaren, respectively. (author)

  14. Synthesis of Some New Condensed Pyrimidine Derivatives

    International Nuclear Information System (INIS)

    Cyclodehydration of 6-amino-5-cyano pyrimidine derivative (2) afforded pyrimidoisoindole derivatives (3). Compound (3) reacted with carbethoxymethylene derivative to give pyridopyrimidine derivatives (5a,b). Compound (3) was also reacted with formamide to give the corresponding pyrimidopyrimdine derivatives (6) that condensed with benzaldehyde to give Schiff's base (7). Refluxing of compound (3) with triethyl orthoformate afforded compound (8) that cyclized with ammonium hydroxide giving the same compound (6). Compound (8) cyclized with hydrazine hydrate giving compound (9) which also cyclized with triethyl orthoformate affording compound (10). Diazotization of compound (3) led to the formation of triazinopyrimidine derivative (11). Cyclization of compound (11) upon treatment with hydrazine hydrate afforded compound (12). Compound (15) was prepared from reaction of compound (3) and ethylenediamine in presence of carbon disulfide. The behaviour of compound (15) toward benzoyl chloride, triethyl orthoformate, nitrous acid and/or carbon disulfide was also described. All proposed structures were supported by elemental analyses, spectroscopic data and some of the new products showed antimicrobial activity

  15. Synthesis and spectral feature of benzophenone-substituted thiosemicarbazones and their Ni(II) and Cu(II) complexes

    Science.gov (United States)

    El-Asmy, A. A.; Al-Hazmi, G. A. A.

    2009-01-01

    The ligational behavior of 2-hydroxybenzophenone and 2-hydroxy-4-methoxybenzophenone N-substituted thiosemicarbazones towards Ni(II) and Cu(II) ions has been investigated. The isolated complexes were identified by elemental analyses, molar conductance, magnetic moment, IR, UV-vis and ESR spectral studies. The IR spectra indicated that the investigated thiosemicarbazones lost the N 2 proton or the N 2 and OH protons and act as mononegative or binegative tridentate ligands. The ligands containing methoxy group facilitate the deprotonation of OH by resonance more than the SH. Most of the Ni(II) complexes measured subnormal magnetic moments due to square-planar + tetrahedral configuration and supported by the electronic spectra. The percentage of square-planar to tetrahedral was calculated and found in agreement with the ligand splitting energy (10Dq). Also, Cu(II) complexes measured subnormal values due to the interaction between copper centers; the lower the value the higher the interaction. It was found that the substitutent has a noticeable effect on the distortion of the complex. The ESR spectra of some solid Cu(II) complexes at room temperature exhibit g|| > g⊥ > 2.0023 confirming a square-planar structure.

  16. Cyclometallated ruthenium(II) carbonyl complexes with 1-pyrenaldehyde 4-R-3-thiosemicarbazones: Regioselective ruthenation of the 1-pyrenyl group

    Indian Academy of Sciences (India)

    Rupesh Narayana Prabhu; Samudranil Pal

    2015-04-01

    A facile method for the synthesis of a series of cyclometallated ruthenium(II) carbonyl complexes with 1-pyrenaldehyde 4-R-3-thiosemicarbazones (H2Ln where the two H’s represent the dissociable thioamide and pyrenyl protons; R = H, Me and Ph) has been described. The characterization of the complexes having the general molecular formula trans-[Ru(Ln)(CO)(EPh33)2] (where E = P or As) were accomplished by elemental (CHN) analysis, magnetic susceptibility and spectroscopic (ESI-MS, IR, UV-Vis, emission and 1H-NMR) measurements. Electronic spectra of the complexes display multiple strong absorptions in the range 440–224 nm due to intraligand transitions. All the complexes exhibit emission bands that are characteristic of ligand centred emissive states. X-ray diffraction studies with representative complexes reveal a pincer-like 5,5-membered fused chelate rings forming CNS coordination mode of the thiosemicarbazonate ligand (Ln)2− via regioselective activation of 1-pyrenyl ortho C–H and formation of a distorted octahedral C2NSE2 coordination sphere around the ruthenium(II) centre.

  17. Vibrational, NMR and UV-Visible spectroscopic investigation, VCD and NLO studies on Benzophenone thiosemicarbazone using computational calculations

    Science.gov (United States)

    Moorthy, N.; Jobe Prabakar, P. C.; Ramalingam, S.; Periandy, S.; Parasuraman, K.

    2016-04-01

    In order to explore the unbelievable NLO property of prepared Benzophenone thiosemicarbazone (BPTSC), the experimental and theoretical investigation has been made. The theoretical calculations were made using RHF and CAM-B3LYP methods at 6-311++G(d,p) basis set. The title compound contains Cdbnd S ligand which helps to improve the second harmonic generation (SHG) efficiency. The molecule has been examined in terms of the vibrational, electronic and optical properties. The entire molecular behavior was studied by their fundamental IR and Raman wavenumbers and was compared with the theoretical aspect. The molecular chirality has been studied by performing vibrational circular dichroism (circularly polarized infrared radiation). The Mulliken charge levels of the compound ensure the perturbation of atomic charges according to the ligand. The molecular interaction of frontier orbitals emphasizes the modification of chemical properties of the compound through the reaction path. The enormous amount of NLO activity was induced by the Benzophenone in thiosemicarbazone. The Gibbs free energy was evaluated at different temperature and from which the enhancement of chemical stability was stressed. The VCD spectrum was simulated and the optical dichroism of the compound has been analyzed.

  18. Toxic effects of bis(thiosemicarbazone) compounds and its palladium(II) complexes on herpes simplex virus growth

    International Nuclear Information System (INIS)

    Here, we present data on the activity of benzyl bis(thiosemicarbazone); 3,5-diacyl-1,2,4-triazole bis(4-methylthiosemicarbazone) and their Pd(II) complexes against the replication of wild type and of acyclovir (ACV)-resistant, herpes simplex virus type 1 (HSV 1) and type 2 (HSV 2) strains. The data were compared to those under the action of acyclovir. The testing of cytotoxic activity suggests that these compounds may be endowed with important antiviral properties. It is interesting to note that the Pd(II)-benzyl bis(thiosemicarbazone) complex, 2, exhibits a significant activity against acyclovir-resistant viruses R-100 (HSV 1) and PU (HSV 2) with an in vitro selectivity index (SI) of 8.0 vs. 0.01 for acyclovir. This complex also negatively influenced the expression of key structural HSV 1 proteins (VP23, gH and gG/gD), thus suppressing simultaneously virus entry, transactivation of virus genome, capsid assembly, and cell-to-cell spread of infectious HSV progeny

  19. Synthesis, spectroscopic characterization, structural studies and antibacterial and antitumor activities of diorganotin complexes with 3-methoxysalicylaldehyde thiosemicarbazone

    Science.gov (United States)

    Khandani, Marzieh; Sedaghat, Tahereh; Erfani, Nasrollah; Haghshenas, Mohammad Reza; Khavasi, Hamid Reza

    2013-04-01

    Three organotin(IV) complexes, Ph2Sn(mstsc) (1), Me2Sn(mstsc) (2) and Bu2Sn(mstsc) (3), have been synthesized from reaction of R2SnCl2 (R = Ph, Me and Bu) with 3-methoxysalicylaldehyde thiosemicarbazone (H2mstsc). The synthesized complexes have been characterized by elemental analysis and FT-IR, 1H, 13C and 119Sn NMR spectroscopy. The structures of 2 and 3 have been also confirmed by X-ray crystallography. On the basis of spectral and structural data thiosemicarbazone acts as a tridentate dianionic ligand and coordinates to tin through phenolic oxygen, the azomethine nitrogen and thiolate sulfur atoms. The metal coordination geometry for 2 and 3 is described as distorted square pyramid and the crystal lattices are stabilized by intermolecular hydrogen bands. On the basis of 119Sn NMR data, coordination number of tin retains five in solution. The in vitro antibacterial activity of ligand and its complexes has been evaluated against one Gram-positive and three Gram-negative bacteria. Complex 2 exhibited good activity along with the standard antibacterial drugs. The in vitro cytotoxicities of the synthesized compounds against Jurkat cells were evaluated by the standard WST-1 assay. The activity decreases in the order 3 > 1 > 2 = H2mstsc.

  20. Comparative evaluation of Bis(thiosemicarbazone)- Biotin and Met-ac-TE3A for tumor imaging

    Science.gov (United States)

    Singh, Sweta; Tiwari, Anjani K.; Varshney, Raunak; Mathur, R.; Shukla, Gauri; Bag, N.; Singh, B.; Mishra, Anil K.

    2016-01-01

    2,2‧,2″-(11-(2-((4-mercapto-1-methoxy-1-oxobutan-2-yl)amino)-2-oxoethyl)-1,4,8,11-tetraaza cyclotetradecane-1,4,8-triyl)triacetic acid, Met-ac-TE3A and (E)-N-methyl-2-((E)-3-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)hydrazinecarbono-thioyl)hydrazonobutan-2-ylidene)hydrazinecarbothioamide, Bis(thiosemicarbazone)- Biotin were synthesized and evaluated for imaging application. The pharmacokinetics of these ligands were determined by tracer methods. In vitro human serum stability of 99mTc Met-ac-TE3A/99mTc Bis(thiosemicarbazone)-Biotin after 24 h was found to be 96.5% and 97.0% respectively. Blood kinetics of both ligands in normal rabbits showed biphasic clearance pattern. Ex vivo biodistribution study revealed significant initial tumor uptake and high tumor/muscles ratio which is a pre-requisite condition for a ligand to work as SPECT-radiopharmaceutical for tumor imaging.