Summary of diamino pyrazoles derived and study their biological activities

International Nuclear Information System (INIS)

Hagui, Marwa

2016-01-01

The work involves the synthesis of new heterocyclic structures diamino pyrazoles derivatives that are present in many natural products and products of pharmacological and therapeutic interests and study their biological activities. In order to develop a radiotracer interest and use in diagnostic nuclear medicine, we are interested to synthesis a pyrazole derivative with the precursor [Re(CO)5Br] and studying the antibacterial and antifungal activity of 3.5-diamino pyrazole and even thioamide complex rhenium. The objectives of our workout: 1/ Synthesis of molecules 3,5-diamino pyrazole and thioamide. 2/ Synthesis of 3,5-diamino pyrazole-rhenium complex. 3/ The in vitro study: Bacteriological Tests (Study of antibacterial and antifungal activity of 3,5-diamino pyrazole and thioamide). The first part of this work concerns the chemical synthesis of molecules such as: thioamide, Amp z1 Ampz2 and then we had synthesized the complex 3,5-diamino pyrazole-rhenium. Similarly we determined the physicochemical characteristics of the compounds synthesized by CLHP, CCM and RMN ( 1 H, 13 C). The second part is devoted to the study in vitro of biological activities of the synthesized molecules and complex 3,5 diaminopyrazole-rhenium with concentration 1 mg/mL and 2 mg/mL. The results allow us to say that the thioamide and Ampz2 have antibacterial activity against S. enterica and Ampz2 has low activity against S. aureus and P. aeruginossa. Other pyrazole derivatives have no significant antibacterial and antifungal activity. The results also show that the synthesized compounds of concentration 2 mg/mL in relation to the inhibition zones of amoxicillin and DMSO: 1/ Escherichia coli, there is antibacterial activity for thioamide, and the Amp z1-Re Ampz2 compound. 2/ Staphylococcus aureus, the complex Ampz 1-Re and the thioamide have significant antibacterial activity. 3/ Salmonella, we observe that the thioamide molecules, Ampz2 and Amp z1-Re have significant antibacterial activity

Consolidating BPR with CALS

DEFF Research Database (Denmark)

Larsen, Michael Holm; Leinsdorff, Torben; Madsen, Claus

1999-01-01

For almost a decade, Business Process Reengineering (BPR) has met a high degree of criticism as project implementations have failed to succeed in industry and public organisations. A vast majority of the reengineering literature recommends that information technology (IT) should enhance the effic......For almost a decade, Business Process Reengineering (BPR) has met a high degree of criticism as project implementations have failed to succeed in industry and public organisations. A vast majority of the reengineering literature recommends that information technology (IT) should enhance...... the likelihood of BPR success. Firstly, CALS contributes to process orientation and process organising in a BPR project. This is partly because CALS satisfies the increased information need of the process team members and partly because CALS breaks down information-based barriers. Secondly, CALS contributes...

Synthesis and antifungal activity of the derivatives of novel pyrazole carboxamide and isoxazolol pyrazole carboxylate.

Science.gov (United States)

Sun, Jialong; Zhou, Yuanming

2015-03-09

A series of pyrazole carboxamide and isoxazolol pyrazole carboxylate derivatives were designed and synthesized in this study. The structures of the compounds were elucidated based on spectral data (infrared, proton nuclear magnetic resonance and mass spectroscopy). Then, all of the compounds were bioassayed in vitro against four types of phytopathogenic fungi (Alternaria porri, Marssonina coronaria, Cercospora petroselini and Rhizoctonia solani) using the mycelium growth inhibition method. The results showed that some of the synthesized pyrazole carboxamides displayed notable antifungal activity. The isoxazole pyrazole carboxylate 7ai exhibited significant antifungal activity against R. solani, with an EC50 value of 0.37 μg/mL. Nonetheless, this value was lower than that of the commercial fungicide, carbendazol.

Synthesis and Antifungal Activity of the Derivatives of Novel Pyrazole Carboxamide and Isoxazolol Pyrazole Carboxylate

Directory of Open Access Journals (Sweden)

Jialong Sun

2015-03-01

Full Text Available A series of pyrazole carboxamide and isoxazolol pyrazole carboxylate derivatives were designed and synthesized in this study. The structures of the compounds were elucidated based on spectral data (infrared, proton nuclear magnetic resonance and mass spectroscopy. Then, all of the compounds were bioassayed in vitro against four types of phytopathogenic fungi (Alternaria porri, Marssonina coronaria, Cercospora petroselini and Rhizoctonia solani using the mycelium growth inhibition method. The results showed that some of the synthesized pyrazole carboxamides displayed notable antifungal activity. The isoxazole pyrazole carboxylate 7ai exhibited significant antifungal activity against R. solani, with an EC50 value of 0.37 μg/mL. Nonetheless, this value was lower than that of the commercial fungicide, carbendazol.

Synthesis and Herbicidal Activity of 5-Heterocycloxy-3-substituted-1-(3-trifluoromethyl)phenyl-1H-pyrazole

Institute of Scientific and Technical Information of China (English)

XU Han; HU Xu-hong; ZOU Xiao-mao; ZHU You-quan; LIU Bin; HU Fang-zhong; YANG Hua-zheng

2012-01-01

The authors synthesized a series of novel 5-heterocycloxy-3-substituted-1-(3-trifluoromethyl)phenyl-1H- pyrazole derivatives.Herbicidal activities of the two intermediate compounds and thirteen target compounds were evaluated via Brassica napus and Echinochloa crusgalli(L.) Beauv tests.Bioassay results show that some of the compounds exhibit better inhibiting activities against Brassica napus and some of the compounds exhibit bleaching activities against Echinochloa crusgalli(L.) Beauv at 100 μg/mL.

Synthesis and Bioactivity of Pyrazole Acyl Thiourea Derivatives

Directory of Open Access Journals (Sweden)

Jian Wu

2012-05-01

Full Text Available Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, ¹H-NMR, ¹³C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.

2-[3-(4-Methoxyphenyl-1-phenyl-1H-pyrazol-5-yl]phenol

Directory of Open Access Journals (Sweden)

2009-03-01

Full Text Available The title compound, C22H18N2O2, was derived from 1-(2-hydroxyphenyl-3-(4-methoxyphenylpropane-1,3-dione. The central pyrazole ring forms dihedral angles of 16.83 (5, 48.97 (4 and 51.68 (4°, respectively, with the methoxyphenyl, phenyl and hydroxyphenyl rings. The crystal packing is stabilized by O—H...N hydrogen bonding.

Design, Synthesis and Fungicidal Activities of Some Novel Pyrazole Derivatives

Directory of Open Access Journals (Sweden)

Xue-Ru Liu

2014-09-01

Full Text Available In order to discover new compounds with good fungicidal activities, 32 pyrazole derivatives were designed and synthesized. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS, and their fungicidal activities against Botrytis cinerea, Rhizoctonia solani Kuhn, Valsa mali Miyabe et Yamada, Thanatephorus cucumeris (Frank Donk, Fusarium oxysporum (S-chl f.sp. cucumerinum Owen, and Fusarium graminearum Schw were tested. The bioassay results indicated that most of the derivatives exhibited considerable antifungal activities, especially compound 26 containing a p-trifluoromethyl- phenyl moiety showed the highest activity, with EC50 values of 2.432, 2.182, 1.787, 1.638, 6.986, and 6.043 μg/mL against B. cinerea, R. solani, V. mali, T. cucumeris, F. oxysporum, and F. graminearum, respectively. Moreover, the activities of compounds such as compounds 27–32 were enhanced by introducing isothiocyanate and carboxamide moieties to the 5-position of the pyrazole ring.

Ultrasound-promoted iodination of pyrazoles in aqueous medium

Directory of Open Access Journals (Sweden)

Jéssica Kunsminskas

2012-06-01

Full Text Available Several pharmacological activities have been devoted to pyrazole containing molecules. In particular, 4-iodopyrazoles have been employed as key starting materials in cross-coupling chemistry and metal-iodine exchange reactions that focus on the synthesis of such biologically important compounds. Unfortunately, existing methods for the synthesis of 4-iodopyrazoles are not in agreement with the environmental requirements due to a series of drawbacks including the use of large excess of reagents, the generation of toxic waste and long reaction times. Recently, we developed a fast and mild reaction condition for the iodination of aromatic compounds using an I2/H2O2 system water as a nonflammable and innocuous solvent and ultrasonic irradiation as energy source. In this work, we present the application of this methodology for the iodination of pyrazoles (Scheme. Initially, a series of pyrazoles were efficiently prepared starting from 1,3-dicarbonyl compounds and hydrazines under ultrasonic irradiation. Three examples from the pyrazoles were subjected to the iodination condition shown above. Iodopyrazoles were obtained in 63-65% yields.

Microwave-assisted synthesis of new pyrazole derivatives bearing 1,2,3-triazole scaffold as potential antimicrobial agents

Directory of Open Access Journals (Sweden)

Ashok Dongamanti

2017-01-01

Full Text Available A new series of (E-3-(3-(4-substituted phenyl-1-phenyl-1H-pyrazol- 4-yl-1-(2-hydroxy-4-((1-aryl-1H-1-2,3-triazol-4-ylmethoxyphenyl- prop-2-en-1-one derivatives was synthesized. The synthesis of the title compounds involved the 1,3-dipolar Cu(I-catalyzed alkyne–azide cycloaddition (CuAAC reaction of (E-3-(3-(4-substituted phenyl-1-phenyl-1H-pyrazol-4- -yl-1-(2-hydroxy-4-(prop-2-yn-1-yloxyphenylprop-2-en-1-ones with aromatic azides. The structures were confirmed by NMR, FT-IR, mass and elemental analysis. All the synthesized compounds (6a–j were evaluated for their antimicrobial activity. Compounds 6a, 6d and 6e demonstrated promising inhibitory effects on both bacterial and fungal strains.

Synthesis and antileishmanial activity of new 1-Aryl-1H-Pyrazole-4- carboximidamides derivatives

Energy Technology Data Exchange (ETDEWEB)

Santos, Mauricio S. dos; Gomes, Adriana O.; Bernardino, Alice M.R.; Souza, Marcos C. de, E-mail: alicerolim@globo.co [Universidade Federal Fluminense (UFF), Niteroi, RJ (Brazil). Programa de Pos-Graduacao em Quimica Organica; Khan, Misbahul A. [The Islamia University of Bahawalpur (Pakistan). Chemistry Dept.; Brito, Monique A. de [Universidade Federal Fluminense (UFF), Niteroi, RJ (Brazil). Fac. de Farmacia. Lab. de Quimica Medicinal Computacional; Castro, Helena C.; Abreu, Paula A. [Universidade Federal Fluminense (LABioMol/GCM/UFF), Niteroi, RJ (Brazil). Inst. de Biologia. Lab. de Antibioticos, Bioquimica e Modelagem Molecular; Rodrigues, Carlos R. [Universidade Federal do Rio de Janeiro (ModMol/UFRJ), RJ (Brazil). Fac. de Farmacia. Lab. de Modelagem Molecular e QSAR; Leo, Rosa M.M. de; Leon, Leonor L.; Canto-Cavalheiro, Marilene M. [Fundacao Oswaldo Cruz (IOC/FIOCRUZ), Rio de Janeiro, RJ (Brazil). Instituto Oswaldo Cruz. Lab. de Bioquimica de Tripanosomatideos

2011-07-01

Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4-carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies. (author)

2-(2,4-Dichlorophenyl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylacetamide

Directory of Open Access Journals (Sweden)

B. Narayana

2013-01-01

Full Text Available In the crystal structure of the title compound, C19H17Cl2N3O2, the molecules form dimers of the R22(10 type through N—H...O hydrogen bonding. As a result of steric repulsion, the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 80.70 (13 and 64.82 (12°, respectively. The dihedral angle between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 48.45 (5° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 56.33 (6°.

Crystal structure of 1-methoxy-2,2,2-tris(pyrazol-1-ylethane

Directory of Open Access Journals (Sweden)

Ganna Lyubartseva

2014-09-01

Full Text Available The title compound, C12H14N6O, consists of three pyrazole rings bound via nitrogen to the distal ethane carbon of methoxy ethane. The dihedral angles between the three pyrazole rings are 67.62 (14, 73.74 (14, and 78.92 (12°. In the crystal, molecules are linked by bifurcated C—H,H...N hydrogen bonds, forming double-stranded chains along [001]. The chains are linked via C—H...O hydrogen bonds, forming a three-dimensional framework structure. The crystal was refined as a perfect (0.5:0.5 inversion twin.

1-[3-(2-Methyl-4-phenylquinolin-3-yl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-propane-1-one

Directory of Open Access Journals (Sweden)

Allaoua Kedjadja

2015-06-01

Full Text Available A novel compound, 1-[3-(2-methyl-4-phenylquinolin-3-yl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-propane-1-one (3 has been synthesized by cyclocondensation of (E-1-(2-methyl-4-phenylquinolin-3-yl-3-phenylprop-2-en-1-one (2 and hydrazine hydrate in propionic acid. The structure of this compound was established by elemental analysis, IR, 1H-NMR, 13C-NMR and MS data.

Analgesic Activity of Some 1,2,4-Triazole Heterocycles Clubbed with Pyrazole, Tetrazole, Isoxazole and Pyrimidine

Directory of Open Access Journals (Sweden)

Ramdas Bhanudas Pandhare

2013-02-01

Full Text Available Purpose: In the present study in vivo analgesic activity of some previously synthesized 1,2,4-triazole derivatives containing pyrazole, tetrazole, isoxazole and pyrimidine ring have been evaluated. Methods: Acetic acid induced writhing method and Hot plate method has been described to study analgesic activity of some 1,2,4-triazole derivatives containing pyrazole, tetrazole, isoxazole and pyrimidine as a pharmacological active lead. Results: Thirty six different derivatives containing 1,2,4-triazole ring were subjected to study their in vivo analgesic activity. Chloro, nitro and methoxy, hydroxy and bromo substituted derivatives showed excellent analgesic activity and dimethylamino, furan and phenyl substituted derivatives showed moderate analgesic activity in both of the methods. Compounds IIIa, IIId, IIIf, IIIi, IIIj, IVa, IVb, IVd, IVf, IVh, IVj IV3a and IIj were found to be superior analgesic agents after screening by Acetic acid induced writhing method. Compounds IIIb, IIId, IIIf, IIIh, IIIj, IVa, IVb, IVd, IVf, IVh, IVi, IV3c, IV3e and IIj were showed analgesic potential after screening of Hot plate method. Conclusion: All tested compounds containing 1,2,4-triazole were found to be promising analgesic agents, for this activity pyrazole, tetrazole, isoxazole and pyrimidine leads might be supported.

5-Isobutyl-4-phenylsulfonyl-1H-pyrazol-3(2H-one

Directory of Open Access Journals (Sweden)

M. Venkatesh

2010-12-01

Full Text Available The title compound, C13H16N2O3S, consists of two crystallographically independent molecules with similar geometries and exists in a keto form, the C=O bond lengths being 1.267 (2 and 1.254 (2 Å. In both molecules, the pyrazole rings are approximately planar, with maximum deviations of 0.017 (2 and 0.010 (2 Å, and the dihedral angles between the pyrazole and phenyl rings are 83.63 (11 and 70.07 (12°. In one molecule, an intramolecular C—H...O hydrogen bond with an S(6 ring motif is observed. In the crystal, intermolecular N—H...O and C—H...O hydrogen bonds link the molecules into two-dimensional networks parallel to the ab plane.

Synthesis, crystal structures, fluorescence and xanthine oxidase inhibitory activity of pyrazole-based 1,3,4-oxadiazole derivatives

Science.gov (United States)

Qi, De-Qiang; Yu, Chuan-Ming; You, Jin-Zong; Yang, Guang-Hui; Wang, Xue-Jie; Zhang, Yi-Ping

2015-11-01

A series of pyrazole-based 1,3,4-oxadiazole derivatives were rationally designed and synthesized in good yields by following a convenient route. All the newly synthesized molecules were fully characterized by IR, 1H NMR and elemental analysis. Eight compounds were structurally determined by single crystal X-ray diffraction analysis. The fluorescence properties of all the compounds were investigated in dimethyl sulfoxide media. In addition, these newly synthesized compounds were evaluated for in vitro inhibitory activity against commercial enzyme xanthine oxidase (XO) by measuring the formation of uric acid from xanthine. Among the compounds synthesized and tested, 3d and 3e were found to be moderate inhibitory activity against commercial XO with IC50 = 72.4 μM and 75.6 μM. The studies gave a new insight in further optimization of pyrazole-based 1,3,4-oxadiazole derivatives with excellent fluorescence properties and XO inhibitory activity.

5-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-ylmethylene]-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H-dione

Directory of Open Access Journals (Sweden)

Salman A. Khan

2010-03-01

Full Text Available The title compound, 5-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-ylmethylene]-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H-dione, has been synthesized by condensation of 1,3-diethyl-2-thiobarbituric acid and 3,5-dimethyl-1-phenylpyrazole-4-carbaldehyde in ethanol in the presence of pyridine. The structure of this new compound was confirmed by elemental analysis, IR, 1H-NMR, 13C-NMR and EI-MS spectral analysis.

Crystal structure of 1-meth-oxy-2,2,2-tris-(pyrazol-1-yl)ethane.

Science.gov (United States)

Lyubartseva, Ganna; Parkin, Sean; Coleman, Morgan D; Mallik, Uma Prasad

2014-09-01

The title compound, C12H14N6O, consists of three pyrazole rings bound via nitro-gen to the distal ethane carbon of meth-oxy ethane. The dihedral angles between the three pyrazole rings are 67.62 (14), 73.74 (14), and 78.92 (12)°. In the crystal, mol-ecules are linked by bifurcated C-H,H⋯N hydrogen bonds, forming double-stranded chains along [001]. The chains are linked via C-H⋯O hydrogen bonds, forming a three-dimensional framework structure. The crystal was refined as a perfect (0.5:0.5) inversion twin.

Organizational Learning as a testbed for BPR

DEFF Research Database (Denmark)

Larsen, Michael Holm; Leinsdorff, Torben

1998-01-01

The fact that a company´s learning ability may prevent strategic drift and the fact that many companies are undertaking BPR projects lead us to inquire into whether all BPR activities promote organizational learning...

IMPLEMENTATION DRIVERS FOR BPR AT SIEMENS TELECOMMUNICATIONS

Directory of Open Access Journals (Sweden)

C.C. Koorts

2012-01-01

Full Text Available <p>ENGLISH ABSTRACT: With the embracing of neV'( management philosophies or redesigned processes, it is becoming a popular opinion that often the practical problem lies with the implementation of the new concept, rather than with the concept itself. By focussing on certain generic critical actions, chances of successful implementation increases for any new philosophy or re-engineered process. This article discusses such critical success actions, or implementation drivers as experience in a BPR project at Siemens Telecommunications.p>>AFRIKAANSE OPSOMMING: 'n Gewilde siening ten opsigte van die bekendstelling van nuwe bestuursfilosofiee, of implementering van herontwerpde prosesse, is dat die probleem gewoonlik Ie by die implementering daarvan, eerder as by die beginsels van die bestuursfilosofie wat geimplementeer word . Deur op generies kritieke faktore te konsentreer, kan die kanse op suksesvolle implementering van bykans enige bestuursfilosofie of herontwerpde proses verbeter word. Hierdie artikel bespreek sulke kritieke sukses aksies, of implementeringsdrywers, aan die hand van 'n gevallestudie soos ervaar in 'n BPR projek by Siemens Telecommunications.p>

Acid catalyzed solvent free synthesis of new 1-acyl-4-benzhydryl substituted pyrazoles

International Nuclear Information System (INIS)

Sher, M.; Kausar, T.; Riaz, N.; Sharif, A.

2016-01-01

A convenient, cost effective and environmentally benign methodology has been developed, which delivered fourteen new 1-acyl-4-benzhyrdyl substituted pyrazole derivatives under solvent free conditions. Target compounds were synthesized in good to excellent yields simply by grinding reactants in a pestle and mortar with catalytic amount of conc. H/sub 2/SO/sub 4/. All the newly formed compounds were fully characterized with the help of detailed spectroscopic techniques including FTIR, NMR and GC-MS. (author)

Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic Acid Amides.

Science.gov (United States)

Du, Shijie; Tian, Zaimin; Yang, Dongyan; Li, Xiuyun; Li, Hong; Jia, Changqing; Che, Chuanliang; Wang, Mian; Qin, Zhaohai

2015-05-08

A series of novel 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-yl)phenyl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide (9m) exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.

Synthesis, Antifungal Activity and Structure-Activity Relationships of Novel 3-(Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic Acid Amides

Directory of Open Access Journals (Sweden)

Shijie Du

2015-05-01

Full Text Available A series of novel 3-(difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amides were synthesized and their activities were tested against seven phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to excellent activities. Among them N-(2-(5-bromo-1H-indazol-1-ylphenyl-3-(difluoro-methyl-1-methyl-1H-pyrazole-4-carboxamide (9m exhibited higher antifungal activity against the seven phytopathogenic fungi than boscalid. Topomer CoMFA was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds. In molecular docking, the carbonyl oxygen atom of 9m could form hydrogen bonds towards the hydroxyl of TYR58 and TRP173 on SDH.

The challenges of ecotox testing of nanomaterials and the BPR

DEFF Research Database (Denmark)

Hansen, Steffen Foss

2015-01-01

The European Biocidal Product Regulation (BPR) requires dedicated risk assessment of nanomaterials. When it comes to ecotoxicological testing of nanomaterials, meeting these requirements is especially challenging. Overall, these challenges fall into four overall categories: 1) materials character......The European Biocidal Product Regulation (BPR) requires dedicated risk assessment of nanomaterials. When it comes to ecotoxicological testing of nanomaterials, meeting these requirements is especially challenging. Overall, these challenges fall into four overall categories: 1) materials...... characterization, 2) exposure preparation, 3) monitoring stability and 4) monitoring time. In this paper, the challenges are presented and discussed. There is no easy manner in which to deal with the challenges related to ecotoxicological testing of nanomaterials in the light of the BPR requirements. It short...

Synthesis of certain fused pyrazoles derived from 2-methyl-3-amino-6-iodo-4(3 H) quinazolinone as possible insecticidal and radiosensitizing agents

International Nuclear Information System (INIS)

Abdel-Hamide, S.G.; Ghorab, M.M.; Ali, G.M.

1996-01-01

The Verisimilar reaction on 3-amino-2-methyl-6-4-quinazolone (1) using P O Cl 3 /DMF afforded 3-formyl pyrazole derivative (2). The condensation products (3 a,b) were obtained via reaction of (2) with malononitrile or ethyl cyano acetate. Heating the condensation products (3 a,b) with acetyl derivatives in the presence of ammonium acetate yielded the corresponding cyano pyridines (9 a-e) and (10 a-e), respectively. Compounds (9 c) and (10 c) were obtained also from the interaction of the chalcone derivative (11) with malononitrile or ethyl cyano acetate. Condensation of (2) with semicarbazide hydrochloride, thio semicarbazide or aromatic amines gave the corresponding (12 a), (12 b) and (13 a-c), respectively. Compound (12 a) could be cyclized to (14) in acid medium. Interaction of compound (12 b) with chloro acetyl chloride gave (15). The Verisimilar reaction on Schiff bass (16) using P O Cl 3 /DMF gave the amino acrolein derivates (17), which was converted into 2-pyrazole derivative (18) and 2-isoxazolinyl derivative (19), respectively. The obtained compounds have been characterized on the basis of their IR, 'H-NMR and Mass spectral data and elemental analysis. Among the synthesized compounds only the formyl pyrazole derivative (2) and the azetidinylthioured derivative (15) showed a remarkable adulticidal activity. In addition the formyl pyrazole derivative (2) acted as a potent radiosensitizer. 2 figs., 3 tabs

Synthesis and characterization of some complexes with imidazole and pyrazole from saccharinate transition ions in oxidation state (II)

International Nuclear Information System (INIS)

Pineda Cedeno, Leslie William

2001-01-01

The synthesis and characterization of metal ions saccharinate of the first serie of transition with the imidazole and pyrazole molecules in water and absolute ethanol were studied. In general, it found that in this series of saccharinate of coordinated water molecules are replaced by imidazole and pyrazole molecules with different substitution patterns, generating neutral complex of molecular formula [M(Sac) 2 (L) n (H 2 O) n-4 ] and cationic complex of molecular formula [M(L) n (H 2 O) 2 ]x2Sac, [M(L) n (H 2 O) 3 ]x2Sac, [M(L) n ]x2Sac, where M = V(II), Cr(II), Mc(II), Fe(II), Co(II), Ni(II) y Zn(II); Sac = saccharinate ion; L = imidazole (imd) and pyrazole (pir) and n = 6,4,3 and 2. These compounds are soluble in DMF and insoluble in all other common solvents. In turn, synthesized compounds in water were characterized by X ray crystallography, where preliminary data of refinement cycles, generate formulas of isostructural type [M(imd) 4 (H 2 O) 2 ]x2Sac and [M(Sac) 2 (pir) 2 (H 2 O) 2 ] where M = Co(II), Ni(II). The imidazole complex crystallize in the triclinic crystal system and space group P-1, while the pyrazole complexes crystallize in the monoclinic crystal system and space group P2 (1)/n. Gradual diminution was observed in the bond distances of M-N (saccharinate ion), M-N (imidazole) and M-N (pyrazole). The complex was characterized by spectroscopic methods, magnetic and electrochemical. (author) [es

Synthesis and antimicrobial evaluation of some new pyrazole, pyrazoline and chromeno[3,4-c]pyrazole derivatives

Energy Technology Data Exchange (ETDEWEB)

Abunada, Nada M.; Miqdad, Omar A. [Al-Aqsa University, Gaza (Palestinian Territory, Occupied). Faculty of Applied Sciences. Dept. of Chemistry; Hassaneen, Hamdi M. [Cairo University, Cairo (Egypt). Faculty of Science. Dept. of Chemistry; Samaha, Ahmed S. M. Abu [Al-Aqsa University, Gaza (Palestinian Territory, Occupied). Faculty of Applied Sciences. Dept. of Biology

2009-07-01

Some new pyrazole-5-carbonitrile derivatives 8,9 and pyrazole-5-carboxamide 13 were synthesized by the cycloaddition reaction of nitrilimines 3,4 to alpha-cyanocinnamonitriles 5a-f and alpha-cyanocinnamamide 12a,b respectively. On the other hand 3,4 add to ethyl alpha-cyanocinnamate 14a-f to give ethyl 2-pyrazoline-5-carboxylate derivatives 15,16. Also, cycloaddition of 3,4 to 3-cyanocoumarin 19a or 3-phenylsulphonylcoumarin 19b or 3-bromocoumarin 19c give chromeno[3,4-c]pyrazol-4(3H)-one derivatives 20. In the same direction, the cycloaddition of 3,4 to 3-acetylcoumarin 22 and 3-benzoylcoumarin 23 gives the corresponding dihydrochromeno[3,4-]pyrazol-4(3H)-one 24 and 25 respectively. Oxidation of 24 and 25 give 20. Most of the prepared compounds showed good to moderate antibacterial and antifungal activities. (author)

Synthesis, Characterization, Antimicrobial Screening and Free-Radical Scavenging Activity of Some Novel Substituted Pyrazoles

Directory of Open Access Journals (Sweden)

Nagwa Mohamed Mahrous Hamada

2015-06-01

Full Text Available The present work deals with the synthesis of acetoxysulfonamide pyrazole derivatives, substituted 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivatives starting from substituted vanillin chalcones. Acetoxysulfonamide pyrazole derivatives were prepared from the reaction of chalcones with p-sulfamylphenylhydrazine followed by treatment with acetic anhydride. At the same time 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivatives were prepared from the reaction of chalcones with either thiosemicarbazide or isonicotinic acid hydrazide, respectively. The synthesized compounds were structurally characterized on the basis of IR, 1H-NMR, 13C-NMR spectral data and microanalyses. All of the newly isolated compounds were tested for their antimicrobial activities. The antimicrobial screening using the agar well-diffusion method revealed that the chloro derivatives are the most active ones. Moreover, the antioxidant and anti-inflammatory activity of these chloro derivatives are also studied using the DPPH radical scavenging and NO radical scavenging methods, respectively.

Synthesis of Functionalized Pyrazoles via 1,3-Dipolar Cycloaddition of α-Diazo-β-ketophosphonates, Sufones and Esters with Electron-Deficient Alkenes.

Science.gov (United States)

Baiju, T V; Namboothiri, Irishi N N

2017-10-01

1,3-Dipolar cycloaddition of diazo compounds with olefinic substrates is a promising atom-economic strategy for the construction of functionalized pyrazoles. Over the last few years, our group has been engaged in the synthesis of phosphonyl/sulfonylpyrazoles and pyrazole esters by employing Bestmann-Ohira Reagent (BOR) and its sulfur and ester analogs as 1,3-dipole precursors with various dipolarophiles. This account describes the novel synthetic methods developed in our laboratory, in the perspective of closely related work by others, for the synthesis of phosphonyl/sulfonylpyrazoles, pyrazole esters and the total synthesis of Withasomnine, a natural product, by using 1,3-dipolar cycloaddition as the key step. © 2017 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Simple and Efficient One-Pot Synthesis, Spectroscopic Characterization and Crystal Structure of Methyl 5-(4-Chlorobenzoyloxy-1-phenyl-1H-pyrazole-3-carboxylate

Directory of Open Access Journals (Sweden)

Imtiaz Khan

2012-07-01

Full Text Available A facile one-pot synthesis of methyl 5-(4-chlorobenzoyloxy-1-phenyl-1H-pyrazole-3-carboxylate (4 is described. The title compound was efficiently synthesized by the reaction of phenyl hydrazine, dimethyl acetylenedicarboxylate and 4-chlorobenzoyl chloride in dichloromethane under reflux in good yield. The structure of the target compound was deduced by modern spectroscopic and analytical techniques and unequivocally confirmed by a single crystal X-ray diffraction analysis. The crystal of the title compound belongs to orthorhombic system, space group P 21 21 21 with cell parameters a = 6.6491(3 Å, b = 7.9627(6 Å, c = 30.621(5 Å, α = β = γ = 90° and Z = 4. The crystal packing of the compound (4 is stabilized by an offset π-stacking between the planar benzoyl-substituted diazole moieties.

Solvent-free one-pot cyclization and acetylation of chalcones: Synthesis of some 1-acetyl pyrazoles and spectral correlations of 1-(3-(3,4-dimethylphenyl-5-(substituted phenyl-4,5-dihydro-1H-pyrazole-1-yl ethanones

Directory of Open Access Journals (Sweden)

G. Thirunarayanan

2016-11-01

Full Text Available One-pot synthesis of some 1N-acetyl pyrazoles including 1-(3-(3,4-dimethylphenyl-5-(substituted phenyl-4,5-dihydro-1H-pyrazole-1-yl ethanones has been achieved via solvent-free microwave irradiation using substituted chalcones, hydrazine hydrate and acetic anhydride in the presence of catalytic amount of fly-ash: PTS catalyst. The yield of these 1N-acetyl pyrazole derivatives is more than 75%. The synthesized 1N-acetyl pyrazoline derivatives were characterized by their physical constants and spectral data. The infrared spectral νCN and CO (cm−1 frequencies, NMR chemical shifts (δ, ppm of Ha, Hb, Hc, CH3 protons, CN, CO and CH3 carbons of 1-(3-(3,4-dimethylphenyl-5-(substituted phenyl-4,5-dihydro-1H-pyrazole-1-yl ethanones have been assigned and correlated with Hammett substituent constants and Swain-Lupton’s parameters using single and multi-regression analysis. From the results of statistical analyses, the effect of substituents on the above group frequencies and chemical shifts of the acetylated pyrazoles were discussed.

5-(2,4-Dichlorophenoxy-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

Directory of Open Access Journals (Sweden)

S. Madan Kumar

2016-07-01

Full Text Available In the crystal structure of the title compound, C17H12Cl2N2O2, the pyrazole ring makes dihedral angles of 65.0 (2 and 43.9 (2° with the dichlorophenyl and phenyl rings, respectively. The dihedral angle between the chlorophenyl and phenyl rings is 59.1 (2°. In the crystal, the molecules are linked by C—H...O hydrogen bonds and weak C—Cl...π and C—H...π interactions, generating a three-dimensional network.

A study of the vaporization enthalpies of some 1-substituted imidazoles and pyrazoles by correlation-gas chromatography.

Science.gov (United States)

Lipkind, Dmitry; Plienrasri, Chatchawat; Chickos, James S

2010-12-23

The vaporization enthalpies of 1-methyl-, 1-ethyl-, 1-phenyl-, and 1-benzylimidazole, 1-methyl- and 1-phenylpyrazole, and trans-azobenzene are evaluated by correlation-gas chromatography (C-GC) using a variety of azines and diazines as standards. The vaporization enthalpies obtained by C-GC when compared to literature values are approximately 14 kJ·mol(-1) smaller for the imidazoles and 6 kJ·mol(-1) smaller for the pyrazoles. The literature vaporization enthalpies of 1-methylpyrrole and 1-methylindole, two closely related compounds with one less nitrogen, are reproduced by C-GC. These results suggest that the magnitude of the intermolecular interactions present in 1-substituted imidazoles and pyrazoles are significantly larger than the those present in the reference compounds and greater than or equal in magnitude to the enhanced intermolecular interactions observed previously in aromatic 1,2-diazines. The vaporization enthalpy and vapor pressure of a trans-1,2-diazine, trans-azobenzene, measured by C-GC using similar standards reproduced the literature values within experimental error.

Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives

Directory of Open Access Journals (Sweden)

Seham Y. Hassan

2013-02-01

Full Text Available A series of 2-pyrazolines 5–9 have been synthesized from α,β-unsaturated ketones 2–4. New 2-pyrazoline derivatives 13–15 bearing benzenesulfonamide moieties were then synthesized by condensing the appropriate chalcones 2–4 with 4-hydrazinyl benzenesulfonamide hydrochloride. Ethyl [1,2,4] triazolo[3,4-c][1,2,4]triazino[5,6-b]-5H-indole-5-ethanoate (26 and 1-(5H-[1,2,4]triazino[5,6-b] indol-3-yl-3-methyl-1H-pyrazol-5(4H-one (32 were synthesized from 3-hydrazinyl-5H-[1,2,4]triazino[5,6-b]indole (24. On the other hand ethyl[1,2,4]triazolo[3,4-c][1,2,4]triazino[5,6-b]-5,10-dihydroquinoxaline- 5-ethanoate (27 and 1-(5,10-dihydro-[1,2,4]triazino[5,6-b]quinoxalin-3-yl-3-methyl-1H-pyrazol-5(4H-one (33 were synthesized from 3-hydrazinyl-5,10-dihydro-[1,2,4]triazino[5,6-b]quinoxaline (25 by reaction with diethyl malonate or ethyl acetoacetate, respectively. Condensation of 6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (1' with compound 24 or 25 afforded the corresponding Schiff's bases 36 and 37, respectively. Reaction of the Schiff's base 37 with benzoyl hydrazine or acetic anhydride afforded benzohydrazide derivative 39 and the cyclized compound 40, respectively. Furthermore, the pyrazole derivatives 42–44 were synthesized by cyclization of hydrazine derivative 25 with the prepared chalcones 2–4. All the newly synthesized compounds have been characterized on the basis of IR and 1H-NMR spectral data as well as physical data. Antimicrobial activity against the organisms E. coli ATCC8739 and P. aeruginosa ATCC 9027 as examples of Gram-negative bacteria, S. aureus ATCC 6583P as an example of Gram-positive bacteria and C. albicans ATCC 2091 as an example of a yeast-like fungus have been studied using the Nutrient Agar (NA and Sabouraud Dextrose Agar (SDA diffusion methods. The best performance was found for the compounds 16, 17, 19 and 20.

Antimalarial activity of 4-(5-trifluoromethyl-1H-pyrazol-1-yl)-chloroquine analogues.

Science.gov (United States)

Cunico, Wilson; Cechinel, Cleber A; Bonacorso, Helio G; Martins, Marcos A P; Zanatta, Nilo; de Souza, Marcus V N; Freitas, Isabela O; Soares, Rodrigo P P; Krettli, Antoniana U

2006-02-01

The antimalarial activity of chloroquine-pyrazole analogues, synthesized from the reaction of 1,1,1-trifluoro-4-methoxy-3-alken-2-ones with 4-hydrazino-7-chloroquinoline, has been evaluated in vitro against a chloroquine resistant Plasmodium falciparum clone. Parasite growth in the presence of the test drugs was measured by incorporation of [(3)H]hypoxanthine in comparison to controls with no drugs. All but one of the eight (4,5-dihydropyrazol-1-yl) chloroquine 2 derivatives tested showed a significant activity in vitro, thus, are a promising new class of antimalarials. The three most active ones were also tested in vivo against Plasmodium berghei in mice. However, the (pyrazol-1-yl) chloroquine 3 derivatives were mostly inactive, suggesting that the aromatic functionality of the pyrazole ring was critical.

1-[3-(4-Chlorophenyl-5-(4-methoxyphenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Directory of Open Access Journals (Sweden)

Hoong-Kun Fun

2012-04-01

Full Text Available In the title compound, C18H17ClN2O2, the benzene rings form dihedral angles of 6.69 (6 and 74.88 (5° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5° with each other. In the crystal, molecules are linked via bifurcated (C,C–H...O hydrogen bonds into chains along [010]. The crystal structure is further consolidated by C—H...π interactions.

Toxicological evaluation of two novel bitter modifying flavour compounds: 3-(1-((3,5-dimethylisoxazol-4-ylmethyl-1H-pyrazol-4-yl-1-(3-hydroxybenzylimidazolidine-2,4-dione and 3-(1-((3,5-dimethylisoxazol-4-ylmethyl-1H-pyrazol-4-yl-1-(3-hydroxybenzyl-5,5-dimethylimidazolidine-2,4-dione

Directory of Open Access Journals (Sweden)

Donald S. Karanewsky

Full Text Available A toxicological evaluation of two novel bitter modifying flavour compounds, 3-(1-((3,5-dimethylisoxazol-4-ylmethyl-1H-pyrazol-4-yl-1-(3-hydroxybenzylimidazolidine-2,4-dione (S6821, CAS 1119831-25-2 and 3-(1-((3,5-dimethylisoxazol-4-ylmethyl-1H-pyrazol-4-yl-1-(3-hydroxybenzyl-5,5-dimethylimidazolidine-2,4-dione (S7958, CAS 1217341-48-4, were completed for the purpose of assessing their safety for use in food and beverage applications. S6821 undergoes oxidative metabolism in vitro, and in rat pharmacokinetic studies both S6821 and S7958 are rapidly converted to the corresponding O-sulfate and O-glucuronide conjugates. S6821 was not found to be mutagenic or clastogenic in vitro, and did not induce micronuclei in bone marrow polychromatic erythrocytes in vivo. S7958, a close structural analog of S6821, was also found to be non-mutagenic in vitro. In short term and subchronic oral toxicity studies in rats, the no-observed-adverse-effect-level (NOAEL for both S7958 and S6821 was 100 mg/kg bw/day (highest dose tested when administered as a food ad-mix for either 28 or 90 consecutive days, respectively. Furthermore, S6821 demonstrated a lack of maternal toxicity, as well as adverse effects on fetal morphology at the highest dose tested, providing a NOAEL of 1000 mg/kg bw/day for both maternal toxicity and embryo/fetal development when administered orally during gestation to pregnant rats. Keywords: S6821, S7958, FEMA GRAS, Subchronic toxicological evaluation, Genetic toxicological evaluation

Standard molar enthalpies of formation of three methyl-pyrazole derivatives

International Nuclear Information System (INIS)

Ribeiro da Silva, Manuel A.V.; Cabral, Joana I.T.A.

2012-01-01

Highlights: ► Combustion calorimetry was used to determine Δ f H m ∘ (cr) of methyl-pyrazole derivatives. ► Vapour pressures were determined by the Knudsen mass-loss effusion technique. ► Gas-phase Δ f H m ∘ of the studied compounds have been derived. - Abstract: The standard (p ° = 0.1 MPa) molar enthalpies of formation of the crystalline 3-methyl-1-pyrazolecarboxamide; 3-methyl-3-pyrazoline-5-one; and 4-methyl-2-pyrazoline-5-one were derived from the standard massic energies of combustion, in oxygen, to yield CO 2 (g), H 2 O (l) and N 2 (g), at T = 298.15 K, measured by static bomb combustion calorimetry. The standard molar enthalpies of sublimation were calculated from the variation of the vapour pressures of each compound with temperature, measured by the Knudsen effusion technique. These two thermodynamic parameters yielded the standard molar enthalpies of formation of the pyrazole derivatives, in the gaseous phase, at T = 298.15 K. The derived standard molar enthalpies of formation, in gaseous state, are analyzed in terms of enthalpic increments and interpreted in terms of molecular structure.

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety

Directory of Open Access Journals (Sweden)

Hong Dai

2016-02-01

Full Text Available In this study, in order to find novel biologically active pyrazole oxime compounds, a series of pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety were synthesized. Preliminary bioassays indicated that most title compounds were found to display good to excellent acaricidal activity against Tetranychus cinnabarinus at a concentration of 200 μg/mL, and some designed compounds still showed excellent acaricidal activity against Tetranychus cinnabarinus at the concentration of 10 μg/mL, especially since the inhibition rates of compounds 8e, 8f, 8l, 8m, 8n, 8p, and 8q were all 100.00%. Interestingly, some target compounds exhibited moderate to good insecticidal activities against Plutella xylostella and Aphis craccivora at a concentration of 200 μg/mL; furthermore, compounds 8e and 8l possessed outstanding insecticidal activities against Plutella xylostella under the concentration of 50 μg/mL.

Synthesis and structure of (bis(3,5-dimethyl-1H-pyrazol-1-yl)methane)diiodocobalt(II)

International Nuclear Information System (INIS)

Bushuev, M.B.; Virovets, A.V.; Peresypkina, E.V.; Naumov, D.Yu.; Lavrenova, L.G.; Potapov, A.S.; Khlebnikov, A.I.; Vasilevskij, S.F.

2005-01-01

Cobalt(II) iodo complex with bis(3,5-dimethyl-1H-pyrazol-1-yl)methane (L), CoLI 2 , is synthesized and its monocrystals are grown. The complex is characterized by electronic spectra and X-ray diffraction. CoLI 2 belongs to the monoclinic crystal system, sp. gr. P2 1 /m, a=8.4044(4), b=13.3120(5), c=14.5824(7) A; β=94.7290(10) deg; Z=4; d clcd =2.112 g/cm 3 . In its structure the complex is molecular and mononuclear one. Ligand L is coordinated in a bidentate-cyclic manner; the cobalt polyhedron is a CoN 2 I 2 tetrahedron formed by nitrogen atoms of the L pyrazole fragments and iodine atoms [ru

Unigene BLAST: CBRC-GGAL-04-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available ndness, protan) (OPN1LW), mRNA /cds=p(9,1097) /gb=NM_205440 /gi=45382134 /ug=Gga.716 /len=1318 1e-30 26% ... ...CBRC-GGAL-04-0034 gnl|UG|Gga#S19184093 Gallus gallus opsin 1 (cone pigments), long-wave-sensitive (color bli

(2E-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl-1-(2,5-dimethyl-3-thienylprop-2-en-1-one

Directory of Open Access Journals (Sweden)

Salman A. Khan

2010-04-01

Full Text Available The title compound, (2E-3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl-1-(2,5-dimethyl-3-thienylprop-2-en-1-one (3 was synthesized in high yield by aldol condensation of 3-acetyl-2,5-dimethylthiophene and 3,5-dimethyl-1-phenylpyrazole-4-carboxaldehyde in ethanolic NaOH at room temperature. Its structure was fully characterized by elemental analysis, IR, 1H NMR, 13C NMR and EI-MS spectral analysis.

1,1′-{1,4-Phenylene bis[3-(6-chloro-2-methyl-4-phenylquinolin-3-yl-4,5-dihydro-1H-pyrazole-5,1-diyl]}dibutan-1-one

Directory of Open Access Journals (Sweden)

Allaoua Kedjadja

2015-10-01

Full Text Available A new polycyclic compound, 1,1′-{1,4-phenylene bis[3-(6-chloro-2-methyl-4-phenylquinolin-3-yl-4,5-dihydro-1H-pyrazole-5,1-diyl]}dibutan-1-one (3 has been synthesized by cyclocondensation of (2E,2′E-1,1′-bis(6-chloro-2-methyl-4-phenylquinolin-3-yl-3,3′-(1,4-phenylenediprop-2-en-1-one (2 and hydrazine hydrate in butanoic acid. The structure of this compound was established by elemental analysis, 1H-NMR, 13C-NMR, mass and IR spectroscopy.

Synthesis and Anti-inflammatory Activity of Some Novel Pyrazole Derivatives of Gallic Acid

Directory of Open Access Journals (Sweden)

S. Arunkumar

2009-01-01

Full Text Available In the present study, a new series of [5-substituted-3-(phenylamino-1H-pyrazol-1yl] (3,4,5-trihydroxyphenyl-methanone (4a-j have been synthesized. 3, 4, 5-Trihydroxy benzohydrazide (1 was synthesized from propyl gallate and hydrazine hydrate in presence of ethanol. Chalcones (2a-j were synthesized from acetanilide and various aromatic aldehydes in presence of ethanol and sodium hydroxide solution. By refluxing the compound (1 and compounds (2a-j in presence of ethanol yielded [5-substituted-3-(phenylamino-4.5-dihydropyrazol-1yl] (3,4,5-trihydroxy phenyl-methanone (3a-j. The final compounds [5-substituted-3-(phenylamino-1H-pyrazol-1yl] (3,4,5-trihydroxyphenyl-methanone (4a-j were synthesized by treating compounds (3a-j with bromine water. The synthesized compounds have been characterized by IR, 1HNMR and Mass spectral data. The compounds were evaluated for in vivo anti-inflammatory activity by carrageenan induced paw edema test. In general all compounds were found to exhibit good anti-inflammatory activity.

3,5-Dimethyl-4-nitroso-1H-pyrazole

Directory of Open Access Journals (Sweden)

Inna Safyanova

2011-09-01

Full Text Available In the unit cell of the title compound, C5H7N3O, there are two conformers (A and B which differ in the position of the oxime group with respect to the protonated pyrazole nitrogen (trans in the A conformer and cis in the B conformer and in the geometric parameters. The oxime group exists in the nitroso form in both conformers. In the crystal, molecules are linked by intermolecular N—H...O and N—H...N hydrogen bonds into zigzag-like chains along the b axis.

4-Methyl-5-phenyl-1H-pyrazol-3-ol

Directory of Open Access Journals (Sweden)

Tara Shahani

2010-07-01

Full Text Available The title compound, C10H10N2O, crystallizes with two independent molecules in the asymmetric unit, having closely comparable geometries. The dihedral angles between the 1H-pyrazole and benzene rings in the two molecules are 39.57 (14 and 41.95 (13°. The two molecules are each connected to neighbouring molecules by pairs of intermolecular O—H...N hydrogen bonds, forming dimers with R22(8 ring motifs. These dimers are further linked into R44(10 ring motifs by intermolecular N—H...O hydrogen bonds, forming chains along [101]. The crystal structure is further stabilized by a C—H...π interaction.

New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.

Directory of Open Access Journals (Sweden)

Amin Mokhlesi

2017-11-01

Full Text Available Three new 2-methoxy acetylenic acids (1–3 and a known derivative (4, in addition to three new natural pyrazole alkaloids (5–7 were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopy as well as by mass spectrometric data. The absolute configuration of the new acetylenic acid derivatives (1–3 was established by ECD spectroscopy. All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells. Compounds 1–4 exhibited strong activity with an IC50 value of 0.3 µM. A plausible biosynthetic pathway for the pyrazole metabolites 5–7 is proposed.

trans-Bis(perchlorato-κOtetrakis(1H-pyrazole-κN2copper(II

Directory of Open Access Journals (Sweden)

Viktor Zapol'skii

2008-10-01

Full Text Available The title compound, [Cu(ClO42(C3H4N24], was obtained unexpectedly by the reaction of copper(II perchlorate hexahydrate with equimolar amounts of 1-chloro-1-nitro-2,2,2-tripyrazolylethane in methanol solution. The crystal structure comprises octahedrally coordinated Cu2+ ions, located on an inversion centre, with four pyrazole ligands in the equatorial plane. The average Cu—N distance is 2.000 (1 Å. Two perchlorate ions are coordinated to copper in trans positions [Cu—O = 2.4163 (11 Å].

Ultrasound Promoted Synthesis of Bis(substituted pyrazol-4-ylcarbonyl-Substituted Thioureas

Directory of Open Access Journals (Sweden)

Li Xiao

2009-03-01

Full Text Available A series of novel bis(substituted pyrazol-4-ylcarbonyl-substituted thioureas have been synthesized by the reactions of substituted pyrazol-4-ylcarbonyl isothiocyanates with different diamines under ultrasound irradiation and classical heating method at 20-25 °C. In general, substantial improvement in rates and modest yields increases were observed when reactions were carried out under sonication, compared with the classical heating method. The structures of these compounds have been elucidated by elemental and spectral (IR, 1H-NMR analysis.

4-Chloroselanyl-3,5-diethyl-1H-pyrazol-2-ium chloride

Directory of Open Access Journals (Sweden)

Maksym Seredyuk

2011-11-01

Full Text Available In the cation of the title compound, C7H12ClN2Se+·Cl−, the ethylene groups and the Se–Cl fragment adopt a cis configuration with a C—Se—Cl angle of 96.09 (6°. In the crystal, intermolecular N—H...Cl hydrogen bonds link two cations and two chlorine anions into centrosymmetric clusters. π–π interactions between the pyrazole rings [centroid–centroid distance of 3.530 (2 Å] link these clusters into columns along [001] with short intermolecular Se...Cl− contacts of 2.995 (1 Å.

X-ray structure, semi-empirical MO calculations and π-electron delocalization of 1-cyanoacetyl-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1 H-pyrazoles

Science.gov (United States)

Martins, Marcos A. P.; Moreira, Dayse N.; Frizzo, Clarissa P.; Campos, Patrick T.; Longhi, Kelvis; Marzari, Mara R. B.; Zanatta, Nilo; Bonacorso, Helio G.

2010-04-01

The structure of three 1-cyanoacetyl-3-alkyl[aryl]-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1 H-pyrazoles ( 1- 3) has been determined by X-ray diffractometry. The 4,5-dihydro-1 H-pyrazole rings were obtained as almost planar structures showing RMS deviation at a range of 0.0196-0.0736 Å. The data demonstrate that the molecular packing is dependent on the substituent present in each molecule. In addition, a computational investigation using semi-empirical AM1 and RM1 methods was performed in order to investigate the correlation between experimental and calculated geometrical parameters. The data obtained suggest that the structural data furnished by the AM1 method is in better agreement with those experimentally determined for the above compounds. An analysis of the π-electron delocalization by HOMA calculations indicate that there is a hyperconjugation effect in the imine group toward to phenyl group at ring 3-position of compound 2, and that this resonance effect decrease in compounds 1 and 3. In addition, it was showed that bond N(1) and C(6) do not have an amide character. Thus, the O(6)-C(6)-N(1)-N(2)-C(3) fragment is not completely delocalized mainly due to the low π-electron delocalization in N(1)-N(2) bond for all compounds.

Synergistic effect of pyrazoles derivatives and doxorubicin in claudin-low breast cancer subtype.

Science.gov (United States)

Saueressig, Silvia; Tessmann, Josiane; Mastelari, Rosiane; da Silva, Liziane Pereira; Buss, Julieti; Segatto, Natalia Vieira; Begnini, Karine Rech; Pacheco, Bruna; de Pereira, Cláudio Martin Pereira; Collares, Tiago; Seixas, Fabiana Kömmling

2018-02-01

Breast cancer is a global public health problem. For some subtypes, such as Claudin-low, the prognosis is poorer and the treatment is still a challenge. Pyrazoles are an important class of heterocyclic compounds and are promising anticancer agents based on their chemical properties. The present study was aimed not only at testing pyrazoles previously prepared by our research group in two breast cancer cell lines characterized by intermediated response to conventional chemotherapy but also at analyzing the possible synergistic effect of these pyrazoles associated with doxorubicin. Four 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-1H pyrazoles were tested for the first time in MCF-7 and MDA-MB-231 culture cells. The pyrazoles with best results in cytotoxicity were used in combination with doxorubicin and compared with this drug alone as standard. The synergic effect was analyzed using Combination Index method. In addition, cell death and apoptosis assays were carried out. Two pyrazoles with cytotoxic effect in MCF-7 and especially in MDA-MB-231 were identified. This activity was markedly higher in pyrazoles containing bromine and chlorine substituents. The combination of these pyrazoles with doxorubicin had a significant synergic effect in both cells tested and mainly in MDA-MB-231. These data were confirmed with apoptosis and cell death analysis. The synergic effect observed with combination of these pyrazoles and doxorubicin deserves special attention in Claudin-low breast cancer subtype. This should be explored in order to improve treatment results and minimize side effects. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Unigene BLAST: CBRC-ATHA-05-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-ATHA-05-0034 gnl|UG|At#S11736431 Arabidopsis thaliana ATMPK19 (Arabidopsis tha...liana MAP kinase 19); MAP kinase (ATMPK19) mRNA, complete cds /cds=p(1,1761) /gb=NM_112333 /gi=30683276 /ug=At.8069 /len=1897 6.9 42% ...

3,5-Dimethyl-4-nitroso-1H-pyrazole

Science.gov (United States)

Safyanova, Inna; Dudarenko, Nikolay M.; Pavlenko, Vadim A.; Iskenderov, Turganbay S.; Haukka, Matti

2011-01-01

In the unit cell of the title compound, C5H7N3O, there are two conformers (A and B) which differ in the position of the oxime group with respect to the protonated pyrazole nitro­gen (trans in the A conformer and cis in the B conformer) and in the geometric parameters. The oxime group exists in the nitroso form in both conformers. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O and N—H⋯N hydrogen bonds into zigzag-like chains along the b axis. PMID:22059058

Polymerization of 1,3-butadiene catalyzed by pincer cobalt(II) complexes derived from 2-(1-arylimino)-6-(pyrazol-1-yl)pyridine ligands

KAUST Repository

Gong, Dirong

2013-08-01

A new class of air stable and structurally well-defined cobalt complexes with unsymmetrical pincer type ligands ([2-(ArNCMe)-6-(Py)C5H 3N]CoCl2) (Ar = C6H5, Py = pyrazol-1-yl, 5a; Ar = 2,4,6-Me3C6H2, Py = pyrazol-1-yl, 5b; Ar = 2,6-iPr2C6H3, Py = pyrazol-1-yl, 5c; Ar = C6H5, Py = 3,5-Me 2pyrazol-1-yl, 5d; Ar = 2,4,6-Me3C6H 2, Py = 3,5-Me2pyrazol-1-yl, 5e; Ar = 2,6- iPr2C6H3, Py = 3,5-Me 2pyrazol-1-yl, 5f; Ar = 2,6-iPr2C 6H3, Py = 3,5-iPr2pyrazol-1-yl, 5g and [2-(OCMe)-6-(3,5-diphenylpyrazol-1-yl)C5H3N]CoCl 2 5h) were prepared and the molecular structures of 5a, 5c and 5f were determined by single crystal X-ray crystallography. Upon activation by methylaluminoxane (MAO) in toluene at room temperature, all complexes initiate polymerization of 1,3-butadiene (polymer yields: 65-99%), affording polybutadiene with excellent cis-1,4 regularity (97.5-98.7%). The polymer yields and properties in terms of molecular weight and distribution are well controlled by the substituents on iminoaryl rings and pyrazole rings. Selectivity switch from cis-1,4 to syndio-1,2 was also achievable by adding phosphine as microstructure regulator. © 2013 Elsevier B.V. All rights reserved.

A Convenient Approach to Heterocyclic Building Blocks: Synthesis of Novel Ring Systems Containing a [5,6]Pyrano[2,3-c]pyrazol-4(1H-one Moiety

Directory of Open Access Journals (Sweden)

Wolfgang Holzer

2007-01-01

Full Text Available Starting from commercially available educts, a straightforward synthetic route to new heterocyclic building blocks is exemplified with the one- or two-step synthesis of tri-, tetra-, or pentacyclic ring systems. Representatives of the following novel ring systems are prepared from 3-methyl-1-phenyl-2-pyrazolin-5-one and the corresponding o-halo-arenecarbonyl chloride using calcium hydroxide in refluxing 1,4-dioxane: pyrimidino[4',5':5,6]pyrano[2,3-c]pyrazol-4(1H-one, thieno[3',2':5,6]pyrano[2,3c]pyrazol- 4-(1H-one, thieno[3',4':5,6]pyrano[2,3-c]pyrazol-4(1H-one, thieno[3'',2'':4',5']thieno[2',3':5,6]-pyrano[2,3-c]pyrazol-4(1H-one, [1,3]dioxolo[5',6'][1]benzothieno[2',3':5,6]pyrano-[2,3-c]- pyrazol-4(1H-one, pyridazino[4',3':5,6]pyrano[2,3-c]pyrazol-4(1H-one and pyrazolo-[4'',3'':5',6']pyrido[3',4':5,6]pyrano[2,3-c]pyrazol-4(1H-one. While the latter two ring systems are directly obtained due to a spontaneous intramolecular substitution reaction, in the other reactions uncyclised 4-aroylpyrazol-5-ols are produced, which are cyclised into the target heterocycles in a subsequent synthetic step (i.e. treatment with NaH in DMF. Detailed NMR spectroscopic investigations (1H-, 13C-, 15N- with the obtained compounds were undertaken to unambiguously prove the new structures.

Microwave assisted synthesis and antimicrobial activity of novel 1-[1/2-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-naphthalen-2/1-yl]-3-(1-phenyl-3-aryl-1H-pyrazol-4-yl-propenones

Directory of Open Access Journals (Sweden)

Dongamanti Ashok

2015-06-01

Full Text Available A series of novel 1-[1/2-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-naphthalen-2/1-yl]-3-(1-phenyl-3-aryl-1H-pyrazol-4-yl-propenones were design and synthesized by Click reaction followed by Claisen-Schmidt condensation under microwave irradiation and conventional heating methods. The structures of newly synthesized compounds have been established on the basis of elemental analysis, IR, 1H & 13C NMR and mass spectral data. All the compounds were screened for their antimicrobial activity.

Antimicrobial activities of pyridinium-tailored pyrazoles bearing 1,3,4-oxadiazole scaffolds

Directory of Open Access Journals (Sweden)

Lei Zhou

2017-11-01

Full Text Available Herein, a series of pyridinium-tailored 5-trifluoromethylpyrazoles containing 1,3,4-oxadiazole moieties were constructed through coupling key pharmaceutical fragments of pyridinium, pyrazole, and 1,3,4-oxadiazole scaffolds in single molecular architecture. Antimicrobial results suggested that this kind of compounds exhibited significant activities against three types of pathogenic bacteria and six fungal strains in vitro. The minimal EC50 values of designed compounds against Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri could reach to 0.467, 1.04, and 0.600 μg/mL, respectively, through tuning and optimizing N-substituents, bridging atom, and alkyl length of the tailor. Antifungal assays revealed that all title molecules possessed considerable activity against Botrytis cinerea with the minimal EC50 value up to 2.71 μg/mL; and compounds I-8, I-10, I-12, II-12, and IV-12 showed the strongest growth suppression toward Rhizoctonia solani with EC50 values ranging from 10.2 to 24.0 μg/mL. Given the above results, this kind of compounds could serve as new lead compounds in the research of antimicrobial chemotherapy.

Anti-Candida, Anti-Enzyme Activity and Cytotoxicity of 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides

Directory of Open Access Journals (Sweden)

Simone Oliveira

2014-05-01

Full Text Available Because of the need for more effective and less harmful antifungal therapies, and interest in the synthesis of new carboximidamides, the goal of this study was to determine the antifungal and anti-enzyme activities of some new pyrazole carboximidamides and their cytotoxicity. For this purpose, tests were performed to evaluate: minimum inhibitory concentration (MIC and minimum fungicidal concentration (MFC; production of proteinases and phospholipase, and cytotoxicity of the extracts. Data were analyzed by ANOVA and Tukey Tests (α = 5%. The results were: MIC and MFC ≥ 62.5 μg/mL (C. albicans, C. parapsilosis, C. famata, C. glabrata, and Rhodotorula mucillaginosa and MIC and MFC ≥ 15.6 μg/mL (C. lipolytica. The values of proteinase and phospholipase (Pz of C. albicans before and after exposure to the compounds were: 0.6 (±0.024 and 0.2 (±0.022 and 0.9 (±0.074 and 0.3 (±0.04, respectively. These proteinase results were not significant (p = 0.69, but those of phospholipase were (p = 0.01, and 15.6 μg/mL was the most effective concentration. The cytotoxicity means were similar among the tests (p = 0.32. These compounds could be useful as templates for further development through modification or derivatization to design more potent antifungal agents. Data from this study provide evidence that these new pyrazole formulations could be an alternative source for the treatment of fungal infections caused by Candida. However, a specific study on the safety and efficacy of these in vivo and clinical trials is still needed, in order to evaluate the practical relevance of the in vitro results.

Synthesis, biological evaluation and molecular docking of novel 5-phenyl-1H-pyrazol derivatives as potential BRAF(V600E) inhibitors.

Science.gov (United States)

Dong, Jing-Jun; Li, Qing-Shan; Wang, Shu-Fu; Li, Cui-Yun; Zhao, Xin; Qiu, Han-Yue; Zhao, Meng-Yue; Zhu, Hai-Liang

2013-10-07

The RAF-MEK-ERK cascade appears to be intimately involved in the regulation of cell cycle progression and apoptosis. The BRAF(V600E) mutant results in constitutive activation of the ERK pathway, which can lead to cellular growth dysregulation. A series of 5-phenyl-1H-pyrazol derivatives (3a-5e) have been designed and synthesized, and their biological activities were evaluated as potential BRAF(V600E) inhibitors. All the compounds were reported for the first time except 3e, and compound 1-(4-bromo-2-hydroxybenzyl)-3-phenyl-1-(5-phenyl-1H-pyrazol-3-yl)urea (5c) displayed the most potent inhibitory activity (BRAF(V600E) IC50 = 0.19 μM). Antiproliferative assay results indicated that compound 5c possessed high antiproliferative activity against cell lines WM266.4 and A375 in vitro, with IC50 values of 1.50 and 1.32 μM, respectively, which were comparable with the positive control vemurafenib. Docking simulations showed that compound 5c binds tightly to the BRAF(V600E) active site and acts as BRAF(V600E) inhibitor. A 3D-QSAR model was also built to provide more pharmacophore understanding towards designing new agents with more potent BRAF(V600E) inhibitory activity.

Antitumor potential of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-1H-pyrazoles in human bladder cancer cells.

Science.gov (United States)

Tessmann, Josiane Weber; Buss, Julieti; Begnini, Karine Rech; Berneira, Lucas Moraes; Paula, Favero Reisdorfer; de Pereira, Claudio Martin Pereira; Collares, Tiago; Seixas, Fabiana Kömmling

2017-10-01

Bladder cancer is a genitourinary malignant disease common worldwide. Current chemotherapy is often limited mainly due to toxicity and drug resistance. Thus, there is a continued need to discover new therapies. Recently evidences shows that pyrazoline derivatives are promising antitumor agents in many types of cancers, but there are no studies with bladder cancer. In order to find potent and novel chemotherapy drugs for bladder cancer, a series of pyrazoline derivatives 2a-2d were tested for their antitumor activity in two human bladder cancer cell lines 5647 and T24. The MTT assay showed that the compounds 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-1H-pyrazole (2a) and 1-thiocarbamoyl-5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole (2c) decrease the cell viability of 5637 cells. Molecular modeling indicated that these compounds had a good oral bioavailability and low toxicities. Clonogenic assay and flow cytometric analysis were used to assess colony formation, apoptosis induction and cell cycle distribution. Overall, our results suggest that pyrazoline 2a and 2c, with the substituents hydrogen and chlorine respectively, may decrease cell viability and colony formation of bladder cancer 5637 cell line by inhibition of cell cycle progression, and for pyrazoline 2a, by induction of apoptosis. As indicated by the physicochemical properties of these compounds, the steric factor influences the activity. Therefore, these pyrazoline derivatives can be considered promising anticancer agents for the treatment of bladder cancer. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

A spin-crossover complex based on a 2,6-bis(pyrazol-1-yl)pyridine (1-bpp) ligand functionalized with a carboxylate group.

Science.gov (United States)

Abhervé, Alexandre; Clemente-León, Miguel; Coronado, Eugenio; Gómez-García, Carlos J; López-Jordà, Maurici

2014-07-07

Combining Fe(ii) with the carboxylate-functionalized 2,6-bis(pyrazol-1-yl)pyridine (bppCOOH) ligand results in the spin-crossover compound [Fe(bppCOOH)2](ClO4)2 which shows an abrupt spin transition with a T1/2 of ca. 380 K and a TLIESST of 60 K due to the presence of a hydrogen-bonded linear network of complexes.

Modification, biological evaluation and 3D QSAR studies of novel 2-(1,3-diaryl- 4,5-dihydro-1H-pyrazol-5-ylphenol derivatives as inhibitors of B-Raf kinase.

Directory of Open Access Journals (Sweden)

Yu-Shun Yang

Full Text Available A series of novel 2-(1,3-diaryl- 4,5-dihydro-1H-pyrazol-5-ylphenol derivatives (C1-C24 have been synthesized. The B-Raf inhibitory activity and anti-proliferation activity of these compounds have been tested. Compound C6 displayed the most potent biological activity against B-RafV600E (IC50 = 0.15 µM and WM266.4 human melanoma cell line (GI50 = 1.75 µM, being comparable with the positive control (Vemurafenib and Erlotinib and more potent than our previous best compounds. The docking simulation was performed to analyze the probable binding models and poses while the QSAR model was built to check the previous work as well as to introduce new directions. This work aimed at seeking more potent inhibitors as well as discussing some previous findings. As a result, the introduction of ortho-hydroxyl group on 4,5-dihydro-1H-pyrazole skeleton did reinforce the anti-tumor activity while enlarging the group on N-1 of pyrazoline was also helpful.

The investigation of the reactions of some pyrazole-3-carboxylic acids with various diamines and diols

Directory of Open Access Journals (Sweden)

Rahmi Kasımoğulları

2012-06-01

Full Text Available In this study, some new derivatives were synthesized of 4-benzoyl-1-(3-nitrophenyl-5-phenyl-1H-pyrazole-3-carboxylic acid (1 and 4-(ethoxycarbonyl-1-(3-nitrophenyl-5-phenyl-1H-pyrazole-3-carboxylic acid (2 that they were pyrazole carboxylic acid derivatives. Firstly, 1 and 2 reacted with SOCl2 to transform them into acyl chlorides (3, 4. Then various bis-carboxamide derivatives (5–8 were obtained from the reaction of 3 and 4 with various diamines and also a ;#946;-hydroxy ester (9 derivative was obtained from the reaction of 3 with ethylene glycol. The structures of synthesized compounds were elucidated with using FT-IR, 1H NMR, 13C NMR and elemental analysis methods.

Microwave-assisted synthesis of N-pyrazole ureas and the p38alpha inhibitor BIRB 796 for study into accelerated cell ageing.

Science.gov (United States)

Bagley, Mark C; Davis, Terence; Dix, Matthew C; Widdowson, Caroline S; Kipling, David

2006-11-21

Microwave irradiation of substituted hydrazines and beta-ketoesters gives 5-aminopyrazoles in excellent yield, which can be transformed to the corresponding N-carbonyl derivatives by treatment with an isocyanate or chloroformate. Derivatization of 4-nitronaphth-1-ol using predominantly microwave heating methods and reaction with an N-pyrazole carbamate provides a rapid route to the N-pyrazole urea BIRB 796 in high purity, as a potent and selective inhibitor of p38alpha mitogen-activated protein kinase for the study of accelerated ageing in Werner syndrome cells.

Crystal structure of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl-1H-pyrazole-4-carbaldehyde

Directory of Open Access Journals (Sweden)

Joel T. Mague

2014-10-01

Full Text Available In the title compound, C15H13N3O, the pyrrolyl and phenyl rings make dihedral angles of 58.99 (5 and 34.95 (5°, respectively, with the central pyrazole ring. In the crystal, weak, pairwise C—H...O interactions across centers of symmetry form dimers, which are further associated into corrugated sheets running approximately parallel to (100 via weak C—H...N interactions.

Synthesis, characterization and antibacterial activity of some 5-aryl-1, 3-Diphenyl 1-4, 5-dihydro-1H-Pyrazoles

International Nuclear Information System (INIS)

Al-Bahtiti, Nawal Hassan

2007-01-01

The condensation of acetophenone (I) with arylaldehyde (II) was investigated and the resulting chalcones 2-Arylidene 1-Acetophenone (III) were reacted with phenyl hydrazine and acetic acid to produce substituted 5-aryl-1, 3-diphenyl-4, 5-dihydro-1H-Pyrazoles (IV). The structures of all products were studied by H-NMR, IR, thermal and elemental analysis. Thermo-gravimetric (TG) and differential thermal analysis (DTA) was applied to investigate the thermal behavior and structure of the synthesized compounds. 2-Pyrazolines (IV) exhibited moderate activity against Streptococcus faecalis ATCC 19433, Klebsiella pneumoniae ATCC 13883, Proteus vulgaris ATCC 25922, Shigella sonnei ATCC 25931 and Peseudom oaeruginosa ATCC 27853. (author)

Synthesis, spectral characterization and X-ray crystal structure studies of 3-(benzo[d][1,3]dioxol-5-yl)-5-(3-methylthiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboxamide: Hirshfeld surface, DFT and thermal analysis

Science.gov (United States)

Kumara, Karthik; Dileep Kumar, A.; Naveen, S.; Ajay Kumar, K.; Lokanath, N. K.

2018-06-01

A novel pyrazole derivative, 3-(benzo[d][1,3]dioxol-5-yl)-5-(3-methylthiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboxamide was synthesized and characterized by elemental analysis, FT-IR, NMR (1H and 13C), MS, UV-visible spectra and finally the structure was confirmed by the single crystal X-ray diffraction studies. The title compound (C16H15N3O3S) crystallized in the triclinic crystal system, with the space group Pī. A dihedral angle of 65.84(1)° between the pyrazole and the thiophene rings confirms the twisted conformation between them. The X-ray structure revealed that the pyrazole ring adopts an E-form and an envelope conformation on C7 atom. The crystal and molecular structure of the title compound is stabilized by inter molecular hydrogen bonds. The compound possesses three dimensional supramolecular self-assembly, in which Csbnd H⋯O and Nsbnd H⋯O chains build up two dimensional arrays, which are extended to 3D network through Csbnd H···Cg and Csbnd O···Cg interactions. The structure also exhibits intramolecular hydrogen bonds of the type Nsbnd H⋯N and π···π stacking interactions, which contributes to the crystal packing. Further, Hirshfeld surface analysis was carried out for the graphical visualization of several short intermolecular interactions on the molecular surface while the 2D finger-print plot provides percentage contribution of each individual atom-to-atom interactions. The thermal decomposition of the compound has been studied by thermogravimetric analysis. The molecular geometries and electronic structures of the compounds were fully optimized, calculated with ab-initio methods by HF, DFT/B3LYP functional in combination of different basis set with different solvent environment and the structural parameters were compared with the experimental data. The Mulliken atomic charges and molecular electrostatic potential on molecular van der Waals (vdW) surface were calculated to know the electrophilic and nucleophilic regions

Formation of a dinuclear copper(II) complex through the cleavage of CN bond of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole

Energy Technology Data Exchange (ETDEWEB)

Shardin, Rosidah; Pui, Law Kung; Yamin, Bohari M. [School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi, Selangor (Malaysia); Kassim, Mohammad B. [School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi, Selangor, Malaysia and Fuel Cell Institute, Universiti Kebangsaan Malaysia, UKM 43600 Bangi, Selangor (Malaysia)

2014-09-03

A simple mononuclear octahedral copper(II) complex was attempted from the reaction of three moles of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole and one mole of copper(II) perchlorate hexahydrate in methanol. However, the product of the reaction was confirmed to be a dinuclear copper(II) complex with μ-(3-(pyridin-2-yl)-pyrazolato) and 3-(pyridin-2-yl)-1H-pyrazole ligands attached to each of the Cu(II) centre atom. The copper(II) ion assisted the cleavage of the C{sub benzoyl}N bond afforded a 3-(pyridin-2-yl)-1H-pyrazole molecule. Deprotonation of the 3-(pyridin-2-yl)-1H-pyrazole gave a 3-(pyridin-2-yl)-pyrazolato, which subsequently reacted with the Cu(II) ion to give the (3-(pyridin-2-yl)-pyrazolato)(3-(pyridin-2-yl)-1H-pyrazole)Cu(II) product moiety. The structure of the dinuclear complex was confirmed by x-ray crystallography. The complex crystallized in a monoclinic crystal system with P2(1)/n space group and cell dimensions of a = 12.2029(8) Å, b = 11.4010(7) Å, c = 14.4052(9) Å and β = 102.414(2)°. The compound was further characterized by mass spectrometry, CHN elemental analysis, infrared and UV-visible spectroscopy and the results concurred with the x-ray structure. The presence of d-d transition at 671 nm (ε = 116 dm{sup 3} mol{sup −1} cm{sup −1}) supports the presence of Cu(II) centres.

A critical review of both the synthesis approach and the receptor profile of the 8-chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4,5,6-tetrahydrobenzo[6,7]cyclohepta[1,2-c]pyrazole-3-carboxamide and analogue derivatives.

Science.gov (United States)

Lazzari, Paolo; Distinto, Rita; Manca, Ilaria; Baillie, Gemma; Murineddu, Gabriele; Pira, Marilena; Falzoi, Matteo; Sani, Monica; Morales, Paula; Ross, Ruth; Zanda, Matteo; Jagerovic, Nadine; Pinna, Gérard Aimè

2016-10-04

8-Chloro-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4,5,6-tetrahydrobenzo[6,7]cyclohepta[1,2-c]pyrazole-3-carboxamide 9a was discovered as potent and selective CB1 antagonist by part of our group few years ago. In particular it was reported to have an affinity towards the CB1 cannabinoid receptor (CB1R), expressed as Ki, of 0.00035 nM. Nevertheless significantly divergent data were reported for the same compound from other laboratories. To unequivocally define the receptor profile of 9a, we have critically reviewed both its synthesis approach and binding data. Here we report that, in contrast to our previously reported data, 9a showed a Ki value for CB1R in the order of nanomolar rather than of fentomolar range. The new determined receptor profile of 9a was also ascertained for analogue derivatives 9b-i, as well as for 12. Moreover, the structural features of the synthesized compounds necessary for CB1R were investigated. Amongst the novel series, effects on CB1R intrinsic activity was highlighted due to the substituents at the position 3 of the pyrazole ring of the 1,4,5,6-tetrahydrobenzo[6,7]cyclohepta[1,2-c]pyrazole scaffold. Although the cannabinoid receptor profile of 9a was reviewed in this work, the relevance of this compound in CB1R antagonist based drug discovery is confirmed. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Crystal structure of N′-diphenylmethylidene-5-methyl-1H-pyrazole-3-carbohydrazide

Directory of Open Access Journals (Sweden)

Khalid Karrouchi

2015-11-01

Full Text Available In the title compound, C18H16N4O, the planes of the phenyl rings are approximately perpendicular to each other [dihedral angle = 78.07 (8°] and form dihedral angles of 56.43 (8 and 24.59 (8° with the pyrazole ring. In the crystal, molecules are linked by N—H...O hydrogen bonds to form one-dimensional chains parallel to the [010] direction.

EU Regulation of Nanobiocides: Challenges in Implementing the Biocidal Product Regulation (BPR

Directory of Open Access Journals (Sweden)

Anna Brinch

2016-02-01

Full Text Available The Biocidal Products Regulation (BPR contains several provisions for nanomaterials (NMs and is the first regulation in the European Union to require specific testing and risk assessment for the NM form of a biocidal substance as a part of the information requirements. Ecotoxicological data are one of the pillars of the information requirements in the BPR, but there are currently no standard test guidelines for the ecotoxicity testing of NMs. The overall objective of this work was to investigate the implications of the introduction of nano-specific testing requirements in the BPR and to explore how these might be fulfilled in the case of copper oxide nanoparticles. While there is information and data available in the open literature that could be used to fulfill the BPR information requirements, most of the studies do not take the Organisation for Economic Co-operation and Development’s nanospecific test guidelines into consideration. This makes it difficult for companies as well as regulators to fulfill the BPR information requirements for nanomaterials. In order to enable a nanospecific risk assessment, best practices need to be developed regarding stock suspension preparation and characterization, exposure suspensions preparation, and for conducting ecotoxicological test.

EU Regulation of Nanobiocides: Challenges in Implementing the Biocidal Product Regulation (BPR).

Science.gov (United States)

Brinch, Anna; Hansen, Steffen Foss; Hartmann, Nanna B; Baun, Anders

2016-02-16

The Biocidal Products Regulation (BPR) contains several provisions for nanomaterials (NMs) and is the first regulation in the European Union to require specific testing and risk assessment for the NM form of a biocidal substance as a part of the information requirements. Ecotoxicological data are one of the pillars of the information requirements in the BPR, but there are currently no standard test guidelines for the ecotoxicity testing of NMs. The overall objective of this work was to investigate the implications of the introduction of nano-specific testing requirements in the BPR and to explore how these might be fulfilled in the case of copper oxide nanoparticles. While there is information and data available in the open literature that could be used to fulfill the BPR information requirements, most of the studies do not take the Organisation for Economic Co-operation and Development's nanospecific test guidelines into consideration. This makes it difficult for companies as well as regulators to fulfill the BPR information requirements for nanomaterials. In order to enable a nanospecific risk assessment, best practices need to be developed regarding stock suspension preparation and characterization, exposure suspensions preparation, and for conducting ecotoxicological test.

A Longitudinal BPR Study in a Danish Manufacturing Company - From Reengineering to Process Management

DEFF Research Database (Denmark)

Larsen, Michael Holm; Wieth, Christian; Domsten, Zenia Vittarp

1998-01-01

, Business Process Reengineering (BPR) is the most applied method for planning and carrying out projects. Novo Nordisk A/S is one of the largest companies in Denmark and the world's largest producer of industrial enzymes with a market share of more than 50%.This paper is a longitudinal study of BPR...... initiatives at Enzyme Business carried out within the time frame of January 1994 to March 1998. The paper provides empirical insight from a number of BPR-projects and related BPR-initiatives, e.g. Business System Reengineering projects. The results of the paper suggest that reengineering with the means...

Structural, optical, mechanical and density functional theory studies of 1H-pyrazol-2-ium hydrogen oxalate crystal

Energy Technology Data Exchange (ETDEWEB)

Devi, P. Karthiga, E-mail: karthvi19@gmail.com; Venkatachalam, K.

2016-11-01

In the present work, we have grown 1H- pyrazol-2-ium hydrogen oxalate single crystal by slow evaporation solution growth technique. The lattice parameters are determined from single crystal X ray diffraction studies. The functional groups present in the compound are confirmed by Fourier transform infrared spectroscopy. UV-Vis analysis shows that the crystal has a wide transparency window. Vicker's hardness test has been carried out to estimate the stiffness constant, fracture toughness, brittleness index and yield strength of the crystal. Density functional study B3LYP method at 6-31 G (d, p) has been performed to study the optimized structure, HOMO-LUMO energy gap, hyperpolarizability and thermodynamic properties. - Highlights: • The title compound was analyzed using FTIR and UV–Vis spectroscopy. • Mechanical study was carried out using Vicker's hardness test. • Optimized molecular geometry was determined using DFT method. • Hydrogen bonding interaction was studied through NBO analysis.

2-(3,5-Dimethyl-1H-pyrazol-1-yl-2-hydroxyimino-N′-[1-(pyridin-2-ylethylidene]acetohydrazide

Directory of Open Access Journals (Sweden)

Maxym O. Plutenko

2012-12-01

Full Text Available In the title compound, C14H16N6O2, the dihedral angles formed by the mean plane of the acetohydrazide group [maximum deviation 0.0629 (12 Å] with the pyrazole and pyridine rings are 81.62 (6 and 38.38 (4° respectively. In the crystal, molecules are connected by N—H...O and O—H...N hydrogen bonds into supramolecular chains extending parallel to the c-axis direction.

1,5-Dimethyl-4-(1-methyl-3-oxo-3-phenylprop-1-enylamino-2-phenyl-1H-pyrazol-3(2H-one

Directory of Open Access Journals (Sweden)

Hualing Zhu

2011-07-01

Full Text Available In the title compound, C21H21N3O2, an intramolecular N—H...O interaction generates an S(6 ring, which stablizes the enamine–keto tautomer. The S(6 ring makes dihedral angles of 33.07 (7, 56.50 (8 and 38.59 (8°, respectively, with the benzoylacetone benzene ring and the antipyrine pyrazole and benzene rings.

3,5-Bis(4-methoxyphenyl-1-phenyl-4,5-dihydro-1H-pyrazole

Directory of Open Access Journals (Sweden)

Zeliha Baktır

2011-02-01

Full Text Available In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å and it makes a dihedral angle of 18.5 (2° with the phenyl ring. The dihedral angles between the phenyl and the two methoxy-substituted phenyl rings are 26.2 (2 and 80.6 (2°. The crystal structure is stabilized by C—H...π stacking interactions and weak π–π interactions [centriod–centroid distance = 3.891 (2 Å].

Toxicological evaluation of a novel cooling compound: 2-(4-methylphenoxy-N-(1H-pyrazol-3-yl-N-(2-thienylmethylacetamide

Directory of Open Access Journals (Sweden)

Donald S. Karanewsky

2015-01-01

Full Text Available A toxicological evaluation of a novel cooling agent, 2-(4-methylphenoxy-N-(1H-pyrazol-3-yl-N-(2-thienylmethyl acetamide (S2227; CAS 1374760-95-8, was completed for the purpose of assessing its safety for use in food and beverage applications. S2227 undergoes rapid oxidative metabolism in vitro, and in rat and dog pharmacokinetic studies is rapidly converted to its component carboxylic acid and secondary amine. S2227 was not found to be mutagenic or clastogenic in vitro, and did not induce micronuclei in polychromatic erythrocytes in vivo. The secondary amine hydrolysis product, N-(2-thienylmethyl-1H-pyrazol-3-amine (M179, was also evaluated for genotoxicity. In subchronic oral toxicity studies in rats, the no-observed-adverse-effect-level (NOAEL for S2227 was 100 mg/kg/day (highest dose tested when administered by oral gavage for 90 consecutive days. Furthermore, S2227 demonstrated a lack of maternal toxicity, as well as adverse effects on fetal morphology at the highest dose tested, providing a NOAEL of 1000 mg/kg/day for both maternal toxicity and embryo/fetal development when administered orally during gestation to pregnant rats.

1-[(6-Chloro-3-pyridylmethyl]-N-(4-ethoxyphenyl-3-phenyl-1H-pyrazole-5-carboxamide

Directory of Open Access Journals (Sweden)

Zheng Tang

2009-04-01

Full Text Available In the title compound, C24H21ClN4O2, the pyrazole ring makes dihedral angles of 7.70 (11, 89.17 (11 and 40.68 (11° with the phenyl, pyridine and ethoxyphenyl rings, respectively. There are some intramolecular C—H...O and C—H...π bonds giving rigidity to the molecule, while weak intermolecular N—H...N and C—H...π hydrogen bonds link the molecules into a two-dimensional structure.

The new 3-(tert-butyl)-1-(2-nitrophenyl)-1H-pyrazol-5-amine: Experimental and computational studies

Science.gov (United States)

Cuenú, Fernando; Muñoz-Patiño, Natalia; Torres, John Eduard; Abonia, Rodrigo; Toscano, Rubén A.; Cobo, J.

2017-11-01

The molecular and supramolecular structure of the title compound, 3-(tertbutyl)-1-(2-nitrophenyl)-1H-pyrazol-5-amine (2NPz) from the single crystal X-ray diffraction (SC-XRD) and spectroscopic data analysis is reported. The computational analysis of the structure, geometry optimization, vibrational frequencies, nuclear magnetic resonance and UV-Vis is also described and compared with experimental data. Satisfactory theoretical aspects were made for the molecule using density functional theory (DFT), with B3LYP and B3PW91 functionals, and Hartree-Fock (HF), with 6-311++G(d,p) basis set, using GAUSSIAN 09 program package without any constraint on the geometry. With VEDA 4 software, vibrational frequencies were assigned in terms of the potential energy distribution while, with the GaussSum software, the percentage contribution of the frontier orbitals at each transition of the electronic absorption spectrum was established. The obtained results indicated that optimized geometry could well reflect the molecular structural parameters from SC-XRD. Theoretical data obtained for the vibrational analysis and NMR spectra are consistent with experimental data.

4-Chloro­selanyl-3,5-diethyl-1H-pyrazol-2-ium chloride

Science.gov (United States)

Seredyuk, Maksym; Znovjyak, Kateryna O.; Sliva, Tetyana Yu.; Haukka, Matti; Fritsky, Igor O.

2011-01-01

In the cation of the title compound, C7H12ClN2Se+·Cl−, the ethyl­ene groups and the Se–Cl fragment adopt a cis configuration with a C—Se—Cl angle of 96.09 (6)°. In the crystal, inter­molecular N—H⋯Cl hydrogen bonds link two cations and two chlorine anions into centrosymmetric clusters. π–π inter­actions between the pyrazole rings [centroid–centroid distance of 3.530 (2) Å] link these clusters into columns along [001] with short inter­molecular Se⋯Cl− contacts of 2.995 (1) Å. PMID:22220089

Green One-pot Synthesis of Novel Polysubstituted Pyrazole Derivatives as Potential Antimicrobial Agents.

Science.gov (United States)

Beyzaei, Hamid; Motraghi, Zahra; Aryan, Reza; Zahedi, Mohammad Mehdi; Samzadeh-Kermani, Alireza

2017-12-01

Various biological properties of natural and synthetic pyrazole derivatives such as anti-inflammatory, antimicrobial, neuroprotective, anticonvulsant, antidepressant and anticancer activities encouraged us to propose a new, fast, green and eco-friendly procedure for the preparation of some novel 5-amino-3-(aryl substituted)-1-(2,4-dinitrophenyl)-1H-pyrazole-4-carbonitriles. They were efficiently synthesized via one-pot two-step process reaction of malononitrile, 2,4-dinitrophenylhydrazine and different benzaldehydes in deep eutectic solvent (DES) glycerol/potassium carbonate. The products yield and reaction times were considerably improved in the presence of applied DES. Antibacterial effects of all newly synthesized pyrazoles in comparison with several common antibiotics were evaluated against a variety of Gram-positive and Gram-negative pathogenic bacteria. In addition to, their inhibitory activities on three fungi were compared to some current antifungal agents. The moderate to good antimicrobial potentials particularly against fungi were observed in the major heterocyclic compounds according to the IZD, MIC, MBC and MFC results.

NCBI nr-aa BLAST: CBRC-GGAL-03-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-GGAL-03-0034 ref|NP_036916.1| cannabinoid receptor 1 (brain) [Rattus norvegicu...s] sp|P20272|CNR1_RAT Cannabinoid receptor 1 (CB1) (CB-R) (Brain-type cannabinoid receptor) emb|CAA39332.1| CB1 cann...abinoid receptor [Rattus norvegicus] gb|AAA99067.1| neuronal cannabinoid receptor gb|EDL98589.1| cann...abinoid receptor 1 (brain) [Rattus norvegicus] prf||1613453A cannabinoid receptor NP_036916.1 0.0 93% ...

Functionalized 3-(benzofuran-2-yl-5-(4-methoxyphenyl-4,5-dihydro-1H-pyrazole scaffolds: A new class of antimicrobials and antioxidants

Directory of Open Access Journals (Sweden)

Javarappa Rangaswamy

2017-05-01

Full Text Available A new class of functionalized 3-(benzofuran-2-yl-5-(4-methoxyphenyl-4,5-dihydro-1H-pyrazole scaffolds (4a–q was synthesized by a four step reaction in good yields. Initially, o-alkyl derivative of salicyaldehyde (1 readily furnished corresponding 2-acetyl benzofuran (2 on treatment with potassium tert-butoxide (t-BuOK in the presence of molecular sieves. Further, Claisen–Schmidt condensation reaction with 4-methoxy benzaldehyde and hydrazine hydrate followed by coupling of benzoyl chlorides afforded target compounds (4a–q. Representative of the synthesized compounds was characterized by IR, 1H NMR, 13C NMR, mass, elemental analysis and evaluated for antimicrobial and antioxidant activities. The results gathered are allowed to conclude that, all newly synthesized analogues exhibit a certain degree of antimicrobial and antioxidant activities. Among the analogues, compounds (4h and (4j showed an excellent antimicrobial activity in the well plate method. Meanwhile, compounds (4e–f, (4l and (4p showed good antioxidant activity, whereas compound (4g and (4q displayed dominant antioxidant efficacy compared to standard butylated hydroxy anisole (BHA.

Effect of Marketing Strategy on Customer Loyalty Bajapuik Savings at PT. BPR Berok Gunung Pangilun Padangn

Directory of Open Access Journals (Sweden)

H. Heryanto

2011-06-01

Full Text Available This study attempts to look and see if the marketing strategy of product, price, and location and upon promotion will affect customer loyalty bajapuik savings on PT.BPR Berok Gunung Pangilun Padang. This study uses primary data, where the object under study here is PT. BPR Berok Gunung Pangilun Padang. Total sample was 100 people taken from the 5750 population of people who gathered from 3 cash offices and 1 center office at PT. BPR Berok Gunung Pangilun Padang. The approach used to test the hypothesis of this study is multiple regression analysis, t-test f-test and anova. From the results showed that a significant difference between variables Marketing Strategies with Customer Loyalty.

Different molecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions.

Science.gov (United States)

Narayana, Badiadka; Yathirajan, Hemmige S; Rathore, Ravindranath S; Glidewell, Christopher

2016-09-01

4-Antipyrine [4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and its derivatives exhibit a range of biological activities, including analgesic, antibacterial and anti-inflammatory, and new examples are always of potential interest and value. 2-(4-Chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, C19H18ClN3O2, (I), crystallizes with Z' = 2 in the space group P\\overline{1}, whereas its positional isomer 2-(2-chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, (II), crystallizes with Z' = 1 in the space group C2/c; the molecules of (II) are disordered over two sets of atomic sites having occupancies of 0.6020 (18) and 0.3980 (18). The two independent molecules of (I) adopt different molecular conformations, as do the two disorder components in (II), where the 2-chlorophenyl substituents adopt different orientations. The molecules of (I) are linked by a combination of N-H...O and C-H...O hydrogen bonds to form centrosymmetric four-molecule aggregates, while those of (II) are linked by the same types of hydrogen bonds forming sheets. The related compound N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(3-methoxyphenyl)acetamide, C20H21N3O3, (III), is isomorphous with (I) but not strictly isostructural; again the two independent molecules adopt different molecular conformations, and the molecules are linked by N-H...O and C-H...O hydrogen bonds to form ribbons. Comparisons are made with some related structures, indicating that a hydrogen-bonded R2(2)(10) ring is the common structural motif.

In vitro biological characterization of a novel, synthetic diaryl pyrazole resorcinol class of heat shock protein 90 inhibitors.

Science.gov (United States)

Sharp, Swee Y; Boxall, Kathy; Rowlands, Martin; Prodromou, Chrisostomos; Roe, S Mark; Maloney, Alison; Powers, Marissa; Clarke, Paul A; Box, Gary; Sanderson, Sharon; Patterson, Lisa; Matthews, Thomas P; Cheung, Kwai-Ming J; Ball, Karen; Hayes, Angela; Raynaud, Florence; Marais, Richard; Pearl, Laurence; Eccles, Sue; Aherne, Wynne; McDonald, Edward; Workman, Paul

2007-03-01

The molecular chaperone heat shock protein 90 (HSP90) has emerged as an exciting molecular target. Derivatives of the natural product geldanamycin, such as 17-allylamino-17-demethoxy-geldanamycin (17-AAG), were the first HSP90 ATPase inhibitors to enter clinical trial. Synthetic small-molecule HSP90 inhibitors have potential advantages. Here, we describe the biological properties of the lead compound of a new class of 3,4-diaryl pyrazole resorcinol HSP90 inhibitor (CCT018159), which we identified by high-throughput screening. CCT018159 inhibited human HSP90beta with comparable potency to 17-AAG and with similar ATP-competitive kinetics. X-ray crystallographic structures of the NH(2)-terminal domain of yeast Hsp90 complexed with CCT018159 or its analogues showed binding properties similar to radicicol. The mean cellular GI(50) value of CCT018159 across a panel of human cancer cell lines, including melanoma, was 5.3 mumol/L. Unlike 17-AAG, the in vitro antitumor activity of the pyrazole resorcinol analogues is independent of NQO1/DT-diaphorase and P-glycoprotein expression. The molecular signature of HSP90 inhibition, comprising increased expression of HSP72 protein and depletion of ERBB2, CDK4, C-RAF, and mutant B-RAF, was shown by Western blotting and quantified by time-resolved fluorescent-Cellisa in human cancer cell lines treated with CCT018159. CCT018159 caused cell cytostasis associated with a G(1) arrest and induced apoptosis. CCT018159 also inhibited key endothelial and tumor cell functions implicated in invasion and angiogenesis. Overall, we have shown that diaryl pyrazole resorcinols exhibited similar cellular properties to 17-AAG with potential advantages (e.g., aqueous solubility, independence from NQO1 and P-glycoprotein). These compounds form the basis for further structure-based optimization to identify more potent inhibitors suitable for clinical development.

catena-Poly[[copper(II-bis[μ-bis(3,5-dimethyl-1H-pyrazol-4-yl selenide

Directory of Open Access Journals (Sweden)

Maksym Seredyuk

2009-11-01

Full Text Available In the title compound, {[Cu(C10H14N4Se2](ClO42}n, the CuII ion is located on a twofold rotation axis and has a tetragonally distorted square-planar geometry constituted by four N atoms. A pair of bis(3,5-dimethyl-1H-pyrazol-4-yl selenide (L ligands bridges the copper centers into a polymeric chain extending along [001]. The perchlorate anions are involved in intermolecular N—H...O hydrogen bonding, which links the chains into layers parallel to the bc plane.

Bis[tris(1H-pyrazol-1-yl-κN2methane]nickel(II bis{[tris(1H-pyrazol-1-yl-κN2methane]tris(thiocyanato-κNnickelate(II} methanol disolvate

Directory of Open Access Journals (Sweden)

Ganna Lyubartseva

2011-12-01

Full Text Available Attempts to prepare the mononuclear [(tpmNiIIL3]−1 [tpm = tris(1H-pyrazol-1-ylmethane and L = thiocyanate] anion yielded the methanol-solvated salt, [(tpm2NiII][(tpmNiII(NCS3]2·2CH3OH or [Ni(C10H10N62][Ni(NCS3(C10H10N6]2·2CH3OH. The asymmetric unit consists of half a centrosymmetric bis[tris(1H-pyrazol-1-ylmethane]nickel(II cation and an octahedral nickelate(II anion bound to one tpm and three L ligands, and a methanol solvent molecule. One of the L ligands is disordered over two positions with occupancy factors of 0.650 (3 and 0.350 (3. There are O—H...S interactions between the methanol and the disordered thiocyanate anion, and a weak C—H...O hydrogen bond between the cation and the methanol O atom.

Preparation of 5-acyl- and 5-aryl-substituted 1-(benzyloxy)pyrazoles via directed ortho-lithiation/transmetalation and palladium catalyzed cross- coupling

DEFF Research Database (Denmark)

Kristensen, Jesper Langgaard; Begtrup, M.; Vedsø, P.

1998-01-01

Palladium(0) catalyzed cross-coupling of 1-(benzyloxy)pyrazol-5-ylzinc halides 3a,b, prepared by transmetalation of 1-(benzyloxy)-5-lithiopyrazole (2), with acyl chlorides produced 5 acyl-1-(benzyloxy)pyrazoles 4a-d in high yields. Similar coupling of the pyrazol-5-ylzinc halide with amino-, hydr...

Polymerization of 1,3-butadiene catalyzed by pincer cobalt(II) complexes derived from 2-(1-arylimino)-6-(pyrazol-1-yl)pyridine ligands

KAUST Repository

Gong, Dirong; Jia, Weiguo; Chen, Tao; Huang, Kuo-Wei

2013-01-01

A new class of air stable and structurally well-defined cobalt complexes with unsymmetrical pincer type ligands ([2-(ArNCMe)-6-(Py)C5H 3N]CoCl2) (Ar = C6H5, Py = pyrazol-1-yl, 5a; Ar = 2,4,6-Me3C6H2, Py = pyrazol-1-yl, 5b; Ar = 2,6-iPr2C6H3, Py

N-{2-[2-(5-Methyl-1H-pyrazol-3-ylacetamido]phenyl}benzamide monohydrate

Directory of Open Access Journals (Sweden)

Karim Chkirate

2017-02-01

Full Text Available The asymmetric unit of the title compound, C19H18N4O2·H2O, comprises the U-shaped pyrazole derivative and a solvent water molecule. The molecular conformation is partly determined by an intramolecular N—H...O hydrogen bond. The crystal packing is directed by an extensive network of O—H...O, N—H...O, N—H...N and C—H...O hydrogen bonds together with C—H...π(ring contacts that generate a three-dimensional network.

3,5-Bis(4-meth-oxy-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazole.

Science.gov (United States)

Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S; Narayana, B; Yathirajan, H S

2011-01-12

In the title compound, C(23)H(22)N(2)O(2), the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two meth-oxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C-H⋯π stacking inter-actions and weak π-π inter-actions [centriod-centroid distance = 3.891 (2) Å].

Synthesis of 5-Substituted 3-Amino-1H-Pyrazole-4-Carbonitriles as Precursors for Microwave Assisted Regiospecific Syntheses of Pyrazolo[1,5-a]Pyrimidines

Directory of Open Access Journals (Sweden)

Fawzia Al-Qalaf

2008-12-01

Full Text Available A simple route to 3-oxoalkanonitrile 5, aprecursor of the title compounds is described. Reaction of enaminones 2 with hydroxylamine hydrochloride in ethanol yielded aldoximes 3 that were converted readily into 5 in basic medium. This method has been successfully applied with a number of substrates and resulted in excellent yields of the products. Reacting 5 with trichloroacetonitrile afforded 3-amino-2-aroyl-4,4,4-trichloro-2-butenenitriles 6 that condensed with hydrazines to yield 3-amino-1H-pyrazole-4-carbonitrilederivatives 8. Substituted pyrazolo[1,5-a]pyridmidines have been prepared with regioselective condensation reactions of 8 with nonsymmetrical dielectrophiles. The structures of compounds obtained were deduced based on 1H-NMR, 1H-15N HMBC- measurements.

BPR implementation process: an analysis of key success and failure factors

Directory of Open Access Journals (Sweden)

Mohamad Reza Khoshlafz

2016-08-01

Full Text Available This paper investigates the effects of different factors influencing on the successful implementation of the business process re-engineering (BPR in Iran. The study selects 386 experts randomly and using some statistical tests examines the effects of four groups of factors including strategic, organizational, methodologic and technological & educational issues on the success of the BPR implementation in Iran. The study designs a questionnaire in Likert scale and distributes it among some experts where Cronbach alpha was calculated as 0.71. The implementation of Pearson correlation ratio has confirmed that technological and educational factors marinated the highest effects (r = 0.523, Sig. = 0.000 followed by strategic (r = 0.505, Sig. = 0.000, organizational (r = 0.352, Sig. = 0.000 and methodologic issues (r = 0.267, Sig. = 0.000. In addition, the implementation of Stepwise regression has confirmed that technological & educational, strategic and methodologic factors influence on BPR in Iran.

BPR best practices for the healthcare domain

NARCIS (Netherlands)

Netjes, M.; Mans, R.S.; Reijers, H.A.; Aalst, van der W.M.P.; Vanwersch, R.J.B.; Rinderle-Ma, S.; Sadiq, S.; Leymann, F.

2010-01-01

Healthcare providers are under pressure to work more efficiently and in a more patient-focused way. One possible way to achieve this is to launch Business Process Redesign (BPR) initiatives, which focus on changing the structure of the involved processes and using IT as an enabler for such changes.

catena-Poly[[copper(II)-bis[μ-bis(3,5-dimethyl-1H-pyrazol-4-yl) selenide

Science.gov (United States)

Seredyuk, Maksym; Haukka, Matti; Pavlenko, Vadim A.; Fritsky, Igor O.

2009-01-01

In the title compound, {[Cu(C10H14N4Se)2](ClO4)2}n, the CuII ion is located on a twofold rotation axis and has a tetra­gonally distorted square-planar geometry constituted by four N atoms. A pair of bis(3,5-dimethyl-1H-pyrazol-4-yl) selenide (L) ligands bridges the copper centers into a polymeric chain extending along [001]. The perchlorate anions are involved in inter­molecular N—H⋯O hydrogen bonding, which links the chains into layers parallel to the bc plane. PMID:21578140

Analgesic Activity of Some 1,2,4-Triazole Heterocycles Clubbed with Pyrazole, Tetrazole, Isoxazole and Pyrimidine

OpenAIRE

Gajanan Khanage, Shantaram; Raju, Appala; Baban Mohite, Popat; Bhanudas Pandhare, Ramdas

2013-01-01

Purpose: In the present study in vivo analgesic activity of some previously synthesized 1,2,4-triazole derivatives containing pyrazole, tetrazole, isoxazole and pyrimidine ring have been evaluated. Methods: Acetic acid induced writhing method and Hot plate method has been described to study analgesic activity of some 1,2,4-triazole derivatives containing pyrazole, tetrazole, isoxazole and pyrimidine as a pharmacological active lead. Results: Thirty six different derivatives con...

Synthesis, Characterization and Antimicrobial Evaluation of Substituted 1,2,4-Triazole Thiones Containing Pyrazole Moiety

Directory of Open Access Journals (Sweden)

ALURU GURU PRASAD

2014-03-01

Full Text Available Aim: To synthesize a series of novel compounds namely, 4-(3-((substituted-1H-pyrazol-3-yl-methylsulphonyl-5-((3,5,6-trichloro-pyridin-2-yl-oxymethyl-[1,2,4]triazol%u20134%u2013yl-methyl-morpholine (8a-g and evaluate their antimicrobial activity. Material and Method: The chemical structures of newly synthesized compounds were elucidated by IR, 1H NMR, mass spectral and elemental analysis data. Their antimicrobial activities against Staphylococus aureus NCCS 2079, Bacillus Cereus, NCCS 2106, Escherichia coli NCCS 2065, Pseudomanas aeruginos NCCS 2200, Aspergillus niger NCCS 1196 and Candida albicans NCCS 2106 were investigated by employing disk diffusion method and minimum inhibitory concentration was found out by broth dilution method. Results: Elemental analysis of the compounds indicated that the values found by the experiments were very close to theoretically calculated values. IR and 1H NMR spectral assignments of critical functional groups were indicated in each case. Mass spectral fragmentation confirmed the formation of the final product to be screened for antimicrobial activity. Antibacterial and antifungal activity of each of the compounds were evaluated and presented. Each member of the series of compounds was found to be active against tested microbes in particular, the derivative %u20188C%u2019 was found exhibit better antimicrobial activity. Discussion: The compounds demonstrated significant antifungal activity once again evidencing the basic trait of 1,2,4-triazoles.

Differences in hepatic microsomal cytochrome P-450 isoenzyme induction by pyrazole, chronic ethanol, 3-methylcholanthrene, and phenobarbital in high alcohol sensitivity (HAS) and low alcohol sensitivity (LAS) rats.

Science.gov (United States)

Lucas, D; Ménez, J F; Berthou, F; Cauvin, J M; Deitrich, R A

1992-10-01

High and low alcohol sensitivity (HAS and LAS) rats have been selected for their differences in ethanol-induced sleep time. Liver monooxygenase activities were studied in HAS and LAS rats before and after treatments with known inducers such as chronic ethanol, pyrazole, 3-methylcholanthrene (3-MC) and phenobarbital (PB) to determine whether the selection procedure also selected for differences in the cytochrome P-450 (P-450) inducibility. This previously has been shown with long sleep (LS) and short sleep (SS) mice, which were selected using a similar criterion. 3-MC and PB, in conjunction with chronic ethanol treatment, were used in order to evaluate the interactions of ethanol with these inducers. Prior to treatment, total P-450 content was slightly lower in LAS than in HAS rats. However, both lines displayed the same microsomal monooxygenase activities related to different P-450 isozymes. This was demonstrated by ethoxyresorufin deethylation (EROD) for cytochrome P-450 1A1 (CYP1A1), acetanilide hydroxylation (ACET) for CYP1A2, pentoxyresorufin dealkylation (PROD) for CYP2B, 1-butanol oxidation (BUTAN) and N-nitrosodimethylamine demethylation (NDMA) for CYP2E1. After the different treatments, HAS rats did not differ from LAS rats in their CYP2E1 inducibility. However, pyrazole, PB and 3-MC treatment led to differences in CYP1A and CYP2B monooxygenase activities between the two lines. The enhancement of PROD by pyrazole treatment was less prominent in LAS (1.7-fold of the control value) than in HAS rats (3.8-fold).(ABSTRACT TRUNCATED AT 250 WORDS)

cyclo-Tetrakis(μ-3-acetyl-4-methyl-1H-pyrazole-5-carboxylato-κ4N2,O3:N1,O5tetrakis[aquacopper(II] tetradecahydrate

Directory of Open Access Journals (Sweden)

Sergey Malinkin

2011-09-01

Full Text Available The title compound, [Cu4(C7H6N2O34(H2O4]·14H2O, a tetranuclear [2 × 2] grid-type complex with S4 symmetry, contains four CuII atoms which are bridged by four pyrazolecarboxylate ligand anions and are additionally bonded to a water molecule. Each CuII atom is coordinated by two O atoms of the carboxylate and acetyl groups, two pyrazole N atoms of doubly deprotonated 3-acetyl-4-methyl-1H-pyrazole-5-carboxylic acid and one O atom of a water molecule. The geometry at each CuII atom is distorted square-pyramidal, with the two N and two O atoms in the equatorial plane and O atoms in the axial positions. O—H...O hydrogen-bonding interactions additionally stabilize the structure. One of the uncoordinated water molecules shows half-occupancy.

NCBI nr-aa BLAST: CBRC-TGUT-05-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-TGUT-05-0034 ref|NP_000854.1| 5-hydroxytryptamine (serotonin) receptor 1B [Hom...o sapiens] ref|NP_001009102.1| 5-hydroxytryptamine (serotonin) receptor 1B [Pan troglodytes] sp|P28222|5HT1B...HT-1B) (Serotonin receptor 1B) (5-HT1B) gb|AAA58675.1| serotonin 1Db receptor gb|AAA36029.1| serotonin recep...tor gb|AAA36030.1| 5-hyroxytryptamine 1D receptor dbj|BAA01763.1| serotonin 1B receptor [Homo sapiens] gb|AAA60316.1| serotonin... 1D receptor emb|CAB51537.1| 5-hydroxytryptamine (serotonin) r

Synthesis of N-(5-(Substitutedphenyl-4,5-dihydro-1H-pyrazol-3-yl-4H-1,2,4-triazol-4-amine from 4-Amino-4H-1,2,4-triazole

Directory of Open Access Journals (Sweden)

Ashvin D. Panchal

2011-01-01

Full Text Available N-(4H-1,2,4-Triazol-4-ylacetamide (2 were prepared by reaction of 4-amino-4H-1,2,4-triazole (1 with acetyl chloride in dry benzene. It has been reacted with various aromatic aldehyde to afford 3-(substitutedphenyl-N-(4H-1,2,4-triazol-4-ylacrylamide (3a-e. The synthesis of N-(5-substitutedphenyl-4,5-dihydro-1H-pyrazol-3-yl-4H-1,2,4-triazol-4-amine (4a-e is achieved by the cyclisation of 3a-e with hydrazine hydrate in ethanol. The structures of synthesized compounds were characterized by 1H NMR and IR spectroscopic studies. The purity of the compounds was checked by thin layer chromatography.

NCBI nr-aa BLAST: CBRC-DSIM-06-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-DSIM-06-0034 ref|NP_000669.1| alpha-1D-adrenergic receptor [Homo sapiens] sp|P...25100|ADA1D_HUMAN Alpha-1D adrenergic receptor (Alpha 1D-adrenoceptor) (Alpha 1D-adrenoreceptor) (Alpha-1A adrenergic... receptor) (Alpha adrenergic receptor 1a) gb|AAB60351.1| adrenergic alpha-1a receptor protein gb|AAB59487.1| alpha 1a/d adre...nergic receptor dbj|BAA06222.1| alpha1A/D adrenergic rec...eptor [Homo sapiens] emb|CAH70478.1| adrenergic, alpha-1D-, receptor [Homo sapiens] emb|CAC00601.2| adrenergic

Molecular and polymeric uranyl and thorium hybrid materials featuring methyl substituted pyrazole dicarboxylates and heterocyclic 1,3-diketones

Science.gov (United States)

Carter, Korey P.; Kerr, Andrew T.; Taydakov, Ilya V.; Cahill, Christopher L.

2018-02-01

A series of seven novel f-element bearing hybrid materials have been prepared from either methyl substituted 3,4 and 4,5-pyrazoledicarboxylic acids, or heterocyclic 1,3- diketonate ligands using hydrothermal conditions. Compounds 1, [UO2(C6H4N2O4)2(H2O)], and 3, [Th(C6H4N2O4)4(H2O)5]·H2O feature 1-Methyl-1H-pyrazole-3,4-dicarboxylate ligands (SVI-COOH 3,4), whereas 2, [UO2(C6H4N2O4)2(H2O)], and 4, [Th(C6H5N2O4)(OH)(H2O)6]2·2(C6H5N2O4)·3H2O feature 1-Methyl-1H-pyrazole-4,5-dicarboxylate moieties (SVI-COOH 4,5). Compounds 5, [UO2(C13H15N4O2)2(H2O)]·2H2O and 6, [UO2(C11H11N4O2)2(H2O)]·4.5H2O feature 1,3-bis(4-N1-methyl-pyrazolyl)propane-1,3-dione and 1,3-bis(4-N1,3-dimethyl-pyrazolyl)propane-1,3-dione respectively, whereas the heterometallic 7, [UO2(C11H11N4O2)2(CuCl2)(H2O)]·2H2O is formed by using 6 as a metalloligand starting material. Single crystal X-ray diffraction indicates that all coordination to either [UO2]2+ or Th(IV) metal centers is through O-donation as anticipated. Room temperature, solid-state luminescence studies indicate characteristic uranyl emissive behavior for 1 and 2, whereas those for 5 and 6 are weak and poorly resolved.

Aquabis(3,5-dimethyl-1H-pyrazole-κN(oxalato-κ2O,O′copper(II

Directory of Open Access Journals (Sweden)

Andrii I. Buvailo

2008-01-01

Full Text Available In the title compound, [Cu(C2O4(C5H8N22(H2O], the CuII atom is coordinated in a slightly distorted square-pyramidal geometry by two N atoms belonging to the two 3,5-dimethyl-1H-pyrazole ligands, two O atoms of the oxalate anion providing an O,O′-chelating coordination mode, and an O atom of the water molecule occupying the apical position. The crystal packing shows a well defined layer structure. Intra-layer connections are realised through a system of hydrogen bonds while the nature of the inter-layer interactions is completely hydrophobic, including no hydrogen-bonding interactions.

Synthesis, structure characterization and biological studies on a new aromatic hydrazone, 5-(2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono)-2,2-dimethyl-1,3-dioxane-4,6-dione, and its transition metal complexes

Science.gov (United States)

Kumar, Shubha S.; Biju, S.; Sadasivan, V.

2018-03-01

A new aromatic hydrazone 5-(2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono)-2,2-dimethyl-1,3-dioxane-4,6-dione has been synthesized by Japp-Klingemann reaction from diazotized 4-aminoantipyrine and Meldrum's acid. A few 3d-metal ion complexes of this hydrazone were synthesized. The compound and its complexes were characterized by UV-Visible, 1H NMR, ESR, Mass spectral, molar conductance and magnetic susceptibility measurements. The compound was found to exist in hydrazone form in solid state and solution from SXRD and 1H NMR study. The influence of pH on the molecule was studied and found that it shows azo/enol-hydrazone tautomerism in solution. This molecule act as a univalent tridentate ligand and the complexes were assigned to have a 1:2 stoichiometry (M:L). The antioxidant properties of the compounds were explored by DPPH assay and found that the ligand possesses better free radical scavenging effect than the complexes. Antimicrobial activities of these compounds were investigated and were found to be active.

An Efficient Synthesis of Novel Pyrazole-Based Heterocycles as Potential Antitumor Agents

Directory of Open Access Journals (Sweden)

Magda A. Abdallah

2017-08-01

Full Text Available A new series of pyrazolylpyridines was prepared by reaction of ethyl-3-acetyl-1,5-diphenyl-1H-pyrazole-4-carboxylate with the appropriate aldehyde, malononitrile, or ethyl acetoacetate and an excess of ammonium acetate under reflux in acetic acid. Similarly, two novel bipyridine derivatives were prepared by the above reaction using terephthaldehyde in lieu of benzaldehyde derivatives. In addition, a series of 1,2,4-triazolo[4,3-a]pyrimidines was synthesized by a reaction of 6-(pyrazol-3-ylpyrimidine-2-thione with a number of hydrazonoyl chlorides in dioxane and in the presence of triethylamine. The structure of the produced compounds was established by elemental analyses and spectral methods, and the mechanisms of their formation was discussed. Furthermore, the pyrazolyl-pyridine derivatives were tested as anticancer agents and the results obtained showed that some of them revealed high activity against human hepatocellular carcinoma (HEPG2 cell lines.

SOCl2 catalyzed cyclization of chalcones: Synthesis and spectral studies of some bio-potent 1H pyrazoles

Directory of Open Access Journals (Sweden)

K. Ranganathan

2014-05-01

Full Text Available Some aryl-aryl 1H pyrazoles have been synthesised by cyclization of aryl chalcones and hydrazine hydrate in the presence of SOCl2. The yields of the pyrazoles are more than 85%. These pyrazoles are characterized by their physical constants and spectral data. The infrared, NMR spectral group frequencies of these pyrazolines have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses the effects of substituent on the spectral frequencies have been studied. The antimicrobial activities of all synthesised pyrazolines have been studied using Bauer-Kirby method. DOI: http://dx.doi.org/10.4314/bcse.v28i2.11

The effect of business process reengineering (BPR) on human ...

African Journals Online (AJOL)

The effect of business process reengineering (BPR) on human resource management in Addis Ababa City Administration. ... The PDF file you selected should load here if your Web browser has a PDF reader plug-in installed (for example, ...

Application of 1-ethyl-3-(2,5-dihydro-4-(3,5-dimethyl-1H-pyrazol-4-yl) -5-oxo-1H-pyrazol-3-yl)thiourea as sensing material for construction of Tm3+-PVC membrane sensor

International Nuclear Information System (INIS)

Zamani, Hassan Ali; Feizyzadeh, Babak; Faridbod, Farnoush; Ganjali, Mohammad Reza

2011-01-01

A thulium(III) membrane sensor was made using 2% sodium tetraphenyl borate (NaTPB), 65% dibutylphthalate (DBP), 30% poly(vinyl chloride) (PVC) and 3% 1-ethyl-3-(2,5-dihydro-4-(3,5-dimethyl-1H-pyrazol-4-yl) -5-oxo-1H-pyrazol-3-yl)thiourea (ET) as an ionophore. Conductometric study shows selectivity of the Et toward Tm 3+ ions. Nernstian response of 19.6 ± 0.4 mV per decade of thulium concentration was observed, and the electrode worked well in concentration range of 1.0 x 10 -6 to 1.0 x 10 -2 mol L -1 with a lower detection limit (LDL) of 7.2 x 10 -7 mol L -1 , in a pH range of 4.3-10.4. The selectivity of the sensor over alkaline, alkaline earth, transition and heavy metal ions was also found to be in a satisfactory range. To check the analytical applicability of the proposed Tm 3+ sensor, it was successfully used as an indicator electrode in analysis of thulium in certified reference materials. - Research highlights: → This work reports development of polymeric membrane sensor for Tm3+ determination in certified reference materials. → The novelty of this work is based on the high affinity of the ionophore toward the Tm3+ ions which causes the high selectivity of the sensor. → The newly developed sensor is superior to the formerly reported Tm3+ sensors in terms of selectivity and detection limit.

Experimental and theoretical studies of a pyrazole-thiazolidin-2,4-di-one hybrid

Science.gov (United States)

Mushtaque, Md.; Avecilla, Fernando; Haque, Ashanul; Perwez, Ahmad; Khan, Md. Shahzad; Rizvi, M. Moshahid Alam

2017-08-01

The present work describes synthesis, characterization and biological evaluations of a hybrid compound 10 composed of two intriguing scaffolds pyrazole and thiazolidin-2,4-di-one. The title compound was obtained via multi-step reaction and characterized by a number of techniques (viz. IR, UV-Visible, 1H-NMR, 13C-NMR and MS) including X-ray crystallography. The structural and photophysical data of compound 10 were well supported by theoretical calculations performed at density functional (DFT) level. In-vitro anticancer studies on different human cancer cell lines indicated moderate to low activity of the compounds. The molecular target of the compound was predicted through in-silico studies. Finding of the studies are presented herein.

3,5-Bis(4-meth­oxy­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

OpenAIRE

Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S.; Narayana, B.; Yathirajan, H. S.

2011-01-01

In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two methoxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C—H...π stacking interactions and weak π–π interactions [cen...

Novel One-Pot Access to 3,3-bis(3-hydroxy-5-substituted-1H-pyrazol-4-yl) indolin-2-ones

International Nuclear Information System (INIS)

Lin, Y.; Fu, Z.; Song, Q.; Shen, T.

2016-01-01

Sodium bicarbonate was applied as catalyst for the synthesis of 3,3-bis(3-hydroxy-5-substituted-1H-pyrazol-4-yl)indolin-2-ones via the reaction of isatins, hydrazine hydrate and ethyl acetoacetate or ethyl benzoylacetate. This reaction was performed in ethanol at 78 degree C, giving 3,3-bis(3-hydroxy-5-substituted-1H-pyrazol-4-yl)indolin-2-one derivatives in good to excellent yields. The structure of 5-bromo-3,3-bis(3-hydroxy-5-methyl-1H-pyrazol-4-yl) indolin-2-one was unambiguously confirmed by X-ray single crystal structure analysis and a plausible reaction mechanism is also proposed. (author)

Synthesis and in vitro biological evaluation of new pyrazole chalcones and heterocyclic diamides as potential anticancer agents

Directory of Open Access Journals (Sweden)

Sankappa Rai U.

2015-05-01

Full Text Available Synthesis and characterization of new heterocyclic pyrazole chalcones (4a–e and diamide (6a–e derivatives are described. Pyrazole chalcones were synthesized by the reaction of pyrazole aldehydes and suitable aromatic ketones. Diamides were synthesized by the reaction of phthalic acid and amines. Newly synthesized compounds were characterized by spectral studies and their biological activity was assessed in vitro using MCF-7 (human breast adenocarcinoma and HeLa (human cervical tumor cells cell lines. Few of the synthesized molecules inhibited the growth of the human breast cancer cell lines and human cervical tumor cell lines at low micromolar to nanomolar concentrations.

Synthesis and antimicrobial screening of novel 2-(5-(4-(allyloxy-3-methoxyphenyl-1H-pyrazol-3-ylphenols analogues of 2-(4-(allyloxy-3-methoxyphenyl-4H-chromen-4-ones

Directory of Open Access Journals (Sweden)

Asha V. Chate

2012-01-01

Full Text Available A series of novel 2-(5-(4-(allyloxy-3-methoxyphenyl-1H-pyrazol-3-ylphenols derivatives have been synthesized via the ring opening of 2-(4-(allyloxy-3-methoxyphenyl-4H-chromen-4-ones in ethanol and hydrazine hydrate under reflux condition. The synthesized compounds were screened for antibacterial and antifungal activity against bacteria Staphylococcus aureus (MRSA E710 and Escherichia coli (ATCC 25922 and fungi Candida albicans and Aspergillus fumigates respectively. Some of the tested compounds showed significant antimicrobial activity. 1H NMR, IR, Mass spectral data and elemental analysis elucidated the structures of the all newly synthesized compounds.

Unigene BLAST: CBRC-DMEL-02-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-DMEL-02-0034 gnl|UG|Dm#S40593060 DMG1C.3_1.C08.C1 MODENCODE_DM_A Drosophila melanogaster cDNA clone DMG...1-chr3R.5.051.a, mRNA sequence /clone=DMG1-chr3R.5.051.a /gb=EW713099 /gi=156142053 /ug=Dm.27239 /len=1584 8e-12 25% ...

Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

Science.gov (United States)

Obasi, L. N.; Kaior, G. U.; Rhyman, L.; Alswaidan, Ibrahim A.; Fun, Hoong-Kun; Ramasami, P.

2016-09-01

The Schiff base, 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (TPMC/AAP) was synthesized by the condensation of 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and trans-para-methoxycinnamaldehyde (trans-3,4-methoxyphenyl-2-propenal) in dry methanol at 75 °C. The compound was characterized using elemental microanalysis, IR, NMR, UV spectroscopies and single-crystal X-ray crystallography. The X-ray structure determination shows that the Schiff base, (TPMC/AAP) is orthorhombic with the Pbca space group. The anti-microbial screening of the compound was carried out with Escherichia coli, Bacillus subtillis, Staphylococcus aureus, Pseudemonas aeruginosa, Candida albicans and Aspergillus niger using agar well diffusion method. The Schiff base possesses significant antimicrobial activity. The minimum inhibitory concentration (MIC) of the compound was also determined and the activity was compared with that of conventional drugs ciprofloxacin and ketoconazole. The compound (TPMC/AAP) showed varying activity against the cultured bacteria and fungi used. To complement the experimental data, density functional theory (DFT) was used to have deeper understanding into the molecular parameters and infrared spectra of the compound.

Application of 1-ethyl-3-(2,5-dihydro-4-(3,5-dimethyl-1H-pyrazol-4-yl) -5-oxo-1H-pyrazol-3-yl)thiourea as sensing material for construction of Tm{sup 3+}-PVC membrane sensor

Energy Technology Data Exchange (ETDEWEB)

Zamani, Hassan Ali, E-mail: haszamani@yahoo.com [Department of Applied Chemistry, Quchan branch, Islamic Azad University, Quchan (Iran, Islamic Republic of); Feizyzadeh, Babak [Department of Applied Chemistry, Quchan branch, Islamic Azad University, Quchan (Iran, Islamic Republic of); Faridbod, Farnoush; Ganjali, Mohammad Reza [Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehran (Iran, Islamic Republic of)

2011-10-10

A thulium(III) membrane sensor was made using 2% sodium tetraphenyl borate (NaTPB), 65% dibutylphthalate (DBP), 30% poly(vinyl chloride) (PVC) and 3% 1-ethyl-3-(2,5-dihydro-4-(3,5-dimethyl-1H-pyrazol-4-yl) -5-oxo-1H-pyrazol-3-yl)thiourea (ET) as an ionophore. Conductometric study shows selectivity of the Et toward Tm{sup 3+} ions. Nernstian response of 19.6 {+-} 0.4 mV per decade of thulium concentration was observed, and the electrode worked well in concentration range of 1.0 x 10{sup -6} to 1.0 x 10{sup -2} mol L{sup -1} with a lower detection limit (LDL) of 7.2 x 10{sup -7} mol L{sup -1}, in a pH range of 4.3-10.4. The selectivity of the sensor over alkaline, alkaline earth, transition and heavy metal ions was also found to be in a satisfactory range. To check the analytical applicability of the proposed Tm{sup 3+} sensor, it was successfully used as an indicator electrode in analysis of thulium in certified reference materials. - Research highlights: {yields} This work reports development of polymeric membrane sensor for Tm3+ determination in certified reference materials. {yields} The novelty of this work is based on the high affinity of the ionophore toward the Tm3+ ions which causes the high selectivity of the sensor. {yields} The newly developed sensor is superior to the formerly reported Tm3+ sensors in terms of selectivity and detection limit.

Structural optimization and biological evaluation of 1,5-disubstituted pyrazole-3-carboxamines as potent inhibitors of human 5-lipoxygenase

Directory of Open Access Journals (Sweden)

Yu Zhou

2016-01-01

Full Text Available Human 5-lipoxygenase (5-LOX is a well-validated drug target and its inhibitors are potential drugs for treating leukotriene-related disorders. Our previous work on structural optimization of the hit compound 2 from our in-house collection identified two lead compounds, 3a and 3b, exhibiting a potent inhibitory profile against 5-LOX with IC50 values less than 1 µmol/L in cell-based assays. Here, we further optimized these compounds to prepare a class of novel pyrazole derivatives by opening the fused-ring system. Several new compounds exhibited more potent inhibitory activity than the lead compounds against 5-LOX. In particular, compound 4e not only suppressed lipopolysaccharide-induced inflammation in brain inflammatory cells and protected neurons from oxidative toxicity, but also significantly decreased infarct damage in a mouse model of cerebral ischemia. Molecular docking analysis further confirmed the consistency of our theoretical results and experimental data. In conclusion, the excellent in vitro and in vivo inhibitory activities of these compounds against 5-LOX suggested that these novel chemical structures have a promising therapeutic potential to treat leukotriene-related disorders.

Exon: CBRC-PABE-11-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-PABE-11-0034 ATGTATAATGTGTATGTGTGtatatatgtgtatacatatatatacatatatacacacatatatgtatatacatatatacacacaca...tatatgtatatacatatatacatatatacacacacatatatgtatatacatatatacatatatacacacacatatgtatatacatatatacacacaca...tatgtatatacatatatacacacatatgtatatacatatacacatatatgtatatacatatatacacacatatatgtatatacatatatacacacatatatgtatatacatatatacacaca...tatatgtatatacatatatacacacatatatgtatatacatatatacacacatatatgtatatacatatatacacaca...tatatgtatacacacatatatacacacatatatgtatacacacatatatacacacatatatgtatatacacacatatatatacacaca

The impact of ISP, BPR, and customization on ERP performance in manufacturing SMEs of Korea

Directory of Open Access Journals (Sweden)

Jong-Weon Kim

2017-01-01

Full Text Available Purpose - This paper aims to assess how enterprise resource planning (ERP performance of Korean small and medium enterprises in manufacturing differs according to different levels of business process reengineering (BPR, information strategic planning (ISP and ERP customization. Design/methodology/approach - A questionnaire survey was carried out in this research. Responses from 96 small and medium manufacturing companies that have adopted ERP systems were analyzed. Findings - The results of this study suggest that ISP and BPR implementation are positively correlated to ERP performance. Originality/value - While consulting and customization costs have positive impacts on ERP performance, the level of customization does not influence performance. As one of the pioneering studies that investigate the impact of BPR, ISP and ERP customization on small and medium manufacturing companies, this research contributes to both theory and practice.

Tetraethylammonium tris(thiocyanato-κN[tris(1H-pyrazol-1-yl-κN2methane]nickelate(II

Directory of Open Access Journals (Sweden)

Ganna Lyubartseva

2012-07-01

Full Text Available The title salt, (C8H20N[Ni(NCS3(C10H10N6], consists of a tetraethylammonium cation and an anion comprising an octahedral NiII atom surrounded by three N atoms from a tripodal tris(pyrazol-1-ylmethane ligand, and three thiocyanate ligands, each bound at the N-atom end. The ligand Ni—N distances range from 2.097 (2 to 2.127 (2 Å for the tripodal ligand and from 2.045 (2 to 2.075 (2 Å for the thiocyanate ligands. The dihedral angles between the three pyrazole rings are 59.03 (12, 53.09 (10 and 67.90 (10°.

Vapour pressures of 1-methyl derivatives of benzimidazole, pyrazole and indole. The energy of the intermolecular hydrogen bond N-H⋯N

International Nuclear Information System (INIS)

Almeida, Ana R.R.P.; Monte, Manuel J.S.

2014-01-01

Highlights: • Vapour pressures of 1-methyl derivatives of benzimidazole, pyrazole and indole. • Enthalpies, entropies and Gibbs free energies of sublimation/vaporisation were derived. • Temperatures and enthalpies of fusion were determined. • Energy of the intermolecular hydrogen bond N-H⋯N was estimated. - Abstract: The vapour pressures of the liquid phase of 1-methylpyrazole, 1-methylbenzimidazole and 1-methylindole were measured over the temperature ranges (253.9 to 293.3) K, (303.2 to 372.5) K, and (268.6 to 341.9) K, respectively, using a static method. The vapour pressures of the crystalline phase of the two latter compounds were also measured at temperatures between (301.2 to 328.9) K and (267.6 to 275.5) K, respectively. The results obtained enabled the determination of the standard molar enthalpies and entropies of sublimation and of vaporisation at the mean temperatures of the measurements and at T = 298.15 K. The temperatures and molar enthalpies of fusion were determined using differential scanning calorimetry. The enthalpies of the intermolecular hydrogen bonds N-H⋯N in the crystalline phase of benzimidazole and pyrazole were determined and compared with the result previously determined for the energy of the intermolecular hydrogen bond in crystalline imidazole

Synthesis and antimicrobial studies of novel derivatives of 4-(4-formyl-3-phenyl-1H-pyrazol-1-yl)benzoic acid as potent anti-Acinetobacter baumanni agents

Science.gov (United States)

Allison, Devin; Delancey, Evan; Ramey, Hunter; Williams, Conrad; Alsharif, Zakeyah Ali; Al-khattabi, Hessa; Ontko, Allyn; Gilmore, David

2017-01-01

Microbial resistance to antibiotics is a global concern. The World Health Organization (WHO) has identified antimicrobial resistance as one the three greatest threats for human beings in the 21st century. Without urgent and coordinated action, the world is moving toward a post-antibiotic era, in which normal infections or minor injuries may become fatal. In an effort to find new agents, we report the synthesis and antimicrobial activities of 40 novel 1,3-diphenyl pyrazole derivatives. These compounds have shown zones of growth inhibition up to 85 mm against Acinetobacter baumannii. We tested the active compounds against this Gram-negative bacterium in minimum inhibitory concentration (MIC) tests and found activity with concentration as low as 4 μg/mL. PMID:28065568

3-Isobutyl-4-phenylsulfanyl-1H-pyrazol-5-ol

Directory of Open Access Journals (Sweden)

Tara Shahani

2011-02-01

Full Text Available The asymmetric unit of the title compound, C13H16N2OS, contains two independent molecules (A and B. The pyrazole ring [maximum deviations = 0.0049 (17 Å in molecule A and 0.0112 (19 Å in molecule B] makes a dihedral angle of 70.23 (11 and 73.18 (12° with the phenyl ring in molecules A and B, respectively. The isobutyl group in molecule B is disordered over two sets of sites with a ratio of refined occupancies of 0.858 (5:0.142 (5. In the crystal, molecules A and B are linked via a pair of intermolecular N—H...O hydrogen bonds, generating an R22(8 ring motif. These ring motifs are further linked into two-dimensional arrays parallel to the bc plane by intermolecular N—H...O and weak C—H...S hydrogen bonds. The crystal is further stablized by weak π–π interactions [centroid–centroid distances = 3.5698 (13 and 3.5287 (12 Å].

3,5-Bis(4-meth­oxy­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

Science.gov (United States)

Baktır, Zeliha; Akkurt, Mehmet; Samshuddin, S.; Narayana, B.; Yathirajan, H. S.

2011-01-01

In the title compound, C23H22N2O2, the central pyrazole ring is nearly planar (r.m.s. deviation = 0.046 Å) and it makes a dihedral angle of 18.5 (2)° with the phenyl ring. The dihedral angles between the phenyl and the two meth­oxy-substituted phenyl rings are 26.2 (2) and 80.6 (2)°. The crystal structure is stabilized by C—H⋯π stacking inter­actions and weak π–π inter­actions [centriod–centroid distance = 3.891 (2) Å]. PMID:21523013

NCBI nr-aa BLAST: CBRC-OSAT-05-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-OSAT-05-0034 gb|AAM20520.1| serine/threonine protein kinase isolog [Arabidopsi...s thaliana] gb|AAO30076.1| serine/threonine protein kinase isolog [Arabidopsis thaliana] AAM20520.1 1e-156 49% ...

NCBI nr-aa BLAST: CBRC-LAFR-01-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-LAFR-01-0034 ref|ZP_01466199.1| mycarose O-acyltransferase [Stigmatella aurant...iaca DW4/3-1] gb|EAU63042.1| mycarose O-acyltransferase [Stigmatella aurantiaca DW4/3-1] ZP_01466199.1 1.2 35% ...

NCBI nr-aa BLAST: CBRC-XTRO-01-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-XTRO-01-0034 ref|ZP_01187932.1| Major facilitator superfamily MFS_1 [Bacillus weihenstep...hanensis KBAB4] gb|EAR72707.1| Major facilitator superfamily MFS_1 [Bacillus weihenstephanensis KBAB4] ZP_01187932.1 2e-28 29% ...

Succinic acid dihydrazide: a convenient N,N-double block for the synthesis of symmetrical and non-symmetrical succinyl-bis[5-trifluoro(chloro)methyl-1H-pyrazoles

International Nuclear Information System (INIS)

Bonacorso, Helio G.; Cechinel, Cleber A.; Pittaluga, Everton P.; Ferla, Adriana; Porte, Liliane M.F; Martins, Marcos A.P; Zanatta, Nilo

2010-01-01

This paper describes the conventional regioselective synthesis of a series of new succinyl spacer bis-(3,5-substituted 2-pyrazolines and 1H-pyrazoles), namely; 1,4-bis[5-(trifluoromethyl)-5- hydroxy-4,5-dihydro-1H-pyrazol-1-yl]butane-1,4-diones (46-88%) and the respective dehydrated system (60-78%), new 1-[5-(trifluoromethyl)-5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl]-4- oxobutane hydrazides (52-81%) and the non-symmetrical 2-pyrazolines derivatives thereof as 1-[5-(trifluoromethyl)- 5-hydroxy-4,5-dihydro-1H-pyrazol-1-yl)-4-(5-(trichloromethyl)-5-hydroxy- 4,5-dihydro-1H-pyrazol-1-yl]butane-1,4-diones (75-91%). All succinyl substituted bispyrazoles were obtained from the cyclocondensation reactions of 4-substituted 4-alkoxy-1,1,1-trihaloalk-3- en-2-ones, where the 4-substituents are H, Me, Ph, 4-FC 6 H 4 , 4-ClC 6 H 4 , 4-OMeC 6 H 4 , 4-NO 2 C 6 H 4 , 1-naphthyl and 2-furyl, with succinic acid dihydrazide in ethanol as solvent under controlled reaction conditions. (author)

NCBI nr-aa BLAST: CBRC-MDOM-03-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-MDOM-03-0034 ref|ZP_04977425.1| possible competence protein EC [Mannheimia hae...molytica PHL213] gb|EDN73821.1| possible competence protein EC [Mannheimia haemolytica PHL213] ZP_04977425.1 0.63 23% ...

NCBI nr-aa BLAST: CBRC-RMAC-03-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-RMAC-03-0034 ref|NP_997055.1| G protein-coupled receptor for asthma susceptibi... (G-protein coupled receptor for asthma susceptibility) (G-protein coupled receptor PGR14) gb|AAQ76966.1| GP

NCBI nr-aa BLAST: CBRC-RNOR-17-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-RNOR-17-0034 ref|NP_350021.1| Membrane export protein, related to SecD/SecF protein exporters...ted to SecD/SecF protein exporters [Clostridium acetobutylicum ATCC 824] NP_350021.1 1.4 39% ...

Effective electroluminescent materials for OLED applications based on lanthanide 1.3-diketonates bearing pyrazole moiety

Energy Technology Data Exchange (ETDEWEB)

Taydakov, Ilya V. [D. Mendeleyev University of Chemical Technology of Russia, Miusskaya pl. 9, 125047 Moscow (Russian Federation); P. N. Lebedev Institute of Physics of RAS, Leninskiy pr-t, 53, 119991 Moscow (Russian Federation); Akkuzina, Alina A.; Avetisov, Roman I.; Khomyakov, Andrew V.; Saifutyarov, Rasim R. [D. Mendeleyev University of Chemical Technology of Russia, Miusskaya pl. 9, 125047 Moscow (Russian Federation); Avetissov, Igor Ch., E-mail: igor_avetisov@mail.ru [D. Mendeleyev University of Chemical Technology of Russia, Miusskaya pl. 9, 125047 Moscow (Russian Federation)

2016-09-15

A series of new pyrazole substituted 1.3-diketones bearing fluorinated alkyl groups were prepared and systematically explored as a ligands for the preparation of luminescent complexes with Eu(III) ion. First triplet levels energy values (T1) of above mentioned ligands were determined by low temperature (77K) phosphorescent spectra measurements of Gd(III) complexes. It was found that 4,4,5,5,6,6,6-heptafluoro-1-(1-methyl-1H-pyrazol-4-yl)hexane-1,3-dione is a superior ligand for synthesis of highly luminescent Eu (III) complexes with 1.10-phenanthroline or similar Lewis bases as auxiliary ligands. The complexes are sufficiently thermal stable, transparent, volatile in high vacuum and soluble in common solvents which make possible to produce OLEDs by dry and wet technology. OLED structures fabricated on the base of the above Eu(III) complexes demonstrated the higher energy efficacy comparing to the standard Eu(TTA){sub 3}(Phen) phosphor.

Magnetocaloric effects in Mn1.35Fe0.65P1−xSix compounds

International Nuclear Information System (INIS)

Geng Yao-Xiang; Tegus O; Bi Li-Ge

2012-01-01

The structural and magnetocaloric properties of Mn 1.35 Fe 0.65 P 1−x Si x compounds are investigated. The Si-substituted compounds, Mn 1.35 Fe 0.65 P 1−x Si x with x = 0.52, 0.54, 0.55, 0.56, and 0.57, are prepared by high-energy ball milling and the solid-state reaction. The X-ray diffraction shows that the compounds crystallize into the Fe 2 P-type hexagonal structure with space group P6-bar2m. The magnetic measurements show that the Curie temperature of the compound increases from 253 K for x = 0.52 to 296 K for x = 0.56. The isothermal magnetic-entropy change of the Mn 1.35 Fe 0.65 P 1−x Si x compound decreases with the Si content increasing. The maximal value of the magnetic-entropy change is about 7.0 J/kg·K in the Mn 1.35 Fe 0.65 P 0.48 Si 0.52 compound with a field change of 1.5 T. The compound quenched in water possesses a larger magnetic entropy change and a smaller thermal hysteresis than the non-quenched samples. The thermal hysteresis of the compound is less than 3.5 K. The maximum adiabatic temperature change is about 1.4 K in the Mn 1.35 Fe 0.65 P 0.45 Si 0.55 compound with a field change of 1.48 T. (condensed matter: electronic structure, electrical, magnetic, and optical properties)

Crystal structure of 3-{5-[3-(4-fluorophenyl-1-isopropyl-1H-indol-2-yl]-1H-pyrazol-1-yl}indolin-2-one ethanol monosolvate

Directory of Open Access Journals (Sweden)

Md. Lutfor Rahman

2016-03-01

Full Text Available The title indolin-2-one compound, C28H23FN4O·C2H6O, crystallizes as a 1:1 ethanol solvate. The ethanol molecule is disordered over two positions with refined site occupancies of 0.560 (14 and 0.440 (14. The pyrazole ring makes dihedral angles of 84.16 (10 and 85.33 (9° with the indolin-2-one and indole rings, respectively, whereas the dihedral angle between indolin-2-one and indole rings is 57.30 (7°. In the crystal, the components are linked by N—H...O and O—H...O hydrogen bonds, forming an inversion molecule–solvate 2:2 dimer with R44(12 ring motifs. The crystal structure is consolidated by π–π interaction between pairs of inversion-related indolin-2-one rings [interplanar spacing = 3.599 (2 Å].

Combinatorial Libraries on Rigid Scaffolds: Solid Phase Synthesis of Variably Substituted Pyrazoles and Isoxazoles

Directory of Open Access Journals (Sweden)

Eduard R. Felder

1997-01-01

Full Text Available The synthesis of combinatorial compound libraries has become a powerful lead finding tool in modern drug discovery. The ability to synthesize rapidly, in high yield, new chemical entities with low molecular weight on a solid support has a recognized strategic relevance (“small molecule libraries”. We designed and validated a novel solid phase synthesis scheme, suitable to generate diversity on small heterocycles of the pyrazole and isoxazole type. Appropriate conditions were worked out for each reaction, and a variety of more or less reactive agents (building blocks was utilized for discrete conversions, in order to exploit the system’s breadth of applicability. Four sequential reaction steps were validated, including the loading of the support with an acetyl bearing moiety, a Claisen condensation, an a-alkylation and a cyclization of a b-diketone with monosubstituted hydrazines. In a second stage, the reaction sequence was applied in a split and mix approach, in order to prepare a combinatorial library built-up from 4 acetyl carboxylic acids (R1, 35 carboxylic esters (R2 and 41 hydrazines (R4 (and 1 hydroxylamine to yield a total of 11,760 compounds divided into 41 pyrazole sublibraries with 140 pairs of regioisomers and 1 isoxazole sublibrary of equal size.

Synthesis, characterization and anticancer studies of new steroidal oxadiazole, pyrrole and pyrazole derivatives

Directory of Open Access Journals (Sweden)

Shamsuzzaman

2015-07-01

Full Text Available In the present study steroidal derivatives, 3β-[5′-mercapto-1′,3′,4′-oxadiazole-2-yl]methoxy cholest-5-ene 2, 3β-[2′,5′-dimethylpyrrole-1-yl]aminocarbonylmethoxycholest-5-ene 3 and 3β-[3′,5′-dimethyl pyrazole-1-yl]carbonylmethoxycholest-5-ene 4 have been synthesized from cholest-5-en-3β-O-acetyl hydrazide 1 using CS2/KOH, acetonyl acetone and acetyl acetone, respectively as reagents and are characterized by IR, 1H NMR,13C NMR, MS and elemental analysis. Compounds 2–4 were also evaluated for anticancer activity against human leukemia cell line (HL-60 by MTT assay and compound 4 displayed the promising behavior by showing better anticancer activity.

Corrosion inhibition properties of pyrazolylindolenine compounds on copper surface in acidic media

Directory of Open Access Journals (Sweden)

Ebadi Mehdi

2012-12-01

Full Text Available Abstract Background The corrosion inhibition performance of pyrazolylindolenine compounds, namely 4-(3,3-dimethyl-3H-indol-2-yl-pyrazole-1-carbothioamide (InPzTAm, 4-(3,3-dimethyl-3H-indol-2-yl-1H-pyrazole-1-carbothiohydrazide (InPzTH and 3,3-dimethyl-2-(1-phenyl-1H-pyrazol-4-yl-3H-indole (InPzPh, on copper in 1M HCl solution is investigated by electrochemical impedance spectroscopy (EIS, open circuit potential (OCP and linear scan voltammetry (LSV techniques. Results The results show that the corrosion rate of copper is diminished by the compounds with the inhibition strength in the order of: InPzTAm> InPzTH > InPzPh. The corrosion inhibition efficiencies for the three inhibitors are 94.0, 91.4 and 79.3, for InPzTAm, InPzTH and InPzPh respectively with the same inhibitor concentration (2 mM. Conclusion From the EIS, OCP and LSV results it was concluded that pyrazolylindolenine compounds with S-atom (with an amine group have illustrated better corrosion inhibition performance compared to hydrazine and phenyl group.

NCBI nr-aa BLAST: CBRC-DRER-16-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-DRER-16-0034 ref|NP_956704.1| solute carrier family 16 (monocarboxylic acid transporters...), member 9a [Danio rerio] gb|AAH54615.1| Solute carrier family 16 (monocarboxylic acid transporters), member 9a [Danio rerio] NP_956704.1 3e-83 51% ...

Synthesis of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives and evaluation of their anticancer activity

Directory of Open Access Journals (Sweden)

Nitin Kumar

2017-05-01

Full Text Available A novel series of 3-(4, 5-dihydro-1-phenyl-5-substituted phenyl-1H-pyrazol-3-yl-2H-chromen-2-one derivatives were synthesized. In the first step salicylaldehyde was reacted with ethylacetoacetate at room temperature by stirring which gives compound (I. Compound (I when refluxed with substituted benzaldehyde and diethylamine in the presence of n-butanol for 4–5 h gives substituted derivatives (IIa–d. Compounds synthesized in step 2 when refluxed with phenyl hydrazine in the presence of pyridine for 6–7 h gives the title compounds (IIIa–d. All the synthesized compounds were sent to NCI for anticancer activity. Synthesized compounds were tested for anticancer activity against 60 different cell lines. From the data thus obtained it was observed that simple coumarin ring derivatives were more effective in inhibiting the growth of cancerous cell lines, than coumarin-pyrazoline derivatives. Among all the synthesized compounds, irrespective of compounds having simple coumarin ring and coumarin-pyrazoline combination, compounds IIa–c, IIIb and IIId were potent anticancer agents. Compounds were active for the single dose therapeutic program at the dose of 1.00E-5 molar concentration. The main anti cancer activity is assumed to be due to the presence of the lactone structure in coumarin moiety.

Synthesis, optical properties and application of a set of novel pyrazole nopinone derivatives

Science.gov (United States)

Yang, Jinlai; Xu, Xu; Rui, Jian; Wang, Zhonglong; Zhang, Yan; Wang, Shifa; Wu, Liangru

2017-08-01

Pyrazole derivatives (4-6) were directly synthesized from β-pinene derivative nopinone, and they were characterized by Fourier transform infrared (FTIR) spectoscope, nuclear magnetic resonance (NMR), and mass spectrometry. Their optical properties were investigated by ultraviolet-visible spectroscopy and fluorescence spectroscopy. The three compounds emitted strong blue fluorescence in ethanol. Using a fluorescence quenching method, compound 4 could be used to detect the content (100.57%) of copper sulfate pentahydrate (≥ 99%) with a RSD of 1.98%, y = - 0.1127 × + 2.7148, R2 = 0.9703 (Cu2 +: 0.5-8.0 × 10- 5 mol/L), and compounds 4-6 also had utility of calculating the content of anhydrous ferric chloride at a wide range of concentration. Thus, compounds 4-6 are new functional fluorescents for detecting the content of some purchased products.

Optimization of a pyrazole hit from FBDD into a novel series of indazoles as ketohexokinase inhibitors

Energy Technology Data Exchange (ETDEWEB)

Zhang, Xuqing; Song, Fengbing; Kuo, Gee-Hong; Xiang, Amy; Gibbs, Alan C.; Abad, Marta C.; Sun, Weimei; Kuo, Lawrence C.; Sui, Zhihua (J); (J-PRD)

2013-11-20

A series of indazoles have been discovered as KHK inhibitors from a pyrazole hit identified through fragment-based drug discovery (FBDD). The optimization process guided by both X-ray crystallography and solution activity resulted in lead-like compounds with good pharmaceutical properties.

Crystal Structure of N,N-bis-(3-Carbomethoxy-5-methyl-pyrazol-1-ylmethylaniline

Directory of Open Access Journals (Sweden)

Taibi Ben-Hadda

2002-09-01

Full Text Available The tripodal ligand N,N-bis-(3-carbomethoxy-5-methylpyrazol-1-ylmethyl aniline (2 has been prepared by the condensation of aniline with two equivalents of N-hydroxymethyl[3-carbomethoxy-5-methyl]pyrazole. The molecule consists of two structurally analogous 3-carbomethoxy-5-methylpyrazol-1-ylmethyl moieties, which adopt a transoidal conformation via a central aniline ring, suggesting that this tripodal ligand is highly flexible and could accommodate many metals by coordination.

Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure-ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine.

Science.gov (United States)

Chagarovskiy, Alexey O; Budynina, Ekaterina M; Ivanova, Olga A; Rybakov, Victor B; Trushkov, Igor V; Melnikov, Mikhail Ya

2016-03-14

A convenient general approach to 2-(pyrazol-4-yl)- and 2-(isoxazol-4-yl)ethanols based on the Brønsted acid-initiated reaction of 3-acyl-4,5-dihydrofurans with hydrazines or hydroxylamine was developed. Further transformation of the alcohol moiety in 2-(pyrazolyl)ethanols affording 2-(pyrazolyl)ethylamine as potent bioactive compounds as well as pyrazole-substituted derivatives of antitumor alkaloid crispine A was elaborated.

Bis[1-methoxy-2,2,2-tris(pyrazol-1-yl-κN2ethane]nickel(II bis(trifluoromethanesulfonate dihydrate

Directory of Open Access Journals (Sweden)

Ganna Lyubartseva

2013-10-01

Full Text Available In the title salt, [Ni(C12H14N6O2](CF3SO32·2H2O, the NiII cation is located on an inversion centre and is coordinated by six N atoms from two tridentate 1-methoxy-2,2,2-tris(pyrazol-1-ylethane ligands in a distorted octahedral geometry. The Ni—N distances range from 2.0594 (12 to 2.0664 (12 Å, intra-ligand N—Ni—N angles range from 84.59 (5 to 86.06 (5°, and adjacent inter-ligand N—Ni—N angles range between 93.94 (5 and 95.41 (5°. In the crystal, inversion-related pyrazole rings are π–π stacked, with an interplanar spacing of 3.4494 (18 Å, forming chains that propagate parallel to the a-axis direction. Intermolecular O—H...O hydrogen bonds are present between water molecules and trifluoromethanesulfonate anions.

EU Regulation of Nanobiocides: Challenges in Implementing the Biocidal Product Regulation (BPR)

DEFF Research Database (Denmark)

Brinch, Anna; Hansen, Steffen Foss; Hartmann, Nanna B.

2016-01-01

The Biocidal Products Regulation (BPR) contains several provisions for nanomaterials (NMs) and is the first regulation in the European Union to require specific testing and risk assessment for the NM form of a biocidal substance as a part of the information requirements. Ecotoxicological data...

DFT, FT-IR, FT-Raman and NMR studies of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles

Science.gov (United States)

Kınalı, Selin; Demirci, Serkan; Çalışır, Zühre; Kurt, Mustafa; Ataç, Ahmet

2011-05-01

We present a detailed analysis of the structural and vibrational spectra of some novel azo dyes. 2-(Substituted phenylazo)malononitriles were synthesized by the coupling reaction of the diazonium salts, which were prepared with the use of various aniline derivatives with malononitrile, and then 4-(substituted phenylazo)-3,5-diamino-1H-pyrazole azo dyes were obtained via the ring closure of the azo compounds with hydrazine monohydrate. The experimental and theoretical vibrational spectra of azo dyes were studied. The structural and spectroscopic analysis of the molecules were carried out by using Becke's three-parameters hybrid functional (B3LYP) and density functional harmonic calculations. The 1H nuclear magnetic resonance (NMR) chemical shifts of the azo dye molecules were calculated using the gauge-invariant-atomic orbital (GIAO) method. The calculated vibrational wavenumbers and chemical shifts were compared with the experimental data of the molecules.

Synthesis of fatty trichloromethyl-β-diketones and new 1H-Pyrazoles as unusual FAMEs and FAEEs

International Nuclear Information System (INIS)

Flores, Alex F.C.; Souto, Alynne A.; Malavolta, Juliana L.; Flores, Darlene C.; Blanco, Rogerio F.

2013-01-01

The efficient synthesis of new fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl 3 CC(O)C(R 2 )=C(R 1 )OMe, where R 1 = n-hexyl, heptyl, nonyl, undecyl, tridecyl and R 2 = H] and 1,1,1-trichloro-2,4-alkanediones [Cl 3 CC(O)CHR 2 C(O)R 1 , where R 1 = n-pentyl and R 2 = Me, R 1 = Et and R 2 = n-butyl, R 1 = n-butyl and R 2 = n-propyl] in good yields (85-95%) from acetal acylation with trichloroacetyl chloride is reported. The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1,1,1-trichloro-2,4-alkanediones were reacted with hydrazine hydrochloride, leading to respective 1 H-pyrazole-5-carboxylates, unusual class of fatty acid methyl (FAMEs) and ethyl (FAEEs) esters. Their structures were confirmed by elemental analysis and 1 H and 13 C nuclear magnetic resonance (NMR). The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1 H-pyrazole derivatives are new oleochemicals with potentially interesting and differential properties. (author)

A second monoclinic polymorph of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-hy­droxy­imino-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide

Science.gov (United States)

Plutenko, Maxym O.; Lampeka, Rostislav D.; Haukka, Matti; Nordlander, Ebbe

2013-01-01

The title compound, C14H16N6O2, is a second monoclinic polymorph of 2-[1-(3,5-dimeth­yl)pyrazol­yl]-2-hy­droxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene] acetohydrazide, with two crystallographically independent mol­ecules per asymmetric unit. The non-planar mol­ecules are chemically equal having similar geometric parameters. The previously reported polymorph [Plutenko et al. (2012 ▶). Acta Cryst. E68, o3281] was described in space group Cc (Z = 4). The oxime group and the O atom of the amide group are anti with respect to the C—C bond. In the crystal, mol­ecules are connected by N—H⋯N hydrogen bonds into zigzag chains extending along the b axis. PMID:23723911

Inorganic pigments doped with tris(pyrazol-1-yl)borate lanthanide complexes: A photoluminescence study

Energy Technology Data Exchange (ETDEWEB)

Gheno, Giulia, E-mail: giulia.gheno@unive.it [Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari di Venezia, Dorsoduro 2137, 30123 Venezia (Italy); Bortoluzzi, Marco; Ganzerla, Renzo [Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari di Venezia, Dorsoduro 2137, 30123 Venezia (Italy); Enrichi, Francesco [CIVEN, Coordinamento Interuniversitario Veneto per le Nanotecnologie, Via delle Industrie 5, 30175 Marghera, Venezia (Italy)

2014-01-15

The inorganic pigments malachite, Egyptian blue, Ercolano blue and chrome yellow have been doped with the neutral homoleptic Ln(III) complex Ln(Tp){sub 3} (Ln=Eu, Tb; Tp=hydrotris(pyrazol-1-yl)borate) in the presence of arabic gum or acrylic emulsion as binders, in order to obtain photoluminescent materials of interest for cultural heritage restoration. The doped pigments have shown emissions associated to f–f transitions in the visible range upon excitation with UV light. Thermal and UV-light ageings have been carried out. In all the cases the photoluminescent behaviour is maintained, but in the cases of acrylic-based paints emission spectra and lifetimes are strongly influenced by thermal treatments. The choice of binder and pigments influences the photoluminescent behaviour of the corresponding film paints. -- Highlights: • Inorganic pigments doped with photoluminescent lanthanide complexes. • Hydrotris(pyrazol-1-yl)borate (Tp) as antenna-ligand for Eu(III) and Tb(III). • Emission associated to f–f transitions upon excitation with UV light. • Photoluminescence of paints influenced by the choice of binder and pigments. • Photoluminescence after ageing depending upon the type of binder.

NCBI nr-aa BLAST: CBRC-MDOM-03-0034 [SEVENS

Lifescience Database Archive (English)

Full Text Available CBRC-MDOM-03-0034 ref|ZP_05988476.1| putative competence protein EC [Mannheimia hae...molytica serotype A2 str. BOVINE] ref|ZP_05990926.1| putative competence protein EC [Mannheimia haemolytica ...serotype A2 str. OVINE] gb|EEY11140.1| putative competence protein EC [Mannheimia haemolytica serotype A2 st...r. OVINE] gb|EEY13570.1| putative competence protein EC [Mannheimia haemolytica serotype A2 str. BOVINE] ZP_05988476.1 0.63 23% ...

Optimization of a pyrazole hit from FBDD into a novel series of indazoles as ketohexokinase inhibitors.

Science.gov (United States)

Zhang, Xuqing; Song, Fengbing; Kuo, Gee-Hong; Xiang, Amy; Gibbs, Alan C; Abad, Marta C; Sun, Weimei; Kuo, Lawrence C; Sui, Zhihua

2011-08-15

A series of indazoles have been discovered as KHK inhibitors from a pyrazole hit identified through fragment-based drug discovery (FBDD). The optimization process guided by both X-ray crystallography and solution activity resulted in lead-like compounds with good pharmaceutical properties. Copyright © 2011 Elsevier Ltd. All rights reserved.

Synthesis of fatty trichloromethyl-{beta}-diketones and new 1H-Pyrazoles as unusual FAMEs and FAEEs

Energy Technology Data Exchange (ETDEWEB)

Flores, Alex F.C.; Souto, Alynne A.; Malavolta, Juliana L.; Flores, Darlene C., E-mail: alex.fcf@ufsm.br [Universidade Federal de Santa Maria (UFSM), RS (Brazil). Departamento de Quimica; Blanco, Rogerio F. [Uniao de Ensino do Sudoeste do Parana (UNISEP), Dois Vizinhos, PR (Brazil). Faculdade de Farmacia

2013-12-01

The efficient synthesis of new fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones [Cl{sub 3}CC(O)C(R{sup 2})=C(R{sup 1})OMe, where R{sup 1} = n-hexyl, heptyl, nonyl, undecyl, tridecyl and R{sup 2} = H] and 1,1,1-trichloro-2,4-alkanediones [Cl{sub 3}CC(O)CHR{sup 2}C(O)R{sup 1}, where R{sup 1} = n-pentyl and R{sup 2} = Me, R{sup 1} = Et and R{sup 2} = n-butyl, R{sup 1} = n-butyl and R{sup 2} = n-propyl] in good yields (85-95%) from acetal acylation with trichloroacetyl chloride is reported. The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and 1,1,1-trichloro-2,4-alkanediones were reacted with hydrazine hydrochloride, leading to respective {sup 1}H-pyrazole-5-carboxylates, unusual class of fatty acid methyl (FAMEs) and ethyl (FAEEs) esters. Their structures were confirmed by elemental analysis and {sup 1}H and {sup 13}C nuclear magnetic resonance (NMR). The fatty 1,1,1-trichloro-4-methoxy-3-alken-2-ones and {sup 1}H-pyrazole derivatives are new oleochemicals with potentially interesting and differential properties. (author)

Nanofibrous matrixes with biologically active hydroxybenzophenazine pyrazolone compound for cancer theranostics

International Nuclear Information System (INIS)

Kandhasamy, Subramani; Ramanathan, Giriprasath; Muthukumar, Thangavelu; Thyagarajan, SitaLakshmi; Umamaheshwari, Narayanan; Santhanakrishnan, V P; Sivagnanam, Uma Tiruchirapalli; Perumal, Paramasivan Thirumalai

2017-01-01

The nanomaterial with the novel biologically active compounds has been actively investigated for application in cancer research. Substantial use of nanofibrous scaffold for cancer research with potentially bioactive compounds through electrospinning has not been fully explored. Here, we describe the series of fabrication of nanofibrous scaffold loaded with novel potential biologically active hydroxybenzo[a]phenazine pyrazol-5(4H)-one derivatives were designed, synthesized by a simple one-pot, two step four component condensation based on Michael type addition reaction of lawsone, benzene-1,2-diamine, aromatic aldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one as the substrates. The heterogeneous solid state catalyst (Fe (III) Y-Zeolite) could effectively catalyze the reaction to obtain the product with high yield and short reaction time. The synthesized compounds (5a–5p) were analyzed by NMR, FTIR and HRMS analysis. Compound 5c was confirmed by single crystal XRD studies. All the compounds were biologically evaluated for their potential inhibitory effect on anticancer (MCF-7, Hep-2) and microbial (MRSA, MTCC 201 and FRCA) activities. Among the compounds 5i exhibited the highest levels of inhibitory activity against both MCF-7, Hep-2 cell lines. Furthermore, the compound 5i (BPP) was evaluated for DNA fragmentation, flow cytometry studies and cytotoxicity against MCF-7, Hep-2 and NIH 3T3 fibroblast cell lines. In addition, molecular docking (PDB ID: (1T46)) studies were performed to predict the binding affinity of ligand with receptor. Moreover, the synthesized BPP compound was loaded in to the PHB-PCL nanofibrous scaffold to check the cytotoxicity against the MCF-7, Hep-2 and NIH 3T3 fibroblast cell lines. The in vitro apoptotic potential of the PHB-PCL-BPP nanofibrous scaffold was assessed against MCF-7, Hep-2 cancerous cells and fibroblast cells at 12, 24 and 48 h respectively. The nanofibrous scaffold with BPP can induce apoptosis and also suppress the

Nanofibrous matrixes with biologically active hydroxybenzophenazine pyrazolone compound for cancer theranostics

Energy Technology Data Exchange (ETDEWEB)

Kandhasamy, Subramani [Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai 600020, Tamilnadu (India); Ramanathan, Giriprasath [Bioproducts Lab, CSIR-Central Leather Research Institute, Chennai 600020, Tamilnadu (India); Muthukumar, Thangavelu [Department of Clinical and Experimental Medicine (IKE), Division of Neuro and Inflammation Sciences (NIV), Linkoping University (Sweden); Thyagarajan, SitaLakshmi [Bioproducts Lab, CSIR-Central Leather Research Institute, Chennai 600020, Tamilnadu (India); Umamaheshwari, Narayanan [Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai 600020, Tamilnadu (India); Santhanakrishnan, V P [Department of Plant Biotechnology, TNAU, Coimbatore, Tamilnadu (India); Sivagnanam, Uma Tiruchirapalli, E-mail: suma67@gmail.com [Bioproducts Lab, CSIR-Central Leather Research Institute, Chennai 600020, Tamilnadu (India); Perumal, Paramasivan Thirumalai, E-mail: ptperumal@gmail.com [Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai 600020, Tamilnadu (India)

2017-05-01

The nanomaterial with the novel biologically active compounds has been actively investigated for application in cancer research. Substantial use of nanofibrous scaffold for cancer research with potentially bioactive compounds through electrospinning has not been fully explored. Here, we describe the series of fabrication of nanofibrous scaffold loaded with novel potential biologically active hydroxybenzo[a]phenazine pyrazol-5(4H)-one derivatives were designed, synthesized by a simple one-pot, two step four component condensation based on Michael type addition reaction of lawsone, benzene-1,2-diamine, aromatic aldehydes and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one as the substrates. The heterogeneous solid state catalyst (Fe (III) Y-Zeolite) could effectively catalyze the reaction to obtain the product with high yield and short reaction time. The synthesized compounds (5a–5p) were analyzed by NMR, FTIR and HRMS analysis. Compound 5c was confirmed by single crystal XRD studies. All the compounds were biologically evaluated for their potential inhibitory effect on anticancer (MCF-7, Hep-2) and microbial (MRSA, MTCC 201 and FRCA) activities. Among the compounds 5i exhibited the highest levels of inhibitory activity against both MCF-7, Hep-2 cell lines. Furthermore, the compound 5i (BPP) was evaluated for DNA fragmentation, flow cytometry studies and cytotoxicity against MCF-7, Hep-2 and NIH 3T3 fibroblast cell lines. In addition, molecular docking (PDB ID: (1T46)) studies were performed to predict the binding affinity of ligand with receptor. Moreover, the synthesized BPP compound was loaded in to the PHB-PCL nanofibrous scaffold to check the cytotoxicity against the MCF-7, Hep-2 and NIH 3T3 fibroblast cell lines. The in vitro apoptotic potential of the PHB-PCL-BPP nanofibrous scaffold was assessed against MCF-7, Hep-2 cancerous cells and fibroblast cells at 12, 24 and 48 h respectively. The nanofibrous scaffold with BPP can induce apoptosis and also suppress the

Regioselective Synthesis of Some Pyrazole Scaffolds Attached to Benzothiazole and Benzimidazole Moieties

Directory of Open Access Journals (Sweden)

Nabila A. Kheder

2014-01-01

Full Text Available Condensation of 2-(benzothiazol-2-ylacetonitrile (1 or 2-(1-methyl-1H-benzimidazol-2-ylacetonitrile (2 with thiophene-2-carbaldehyde afforded the corresponding acrylonitrile derivatives 3 or 4, respectively. The 1,3-dipolar cycloaddition reaction of the acrylonitrile 3 or 4 with nitrile-imine 6 gave novel pyrazole derivatives pendant to benzothiazole and benzimidazole. The pyrazoline derivative 7 was converted into the corresponding pyrazole derivative 11 via thermal elimination of hydrogen cyanide upon heating in sodium ethoxide solution. The structures of the synthesized products were confirmed by IR, 1H NMR, and mass spectral techniques.

PENGARUH DISIPLIN KERJA, KOMPETENSI DAN KEPUASAN KERJA SUMBER DAYA MANUSIA TERHADAP PRODUKTIVITAS KERJA KARYAWAN PADA PT. BPR PATARU LABA CABANG BULUKUMBA

Directory of Open Access Journals (Sweden)

JUMARNI _

2017-05-01

This research aims to find out and analyze the influence of the working Discipline, competence and job satisfaction to productivity of human resources Employee At PT BPR Pataru Laba Cabang Bulukumba.The population was used as the target of this research is the parties associated with the Discipline of work, competence and job satisfaction to productivity of human resources Employee At PT BPR Pataru Laba Cabang Bulukumba, and entirely become respondents by using Multiple linear regression analysis models.The results of this research indicate that all the variables, namely: work discipline, competence and job satisfaction has a positive and significant effect simultaneously against work productivity of employees At PT BPR Pataru Laba Cabang Bulukumba. Are partially found that discipline work that has significant influence are the most dominant against employee productivity.

Magnetic properties and magnetocaloric effects in Mn1.2Fe0.8P1-xGex compounds

International Nuclear Information System (INIS)

Ou, Z Q; Wang, G F; Lin Song; Tegus, O; Brueck, E; Buschow, K H J

2006-01-01

We have studied the magnetic properties and magnetocaloric effects in the Mn 1.2 Fe 0.8 P 1-x Ge x compounds with x = 0.2, 0.22, 0.3, 0.4 and 0.5. X-ray diffraction patterns show that the Mn 1.2 Fe 0.8 P 1-x Ge x compounds crystallize in the hexagonal Fe 2 P-type crystal structure. The magnetic moments of the Mn 1.2 Fe 0.8 P 1-x Ge x compounds measured at 5 K and 5 T increase with increasing Ge content. The Curie temperature increases strongly and the magnetic entropy change has a maximum around 233 K for the compound with x = 0.22, which is about 19 and 31 J kg -1 K -1 for a field change of 2 and 5 T, respectively

Pyrazole carboxamides and carboxylic acids as protein kinase inhibitors in aberrant eukaryotic signal transduction

DEFF Research Database (Denmark)

Persson, Tobias; Yde, Christina W.; Rasmussen, Jakob Ewald

2007-01-01

Densely functionalised pyrazole carboxamides and carboxylic acids were synthesised in an expedient manner through saponification and transamidation, respectively, of ester-functionalised pyrazoles. This synthetic protocol allowed for three diversifying steps in which appendages on the pyrazole...

Synthesis of novel N1-substituted bicyclic pyrazole amino acids and evaluation of their interaction with glutamate receptors

DEFF Research Database (Denmark)

Conti, Paola; Grazioso, Giovanni; di Ventimiglia, Samuele Joppolo

2005-01-01

N1-substituted bicyclic pyrazole amino acids (S)-9a-9c and (R)-9a-9c, which are conformationally constrained analogues of glutamic acid, were prepared via a strategy based on a 1,3-dipolar cycloaddition. The new amino acids were tested for activity at ionotropic and metabotropic glutamate receptors...

Crystal structure of ethyl (2Z-2-cyano-3-[(3-methyl-1-phenyl-1H-pyrazol-5-ylamino]prop-2-enoate

Directory of Open Access Journals (Sweden)

Joel T. Mague

2014-11-01

Full Text Available The title compound, C16H16N4O2, crystallizes with two molecules in the asymmetric unit, one of which shows disorder of the acetate group over two sets of sites in a 0.799 (2:0.201 (2 ratio. The phenyl group has a similar but opposite sense of twist relative to the pyrazole ring in the two molecules, as indicated by the syn N—N—Car—Car (ar = aromatic torsion angles of 39.7 (2 and −36.9 (2°. Each molecule features an intramolecular N—H...O hydrogen bond, which closes an S(6 ring. In the crystal, C—H...O and C—H...N interactions direct the packing into a layered structure parallel to (110.

The Malaysian microfinance system and a comparison with the Grameen Bank (Bangladesh and Bank Perkreditan Rakyat (BPR-Indonesia

Directory of Open Access Journals (Sweden)

Suraya Hanim Mokhtar

2013-06-01

Full Text Available Microfinance programme in Malaysia has been implemented since 1987 as one of the poverty eradication strategies in the country. There are three large microfinance institutions in Malaysia namely AIM, YUM and TEKUN that targeted to different groups of people. Each of the microfinance institution has its own lending systems and has been subsidised by the government since their existence. This paper compares the Malaysian subsidised microfinance institutions’ lending systems with the unsubsidised microfinance institutions such as the Grameen Bank in Bangladesh and People’s Bank (Bank Perkreditan Rakyat/BPR in Indonesia. This study found the Grameen Bank and BPR have more variety of microfinance services and flexible lending systems compared with Malaysian microfinance institutions.

Synthesis, Structure and Electrochemistry of Tetranuclear Oxygen-Centered Copper(II) Clusters with Acetylacetone and Benz-pyrazole Hydrolyzed Derivatives as Ligand.

Science.gov (United States)

Vafazadeh, Rasoul; Willis, Anthony C

2016-01-01

Two copper(II) clusters Cu(4)OCl(6)(pyrazole)4, 1, and Cu(4)OBr(6)(Br-pyrazole)4, 2, have been synthesized by reacting acetylacetone and benzohydrazide (1:1 ratio) with CuX(2) (X = Cl for 1 and X= Br for 2) in methanol solutions. The structures of both clusters have been established by X-ray crystallography. The clusters contain four Cu, one O, six μ(2)-X atoms, and four pyrazole ligands. The pyrazoles was prepared in situ by the reaction of acetylacetone with benzohydrazide in methanol under reflux. In 2, the methine hydrogens of the pyrazole ligands have been replaced by bromine atoms. The four copper atoms encapsulate the central O atom in a tetrahedral arrangement. All copper atoms are five-coordinate and have similar coordination environments with slightly distorted trigonal bipyramidal geometry. The cyclic voltammogram of the clusters 1 and 2 show a one-electron quasi-reversible reduction wave in the region 0.485 to 0.731 V, and a one-electron quasi-reversible oxidation wave in the region 0.767 to 0.898 V. In 1, one irreversible oxidative response is observed on the positive of side of the voltammogram at 1.512 V and this can be assigned to Cu(II) to Cu(III) oxidation.

Synthesis, basicity and complexation properties versus Zn (II) of a new acyclic acceptor of proton-ionizing pyrazole and pyridine; Sintesis, basicidad y propiedades complejantes frente a Zn (II) de un nuevo receptor aciclico de pirazol y piridina proton-ionizable

Energy Technology Data Exchange (ETDEWEB)

Bueno, J.M.; Campayo, L.; Navarro, P.; Acerete, C. [Instituto de Quimica Medica, CSIC (Spain)

1995-12-31

The synthesis of bis (2`-pyridyl methyl) N{sub 1}-H pyrazole 3,5-dicarboxylate 1[L] is reported. The formation of its sodium pyrazolate salt 1`[L] has been studied by ``13 CNMR, and the deprotonation pKa value of the pyrazole ring of 1 and those corresponding to the protonation of their pyridine rings have been measured using potentiometric methods in H{sub 2}O-MeOH (v/v 9:1) Starting from 1[L] or 1`[L-], the formation of mono- and dinuclear complexes 2 Zn[L] and 3[Zn]{sub 2}[L-]``3+ respectively has been studied. (Author) 17 refs.

Experimental and computational approaches to the analysis of the molecular structure of (E)-3-(3-(4-nitrophenyl)triaz-1-en-1-yl)-1H-pyrazole-4-carbonitrile

Science.gov (United States)

Al-Azmi, Amal; Shalaby, Mona Abbas

2018-03-01

A green, fast and straightforward procedure for the synthesis of (E)-3-(3-(4-nitrophenyl)triaz-1-en-1-yl)-1H-pyrazole-4-carbonitrile is described in this paper. The method uses a coupling reaction between 4- nitrophenyl diazonium chloride and 5-aminopyrazole-4-carbonitrile. The structure is confirmed by different spectroscopic studies such as IR, NMR, HRMS and UV-vis spectroscopy in addition to X-ray single-crystal determination. The molecular geometry, vibrational frequencies and gauge-invariant atomic orbital (GIAO) 1H and 13C NMR chemical shift values of (E)-3-(3-(4-nitrophenyl)triaz-1-en-1-yl)-1H-pyrazole-4-carbonitrile are calculated in the ground state using the Hartree-Fock (HF) method and density functional theory (DFT) with the 6-31G(d) basis set, and are compared with the experimental data. The natural bond orbital (NBO) analysis is performed so as to discuss the stability of the molecule that arises from hyper conjugative interactions and charge delocalization. The electronic properties, such as HOMO and LUMO energies, were calculated using time dependent density functional theory (TD-DFT) approach.

Partial deletion of argininosuccinate synthase protects from pyrazole plus lipopolysaccharide-induced liver injury by decreasing nitrosative stress

Science.gov (United States)

Lu, Yongke; Leung, Tung Ming; Ward, Stephen C.

2012-01-01

Argininosuccinate synthase (ASS) is the rate-limiting enzyme in the urea cycle. Along with nitric oxide synthase (NOS)-2, ASS endows cells with the l-citrulline/nitric oxide (NO·) salvage pathway to continually supply l-arginine from l-citrulline for sustained NO· generation. Because of the relevant role of NOS in liver injury, we hypothesized that downregulation of ASS could decrease the availability of intracellular substrate for NO· synthesis by NOS-2 and, hence, decrease liver damage. Previous work demonstrated that pyrazole plus LPS caused significant liver injury involving NO· generation and formation of 3-nitrotyrosine protein adducts; thus, wild-type (WT) and Ass+/− mice (Ass−/− mice are lethal) were treated with pyrazole plus LPS, and markers of nitrosative stress, as well as liver injury, were analyzed. Partial ablation of Ass protected from pyrazole plus LPS-induced liver injury by decreasing nitrosative stress and hepatic and circulating TNFα. Moreover, apoptosis was prevented, since pyrazole plus LPS-treated Ass+/− mice showed decreased phosphorylation of JNK; increased MAPK phosphatase-1, which is known to deactivate JNK signaling; and lower cleaved caspase-3 than treated WT mice, and this was accompanied by less TdT-mediated dUTP nick end labeling-positive staining. Lastly, hepatic neutrophil accumulation was almost absent in pyrazole plus LPS-treated Ass+/− compared with WT mice. Partial Ass ablation prevents pyrazole plus LPS-mediated liver injury by reducing nitrosative stress, TNFα, apoptosis, and neutrophil infiltration. PMID:22052013

Evaluasi Sistem Pemberian Kredit Modal USAha Dan Penerimaan Angsuran Dalam Upaya Meningkatkan Efektivitas Pengendalian Intern (Studi Pada Kantor Pusat Pd. Bpr. Bank Jombang)

OpenAIRE

Hindarto, Andreas Eko

2014-01-01

The accuracy of credit will always affect the smooth running of the business on the whole rural banks , so if there is an error in the analysis of credit may result in loss of business continuity and disrupt the rural banks . Researchers took place in PD research . BPR . Bank Jombang . The purpose of this study is to determine the implementation of systems and procedures for granting loans and venture capital installment receipts on PD . BPR . Bank Jombang . The elements that must be met is t...

Superconductivity in Ti3P-type compounds

International Nuclear Information System (INIS)

Wills, J.O.; Hein, R.A.; Waterstrat, R.M.

1978-01-01

A study of 12 intermetallic A 3 B compounds which crsytallize in the tetragonal Ti 3 P-type structure has revealed five new superconductors with transition temperatures below 1 K: Zr 3 Si, Zr 3 Ge, Zr 3 P, V 3 P, and Nb 3 Ge (extrapolated from the alloy series Nb-Ge-As). In addition, two compounds, Zr 3 Sb and Ta 3 Ge, having the Ni 3 P structure type are found to be superconducting below 1 K. Within the Ti 3 P-type compounds, those with the lighter ''B'' elements in a given column of the Periodic Table have the higher transition temperatures. Critical-magnetic-field and electrical-resistivity data are reported for the superconducting Ti 2 P-type compound Nb 3 P, which permit one to estimate the Ginzburg-Landau kappa parameter and the electronic-specific-heat coefficient γ. The kappa value of 8.4 indicates that this material is type II, and the γ value of 1.3 mJ/mole K 2 for Nb 3 P is probably related to its low transition temperature relative to many A15 compounds

Regio- and enantioselective synthesis of N-substituted pyrazoles by rhodium-catalyzed asymmetric addition to allenes.

Science.gov (United States)

Haydl, Alexander M; Xu, Kun; Breit, Bernhard

2015-06-08

The rhodium-catalyzed asymmetric N-selective coupling of pyrazole derivatives with terminal allenes gives access to enantioenriched secondary and tertiary allylic pyrazoles, which can be employed for the synthesis of medicinally important targets. The reaction tolerates a large variety of functional groups and labelling experiments gave insights into the reaction mechanism. This new methodology was further applied in a highly efficient synthesis of JAK 1/2 inhibitor (R)-ruxolitinib. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

catena-Poly[[[trans-diaquabis(pyridine-κNcobalt(II]-μ-(4-{N′-[1-(3-acetyl-4-methyl-1H-pyrazol-5-ylethylidene]hydrazino}benzoato-κ3O:N,N′-[bis(pyridine-κNcobalt(III]-μ-(4-{N′-[1-(3-acetyl-4-methyl-1H-pyrazol-5-ylethylidene]hydrazino}benzoato-κ3N,N′:O]perchlorate 3.66-hydrate

Directory of Open Access Journals (Sweden)

Igor O. Fritsky

2008-02-01

Full Text Available The title compound, {[Co2(C15H14N4O32(C5H5N4(H2O2]ClO4·3.66H2O}n, is a one-dimensional coordination polymer, with both CoII and CoIII centres in its structure. The ligand environment surrounding CoIII is formed by two N,N-chelating pyrazole-containing ligands and two pyridine molecules in axial positions. The high-spin CoII ions, situated at crystallographic centres of inversion, exhibit a distorted octahedral coordination mode. The ClO4− anion is linked to the polymer chain via hydrogen bonds. The chains are connected by hydrogen bonds to produce a three-dimensional structure.

QTAIM investigation of bis(pyrazol-1-ylmethane derivative and its Zn(II complexes (ZnLX2, X=Cl, Br or I

Directory of Open Access Journals (Sweden)

Dehestani Maryam

2015-01-01

Full Text Available Topological analyses of the electron density using the quantum theory of atoms in molecules (QTAIM have been carried out at the B3PW91/6-31g (d theoretical level, on bis(pyrazol-1-ylmethanes derivatives 9-(4-(di (1H-pyrazol-1-yl-methylphenyl-9H-carbazole (L and its zinc(II complexes: ZnLCl2 (1, ZnLBr2 (2 and ZnLI2 (3. The topological parameters derived from Bader theory were also analyzed; these are characteristics of Zn-bond critical points and also of ring critical points. The calculated structural parameters are the frontier molecular orbital energies highest occupied molecular orbital energy (EHOMO, lowest unoccupied molecular orbital energy (ELUMO, hardness (η, softness (S, the absolute electronegativity (χ, the electrophilicity index (ω and the fractions of electrons transferred (ΔN from ZnLX2 complexes to L. The numerous correlations and dependencies between energy terms of the Symmetry Adapted Perturbation Theory approach (SAPT, geometrical, topological and energetic parameters were detected and described.

IMPROVING COMPETITIVE POWER PRODUCTS BY STRATEGIC ENVIRONMENTAL ANALYSIS: CASE STUDY CREDITS PRODUCTS’ EMPLOYEES OF BANK BPR

Directory of Open Access Journals (Sweden)

Kunto Ajibroto

2017-09-01

Full Text Available Strategic environment analysis is part of strategic planning component and is a process to always put the company in a strategic position, so that in its development will always be in a favorable position. By analyzing external factors and internal factors, it will be possible to find out the most appropriate strategy formulation for BPR Bhakti Daya Ekonomi in facing the increasingly fierce competition. The research method used is qualitative with data collection using interview and observation, while for data analysis using SWOT method which also use analysis of EFAS and IFAS. The results of this study indicate that the position of BPR Bhakti Daya Ekonomi for Credit Employees products is located in quadrant IV. In this quadrant the bank is in a position where its internal advantage is relatively more dominant than its weakness. However, in the face of the threat environment is relatively greater than the chances. This means that the bank has a relatively better internal capability to expand its business, especially by utilizing some of its internal strengths.

Evidências de validade da bateria de provas de raciocínio (BPR-5 para seleção de pessoal Evidences on the validity of the battery of reasoning tests (BPR-5 for employment selection

Directory of Open Access Journals (Sweden)

Viviane de Oliveira Baumgartl

2006-01-01

Full Text Available A utilização de testes psicológicos é uma prática comum em empresas brasileiras. Estas avaliações, no entanto, muitas vezes são realizadas sem levar em conta a eficácia dos instrumentos utilizados em discriminar critérios relevantes para um bom de desempenho do funcionário em seu posto de trabalho. Nesse sentido o presente estudo teve como objetivo verificar as evidências de validade do BPR-5 em um contexto organizacional. Os participantes foram 79 funcionários de uma empresa de energia elétrica brasileira. Como critério foi utilizado o número de acidentes de trabalho dos funcionários. Os dados foram analisados por meio de estatísticas descritivas e análises correlacionais. Nos resultados, o critério utilizado, referente ao número de acidentes de trabalho, correlacionou-se com a inteligência principalmente para funcionários com menor tempo na função (-0,39; pThe use of psychological tests is a common practice among Brazilian companies. These evaluations, however, are done many times without taking into account the efficiency of the instruments that are used for discriminating relevant criteria for a good performance of the employee at work. The purpose of this study was to check evidences on the validity of the BPR-5 test in an organizational context. The sample consisted of 79 employees of a Brazilian electric company. The number of injuries at the workplace was used as criteria. The data was analyzed using descriptive statistics and correlation analyses. The results showed that the criteria of injuries at the workplace presented significant correlations with the tests, indicating correlation with intelligence, especially for employees with less job experience (-0,39; p<0,05. The implications of these results for both research and practice are discussed.

Double-edged swords as cancer therapeutics: novel, orally active, small molecules simultaneously inhibit p53-MDM2 interaction and the NF-κB pathway.

Science.gov (United States)

Zhuang, Chunlin; Miao, Zhenyuan; Wu, Yuelin; Guo, Zizhao; Li, Jin; Yao, Jianzhong; Xing, Chengguo; Sheng, Chunquan; Zhang, Wannian

2014-02-13

Simultaneous inactivation of p53 and hyperactivation of nuclear factor-κB (NF-κB) is a common occurrence in human cancer. Currently, antitumor agents are being designed to selectively activate p53 or inhibit NF-κB. However, there is no concerted effort yet to deliberately design inhibitors that can simultaneously do both. This paper provided a proof-of-concept study that p53-MDM2 interaction and NF-κB pathway can be simultaneously targeted by a small-molecule inhibitor. A series of pyrrolo[3,4-c]pyrazole derivatives were rationally designed and synthesized as the first-in-class inhibitors of p53-MDM2 interaction and NF-κB pathway. Most of the compounds were identified to possess nanomolar p53-MDM2 inhibitory activity. Compounds 5q and 5s suppressed NF-κB activation through inhibition of IκBα phosphorylation and elevation of the cytoplasmic levels of p65 and phosphorylated IKKα/β. Biochemical assay for the kinases also supported the fact that pyrrolo[3,4-c]pyrazole compounds directly targeted the NF-κB pathway. In addition, four compounds (5j, 5q, 5s, and 5u) effectively inhibited tumor growth in the A549 xenograft model. Further pharmacokinetic study revealed that compound 5q exhibited excellent oral bioavailability (72.9%).

[2,9-Bis(3,5-dimethyl-1H-pyrazol-1-yl-κN2-1,10-phenanthroline-κ2N,N′]bis(thiocyanato-κNcadmium(II

Directory of Open Access Journals (Sweden)

Yan Hui Chi

2011-01-01

Full Text Available In the title complex, [Cd(NCS2(C22H20N6], the CdII ion is in a CdN6 coordination geometry which is intermediate between octahedral and trigonal–prismatic. The dihedral angles formed between the mean planes of the pyrazole rings and the phenanthroline system are 15.74 (15 and 16.30 (13°. In the crystal, there is a π–π stacking interaction involving two symmetry-related pyrazole rings, with a centroid–centroid distance of 3.664 (3 Å. In addition, there is a relatively short intermolecular contact between C atoms [C...C = 3.399 (6 Å] involving symmetry-related pyridine rings along the a axis.

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs.

Science.gov (United States)

Nakao, Syuhei; Mabuchi, Miyuki; Shimizu, Tadashi; Itoh, Yoshihiro; Takeuchi, Yuko; Ueda, Masahiro; Mizuno, Hiroaki; Shigi, Naoko; Ohshio, Ikumi; Jinguji, Kentaro; Ueda, Yuko; Yamamoto, Masatatsu; Furukawa, Tatsuhiko; Aoki, Shunji; Tsujikawa, Kazutake; Tanaka, Akito

2014-02-15

A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5-methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects. Copyright © 2014 Elsevier Ltd. All rights reserved.

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Directory of Open Access Journals (Sweden)

Smaail Radi

2015-11-01

Full Text Available Recently, a new generation of highly promising inhibitors bearing β-keto-enol functionality has emerged. Reported herein is the first synthesis and use of novel designed drugs based on the β-keto-enol group embedded with heterocyclic moieties such as pyrazole, pyridine, and furan, prepared in a one-step procedure by mixed Claisen condensation. All the newly synthesized compounds were characterized by FT-IR, 1H-NMR, 13C-NMR, ESI/LC-MS, elemental analysis, and evaluated for their in vitro antiproliferative activity against breast cancer (MDA-MB241 human cell lines and fungal strains (Fusarium oxysporum f.sp albedinis FAO. Three of the synthesized compounds showed potent activity against fungal strains with IC50 values in the range of 0.055–0.092 µM. The results revealed that these compounds showed better IC50 values while compared with positive controls.

New octahedral ZnII and CdII complexes based on azo derivatives and azomethines of pyrazole-5-thione

International Nuclear Information System (INIS)

Uraev, A.I.; Vasil'chenko, I.S.; Borodkin, G.S.; Borodkina, I.G.; Vlasenko, V.G.; Burlov, A.S.; Divaeva, L.N.; Garnovskij, A.D.; Lysenko, K.A.; Antipin, M.Yu.

2005-01-01

New metal chelates of Zn II and Cd II (ML 2 ) based on (4Z)-3-methyl-1-phenyl-5-thioxo- 1,5-dihydro-4H-pyrazol-4-one quinolin-8-ylhydrazone (HL 1 ) and (4Z)-5-methyl-2-phenyl- 4-[(quinolin-8-ylimino)methyl]-2,4-dihydro-3H-pyrazole-3-thione (HL 2 ) were synthesized. The structures of the metal chelates were studied by EXAFS and NMR ( 1 H, 13 C, and 111 Cd) spectroscopy. The structure of the Cd(L 1 ) 2 complex was established by X-ray diffraction analysis. The complexes have pseudo octahedral structures with the N 4 S 2 ligand environment [ru

Synthesis and antitumor activity of some novel thiophene, pyrimidine, coumarin, pyrazole and pyridine derivatives

Directory of Open Access Journals (Sweden)

Albratty Mohammed

2017-03-01

Full Text Available 2-Cyano-N-(thiazol-2-yl acetamide (2a and 2-cyano-N-(oxazol- 2-yl acetamide (2b were obtained via the reaction of ethyl cyanoacetate with either 2-aminothiazole (1a or 2-aminooxazole (1b. The formed products were directed toward the reaction with cyclopentanone and elemental sulfur in the presence of triethylamine to give cyclopenta[b]thiophene derivatives (3a,b. The latter products were reacted with either ethyl cyanoacetate or malononitrile to form compounds 4a,b and 5a,b, respectively. Compounds 4a,b were aimed at synthesizing some heterocyclic compounds; thus internal cyclization reactions were introduced to form compounds 6a,b. Also, compounds 4a,b reacted with salicylaldehyde, hydrazine derivatives and either urea or thiourea to produce coumarin derivatives (7a,b, pyrazole derivatives (8a-d and pyrimidine derivatives (9a-d, respectively. Reaction of either benzaldehyde or benzene diazonium chloride (11 with compounds 4a,b afforded compounds 10a,b and 12a,b, respectively. On the other hand, compounds 5a,b underwent internal cyclization to form pyrimidine derivatives 13a,b. Also, when compounds 5a,b reacted with either ethyl cyanoacetate or malononitrile, they gave pyridine derivatives (15a-d through the formation of intermediates (14a-d. Finally, formation of fused pyrimidine derivatives (17a,b was achieved through the reaction of compounds 5a,b and salicylaldehyde applying two different pathways. The first pathway used a catalytic amount of piperidine to form compounds 16a,b; the latter products underwent cyclization to give compounds 17a,b. The second pathway, using a catalytic amount of sodium ethoxide solution directly in one step, afforded compounds 17a,b. Structures of the newly synthesized compounds were established using IR, 1H NMR, 13C NMR and mass spectrometry and their antitumor activity was investigated. Some of these compounds showed promising inhibitory effects on three different cell lines. However, fused pyrimidine

STRUCTURAL STUDY OF BIS(2,6-BIS(PYRAZOL-3-YLPYRIDINENICKEL(II BY CALORIMETRY AND EXAFS SPECTROMETRY

Directory of Open Access Journals (Sweden)

Kristian H Sugiyarto

2010-06-01

Full Text Available The main aim of this work is to reveal the complex formation of 2,6-bis(pyrazol-3-ylpyridine, bpp, with nickel(II perchlorate in DMF by calorimetric stepwise complex formation and then followed by EXAFS spectrometry. It was found that the complex formation follows two stepwise pathways namely the formation of mono pyrazolyl-pyridine, [Ni(DMF3 bpp]2+, and bis pyrazolyl-pyridine, [Ni(bpp2]2+;  the formation constants being  log β1 = 6.57, and log β2 = 5.02, and the total value of log β  = 11.58. The final formation of six-coordinated compound was confirmed by EXAFS analysis with the mean Ni-Nbpp bond length of 2.0646(0.0014 Å.   Keywords: nickel(II, bpp, EXAFS

Structure-based design synthesis of functionalized 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs and indigenous plant extracts and their antimalarial potential

Science.gov (United States)

Olayinka, Ajani; Grace, Olasehinde; Titilope, Dokunmu; Ruth, Diji-Geske; Olabode, Onileere; John, Openibo; Oreoluwa, Oluseye; Tochukwu, Chileke; Ezekiel, Adebiyi

2018-04-01

Resistance of the malaria parasite to conventional therapeutic agents calls for increased efforts in antimalarial drug discovery. Current efforts should be targeted at developing safe and affordable new agents to counter the spread of malaria parasites that are resistant to existing therapy. In this study, toxicological and in vivo antiplasmodial properties of 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-42H-chromen-2, Mangifera indica and Tithonia diversifolia in swiss albino mice models, Musmusculus were investigated. 2H-Chromen-2-one also known as coumarin is highly privileged oxygen-containing heterocyclic entity which are present in plant kingdom as secondary metabolites. The maceration technique of crude drug extraction was employed using cold water extraction. Toxicological analysis was carried out using Lorke's method for acute toxicity testing while the chemosuppressive activity was carried out using Peter's four day test on early infection. We also report the synthesis of functionalized 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs via microwave assisted synthetic approach and isolation of indigenous plant extract in order to investigate their antimalarial efficacy. The condensation reaction of 3-acetylcoumarin with various benzaldehyde derivatives resulted in the formation of 3-[3-acryloyl]-2H-chromen-2-one which was subsequently reaction the hydrazine hydrate via microwave assisted hydrazinolysis to afford the targeted 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs. The chemical structures were confirmed by analytical data and spectroscopic means such as FT-IR, UV, 1H NMR, 13C NMR and DEPT-135. The microwave assisted reaction was remarkably successful and gave targeted 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs in higher yields at lesser reaction time compared to conventional heating method. The LD50 of the aqueous extracts of the leaves and stem bark Mangifera indica was established to be ± 707.11 mg/kg b.w., p.o. (body weight

Synthesis and anti-bacterial activity of novel 1,3-phenylene-bis-N-acetyl-and N-phenylenepyrazole derivatives

Directory of Open Access Journals (Sweden)

Gökçe Demir

2017-04-01

Full Text Available The 1,1'-(5,5'-(1,3-phenylenebis(3-aryl-4,5-dihydro-1H-pyrazole-5,1-diyldi-ethanone (5a-e and 1,3-bis(1-phenyl-3-(aryl-4,5-dihydro-1H-pyrazol-5-ylbenzene (6a-e were synthesized by addition of hydrazine hydrate and/or phenylhydrazine to 1,3-phenylene-bis-chalcone derivatives (3a-e, respectively. The structures of obtained compounds (5a-e and 6a-e were characterized using the spectroscopic methods (NMR, IR and elemental analysis. Addition, the in vitro antibacterial activities of compounds (5a-e was tested against the five human pathogenic bacteria. Gentamycin and Fluconazole were used as positive control. The results were given as inhibition zone (mm and the compounds 5d and 5e showed the same activity with standard (Fluconazole against C. albinas.

Single-electron transfer in palladium complexes of 1,4-naphthoquinone-containing bis(pyrazol-1-yl)methane ligands.

Science.gov (United States)

Scheuermann, Sebastian; Sarkar, Biprajit; Bolte, Michael; Bats, Jan W; Lerner, Hans-Wolfram; Wagner, Matthias

2009-10-05

A 1,4-naphthoquinone-substituted bis(pyrazol-1-yl)methane ligand (N--N) has been synthesized and transformed into its corresponding Pd(II) chelate complex [(N--N)PdCl(2)]. Both N--N and [(N--N)PdCl(2)] have been fully characterized by NMR spectroscopy, spectro-electrochemistry, and X-ray crystallography. After treatment of [(N--N)PdCl(2)] with NEt(3), the signature of a 1,4-naphthosemiquinonate radical is visible in the UV-vis- and electron paramagnetic resonance (EPR) spectrum of the reaction mixture; the free ligand N--N does not react with NEt(3) under the conditions applied. It is therefore concluded that NEt(3) first reduces the Pd(II)-ion of [(N--N)PdCl(2)] to the zero-valent state and that this reaction is followed by a single-electron transfer from the metal atom to the 1,4-naphthoquinone moiety. The complex has been specifically designed to disfavor any direct Pd-to-naphthoquinone coordination. Electron transfer thus proceeds through space or, less likely, via sigma-bonds of the ligand framework.

Pyrazole Based Inhibitors against Enzymes of Staphylococcus aureus

DEFF Research Database (Denmark)

Jagadeesan, G.; Vijayakuma, Vinodhkumar; Palayam, Malathy

2015-01-01

agents. The current study focuses on molecular docking and dynamics studies of pyrazole derivatives against Nucleosidase and DNA gyrase B of Staphylococcus aureus. Molecular docking and dynamics studies reveal that some of these derivatives show better binding abilities than some of the current drugs...

Reingeniería de procesos de negocio (BPR: análisis de un caso desde la perspectiva del nuevo institucionalismo sociológico

Directory of Open Access Journals (Sweden)

José María González González

2012-12-01

Full Text Available El BPR (Business Process Reengineering se ha difundido recientemente entre las organizaciones para la implantación de los sistemas ERP (Enterprise Resource Planning. Este trabajo emplea el Nuevo Institucionalismo Sociológico y la Teoría de la Estructuración como enfoques teóricos complementarios para conocer mejor cómo pueden influir los entornos social y organizativo sobre la adopción del BPR para la implantación de un sistema ERP, así como las repercusiones que este cambio puede tener sobre las estructuras sociales a nivel de organización, prestando especial atención al papel desarrollado por los emprendedores institucionales. Para alcanzar este objetivo, hemos desarrollado un estudio de caso en un grupo multinacional de electricidad español que emprendió la reingeniería de sus procesos económico-financieros para la implantación de un sistema ERP. Los resultados del estudio evidencian la influencia de presiones tanto competitivas como institucionales sobre la organización para la adopción del BPR, así como los factores que motivaron a los actores dominantes a emprender un cambio radical. Asimismo, el estudio pone de manifiesto cómo el cambio analizado impactó sobre las estructuras sociales, pero también fue limitado por éstas.

Unexpected formation and crystal structure of tetrakis(1H-pyrazole-κN2palladium(II dichloride

Directory of Open Access Journals (Sweden)

Thomas Wagner

2014-12-01

Full Text Available The title salt, [Pd(C3H4N24]Cl2, was obtained unexpectedly by the reaction of palladium(II dichloride with equimolar amounts of 1-chloro-1-nitro-2,2,2-tris(pyrazolylethane in methanol solution. The Pd2+ cation is located on an inversion centre and has a square-planar coordination sphere defined by four N atoms of four neutral pyrazole ligands. The average Pd—N distance is 2.000 (2 Å. The two chloride anions are not coordinating to Pd2+. They are connected to the complex cations through N—H...Cl hydrogen bonds. In addition, C—H...Cl hydrogen bonds are observed, leading to a three-dimensional linkage of cations and anions.

Synthesis and antimicrobial, antifungal and anthelmintic activities of 3H-1,5-benzodiazepine derivatives

Directory of Open Access Journals (Sweden)

RAJESH KUMAR

2008-10-01

Full Text Available The diazonium salt of 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide in the presence of sodium hydroxide was condensed with different β-diketones/β-ketoesters, 3a–e, to obtain new β-diketones/β-ketoesters, 4a–e. The β-diketones/β-ketoesters 4a–e were condensed with o-phenylenediamine (o-PDA in presence of p-toluenesulfonic acid/SiO2 to give biologically active 3H-1,5-benzodiazepines, 5a–e. All the newly synthesized compounds were characterized by elemental analysis and spectral studies. The compounds 5a–e was screened for their antimicrobial, antifungal and anthelmintic activities.

Magnetocaloric effects in MnFeP1-x As x -based compounds

International Nuclear Information System (INIS)

Brueck, E.; Ilyn, M.; Tishin, A.M.; Tegus, O.

2005-01-01

Here we present the results of an investigation of some magnetic and thermal properties of the compounds MnFeP 0.45 As 0.55 , MnFeP 0.47 As 0.53 , and Mn 1.1 Fe 0.9 P 0.47 As 0.53 which can be regarded as possible magnetic refrigerants for room temperature applications. Magnetization measurements are performed in the temperature range 250-330 K, in magnetic fields up to 5 T. The coexistence of the magnetic and structural first-order phase transitions is revealed in all three samples, suggesting its key role in the large values observed for the magnetocaloric effect. The adiabatic temperature change measured directly was up to 4.0, 3.4, and 4.2 K for a magnetic field change of 1.45 T

Azomethines, isoxazole, N-substituted pyrazoles and pyrimidine containing curcumin derivatives: Urease inhibition and molecular modeling studies.

Science.gov (United States)

Ahmed, Mahmood; Qadir, Muhammad Abdul; Hameed, Abdul; Arshad, Muhammad Nadeem; Asiri, Abdullah M; Muddassar, Muhammad

2017-08-19

Curcumin has shown large number of pharmacological properties against different phenotypes of various disease models. Different synthetic routes have been employed to develop its various derivatives for diverse biological functions. In this study, curcumin derived azomethine, isoxazole, pyrimidines and N-substituted pyrazoles were synthesized to investigate their urease enzyme inhibition. The structures of newly synthesized compounds were described by IR, MS, 1 H NMR and 13 C NMR spectral data. Urease enzyme inhibition was evaluated through in vitro assays in which compound 8b was found to be the most potent (IC 50  = 2.44 ± 0.07 μM) among the tested compounds. The compounds with diazine ring system except the 4d showed better urease inhibition (IC 50  = 11.43 ± 0.21-19.63 ± 0.28 μM) than the standard urease inhibitor thiourea (IC 50  = 22.61 ± 0.23 μM). Similarly enzyme kinetics data revealed that compounds 3c-3e and 8b were competitive inhibitors with Ki values of 20.0, 19.87, 20.23 and 19.11 μM respectively while the compounds 4b, 4c and 4e were mixed type of inhibitors with Ki values 6.72, 19.69 and 6.72 μM respectively. Molecular docking studies were also performed to identify the plausible binding modes of the most active compounds. Copyright © 2017 Elsevier Inc. All rights reserved.

The ferromagnetic Kondo-lattice compound SmFe sub 4 P sub 1 sub 2

CERN Document Server

Takeda, N

2003-01-01

We report on the magnetic properties of a filled skutterudite compound, SmFe sub 4 P sub 1 sub 2. Magnetic susceptibility and specific heat measurements revealed a ferromagnetic transition at 1.6 K. The temperature dependence of the electrical resistivity exhibits a Kondo-lattice behaviour and the electronic specific heat coefficient attains values as large as 370 mJ mol sup - sup 1 K sup - sup 2. This compound is thereby the first Sm-based heavy-fermion system found with a ferromagnetic ground state. The Kondo temperature is estimated to be about 30 K. (letter to the editor)

Stability Constants of Some Biologically Important Pyrazoles and Their Ni2+ Complexes in Different Dielectric Constant of Medium

Directory of Open Access Journals (Sweden)

S. D. Deosarkar

2012-01-01

Full Text Available The proton-ligand stability constants of some biologically important new pyrazoles and formation constants of their complexes with Ni(II were determined at 0.1 mol dm-3 ionic strength and at 303.15 K in different dielectric constant of dioxane-water mixture by potentiometric method. The Calvin-Bjerrum's pH-titration technique as used by Irving and Rossotti was used for determination of stability constants. The results enabled to study the electrostatic forces of attraction between metal ion and ligand with changes in dielectric constant of the medium.

Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety

Science.gov (United States)

Darwish, Elham S.; Abdel Fattah, Azza M.; Attaby, Fawzy A.; Al-Shayea, Oqba N.

2014-01-01

This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide (3). The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13a–e. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl)-2H-chromen-2-one and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl) phenyl]-2-cyano-2-(1,3-dithian-2-ylidene)acetamide product 22. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results. PMID:24445259

Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety

Directory of Open Access Journals (Sweden)

Elham S. Darwish

2014-01-01

Full Text Available This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonylphenyl]-2-cyanoacetamide (3. The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13a–e. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl-2H-chromen-2-one and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl phenyl]-2-cyano-2-(1,3-dithian-2-ylideneacetamide product 22. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results.

Effect of Cu(II) coordination compounds on the activity of antioxidant enzymes catalase and superoxide dismutase in patients with colorectal cancer.

Science.gov (United States)

Kubiak, Katarzyna; Malinowska, Katarzyna; Langer, Ewa; Dziki, Łukasz; Dziki, Adam; Majsterek, Ireneusz

2011-03-01

Colorectal cancer (CRC) is a serious medical and economical problem of our times. It is the most common gastrointestinal cancer in the world. In Poland, the treatment and detection of CRC are poorly developed and the pathogenesis is still unclear. One hypothesis suggests a role of reactive oxygen species (ROS) in the pathogenesis of CRC. Experimental studies in recent years confirm the participation of ROS in the initiation and promotion of CRC. The aim of the study was to examine the effect of the following coordination compounds coordination compounds: dinitrate (V) tetra(3,4,5-trimethyl-N1-pyrazole-κN2) copper(II), dichloro di(3,4,5-trimethyl-N1-pyrazole-κN2) copper(II), dinitrate (V) di(1,4,5-trimethyl-N1-pyrazole-κN2) copper(II), dichloro di(1,3,4,5-tetramethyl-N1-pyrazole-κN2) copper(II) on the activity of antioxidant enzymes superoxide dismutase (SOD, ZnCu-SOD) and catalase (CAT) in a group of patients with colorectal cancer (CRC) and in the control group consisting of patients with minor gastrointestinal complaints. The study was conducted in 20 patients diagnosed with colorectal cancer at the age of 66.5±10.2 years (10 men and 10 women) versus the control group of 20 people (10 men and 10 women) aged 57.89±17.10 years without cancer lesions in the biological material - hemolysate prepared in a proportion of 1ml of water per 1 ml of blood. CAT activity was measured by the Beers method (1952), while SOD activity was measured by the Misra and Fridovich method (1972). We found that patients with CRC showed a statistically significant decrease of SOD and CAT activity (CAT - 12,75±1.97 U/g Hb, SOD - 1111.52±155.52 U/g Hb) in comparison with the control group (CAT - 19.65±2,17 U/g Hb, SOD - 2046.26±507.22 U/g Hb). Simultaneously, we observed that the investigated coordination compounds of Cu(II) significantly increased the antioxidant activity of CAT and SOD in patients with CRC (mean: CAT 25.23±4.86 U/g Hb, SOD - 3075.96±940.20 U/g Hb). Patients with

Experimental and theoretical study of pyrazole N-alkylation catalyzed by basic modified molecular sieves

Czech Academy of Sciences Publication Activity Database

Matos, I.; Pérez-Mayoral, E.; Soriano, E.; Zukal, Arnošt; Martín-Aranda, R. M.; López-Peinado, A. J.; Fonseca, I.; Čejka, Jiří

2010-01-01

Roč. 161, č. 3 (2010), s. 377-383 ISSN 1385-8947 R&D Projects: GA AV ČR 1QS400400560 Institutional research plan: CEZ:AV0Z40400503 Keywords : pyrazole alkylation * basic mesoporous materials * reaction mechanism Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 3.074, year: 2010

New Pyrazole-Hydrazone Derivatives: X-ray Analysis, Molecular Structure Investigation via Density Functional Theory (DFT) and Their High In-Situ Catecholase Activity.

Science.gov (United States)

Karrouchi, Khalid; Yousfi, El Bekkaye; Sebbar, Nada Kheira; Ramli, Youssef; Taoufik, Jamal; Ouzidan, Younes; Ansar, M'hammed; Mabkhot, Yahia N; Ghabbour, Hazem A; Radi, Smaail

2017-10-25

The development of low-cost catalytic systems that mimic the activity of tyrosinase enzymes (Catechol oxidase) is of great promise for future biochemistry technologic demands. Herein, we report the synthesis of new biomolecules systems based on hydrazone derivatives containing a pyrazole moiety ( L1 - L6 ) with superior catecholase activity. Crystal structures of L1 and L2 biomolecules were determined by X-ray single crystal diffraction (XRD). Optimized geometrical parameters were calculated by density functional theory (DFT) at B3LYP/6-31G (d, p) level and were found to be in good agreement with single crystal XRD data. Copper (II) complexes of the compounds ( L1 - L6 ), generated in-situ, were investigated for their catalytic activities towards the oxidation reaction of catechol to ortho -quinone with the atmospheric dioxygen, in an attempt to model the activity of the copper containing enzyme tyrosinase. The studies showed that the activities depend on four parameters: the nature of the ligand, the nature of counter anion, the nature of solvent and the concentration of ligand. The Cu(II)-ligands, given here, present the highest catalytic activity (72.920 μmol·L -1 ·min -1 ) among the catalysts recently reported in the existing literature.

Synthesis, structural characterization and theoretical studies of a new Schiff base 4-(((3-(tert-Butyl)-(1-phenyl)pyrazol-5-yl) imino)methyl)phenol

Science.gov (United States)

Cuenú, Fernando; Londoño-Salazar, Jennifer; Torres, John Eduard; Abonia, Rodrigo; D'Vries, Richard F.

2018-01-01

4-(((3-(tert-Butyl)-(1-phenyl)pyrazol-5-yl)imino)methyl)phenol (4-OHFPz) was synthesized and characterized by FT-IR, MS, NMR, and single-crystal X-ray diffraction. Optimization of molecular geometry, vibrational frequencies, and chemical shifts were calculated by using the methods of density functional theory (DFT) with B3LYP and B3PW91 as functionals and Hartree-Fock with 6-311G++(d,p) as basis set using the GAUSSIAN 09 program package. With the VEDA 4 software, the vibrational frequencies were assigned in terms of the potential energy distribution (PED). The equilibrium geometries calculated by all methods were compared with X-ray diffraction results, indicating that the theoretical results matches well with the experimental ones. The data obtained from the vibrational analysis and the calculated NMR are consistent with the experimental spectra.

Pengaruh segmentasi pasar terhadap kepuasan pelanggan (nasabah pada Bank BPR Jatim Cabang Ponorogo

Directory of Open Access Journals (Sweden)

Elis Tri Wahyuni

2017-01-01

Full Text Available This study aims to determine the effect of market segmentation of customer satisfaction (Customer in bank BPR Jatim Branch of Ponorogo. Market Segmentation effect on customer satisfaction as evidenced from t value on the market cementation variable (X is from a significant level of 0.000 t less than 0.05 then the research hypothesis H0 and menerimaHa resisting. And it can be seen the value rhitung is 0.748 while rtabel 0,138. This  constant value of 10.264 means if the variable value market segmentation fixed or constant, the amount of customer satisfaction (customers amounted to 10.264. This means that in the absence of market segmentation variables pegaruh then customer satisfaction still has a value of 10.264.

Synthesis and Antimicrobial Evaluation of Some Novel 2-(4-Chlorophenylimino) thiazolidin-4-one Derivatives

Energy Technology Data Exchange (ETDEWEB)

B' Bhatt, H.; Sharma, S. [Hemchandracharya North Gujarat Univ., Gujarat (India)

2012-06-15

A series of 2-(4-chlorophenylimino)-5-((3-(p-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl) methylene) thiazolidin-4-one (3a-h) compounds were prepared from the 2-(4-chlorophenylimino) thiazolidin-4-one (1) and 1-phenyl-3-(psubstituted phenyl)-1H-pyrazole-4-carbaldehyde (2a-h). All compounds were characterized by elemental (C, H, N) analysis and spectral (FT-IR, {sup 1}H NMR and GC-MS) analysis. These newly synthesized compounds were screened for their antibacterial and antifungal activities. Antimicrobial activity was observed and evaluated against the bacterial strains like Eschericha coli (MTCC 443), Pseudomonas aeruginosa (MTCC 1688), Staphylococcus aureus (MTCC 96), Streptococcus pyogenes (MTCC 442) and against the fungal strains like Candida albicans (MTCC 227), Aspergillus niger (MTCC 282) and Aspergillus clavatus (MTCC 1323). All the synthesized compounds were found to possess moderate to excellent antimicrobial activity against above selected strains.

Synthesis of some Heterocyclic Compounds Derived from 2-Chloro-N-p-Tolylacetamide

Directory of Open Access Journals (Sweden)

Hanan Gh Shaaban

2017-02-01

Full Text Available This research includes preparation of (2-chloro-N-p-tolylacetamide (1 from the reaction of (p-aminotoluene with chloro acetyl chloride. Compound (1 reacted with thiosemi carbazide and gave compound (2, and when compound (1 reacted with semicarbazide gave compound (3. While when compound (1 reacted with thiourea it produced compound (4. Compounds (2-4 when reacted with appropriate aromatic aldehydes or ketones produced Shiff bass (5-16, which in turn reacted with chloro acetyl chloride in the present of tri ethyl amine and dioxin gave β-lactam derivatives (14-22. The structures of these compounds were characterized from their melting points, FT-IR, and NMR.

Molecular Self-Assembly of Group 11 Pyrazolate Complexes as Phosphorescent Chemosensors for Detection of Benzene

Science.gov (United States)

Ghazalli, N. F.; Yuliati, L.; Lintang, H. O.

2018-01-01

We highlight the systematic study on vapochromic sensing of aromatic vapors such as benzene using phosphorescent trinuclear pyrazolate complexes (2) with supramolecular assembly of a weak intermolecular metal-metal interaction consisting of 4-(3,5-dimethoxybenzyl)-3,5-dimethyl pyrazole ligand (1) and group 11 metal ions (Cu(I), Ag(I), Au(I)). The resulting chemosensor 2(Cu) revealed positive response to benzene vapors in 5 mins by blue-shifting its emission band in 44 nm (from 616 to 572 nm) and emitted bright orange to green, where this change cannot be recovered even with external stimuli. Comparing to 2(Ag) with longer metal-metal distance (473 nm) with same sensing time and quenching in 37%, 2(Au) gave quenching in 81% from its original intensity at 612 nm with reusability in 82% without external stimuli and emitted less emissive of red-orange from its original color. The shifting phenomenon in 2(Cu) suggests diffusion of benzene vapors to inside molecules for formation of intermolecular interaction with Cu(I)-Cu(I) interaction while quenching phenomenon in 2(Au) suggests diffusion of benzene vapors to between the Au(I)-Au(I) interaction. These results indicate that suitable molecular structure of ligand and metal ion in pyrazolate complex is important for designing chemosensor in the detection of benzene vapors.

Free radical reactions of isoxazole and pyrazole derivatives of hispolon: kinetics correlated with molecular descriptors.

Science.gov (United States)

Shaikh, Shaukat Ali M; Barik, Atanu; Singh, Beena G; Modukuri, Ramani V; Balaji, Neduri V; Subbaraju, Gottumukkala V; Naik, Devidas B; Priyadarsini, K Indira

2016-12-01

Hispolon (HS), a natural polyphenol found in medicinal mushrooms, and its isoxazole (HI) and pyrazole (HP) derivatives have been examined for free radical reactions and in vitro antioxidant activity. Reaction of these compounds with one-electron oxidant, azide radicals ([Formula: see text]) and trichloromethyl peroxyl radicals ([Formula: see text]), model peroxyl radicals, studied by nanosecond pulse radiolysis technique, indicated formation of phenoxyl radicals absorbing at 420 nm with half life of few hundred microseconds (μs). The formation of phenoxyl radicals confirmed that the phenolic OH is the active centre for free radical reactions. Rate constant for the reaction of these radicals with these compounds were in the order k HI ≅ k HP  >   k HS . Further the compounds were examined for their ability to inhibit lipid peroxidation in model membranes and also for the scavenging of 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical and superoxide ([Formula: see text]) radicals. The results suggested that HP and HI are less efficient than HS towards these radical reactions. Quantum chemical calculations were performed on these compounds to understand the mechanism of reaction with different radicals. Lower values of adiabatic ionization potential (AIP) and elevated highest occupied molecular orbital (HOMO) for HI and HP compared with HS controlled their activity towards [Formula: see text] and [Formula: see text] radicals, whereas the contribution of overall anion concentration was responsible for higher activity of HS for DPPH, [Formula: see text], and lipid peroxyl radical. The results confirm the role of different structural moieties on the antioxidant activity of hispolon derivatives.

Synthesis, physical-chemical and biological properties of 1,8-disubstituted compounds of theobromine. III. 8-Amino-p-chlorobenzyltheobromines

Directory of Open Access Journals (Sweden)

D. G. Ivanchenko

2014-08-01

Full Text Available Introduction. This work is a follow-up to a series of research activities dedicated to the search of biologically active compounds among the xanthine derivatives. Aim of the Work.Development of simple laboratory-based methods for 8-amino-1-p-chlorobenzyltheobromines synthesis and the study of antioxidant, antimicrobial and antifungal effect of the synthesized compounds. Materials and Methods of Research.The melting point has been determined with the help of an open capillary method with TAP device (M. Elemental analysis has been performed with the helpof the instrument ElementarVario L cube, NMR-spectra have been taken on a spectrometer Bruker SF-400 (operating frequency of 400 MHz, solvent DMSO-d6 or DMSO-d6 + CDCl3, internal standard – TMS. These data correspond to thecalculated elemental analysis. The synthesis of 8-aminosubstituted 1-p-chlorobenzyltheobromine (2,3.Mixture 0.01 mole of8-bromo-1-p-chlorobenzyltheobromine (1, 0.03 mole of pyrrolidine (2 or piperidine (3, 40 ml of cellosolve is boiled during 4 hours, then it is allowed to steam out dry in a vacuum. Dry residue is processed with water, then residual matter which has been formed is filtered out, washed with water and recrystallized from the aqueous ethanol. The synthesis of 8-amino-1-p-chlorobenzyltheobromines (4-7. Mixture 0.01 mole of initial compound (1, 0.03 mole of the respective amine and 40 ml of cellosolve is boiled during 4 hours, thenit is allowed to cool down and is diluted with water. After this, residual matter which has been formed is filtered out, washed with water and aqueous propanol-2 and recrystallized from the water ethanol. Molecular descriptors have been calculated using the computer programs ALOGPS and DRAGON, whereas biological properties of the synthesized compounds have been calculated with the help of GUSAR and ACD / Percepta Platform. Antioxidant activity (AOA has been studied in vitro applying the method of nonenzymic initiation of free

NQRS Data for AlDO28Si13 (Subst. No. 0034)

Science.gov (United States)

Chihara, H.; Nakamura, N.

This document is part of Subvolume A `Substances Containing Ag … C10H15' of Volume 48 `Nuclear Quadrupole Resonance Spectroscopy Data' of Landolt-Börnstein - Group III `Condensed Matter'. It contains an extract of Section `3.2 Data tables' of the Chapter `3 Nuclear quadrupole resonance data' providing the NQRS data for AlDO28Si13 (Subst. No. 0034)

A Bateria de Provas de Raciocínio (BPR-5 aplicada a um contexto organizacional The Bateria de Provas de Raciocínio (BPR-5 applied to an organizational context

Directory of Open Access Journals (Sweden)

Viviane de Oliveira Baumgartl

2004-06-01

Full Text Available O presente estudo relata os resultados de uma pesquisa de estabelecimento de normas para a Bateria de Provas de Raciocínio (BPR-5 e de investigação da relação entre variáveis demográficas e ocupacionais e os desempenhos na referida bateria. As normas foram estabelecidas especificamente para os funcionários do setor elétrico de uma companhia energética de Minas Gerais, por ocasião da reimplantação do processo de avaliação psicológica. A amostra foi composta por 57 funcionários, que possuíam escolaridade de, pelo menos, 2o grau incompleto. Em razão do nível de escolaridade foi utilizada no estudo a forma B da bateria. Os resultados revelaram correlações significativas entre as idades dos sujeitos, a escolaridade e o desempenho geral na prova. Evidenciou-se, portanto, a importância do estabelecimento de normas para a empresa, visto que a amostra organizacional apresenta características peculiares em relação à amostra original de estudo da respectiva bateria.This study shows the results of a test-norms establishment research for the Bateria de Provas de Raciocínio (BPR-5 and the investigation of relations between demographic and occupational variables and the performance of employees on the battery. The test-norms were established specifically for employees of the electricity sector of an energy company when the psychological assessment process was reintroduced. The sample consisted of 57 employees who had achieved high school at least. Because of that, only the B type of the battery was used in the research. The results showed significative relations among the age, schooling and general performance on the battery. Therefore, the importance of establishing test-norms for the company became evident, since the organizational sample shows peculiar characteristics when compared to the original study sample of the battery.

Regioconvergent and Enantioselective Rhodium-Catalyzed Hydroamination of Internal and Terminal Alkynes: A Highly Flexible Access to Chiral Pyrazoles.

Science.gov (United States)

Haydl, Alexander M; Hilpert, Lukas J; Breit, Bernhard

2016-05-04

The rhodium-catalyzed asymmetric N-selective coupling of pyrazole derivatives with internal and terminal alkynes features an utmost chemo-, regio-, and enantioselective access to enantiopure allylic pyrazoles, readily available for incorporation in small-molecule pharmaceuticals. This methodology is distinguished by a broad substrate scope, resulting in a remarkable compatability with a variety of different functional groups. It furthermore exhibits an intriguing case of regio-, position-, and enantioselectivity in just one step, underscoring the sole synthesis of just one out of up to six possible products in a highly flexible approach to allylated pyrazoles by emanating from various internal and terminal alkynes. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine.

Science.gov (United States)

Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo

2014-03-07

The reaction of terminal alkynes with n-BuLi, and then with aldehydes, followed by the treatment with molecular iodine, and subsequently hydrazines or hydroxylamine provided the corresponding 3,5-disubstituted pyrazoles or isoxazoles in good yields with high regioselectivity, through the formations of propargyl secondary alkoxides and α-alkynyl ketones. The present reactions are one-pot preparation of 3,5-disubstituted pyrazoles from terminal alkynes, aldehydes, molecular iodine, and hydrazines, and 3,5-disubstituted isoxazoles from terminal alkynes, aldehydes, molecular iodine, and hydroxylamine.

From proton nuclear magnetic resonance spectra to pH. Assessment of {sup 1}H NMR pH indicator compound set for deuterium oxide solutions

Energy Technology Data Exchange (ETDEWEB)

Tynkkynen, Tuulia, E-mail: tuulia.tynkkynen@uku.fi [Laboratory of Chemistry, Department of Biosciences, University of Kuopio, PO Box 1627, 70211 Kuopio (Finland); Tiainen, Mika; Soininen, Pasi; Laatikainen, Reino [Laboratory of Chemistry, Department of Biosciences, University of Kuopio, PO Box 1627, 70211 Kuopio (Finland)

2009-08-19

In this study, a protocol for pH determination from D{sub 2}O samples using {sup 1}H NMR pH indicator compounds was developed and assessed by exploring the pH-dependency of 13 compounds giving pH-dependent {sup 1}H NMR signals. The indicators cover the pH range from pH* 0 to 7.2. Equations to transform the indicator chemical shifts to pH estimates are given here for acetic acid, formic acid, chloroacetic acid, dichloroacetic acid, creatine, creatinine, glycine, histidine, 1,2,4-triazole, and TSP (2,2,3,3-tetradeutero-3-(trimethylsilyl)-propionic acid). To characterize the method in presence of typical solutes, the effects of common metabolites, albumin and ionic strength were also evaluated. For the ionic strengths, the effects were also modelled. The experiments showed that the use of pH sensitive {sup 1}H NMR chemical shifts allows the pH determination of typical metabolite solutions with accuracy of 0.01-0.05 pH units. Also, when the ionic strength is known with accuracy better than 0.1 mol dm{sup -3} and the solute concentrations are low, pH{sub nmr}{sup *} (the NMR estimate of pH) can be assumed to be within 0.05 pH units from potentiometrically determined pH.

The regulatory effect of SC-236 (4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-l] benzenesulfonamide) on stem cell factor induced migration of mast cells

International Nuclear Information System (INIS)

Kim, Su-Jin; Jeong, Hyun-Ja; Park, Rae-Kil; Lee, Kang-Min; Kim, Hyung-Min; Um, Jae-Young; Hong, Seung-Heon

2007-01-01

SC-236 (4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-]benzenesulfonamide; C 16 H 11 ClF 3 N 3 O 2 S), is a highly selective cyclooxygenase (COX)-2 inhibitor. Recently, there have been reports that SC-236 protects against cartilage damage in addition to reducing inflammation and pain in osteoarthritis. However, the mechanism involved in the inflammatory allergic reaction has not been examined. Mast cells accumulation can be related to inflammatory conditions, including allergic rhinitis, asthma, and rheumatoid arthritis. The aim of the present study is to investigate the effects of SC-236 on stem cell factor (SCF)-induced migration, morphological alteration, and cytokine production of rat peritoneal mast cells (RPMCs). We observed that SCF significantly induced the migration and morphological alteration. The ability of SCF to enhance migration and morphological alteration was abolished by treatment with SC-236. In addition, production of tumor necrosis factor (TNF)-α, interleukin (IL)-1β, and vascular endothelial growth factor (VEGF) production induced by SCF was significantly inhibited by treatment with SC-236. Previous work has demonstrated that SCF-induced migration and cytokine production of mast cells require p38 MAPK activation. We also showed that SC-236 suppresses the SCF-induced p38 MAPK activation in RPMCs. These data suggest that SC-236 inhibits migration and cytokine production through suppression of p38 MAPK activation. These results provided new insight into the pharmacological actions of SC-236 and its potential therapeutic role in the treatment of inflammatory allergic diseases

Synthesis of Heteroaromatic Compounds by Oxidative Aromatization Using an Activated Carbon/Molecular Oxygen System

Directory of Open Access Journals (Sweden)

Masahiko Hayashi

2009-08-01

Full Text Available A variety of heteroaromatic compounds, such as substituted pyridines, pyrazoles, indoles, 2-substituted imidazoles, 2-substituted imidazoles, 2-arylbenzazoles and pyrimidin-2(1H-ones are synthesized by oxidative aromatization using the activated carbon and molecular oxygen system. Mechanistic study focused on the role of activated carbon in the synthesis of 2-arylbenzazoles is also discussed. In the final section, we will disclose the efficient synthesis of substituted 9,10-anthracenes via oxidative aromatization.

Cinnamoyl compounds as simple molecules that inhibit p300 histone acetyltransferase.

Science.gov (United States)

Costi, Roberta; Di Santo, Roberto; Artico, Marino; Miele, Gaetano; Valentini, Paola; Novellino, Ettore; Cereseto, Anna

2007-04-19

Cinnamoly compounds 1a-c and 2a-d were designed, synthesized, and in vitro tested as p300 inhibitors. At different degrees, all tested compounds were proven to inactivate p300, particularly, derivative 2c was the most active inhibitor, also showing high specificity for p300 as compared to other histone acetyltransferases. Most notably, 2c showed anti-acetylase activity in mammalian cells. These compounds represent a new class of synthetic inhibitors of p300, characterized by simple chemical structures.

Synthesis of novel pyrazoline based bis (1,2,3-triazole scaffolds via click chemistry

Directory of Open Access Journals (Sweden)

Kiran Kothuri

2017-01-01

Full Text Available A series of novel bis(1,2,3-triazoles derivatives 7a–m were synthesized by the 1,3-dipolar cycloaddition (click-reaction of 1-methyl-3,5-bis(2- -(prop-2-yn-1-yloxyphenyl-4,5-dihydro-1H-pyrazole (5 with various aralkyl azides 6a–m in the presence of sodium ascorbate and copper sulphate with good yields. The required precursor 5 was synthesized by reacting (E-1,3- -bis(2-hydroxyphenylprop-2-en-1-one (3 with methylhydrazine hydrate via 2,2′-(1-methyl-4,5-dihydro-1H-pyrazole-3,5-diyldiphenol 4, followed by reaction with propargyl bromide. The homogeneity of all the newly synthesized compounds was checked by TLC. The IR, NMR, mass spectral data and elemental analysis were in accord with the assigned structure. The title compounds were evaluated for their antibacterial activity against various bacterial strains, i.e., Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis; compounds 7f–7h and 7j were found to be moderately active against the bacteria, when compared with that of the standard drug. Furthermore, the same library of compounds was evaluated for their antioxidant activity using the nitric oxide radical scavenging activity. The results of the study showed that compounds 7e–7h and 7k–7m showed good radical scavenging activity.

Coordination of bis(pyrazol-1-ylamine to palladium(II: influence of the co-ligands and counter-ions on the molecular and crystal structures

Directory of Open Access Journals (Sweden)

María de los Angeles Mendoza

2015-01-01

Full Text Available The structures of a series of complexes with general formula n[Pd(pzaX]Y·mH2O (n = 1, 2; X = Cl, Br, I, N3, NCS; Y = NO3, I, N3, [Pd(SCN4]; m = 0, 0.5, 1 have been determined, where pza is the tridentate ligand bis[2-(3,5-dimethylpyrazol-1-ylethyl]amine, C14H23N5. In all complexes, {bis[2-(3,5-dimethylpyrazol-1-yl-κN2ethyl]amine-κN}chloridopalladium nitrate, [Pd(pzaCl]NO3, (1, {bis[2-(3,5-dimethylpyrazol-1-yl-κN2ethyl]amine-κN}bromidopalladium nitrate, [Pd(pzaBr]NO3, (2, {bis[2-(3,5-dimethylpyrazol-1-yl-κN2ethyl]amine-κN}iodidopalladium iodide hemihydrate, [Pd(pzaI]I·0.5H2O, (3, azido{bis[2-(3,5-dimethylpyrazol-1-yl-κN2ethyl]amine-κN}palladium azide monohydrate, [Pd(pzaN3]N3·H2O, (4, and bis[{bis[2-(3,5-dimethylpyrazol-1-yl-κN2ethyl]amine-κN}(thiocyanato-κNpalladium] tetrakis(thiocyanato-κSpalladate, [Pd(pzaNCS]2[Pd(SCN4], (5, the [Pd(pzaX]+ complex cation displays a square-planar coordination geometry, and the pza ligand is twisted, approximating twofold rotation symmetry. Although the pza ligand is found with the same conformation along the series, the dihedral angle between pyrazole rings depends on the co-ligand X. This angle span the range 79.0 (3–88.6 (1° for the studied complexes. In (3, two complex cations, two I− anions and one water molecule of crystallization are present in the asymmetric unit. In (5, the central amine group of pza is disordered over two positions [occupancy ratio 0.770 (18:0.230 (18]. The complex [Pd(SCN4]2− anion of this compound exhibits inversion symmetry and shows the Pd2+ transition metal cation likewise in a square-planar coordination environment. Compound (5 is also a rare occurrence of a non-polymeric compound in which the pseudohalide ligand NCS− behaves both as thiocyanate and isothiocyanate, i.e. is coordinating either through the N atom (in the cation or the S atom (in the anion.

Ultrasonics Promoted Synthesis of 5-(Pyrazol-4-yl-4,5-Dihydropyrazoles Derivatives

Directory of Open Access Journals (Sweden)

Manuel Nogueras

2013-04-01

Full Text Available A series of new 1,3-diaryl-5-(1-phenyl-3-methyl-5-chloropyrazol-4-yl-4,5-dihydropyrazole derivatives have been synthesized under sonication conditions in ethanol or methanol/glacial acetic acid mixture (5/1 ratio with two equivalents of hydrazines and seven kinds of chalcone-like heteroanalogues obtained from 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde. The structures were established on the basis of NMR, IR, MS and element analysis. This method provides several advantages over current reaction methodologies, including a simple work-up procedure, shorter reaction times (2–20 min and good yields (65%–80%.

Crystal structure of an organic–inorganic supra­molecular salt based on a 4,4′-methyl­enebis(3,5-dimethyl-1H-pyrazol-2-ium) cation and a β-octa­molybdate anion

Science.gov (United States)

Amarante, Tatiana R.; Gonçalves, Isabel S.; Almeida Paz, Filipe A.

2016-01-01

The asymmetric unit of the title compound, bis­[4,4′-methyl­enebis(3,5-dimethyl-1H-pyrazol-2-ium)] β-octa­molybdate, (C11H18N4)2[Mo8O26] or (H4mbdpz)2[Mo8O26], is composed of an H4mbdpz2+ cation and half of the β-octa­molybdate anion which is completed by inversion symmetry. The organic mol­ecular units are engaged in a series of N—H⋯O hydrogen bonds with neighbouring anions, with N⋯O distances and N—H⋯O angles in the ranges 2.730 (2)–2.941 (2) Å and 122–166°, respectively. These inter­actions lead to the formation of a supra­molecular two-dimensional network parallel to the (010) plane. PMID:26958369

Identification of 5-(1-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)thiophene-2-Carboxamides as Novel and Selective Monoamine Oxidase B Inhibitors Used to Improve Memory and Cognition.

Science.gov (United States)

Kaplan, Alan P; Keenan, Terence; Scott, Roderick; Zhou, Xianbo; Bourchouladze, Rusiko; McRiner, Andrew J; Wilson, Mark E; Romashko, Darlene; Miller, Regina; Bletsch, Matthew; Anderson, Gary; Stanley, Jennifer; Zhang, Adia; Lee, Dong; Nikpur, John

2017-12-20

Initial work in Drosophila and mice demonstrated that the transcription factor cyclic adenosine monophosphate (cAMP) response element binding protein (CREB) is a master control gene for memory formation. The relationship between CREB and memory has also been found to be true in other species, including aplysia and rats. It is thus well-established that CREB activation plays a central role in memory enhancement and that CREB is activated during memory formation. On the basis of these findings, a phenotypic high-throughput screening campaign utilizing a CRE-luciferase (CRE-Luci) SK-N-MC cell line was performed to identify compounds that enhance transcriptional activation of the CRE promoter with a suboptimal dose of forskolin. A number of small-molecule hits of unknown mechanisms of action were identified in the screening campaign, including HT-0411. Follow-up studies suggested that the CREB activation by HT-0411 is attributed to its specific and selective inhibition of monoamine oxidase B (MAO-B). Further, HT-0411 was shown to improve 24 h memory in rodents in a contextual fear conditioning model. This report describes the lead optimization of a series of 5-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) thiophene-2-carboxamides that were identified as novel, potent, and selective inhibitors of MAO-B. Extensive SAR studies and in vivo behavioral evaluations of this and other related analogue series identified a number of potential clinical development candidates; ultimately, compound 8f was identified as a candidate molecule with high selectivity toward MAO-B (29-56 nM) over MAO-A (19% inhibition at a screening concentration of 50 μM), an excellent profile against a panel of other enzymes and receptors, good pharmacokinetic properties in rodents and dogs, and efficacy in multiple rodent memory models.

Three-phase Bone Scintigraphy Can Predict the Analgesic Efficacy of Ketamine Therapy in CRPS.

Science.gov (United States)

Sorel, Marc; Beatrix, Jacques-Christian; Locko, Blanche; Armessen, Catherine; Domec, Anne-Marie; Lecompte, Otilia; Boucheneb, Sofiane; Harache, Benoit; Robert, Jacques; Lefaucheur, Jean-Pascal

2018-03-13

The efficacy of ketamine in relieving complex regional pain syndrome (CRPS) lacks predictive factors. The value of three-phase bone scintigraphy (TPBS) was assessed or this purpose. TPBS was performed in 105 patients with unilateral, focal CRPS of type 1 before 5 days of ketamine infusions. Tracer uptake was measured in the region of interest concerned by CRPS and the contralateral homologous region. For the three scintigraphic phases (vascular, tissular, and bone phases), an asymmetry ratio of fixation was calculated between the affected and the unaffected sides (VPr, TPr, and BPr). Ketamine efficacy was assessed on pain intensity scores. Ketamine-induced pain relief did not correlate with VPr, TPr, and BPr, but with the ratios of these ratios: BPr/TPr (r=0.32, P=0.009), BPr/VPr (r=0.34, P=0.005), and TPr/VPr (r=0.23, P=0.02). The optimum cut-off value for predicting the response to ketamine therapy was >1.125 for BPr/TPr, >1.075 for BPr/VPr, and >0.935 for TPr/VPr. The combination of increased values of BPr/TPr, BPr/VPr, and TPr/VPr was extremely significantly associated with ketamine therapy outcome. The relative hyperfixation of the radioactive tracer in the limb region concerned by CRPS in phases 2 and 3 versus phase 1 of TPBS correlated positively to the analgesic efficacy of ketamine. This study shows for the first time the potential predictive value of TPBS regarding ketamine therapy outcome. In addition, these results suggest that the analgesic action of ketamine is not restricted to "central" mechanisms, but may also involve "peripheral" mechanisms related to tissue inflammation and bone remodeling.

Crystal Structure of N,N,N’,N’-tetra-[(3,5-dimethyl-1-pyrazolyl methyl]-para-phenylenediamine

Directory of Open Access Journals (Sweden)

Taibi Ben-Hadda

2003-02-01

Full Text Available The title compound, molecular formula C30H40N10, crystallizes and exhibits a cisoidal conformation around a central p-phenylenediamine ring suggesting that this bis-tripodal ligand is highly flexible and could be accommodated by many and original metal coordinations. All four five-membered pyrazole rings are identical. The molecule presents an inversion centre that coincides with the phenyl ring centre: pyrazole rings are two-by-two equivalent. The electrostatic spatial intramolecular repulsion between N4 and N5 is probably responsible for this general arrangement. These data emphasize the basic character of nitrogens N4 and N5.

Antiferromagnetic Coupling in the Polynuclear Compound [Cu(II) (Allopurinolate) (OH-)] n

Science.gov (United States)

Acevedo-Chávez, Rodolfo; Costas, María. Eugenia; Escudero-Derat, Roberto

1994-11-01

Synthetic, spectral, and magnetic studies of the Cu(II) polynuclear coordination compound [Cu(HL(OH-)]n with bridging OH- and HL (allopurinolate; C5H3N4O-) ligands are reported. The compound is obtained from aqueous media (at several pH values and from CI-, Br-, NO-3, SO2-4, ClO-4, and CH3CO-2 Cu(II) salts), from DMSO at ca. 70°C using several of the above salts, and under refluxing methanol employing Cu(SO4) or Cu(CH3CO2)2. The results suggest that the compound [Cu(HL)(OH-)]n has a polynuclear form in which the bridging allopurinolate is coordinated through the N(1) and N(2) atoms of the pyrazolic moiety. All attempts to grow crystals suitable for X-ray studies were unsuccessful, and an amorphous compound was always obtained. Magnetic studies show the existence of a strong antiferromagnetic coupling, which may be associated with a favorable structural arrangement between the metallic centers and the bridging ligands. This magnetic behavior is remarkable for a Cu(II) polynuclear coordination compound. Spectral and magnetic results together with the coordination modes of the bridging groups let us postulate as a possible arrangement a cyclic polynuclear structure presenting the allopurinolate and OH- bridging ligands in a mutually trans configuration. This work is the first EPR spectral and magnetic study reported for a coordination compound with the allopurinol heterocycle as a ligand and, thus for the first example of a polynuclear coordination compound combining allopurinolate and OH- as bridging groups.

Synthesis and Antibacterial Evaluation of Novel Heterocyclic Compounds Containing a Sulfonamido Moiety

Directory of Open Access Journals (Sweden)

Eman A. El-Bordany

2013-01-01

Full Text Available Aiming for the synthesis of new heterocyclic compounds containing a sulfonamido moiety suitable for use as antibacterial agents, the precursor ethyl {[4-N-(4,6-dimethylpyrimidin-2-ylsulfamoyl]phenylazo}cyanoacetate was reacted with a variety of active methylene compounds producing pyran, pyridine and pyridazine derivatives. Also, the reactivity of the precursor hydrazone towards hydrazine derivatives to give pyrazole and oxazole derivatives was studied. On the other hand, treatment of the same precursor with urea, thiourea and/or guanidine hydrochloride furnished pyrimidine and thiazine derivatives, respectively. The newly synthesized compounds were tested for antibacterial activity, whereby eight compounds were found to have high activities.

Crystallization of the virulent and benign subtilisin-like proteases from the ovine footrot pathogen Dichelobacter nodosus

International Nuclear Information System (INIS)

Wong, Wilson; Kennan, Ruth M.; Rosado, Carlos J.; Rood, Julian I.; Whisstock, James C.; Porter, Corrine J.

2010-01-01

The subtilisin-like proteases AprV2 and BprV from virulent strains and AprB2 and BprB from benign strains of D. nodosus have been crystallized and X-ray diffraction data have been collected to 2.0, 2.0, 1.7 and 1.8 Å resolution, respectively. Dichelobacter nodosus is the principal causative agent of ovine footrot, a disease of significant economic importance to the sheep industry. D. nodosus secretes a number of subtilisin-like serine proteases which mediate tissue damage and presumably contribute to the pathogenesis of footrot. Strains causing virulent footrot secrete the proteases AprV2, AprV5 and BprV and strains causing benign footrot secrete the closely related proteases AprB2, AprB5 and BprB. Here, the cloning, purification and crystallization of AprV2, AprB2, BprV and BprB are reported. Crystals of AprV2 and AprB2 diffracted to 2.0 and 1.7 Å resolution, respectively. The crystals of both proteases belonged to space group P1, with unit-cell parameters a = 43.1, b = 46.0, c = 47.2 Å, α = 97.8, β = 115.2, γ = 115.2° for AprV2 and a = 42.7, b = 45.8, c = 45.7 Å, α = 98.4, β = 114.0, γ = 114.6° for AprB2. Crystals of BprV and BprB diffracted to 2.0 and 1.8 Å resolution, respectively. The crystals of both proteases belonged to space group P2 1 , with unit-cell parameters a = 38.5, b = 89.6, c = 47.7 Å, β = 113.6° for BprV and a = 38.5, b = 90.5, c = 44.1 Å, β = 109.9° for BprB. The crystals of all four proteases contained one molecule in the asymmetric unit, with a solvent content ranging from 36 to 40%

Alum as a Catalyst for the Synthesis of Bispyrazole Derivatives

Directory of Open Access Journals (Sweden)

Mohammad Ali Zolfigol

2016-01-01

Full Text Available Compounds with pyrazolemoieties as nitrogen-containing heterocyclic systems have received attention owing to their diverse biological activities. Alum (KAl(SO42∙12H2O is an inexpensive, reusable and nontoxic catalyst used to synthesize 1H-pyrazole derivatives via the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H-one and carbonyl compound under solvent-free conditions at 60 °C. The proposed method has been used for the preparation of 1H-pyrazole derivatives to yield green products for cleaning-in-place and to avoid toxic catalysts and hazardous solvents in accordance with the philosophy of sustainable chemistry.

Lymphatic absorption of hypolipidemic compound, 1-O-[p-(myristyloxy)-alpha-methylcinnamoyl] glycerol (LK-903).

Science.gov (United States)

Sugihara, J; Furuuchi, S

1988-02-01

The intestinal absorption process of 1-O-[p-(myristyloxy)-alpha-methylcinnamoyl] glycerol (LK-903), a new hypolipidemic compound, was studied in rats. When 3H-LK-903 or 3H-LKA [3H-p- (myristyloxy)-alpha-methyl cinnamic acid], labeled at the cinnamic acid moiety, or 14C-LK-903, labeled at the glycerol moiety, were administered orally to thoracic duct-cannulated rats at a dose of 0.233 mmol/kg, 31.1, 6.7 and 18.1% of the dose, respectively, appeared in the lymph within 24 h. In this case, radioactive compounds in the lymph lipids consisted of LKA (radioactivity was not detected in the fraction of LKA with 14C-LK-903), LK-903, diglyceride analogues and triglyceride analogues. The percentages of the triglyceride analogues were the highest, followed by the diglyceride analogues. On the other hand, when doubly labeled LK-903 (3H/14C = 1, corrected ratio) was administered orally, the values of 3H/14C for the monoglyceride, diglyceride and triglyceride analogues in the lymph were 1.2-1.5, 1.7-1.9 and 1.9-2.7, respectively. The lymphatic absorption of LK-903 was stimulated by the presence of lecithin but inhibited by a high dose of triolein. The results indicated that (1) LK-903 formed micelles in the intestine, (2) a large part of LK-903 was absorbed as such, (3) a part of LK-903 was hydrolyzed in the intestinal mucosa, and (4) a part of LKA formed by hydrolysis was again utilized to synthesize the higher glycerides and absorbed via the lymphatic absorption route for lipids.

Spacer type mediated tunable spin crossover (SCO) characteristics of pyrene decorated 2,6-bis(pyrazol-1-yl)pyridine (bpp) based Fe(ii) molecular spintronic modules.

Science.gov (United States)

Kumar, Kuppusamy Senthil; Šalitroš, Ivan; Moreno-Pineda, Eufemio; Ruben, Mario

2017-08-14

A simple "isomer-like" variation of the spacer group in a set of Fe(ii) spin crossover (SCO) complexes designed to probe spin state dependence of electrical conductivity in graphene-based molecular spintronic junctions led to the observation of remarkable variations in the thermal- and light-induced magnetic characteristics, paving a simple route for the design of functional SCO complexes with different temperature switching regimes based on a 2,6-bis(pyrazol-1-yl)pyridine ligand skeleton.

Preparation, structure and luminescent characterization of a series of metal-organic frameworks based on flexible ligands with nitrogen heterocycles and carboxyl

Science.gov (United States)

Dai, Hai-yu; Tang, Yu-yuan; Wang, Cui-juan; Chen, Shuang; Tong, Yan; Zhang, Zhi-Bing

2017-12-01

Seven new compounds, [Zn(pypymba)2]n(1), [Co(pypymba)2]n(2), [Cd(pypymba)2]n(3), [Cd(Hpypymba)Cl2]n(4), {[Cd(pypymba)Cl]·C2H5OH·H2O}n(5), [Cd(pypyaa)Cl]n(6), {[Cd2(pyznpy)2Cl2H2O]·H2O}n(7) [Hpypymba = 4-((3-(pyrazin-2-yl)-1H-pyrazol-1-yl)methyl)benzoic acid, Hpyznpy = 4-((3-(pyridin-2-yl)-1H-pyrazol-1-yl)methyl)benzoic acid, Hpypyaa = 2-(3-pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid], were hydrothermally synthesized by tuning the metal ion's species, counter anions, solvents and pH values and characterized by routine methods: XRD, elemental analysis, fluorescence properties analysis, TGA and crystal structure analysis and single-crystal X-ray crystallography. The main structures of the compounds 1, 2, and 3 are extended to similar 3D structures by C-H…N, C-H…O hydrogen bonds and π…π stacking under the same synthesis method. Each Cd(II) node of compound 4 has four chlorine bridges (two pairs of double chlorine); Each Cd(II) node of compounds 5, 6 has two chlorine bridges (a pair of double chlorine bridges), while their spatial structures are expanded in different ways. Compound 7 also contains chlorine atoms, but does not contain chlorine bridged structures. The luminescent properties of compound 7 and the ones immersed in various kinds of organic compounds and nitrate@EtOH solutions have been investigated. Importantly, 7 shows highly sensitive response to nitrobenzene and Fe3+ through luminescence quenching effects, making it a promising luminescent sensor for nitrobenzene and Fe3+.

AcEST: DK958157 [AcEST

Lifescience Database Archive (English)

Full Text Available Ca... 31 3.8 sp|P42268|NDD_BPR70 Nuclear disruption protein OS=Enterobacteria... 31 5.0 sp|Q8N2S1|LTBP4_HUMA...MKYCLFCGLCV 97 >sp|P42268|NDD_BPR70 Nuclear disruption protein OS=Enterobacteria phage RB70 GN=ndd PE=4 SV=1

A Novel Hydroxamate-Based Compound WMJ-J-09 Causes Head and Neck Squamous Cell Carcinoma Cell Death via LKB1-AMPK-p38MAPK-p63-Survivin Cascade.

Science.gov (United States)

Yen, Chia-Sheng; Choy, Cheuk-Sing; Huang, Wei-Jan; Huang, Shiu-Wen; Lai, Pin-Ye; Yu, Meng-Chieh; Shiue, Ching; Hsu, Ya-Fen; Hsu, Ming-Jen

2018-01-01

Growing evidence shows that hydroxamate-based compounds exhibit broad-spectrum pharmacological properties including anti-tumor activity. However, the precise mechanisms underlying hydroxamate derivative-induced cancer cell death remain incomplete understood. In this study, we explored the anti-tumor mechanisms of a novel aliphatic hydroxamate-based compound, WMJ-J-09, in FaDu head and neck squamous cell carcinoma (HNSCC) cells. WMJ-J-09 induced G2/M cell cycle arrest and apoptosis in FaDu cells. These actions were associated with liver kinase B1 (LKB1), AMP-activated protein kinase (AMPK) and p38 mitogen-activated protein kinase (p38MAPK) activation, transcription factor p63 phosphorylation, as well as modulation of p21 and survivin. LKB1-AMPK-p38MAPK signaling blockade reduced WMJ-J-09's enhancing effects in p63 phosphorylation, p21 elevation and survivin reduction. Moreover, WMJ-J-09 caused an increase in α-tubulin acetylation and interfered with microtubule assembly. Furthermore, WMJ-J-09 suppressed the growth of subcutaneous FaDu xenografts in vivo . Taken together, WMJ-J-09-induced FaDu cell death may involve LKB1-AMPK-p38MAPK-p63-survivin signaling cascade. HDACs inhibition and disruption of microtubule assembly may also contribute to WMJ-J-09's actions in FaDu cells. This study suggests that WMJ-J-09 may be a potential lead compound and warrant the clinical development in the treatment of HNSCC.

(μ-3-Acetyl-5-carboxylato-4-methylpyrazolido-1:2κ4N2,O3:N1,O5-μ-chlorido-tetrapyridine-1κ2N,2κ2N-chlorido-1κCl-dicopper(II propan-2-ol solvate

Directory of Open Access Journals (Sweden)

Sergey Malinkin

2009-10-01

Full Text Available The title compound, [Cu2(C7H6N2O3Cl2(C5H5N4]·C3H8O, is a binuclear pyrazolate complex, in which the two CuII atoms have different coordination numbers and are connected by a bridging Cl atom. One CuII atom has a distorted square-pyramidal coordination environment formed by two pyridine N atoms, one bridging Cl atom and an N,O-chelating pyrazolate ligand. The other CuII atom adopts an octahedral geometry defined by two pyridine N atoms at the axial positions, two Cl atoms and the coordinated pyrazolate ligand in the equatorial plane. An O—H...O hydrogen bond connects the complex molecules and propan-2-ol solvent molecules into pairs. These pairs form columns along the a axis.

Tunable Cascade Reaction of Aryl Diazonium Salts and Trialkylamine: Synthesis of Monofluorinated Arylhydrazones and gem-Difluorinated Azo Compounds.

Science.gov (United States)

Guo, Rui; Zhang, Zhengjuan; Shi, Feng; Tang, Pingping

2016-03-04

The first example of a mild and tunable cascade reaction of aryl diazonium salts and trialkylamine in the presence of Selectfluor to prepare monofluorinated arylhydrazones and gem-difluorinated azo compounds without metal has been explored. In the presence of H2O, the monofluorinated arylhydrazones were observed in moderate to good yield. In the absence of H2O, the gem-difluorinated azo compounds were obtained. The fluorinated arylhydrazones were utilized to synthesize fluorinated pyrazoles and other nitrogen-containing compounds.

Dichlorido{2-[(5-methyl-1H-pyrazol-3-yl-κN2methyl]-1H-1,3-benzimidazole-κN3}zinc

Directory of Open Access Journals (Sweden)

Karim Chkirate

2017-01-01

Full Text Available The asymmetric unit of the title complex, [ZnCl2(C12H12N4], contains two independent molecules having similar conformations. The coordination about the ZnII atom is distorted tetrahedral, with the geometrical constraints of the chelating ligand responsible for the observed distortion. Each of the independent molecules forms chains in the crystal through pairs of N—H...Cl hydrogen bonds, using the pyrazole and benzimidazole N—H groups as donors. The first molecule forms chains running parallel to the b axis, while the other molecule affords the same kind of one-dimensional supramolecular structure parallel to the a axis. The structure was refined as a two-component twin with BASF = 0.0437 (4.

Heterocyclic Analogues of Xanthone and Xanthione. 1H-Pyrano[2,3-c:6,5-c]dipyrazol-4(7H-ones and Thiones: Synthesis and NMR Data

Directory of Open Access Journals (Sweden)

Wolfgang Holzer

2010-09-01

Full Text Available The synthesis of the title compounds is described. Reaction of 1-substituted 2-pyrazolin-5-ones with 5-chloro-1-phenyl-1H-pyrazole-4-carbonyl chloride or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl chloride, respectively, using calcium hydroxide in refluxing 1,4-dioxane gave the corresponding 4-heteroaroylpyrazol-5-ols, which were cyclized into 1H-pyrano[2,3-c:6,5-c]dipyrazol-4(7H-ones by treatment with K2CO3/DMF. The latter were converted into the corresponding thiones upon reaction with Lawesson’s reagent. Detailed NMR spectroscopic investigations (1H, 13C, 15N of the ring systems and their precursors are presented.

Assessment of genetic integrity, splenic phagocytosis and cell death potential of (Z-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3dihydro-1H-pyrazol-4-yl amino-4-oxobut-2-enoic acid and its effect when combined with commercial chemotherapeutics

Directory of Open Access Journals (Sweden)

Rodrigo Juliano Oliveira

2018-02-01

Full Text Available Abstract The increased incidence of cancer and its high treatment costs have encouraged the search for new compounds to be used in adjuvant therapies for this disease. This study discloses the synthesis of (Z-4-((1,5-dimethyl-3-oxo-2-phenyl-2,3dihydro-1H-pyrazol-4-yl amino-4-oxobut-2-enoic acid (IR-01 and evaluates not only the action of this compound on genetic integrity, increase in splenic phagocytosis and induction of cell death but also its effects in combination with the commercial chemotherapeutic agents doxorubicin, cisplatin and cyclophosphamide. IR-01 was designed and synthesized based on two multifunctionalyzed structural fragments: 4-aminoantipyrine, an active dipyrone metabolite, described as an antioxidant and anti-inflammatory agent; and the pharmacophore fragment 1,4-dioxo-2-butenyl, a cytotoxic agent. The results indicated that IR-01 is an effective chemoprotector because it can prevent clastogenic and/or aneugenic damage, has good potential to prevent genomic damage, can increase splenic phagocytosis and lymphocyte frequency and induces cell death. However, its use as an adjuvant in combination with chemotherapy is discouraged since IR-01 interferes in the effectiveness of the tested chemotherapeutic agents. This is a pioneer study as it demonstrates the chemopreventive effects of IR-01, which may be associated with the higher antioxidant activity of the precursor structure of 4-aminoantipyrine over the effects of the 1,4-dioxo-2-butenyl fragment.

Combining silver- and organocatalysis: an enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles.

Science.gov (United States)

Hack, Daniel; Chauhan, Pankaj; Deckers, Kristina; Mizutani, Yusuke; Raabe, Gerhard; Enders, Dieter

2015-02-11

A one-pot asymmetric Michael addition/hydroalkoxylation sequence, catalyzed by a sequential catalytic system consisting of a squaramide and a silver salt, provides a new series of chiral pyrano-annulated pyrazole derivatives in excellent yields (up to 95%) and high enantioselectivities (up to 97% ee).

Synthesis of new trihalo methylated and non-symmetrical substituted 2-(1H-pyrazolyl)-5-(1H-pyrazolylcarbonyl)pyridines

International Nuclear Information System (INIS)

Bonacorso, Helio G.; Paim, Gisele R.; Guerra, Carolina Z.; Sehnem, Ronan C.; Cechinel, Cleber A.; Porte, Liliane M. F.; Martins, Marcos A. P.; Zanatta, Nilo

2009-01-01

This paper describes the synthesis of a new series of 2-[3-alkyl(aryl/heteroaryl)-5-trifluoro(chloro)methyl-5-hydroxy-4,5-dihydro -1H-pyrazol-1-yl]-5- [3-alkyl(aryl/heteroaryl)-5-trifluoro(chloro)methyl-5-hydroxy= -4,5-dihydro-1H-pyrazol-1-yl-1-carbonyl] pyridines by the cyclocondensation reaction of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1- trifluoro(chloro) -3-alken- 2-ones [CX 3 C(O)CH=CR 1 OR, where R = Me, Et; R 1 = H, Me, Ph, 4-MeOPh, 4-NO 2 Ph, 4,4'-Biphenyl, 1-Naphthyl, Fur-2-yl, Thien-2-yl and X = F, Cl] with 6-hydrazinonicotinic hydrazide hydrate. Yields of 62 to 97% were obtained when the reactions were performed in ethanol as solvent at 78 deg C for 4 hours. In a subsequent step, the dehydration reactions of 2-(5-hydroxy-1H-pyrazol-1-yl)-5-(5-hydroxy-1H?pyrazol-1-yl-1-carbonyl) pyridines were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of 2- [3-alkyl(aryl/heteroaryl)-5-trifluoro(chloro)methyl-1H-pyrazol-1-yl]-5- [3-alkyl(aryl/heteroaryl)-5 -trifluoro(chloro)methyl-1H-pyrazol-1-yl-1-carbonyl]pyridi= nes, in 64 to 86% yields. (author)

Design and Synthesis of Novel and Selective Glycine Transporter-1 (GlyT1) Inhibitors with Memory Enhancing Properties.

Science.gov (United States)

Santora, Vincent J; Almos, Theresa A; Barido, Richard; Basinger, Jillian; Bellows, Chris L; Bookser, Brett Carder; Breitenbucher, J Guy; Broadbent, Nicola J; Cabebe, Clifford; Chai, Chih-Kun; Chen, Mi; Chow, Stephine; Chung, De Michael; Crickard, Lindsay; Danks, Anne M; Freestone, Graeme; Gitnick, Dany; Gupta, Varsha; Hoffmaster, Christine; Hudson, Andrew R; Kaplan, Alan P; Kennedy, Michael R; Lee, Dong; Limberis, James; Ly, Kiev; Mak, Chi Ching; Masatsugu, Brittany; Morse, Andrew C; Na, Jim; Neul, David; Nikpur, John; Peters, Marco; Petroski, Robert E; Renick, Joel; Sebring, Kristen; Sevidal, Samantha; Tabatabaei, Ali; Wen, Jenny; Yan, Yingzhuo; Yoder, Zachary W; Zook, Douglas

2018-06-11

We report here the identification and optimization of a novel series of potent GlyT1 inhibitors. A ligand design campaign that utilized known GlyT1 inhibitors as starting points led to the identification of a novel series of pyrrolo[3,4-c]pyrazoles amides (21-50) with good in vitro potency. Subsequent optimization of physicochemical and in vitro ADME properties produced several compounds with promising pharmacokinetic profiles. In vivo inhibition of GlyT1 was demonstrated for select compounds within this series by measuring the elevation of glycine in the cerebrospinal fluid (CSF) of rats after a single oral dosing of 10 mg/kg. Ultimately, an optimized lead, compound 46, demonstrated in vivo efficacy in a rat Novel Object Recognition (NOR) assay after oral dosing at 0.1, 1, and 3 mg/kg.

Lipophilicity screening of novel drug-like compounds and comparison to clog P.

Science.gov (United States)

Lu, Dujuan; Chambers, Peter; Wipf, Peter; Xie, Xiang-Qun; Englert, Danielle; Weber, Stephen

2012-10-05

We determined the distribution coefficients of solutes between a polymer film phase (polyvinyl chloride (PVC) with 67% (w/w) dioctyl sebacate (DOS)) and an aqueous phase in a 96-well format. The parallel measurement approach is efficient and uses very little material. Polymer-water distribution coefficients (D(pw)) at different pH values yield the pKa and polymer-water partition coefficient values (P(pw)) of the solutes. log P(pw) of a prominent drug-like compound, 2H-1,2,6-thiadiazine, 3-methyl-5-phenyl-,1,1-dioxide, is in good agreement with clog P, while the pK(a) value is substantially different from calculated values. This method has been also successfully applied to a library of novel drug-like compounds. log D(pw) values (at pH 4.0, 7.0, 10.0) of 24 novel drug-like compounds have been determined with good reproducibility with the 96-well plate approach. Differences between experimental values and a variety of available calculated values are significant. This emphasizes the need for laboratory separations-based measurements of log D. Copyright © 2012 Elsevier B.V. All rights reserved.

Bromopyrogallol red: a new microanalytical reagent for amperometric estimation of Dy (III) and Gd (III)

International Nuclear Information System (INIS)

Sahu, G.P.; Lavale, S.C.

2000-01-01

Bromopyrogallol red (BPR) has been extensively used as an indicator but its electro-reducibility has proved it to be a very useful amperometric reagent. BPR reduces on a DME in KNO 3 in the entire pH range 2.4 to 9.5. It produces single stage reduction wave below pH 4, but a two stage reduction wave in the basic range. Progressive ionization of hydroxyl group and distinct colour species of BPR, have also been studied using a Bausch and Lomb spectronic-20 spectrophotometer in order to support electroanalytical studies. On performing amperometric titrations of Dy(III) and Gd(III) with BPR at its plateau potential 1.0 V at pH 2.6 and μ = 0.4, reversed L-shaped titration curves have been observed indicating metal to BPR ratio 1:1 and the colour changes from claret red to orange yellow. The reagents have been tested in presence of various diverse ions and tolerance limits have been computed. Na + , K + , Li + , Cl - , ClO 4 - , CH 3 COO - , Pd 2+ , Fe 3+ ions did not interfere in the titrimetric procedure. However, small amounts of Bi 3+ , Pb 2+ , Ni 2+ , Co 2+ , Cd 2+ , Mg 2+ and rare earth metals have hampered the titrimetric estimations. (author)

Exploring selectivity requirements for COX-2 versus COX-1 binding of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines using topological and physico-chemical parameters.

Science.gov (United States)

Chakraborty, Santanu; Sengupta, Chandana; Roy, Kunal

2005-04-01

Considering the current need for development of selective cyclooxygenase-2 (COX-2) inhibitors, an attempt has been made to explore physico-chemical requirements of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines for binding with COX-1 and COX-2 enzyme subtypes and also to explore the selectivity requirements. In this study, E-states of different common atoms of the molecules (calculated according to Kier & Hall), first order valence connectivity and physicochemical parameters (hydrophobicity pi, Hammett sigma and molar refractivity MR of different ring substituents) were used as independent variables along with suitable dummy parameters in the stepwise regression method. The best equation describing COX-1 binding affinity [n = 25, Q2 = 0.606, R(a)2 = 0.702, R2 = 0.752, R = 0.867, s = 0.447, F = 15.2 (df 4, 20)] suggests that the COX-1 binding affinity increases in the presence of a halogen substituent at R1 position and a p-alkoxy or p-methylthio substituent at R2 position. Furthermore, a difluoromethyl group is preferred over a trifluoromethyl group at R position for the COX-1 binding. The best equation describing COX-2 binding affinity [n = 32, Q2 = 0.622, R(a)2= 0.692, R2 = 0.732, R = 0.856, s = 0.265, F = 18.4 (df 4, 27)] shows that the COX-2 binding affinity increases with the presence of a halogen substituent at R1 position and increase of size of R2 substituents. However, it decreases in case of simultaneous presence of 3-chloro and 4-methoxy groups on the phenyl nucleus and in the presence of highly lipophilic R2 substituents. The best selectivity relation [n = 25, Q2 = 0.455, R(a)2 = 0.605, R2 = 0.670, R = 0.819, s = 0.423, F = 10.2 (df 4, 20)] suggests that the COX-2 selectivity decreases in the presence of p-alkoxy group and electron-withdrawing para substituents at R2 position. Again, a trifluoro group is conductive for the selectivity instead of a difluoromethyl group at R position. Furthermore, branching may also play significant role in

Synthesis and antimicrobial activities of novel 1,4-benzothiazine derivatives

Directory of Open Access Journals (Sweden)

Vijay V. Dabholkar

2016-09-01

Full Text Available A series of 2H,4H-2-[3,5-dimethyl-4-(substituted phenyl azo pyrazol-1-yl] carbonyl methyl-3-oxo-1,4-benzothiazine derivatives have been synthesized by the reaction of 2H,4H-2-hydrazino carbonyl methyl-3-oxo-1,4-benzothiazine with acetyl acetone derivatives using ultrasound in lesser time with higher yields. All the synthesized compounds were investigated for their antibacterial activities. The result indicated that the compounds show convincing activities against Gram-positive bacteria (Bacillus subtilis and Streptococcus lactis when compared with standard drug (ampicillin trihydrate. These compounds were also synthesized by conventional method and their structures have been elucidated on the basis of spectral analyses and chemical reactions.

USE OF TRANSESTERIFIED 1,3-DIKETOESTERS IN THE ...

African Journals Online (AJOL)

Preferred Customer

Pyrazoles are important class of nitrogen containing five membered heterocyclic compounds. Compounds .... The chemical shift value of the methoxy carbon in 13C NMR is observed at δ 53 ppm (-OCH3), the carbon atoms connected to methoxy group are observed at the δ 156-167 ppm range, signal δ 167 ppm is due to ...

Studies on the effect of a newly synthesized Schiff base compound from phenazone and vanillin on the corrosion of steel in 2M HCl

International Nuclear Information System (INIS)

Emreguel, Kaan C.; Hayvali, Mustafa

2006-01-01

The inhibiting action of a Schiff base 4-[(4-hydroxy-3-hydroxymethyl-benzylidene)-amino]-1,5-dimethyl-2-phenyl-1,2 -dihydro-pyrazol-3-one (phv), derived from 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (phz) and 4-hydroxy-3-methoxy-benzaldehyde (vn), towards the corrosion behavior of steel in 2M HCl solution has been studied using weight loss, polarization and electrochemical impedance spectroscopy (EIS) techniques. Although vn and phz were found to retard the corrosion rate of steel, the compound synthesized from vn and phz was seen to retard the corrosion rate even more. At constant temperature, the corrosion rate decreases with increasing inhibitor concentration. However, at any inhibitor concentration the increase in temperature leads to an increase in the corrosion rate of steel. The activations energies, ΔE a , as well as other thermodynamic parameters (ΔG ads 0 , ΔH ads 0 ) for the inhibitor process were calculated. The inhibitor efficiencies calculated from all the applied methods were in agreement and were found to be in the order: phv>phz>vn

Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of some new 4,6-dimethoxy-5-(heterocyclesbenzofuran starting from naturally occurring visnagin

Directory of Open Access Journals (Sweden)

E.R. El-Sawy

2014-12-01

Full Text Available Novel 3-(4,6-dimethoxybenzofuran-5-yl-1-phenyl-1H-pyrazole-4-carboxaldehyde (3 and 3-chloro-3-(4,6-dimethoxybenzofuran-5-ylpropenal (4 were prepared via Vilsmeier–Haack reaction of 1-(4,6-dimethoxybenzofuran-5-ylethanone (1 and its hydrazone derivative 2. Reaction of compound 4 with some hydrazine derivatives, namely hydrazine hydrate, phenylhydrazine and benzylhydrazine hydrochloride led to the formation of pyrazole derivatives 5–8, respectively. On the other hand, reaction of compound 4 with thiourea, urea or guanidine gave the pyrimidine derivatives 9–11, respectively. Reaction of amino compound 11 with acetic anhydride, benzoyl chloride and benzenesulphonyl chloride yielded N-substituted pyrimidine derivatives 12–14, respectively. Reaction of diazonium salt of compound 11 with sodium azide afforded azidopyrimidine derivative 15, which upon reaction with ethyl acetoacetate gave 1,2,3-triazole derivative 16. Acid catalyzed reaction of 11 with p-nitrobenzaldehyde gave Schiff base 17, which cyclized upon reaction with thioglycolic acid or chloroacetyl chloride to give thiazolidin-4-one 18 and azetidin-2-one 19, respectively. The newly synthesized compounds were tested for their anti-inflammatory, analgesic and anticonvulsant activities. Depending on the obtained results, the newly synthesized compounds possess significant anti-inflammatory, analgesic and anticonvulsant activities.

Modulation of 17{beta}-estradiol-induced responses in fish by cytochrome P4501A1 inducing compounds

Energy Technology Data Exchange (ETDEWEB)

Anderson, M.J.; Hinton, D.E. [Univ. of California, Davis, CA (United States)

1995-12-31

Some compounds which induce cytochrome P4501A1 (CYP1A1) are antiestrogenic in mammalian bioassay, and this effect is linked to aryl hydrocarbon (Ah) receptor. Liver of fish synthesizes estrogen-inducible egg yolk precursor protein vitellogenin (Vg) which is critical for oocyte maturation and ovarian development. To determine if Ah receptor-linked endocrine modulation could occur in fish liver, primary cultures of juvenile rainbow trout (Oncorhynchus mykiss) liver cells were co-administered 17{beta}-estradiol and CYP1A1 inducing compounds. Vitellogenin and albumin, estimated by ELISA measurement of concentration in the media 48 hrs after treatment, formed the basis for the test. Cellular CYP1A1 protein content and catalytic activity was estimated by ELISA and ethoxyresorufin-O-deethylase (EROD) activity assays respectively. Equivalent viability (mitochondrial dehydrogenase activity) and secretary functional capacity (albumin synthesis) were estimated and correlated with other results. In descending order, 2,3,4,7,8 pentachlorodibenzofuran (10{sup {minus}12} to 10{sup {minus}8} M) > 2,3,7,8 tetrachlorodibenzo-p-dioxin {approx_equal} 2,3,7,8 tetrachlorodibenzofuran (10{sup {minus}11} to 10{sup {minus}8} M) > {beta}-naphthoflavone (10{sup {minus}7} to 10{sup {minus}6} M) inhibited Vg synthesis in 17{beta}-estradiol treated liver cells. Potency of inhibition directly related to strength as an inducer of CYP1A1 protein. At 10-8 M, PCB congeners 77, 126, and 156 did not inhibit Vg synthesis and induced no or only moderate CYP1A1 protein. At 10-8 M, PCB congener 114, a weak CYP1A1 inducer, potentiated Vg synthesis relative to cells treated with 17{beta}-estradiol alone. This study increases their understanding of the consequences of hepatic CYP1A1 induction, forewarns of reproductive impairment of sexually maturing fishes exposed to CYP1A1 inducing compounds and argues for further, more detailed in vivo investigation.

(μ-3-Acetyl-5-carboxyl­ato-4-methyl­pyrazolido-1:2κ4 N 2,O 3:N 1,O 5)-μ-chlorido-tetra­pyridine-1κ2 N,2κ2 N-chlorido-1κCl-dicopper(II) propan-2-ol solvate

Science.gov (United States)

Malinkin, Sergey; Penkova, Larisa; Pavlenko, Vadim A.; Haukka, Matti; Fritsky, Igor O.

2009-01-01

The title compound, [Cu2(C7H6N2O3)Cl2(C5H5N)4]·C3H8O, is a binuclear pyrazolate complex, in which the two CuII atoms have different coordination numbers and are connected by a bridging Cl atom. One CuII atom has a distorted square-pyramidal coordination environment formed by two pyridine N atoms, one bridging Cl atom and an N,O-chelating pyrazolate ligand. The other CuII atom adopts an octa­hedral geometry defined by two pyridine N atoms at the axial positions, two Cl atoms and the coordinated pyrazolate ligand in the equatorial plane. An O—H⋯O hydrogen bond connects the complex mol­ecules and propan-2-ol solvent mol­ecules into pairs. These pairs form columns along the a axis. PMID:21577764

Organically Modified Silica with Pyrazole-3-carbaldehyde as a New Sorbent for Solid-Liquid Extraction of Heavy Metals

Directory of Open Access Journals (Sweden)

Smaail Radi

2013-12-01

Full Text Available A new chelating matrix, SiNP, has been prepared by immobilizing 1.5-dimethyl-1H-pyrazole-3-carbaldehyde on silica gel modified with 3-aminopropyl-trimethoxysilane. This new chelating material was well characterized by elemental analysis, FT-IR spectroscopy, cross polarization magic angle spinning solid state 13C-NMR, nitrogen adsorption-desorption isotherm, BET surface area, BJH pore size, and scanning electron microscopy (SEM. The new product exhibits good chemical and thermal stability as determined by thermogravimetry curves (TGA. The new prepared material was used as an adsorbent for the solid-phase extraction (SPE of Pb(II, Cd(II, Cu(II and Zn(II from aqueous solutions using a batch method, prior to their determination by flame atomic adsorption spectrometry. The adsorption capacity was investigated using kinetics and pH effects. Common coexisting ions did not interfere with separation and determination.

Crystal structure of 1-{3-(4-methylphenyl-5-[(E-2-phenylethenyl]-4,5-dihydro-1H-pyrazol-1-yl}ethan-1-one

Directory of Open Access Journals (Sweden)

Farook Adam

2015-12-01

Full Text Available The title compound, C20H20N2O, was studied as a part of our work on pyrazoline derivatives. It represents a trans-isomer. The central pyrazoline ring adopts an envelope conformation with the asymmetric C atom having the largest deviation of 0.107 (1 Å from the mean plane. It forms dihedral angles of 6.2 (1 and 86.4 (1° with the adjacent p-tolyl and styrene groups, respectively. In the crystal, C—H...O interactions link molecules into infinite chains along the c axis.

Tannin structural elucidation and quantitative ³¹P NMR analysis. 1. Model compounds.

Science.gov (United States)

Melone, Federica; Saladino, Raffaele; Lange, Heiko; Crestini, Claudia

2013-10-02

Tannins and flavonoids are secondary metabolites of plants that display a wide array of biological activities. This peculiarity is related to the inhibition of extracellular enzymes that occurs through the complexation of peptides by tannins. Not only the nature of these interactions, but more fundamentally also the structure of these heterogeneous polyphenolic molecules are not completely clear. This first paper describes the development of a new analytical method for the structural characterization of tannins on the basis of tannin model compounds employing an in situ labeling of all labile H groups (aliphatic OH, phenolic OH, and carboxylic acids) with a phosphorus reagent. The ³¹P NMR analysis of ³¹P-labeled samples allowed the unprecedented quantitative and qualitative structural characterization of hydrolyzable tannins, proanthocyanidins, and catechin tannin model compounds, forming the foundations for the quantitative structural elucidation of a variety of actual tannin samples described in part 2 of this series.

Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents

Directory of Open Access Journals (Sweden)

Abdou O. Abdelhamid

2016-07-01

Full Text Available 2-(3-(1H-Indol-3-yl-5-(p-tolyl-4,5-dihydro-1H-pyrazol-1-yl-4-substituted-5-(substituted diazenylthiazoles and 2-(1H-indol-3-yl-9-substituted-4,7-disubstituted pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(7H-ones were synthesized via reaction of hydrazonoyl halides with each of 3-(1H-indol-2-yl-5-(p-tolyl-4,5-dihydro-1H-pyrazole-1-carbothioamide and 7-(1H-indol-3-yl-2- thioxo-5-substituted-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H-ones, respectively. Also, hydrazonoyl halides were reacted with N’-(1-(1H-indol-3-ylethylidene-2-cyanoacetohydrazide to afford 1,3,4-thiadiazole derivatives. Structures of the new synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Fifteen of the new compounds have been evaluated for their antitumor activity against the MCF-7 human breast carcinoma cell line. The results indicated that many of the tested compounds showed moderate to high anticancer activity when compared with doxorubicin as a reference drug.

ALK5 kinase inhibitory activity and synthesis of 2,3,4-substituted 5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles

Czech Academy of Sciences Publication Activity Database

Řezníčková, Eva; Tenora, L.; Pospíšilová, Pavlína; Galeta, J.; Jorda, Radek; Berka, K.; Majer, Pavel; Potáček, M.; Kryštof, Vladimír

2017-01-01

Roč. 127, FEB 15 (2017), s. 632-642 ISSN 0223-5234 R&D Projects: GA MŠk(CZ) LO1204; GA ČR(CZ) GA15-15264S; GA MŠk(CZ) LM2015047 Institutional support: RVO:61389030 ; RVO:61388963 Keywords : i-receptor kinase * beta signaling pathway * small- molecule inhibitor * tgf-beta * domain inhibitors * growth * fibrosis * cancer * potent * series * Transforming growth factor beta receptor I * Protein kinase * Inhibitor * Substituted pyrrolo[1,2-b]pyrazoles Subject RIV: FR - Pharmacology ; Medidal Chemistry OBOR OECD: Pharmacology and pharmacy; Pharmacology and pharmacy (UOCHB-X) Impact factor: 4.519, year: 2016

4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H-one

Directory of Open Access Journals (Sweden)

Sergey A. Smolnikov

2017-12-01

Full Text Available Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H-one (4 via S-alkylation of 2-phenyl-4-thioxopyrazolo[1,5-a][1,3,5]triazine-7(6H-one (3, prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2 with alkali. The antiproliferative activity of 4 against human lung cancer (A549 and human breast cancer (MDA-MB231 cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells.

EXAFS study of Mn1.28Fe0.67P0.46Si0.54 compound with first-order phase transition

International Nuclear Information System (INIS)

L, Yingjie; Huliyageqi, B; Haschaolu, W; Song, Zhiqiang; Tegus, O; Nakai, Ikuo

2014-01-01

Highlights: • We have investigated the Fe and Mn K edge XAFS spectra of the Mn 1.28 Fe 0.67 P 0.46 Si 0.54 compound at 25 K and 295 K. • The site occupation of the Fe and Mn atoms and local structure of Mn 1.28 Fe 0.67 P 0.46 Si 0.54 are determined. • The atomic distances between Fe–Fe in c-plane for the ferromagnetic state are larger than those in the paramagnetic state. - Abstract: The Fe 2 P-type MnFe(P,Si) compounds are investigated by means of magnetic measurements and X-ray absorption fine structure spectroscopy. Magnetic measurements show that the Mn 1.28 Fe 0.67 P 0.46 Si 0.54 compound undergoes a first-order phase transition at the Curie temperature of 254 K. The Fe K-edge and Mn K-edge X-ray absorption fine structure spectra show that Mn atom mainly located at the 3g sites, while the 3f sites are occupied by Fe atoms and Mn atom randomly. The distances between the Fe atom and its nearest neighbor atoms in a triangle Fe–Mn–Fe change from 2.80 Å at 25 K to 2.74 Å at 300 K. On the other hand, the distances between Fe atom and its second neighbor atoms change from 4.06 Å at 25 K to 4.02 Å at 300 K

Ab Initio Ligand Field Molecular Mechanics and the Nature of Metal-Ligand π-Bonding in Fe(II) 2,6-di(pyrazol-1-yl)pyridine Spin Crossover Complexes.

Science.gov (United States)

Deeth, Robert J; Halcrow, Malcolm A; Kershaw Cook, Laurence J; Raithby, Paul R

2018-04-06

A ligand field molecular mechanics (LFMM) force field has been constructed for the spin states of [Fe(bpp) 2 ] 2+ (bpp=2,6-di(pyrazol-1-yl)pyridine) and related complexes. A new charge scheme is employed which interpolates between partial charges for neutral bpp and protonated [H 3 bpp] 3+ to achieve a target metal charge. The LFMM angular overlap model (AOM) parameters are fitted to fully ab initio d orbital energies. However, several AOM parameter sets are possible. The ambiguity is resolved by calculating the Jahn-Teller distortion mode for high spin, which indicates that in [Fe(bpp) 2 ] 2+ pyridine is a π-acceptor and pyrazole a weak π-donor. The alternative fit, assumed previously, where both ligands act as π-donors leads to an inconsistent distortion. LFMM optimisations in the presence of [BF 4 ] - or [PF 6 ] - anions are in good agreement with experiment and the model also correctly predicts the spin state energetics for 3-pyrazolyl substituents where the interactions are mainly steric. However, for 4-pyridyl or 4-pyrazolyl substituents, LFMM only treats the electrostatic contribution which, for the pyridyl substituents, generates a fair correlation with the spin crossover transition temperatures, T 1/2 , but in the reverse sense to the dominant electronic effect. Thus, LFMM generates its smallest spin state energy difference for the substituent with the highest T 1/2 . One parameter set for all substituted bpp ligands is insufficient and further LFMM development will be required. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis and anticonvulsant activity of some 2-pyrazolines derived from chalcones

Directory of Open Access Journals (Sweden)

Nagihan Beyhan

2017-05-01

All compounds were tested for their anticonvulsant activity using pentylenetetrazole induced seizure (PTZ and maximal electroshock seizure (MES tests in mice at a dose level of 50 mg/kg. Among the 2-pyrazoline-1-carbothioamide derivatives, 5-(2,6-dichlorophenyl-3-(thiophen-2-yl-4,5-dihydro-1H-pyrazole-1-carbothioamide (2e reduced grade-5 seizure activity and also increased survival rate in PTZ test. In MES test, 5-(4-methoxyphenyl-3-[4-(methylsulphonylphenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide(2g has not only decreased seizure severity, but also increased survival rate. Among the 2-pyrazoline-1-carboxamide derivatives, 3-(5-bromothiophen-2-yl-N-(4-chlorophenyl-5-(2,6-dichlorophenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (3d having 5-bromothiophen and 2,6-dichlorophenyl moieties and N-(4-chlorophenyl-5-(2,6-dichlorophenyl-3-(5-chlorothiophen-2-yl-4,5-dihydro-1H-pyrazole-1-carboxamide (3e having 5-chlorothiophen and 2,6-dichlorophenyl moieties showed remarkable activities in PTZ test. Among all tested derivatives, compound 3d was found to be the most active one and reduced grade-5 seizure severity and also increased survival rate.

Late-stage optimization of a tercyclic class of S1P3-sparing, S1P1 receptor agonists.

Science.gov (United States)

Horan, Joshua C; Kuzmich, Daniel; Liu, Pingrong; DiSalvo, Darren; Lord, John; Mao, Can; Hopkins, Tamara D; Yu, Hui; Harcken, Christian; Betageri, Raj; Hill-Drzewi, Melissa; Patenaude, Lori; Patel, Monica; Fletcher, Kimberly; Terenzzio, Donna; Linehan, Brian; Xia, Heather; Patel, Mita; Studwell, Debbie; Miller, Craig; Hickey, Eugene; Levin, Jeremy I; Smith, Dustin; Kemper, Raymond A; Modis, Louise K; Bannen, Lynne C; Chan, Diva S; Mac, Morrison B; Ng, Stephanie; Wang, Yong; Xu, Wei; Lemieux, René M

2016-01-15

Poor solubility and cationic amphiphilic drug-likeness were liabilities identified for a lead series of S1P3-sparing, S1P1 agonists originally developed from a high-throughput screening campaign. This work describes the subsequent optimization of these leads by balancing potency, selectivity, solubility and overall molecular charge. Focused SAR studies revealed favorable structural modifications that, when combined, produced compounds with overall balanced profiles. The low brain exposure observed in rat suggests that these compounds would be best suited for the potential treatment of peripheral autoimmune disorders. Copyright © 2015 Elsevier Ltd. All rights reserved.

Surface induces different crystal structures in a room temperature switchable spin crossover compound.

Science.gov (United States)

Gentili, Denis; Liscio, Fabiola; Demitri, Nicola; Schäfer, Bernhard; Borgatti, Francesco; Torelli, Piero; Gobaut, Benoit; Panaccione, Giancarlo; Rossi, Giorgio; Degli Esposti, Alessandra; Gazzano, Massimo; Milita, Silvia; Bergenti, Ilaria; Ruani, Giampiero; Šalitroš, Ivan; Ruben, Mario; Cavallini, Massimiliano

2016-01-07

We investigated the influence of surfaces in the formation of different crystal structures of a spin crossover compound, namely [Fe(L)2] (LH: (2-(pyrazol-1-yl)-6-(1H-tetrazol-5-yl)pyridine), which is a neutral compound thermally switchable around room temperature. We observed that the surface induces the formation of two different crystal structures, which exhibit opposite spin transitions, i.e. on heating them up to the transition temperature, one polymorph switches from high spin to low spin and the second polymorph switches irreversibly from low spin to high spin. We attributed this inversion to the presence of water molecules H-bonded to the complex tetrazolyl moieties in the crystals. Thin deposits were investigated by means of polarized optical microscopy, atomic force microscopy, X-ray diffraction, X-ray absorption spectroscopy and micro Raman spectroscopy; moreover the analysis of the Raman spectra and the interpretation of spin inversion were supported by DFT calculations.

A structural, magnetic and Moessbauer spectral study of the magnetocaloric Mn1.1Fe0.9P1-xGex compounds

International Nuclear Information System (INIS)

Sougrati, Moulay T; Hermann, Raphael P; Grandjean, Fernande; Long, Gary J; Brueck, E; Tegus, O; Trung, N T; Buschow, K H J

2008-01-01

The structural, magnetic and Moessbauer spectral properties of the magnetocaloric Mn 1.1 Fe 0.9 P 1-x Ge x compounds, with 0.19 1.1 Fe 0.9 P 0.74 Ge 0.26 . The temperature dependence of the magnetization reveals a ferromagnetic to paramagnetic transition with a Curie temperature between approximately 250 and 330 K and hysteresis width of 10 to 4 K, for 0.19 1.1 Fe 0.9 P 0.78 Ge 0.22 shows the largest isothermal entropy change of approximately 10 J/(kgKT) at 290 K. The Moessbauer spectra have been analysed with a binomial distribution of hyperfine fields correlated with a change in isomer shift and quadrupole shift, a distribution that results from the distribution of phosphorus and germanium among the near neighbours of the iron. The coexistence of paramagnetic and magnetically ordered phases in ranges of temperature of up to 50 K around the Curie temperature is observed in the Moessbauer spectra and is associated with the first-order character of the ferromagnetic to paramagnetic transition. The temperature dependence of the weighted average hyperfine field is well fitted within the magnetostrictive model of Bean and Rodbell. Good fits of the Moessbauer spectra could only be achieved by introducing a difference between the isomer shifts in the paramagnetic and ferromagnetic phases, a difference that is related to the magnetostriction and electronic structure change.

Solvent extraction of Zr(IV) and Nb(V) with 1-phenyl-3-methyl-4benzoyl-pyrazole-5-one and tri-iso-octylamine from different mineral acid solutions

International Nuclear Information System (INIS)

Mirza, M.Y.; Nwabue, F.I.; Ahmed, S.

1981-01-01

The extraction of Zr(IV) and Nb(V) from aqueous solutions of mineral acids with 1% 1-phenyl-3-methyl-4-benzoyl-pyrazole-5-one and 5% tri-iso-octylamine solutions in chloroform has been investigated respectively. The mechanism of extraction and the composition of the extracted species have been suggested and the effect of complexing and salting-out agents also determined. Separation factors of various metals with respect to niobium have been estimated and separation from zirconium and many other elements has been achieved. Procedures are recommended for the separation of 95 Nb from 95 Zr- 95 Nb mixture as well as from the fission products. (orig.) [de

Small organic compounds enhance antigen loading of class II major histocompatibility complex proteins by targeting the polymorphic P1 pocket

DEFF Research Database (Denmark)

Höpner, Sabine; Dickhaut, Katharina; Hofstätter, Maria

2006-01-01

the peptide loading rate. The effect was evident only for an allelic subset and strictly correlated with the presence of glycine at the dimorphic position beta86 of the HLA-DR molecule. The residue forms the floor of the conserved pocket P1, located in the peptide binding site of MHC molecule. Apparently......, transient occupation of this pocket by the organic compound stabilizes the peptide-receptive conformation permitting rapid antigen loading. This interaction appeared restricted to the larger Gly(beta86) pocket and allowed striking enhancements of T cell responses for antigens presented by these "adamantyl......-susceptible" MHC molecules. As catalysts of antigen loading, compounds targeting P1 may be useful molecular tools to amplify the immune response. The observation, however, that the ligand repertoire can be affected through polymorphic sites form the outside may also imply that environmental factors could induce...

A Sequential Method to Prepare Polymorphs and Solvatomorphs of [Fe(1,3-bpp)2 ](ClO4 )2 ⋅nH2 O (n=0, 1, 2) with Varying Spin-Crossover Behaviour.

Science.gov (United States)

Bartual-Murgui, Carlos; Codina, Carlota; Roubeau, Olivier; Aromí, Guillem

2016-08-26

Two polymorphs of the spin crossover (SCO) compound [Fe(1,3-bpp)2 ](ClO4 )2 (1 and 2; 1,3-bpp=2-(pyrazol-1-yl)-6-(pyrazol-3-yl)pyridine) were prepared using a novel, stepwise procedure. Crystals of 1 deposit from dry solvents, while 2 is obtained from a solid-state procedure, by sequentially removing lattice H2 O molecules from the solvatomorph [Fe(1,3-bpp)2 ](ClO4 )2 ⋅2 H2 O (2⋅2 H2 O), using single-crystal-to-single-crystal (SCSC) transformations. Hydrate 2⋅2 H2 O is obtained through the same reaction as 1, now with 2.5 % of water added. Compounds 2 and 2⋅2 H2 O are unstable in the atmosphere and absorb or lose one equivalent of water, respectively, to both yield the stable solvatomorph [Fe(1,3-bpp)2 ](ClO4 )2 ⋅H2 O (2⋅H2 O), also following SCSC processes. The four derivatives have been characterised by single-crystal X-ray diffraction (SCXRD). Furthermore, the homogeneity of the various compounds as well as their SCSC interconversions have been confirmed by powder X-ray diffraction (PXRD). Polymorphs 1 and 2 exhibit abrupt SCO behaviour near room temperature with T1/2↑ =279/316 K and T1/2↓ =276/314 K (near 40 K of shift) and different cooperativity. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis and Anti-Bacterial Activities of Some Novel Schiff Bases Derived from Aminophenazone

Directory of Open Access Journals (Sweden)

Salman A Khan

2010-10-01

Full Text Available A series of 1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one-containing Schiff bases were synthesized, characterized and screened for their antibacterial activities. The structures of the synthesized compounds were established by spectroscopic (FT-IR, 1H-NMR, 13C-NMR, MS and elemental analyses. The anti-bacterial activities (with MIC values of compounds were evaluated. The anti-bacterial screening results reveal that among the six compounds screened, four compounds showed moderate to good anti-bacterial activity. Among the tested compounds, the most effective compounds against four bacterial strains, viz. Escherichia coli, Staphylococcus aureus, Salmonella typhimurium and Streptococcus pyogenes, are [(2-Chlorobenzylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one (4 and [(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yliminomethyl]benzonitrile (5 with MIC values of 6.25 μg/mL.

Magnetic properties of the filled skutterudite-type structure compounds GdRu4P12 and TbRu4P12 synthesized under high pressure

OpenAIRE

Sekine, C; Uchiumi, T; Shirotani, I; Matsuhira, kazuyuki; Sakakibara, T; Goto, T; Yagi, T

2000-01-01

We have succeeded in synthesizing filled skutterudite-type structure compounds GdRu4P12 and TbRu4P12 under high pressure. The magnetic properties of GdRu4P12 and TbRu4P12 have been studied by means of electrical resistivity, magnetic susceptibility, and magnetization measurements. Magnetic experiments suggest that the Gd and Tb ions in the compounds have trivalent state. The compound GdRu4P12 displays features that suggest the occurrence of antiferromagnetic ordering below TN=22 K. In TbRu4P1...

Ethyl 2-(3,4-dimethyl-5,5-dioxo-1H,4H-benzo[e]pyrazolo[4,3-c][1,2]thiazin-1-ylacetate

Directory of Open Access Journals (Sweden)

Sana Aslam

2012-10-01

Full Text Available In the title molecule, C15H17N3O4S, the heterocyclic thiazine ring adopts a twist-boat conformation, which differs from that in related compounds, with adjacent S and C atoms displaced by 0.981 (4 and 0.413 (5 Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The mean plane of the benzene ring makes a dihedral angle of 23.43 (14° with the mean plane of the pyrazole ring. In the crystal, molecules are connected by weak C—H...O hydrogen bonds to form a three-dimensional network. The H atoms of the methyl group attached to the pyrazole ring were refined over six sites with equal occupancies.

Assessment of two-dimensional (2D) and three-dimensional (3D) lower limb measurements in adults: Comparison of micro-dose and low-dose biplanar radiographs

International Nuclear Information System (INIS)

Rosskopf, Andrea B.; Pfirrmann, Christian W.A.; Buck, Florian M.

2016-01-01

To evaluate reliability of 2D and 3D lower limb measurements in adults using micro-dose compared to low-dose biplanar radiographs(BPR). One hundred patients (mean 54.9 years) were examined twice using micro-dose and low-dose BPR. Length and mechanical axis of lower limbs were measured on the antero-posterior(ap) micro-dose and low-dose images by two independent readers. Femoral and tibial torsions of 50 patients were measured by two independent readers using reconstructed 3D-models based on the micro-dose and low-dose BPR. Intermethod and interreader agreements were calculated using descriptive statistics, intraclass-correlation-coefficient(ICC), and Bland-Altman analysis. Mean interreader-differences on micro-dose were 0.3 cm(range 0-1.0)/ 0.7 (0-2.9) for limb length/axis and 0.4 cm (0-1.0)/0.8 (0-3.3) on low-dose BPR. Mean intermethod-difference was 0.04 cm ± 0.2/0.04 ± 0.6 for limb length/axis. Interreader-ICC for limb length/axis was 0.999/0.991 on micro-dose and 0.999/0.987 on low-dose BPR. Interreader-ICC for micro-dose was 0.879/0.826 for femoral/tibial torsion, for low-dose BPR was 0.924/0.909. Mean interreader-differences on micro-dose/low-dose BPR were 3 (0-13 )/2 (0 -12 ) for femoral and 4 (0-18 )/3 (0 -10 ) for tibial torsion. Mean intermethod-difference was -0.1 ± 5.0/-0.4 ± 2.9 for femoral/tibial torsion. Mean dose-area-product was significantly lower (9.9 times;p < 0.001) for micro-dose BPR. 2D-and 3D-measurements of lower limbs based on micro-dose BPR are reliable and provide a 10-times lower radiation dose. (orig.)

Compound list: buspirone [Open TG-GATEs

Lifescience Database Archive (English)

Full Text Available buspirone BPR 00173 ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Human/in..._vitro/buspirone.Human.in_vitro.Liver.zip ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Rat/in_vitro/buspirone.Rat.in_vitro.Liver.zip ...

Sphingosine-1-phosphate (S1P) displays sustained S1P1 receptor agonism and signaling through S1P lyase-dependent receptor recycling.

Science.gov (United States)

Gatfield, John; Monnier, Lucile; Studer, Rolf; Bolli, Martin H; Steiner, Beat; Nayler, Oliver

2014-07-01

The sphingosine-1-phosphate (S1P) type 1 receptor (S1P1R) is a novel therapeutic target in lymphocyte-mediated autoimmune diseases. S1P1 receptor desensitization caused by synthetic S1P1 receptor agonists prevents T-lymphocyte egress from secondary lymphoid organs into the circulation. The selective S1P1 receptor agonist ponesimod, which is in development for the treatment of autoimmune diseases, efficiently reduces peripheral lymphocyte counts and displays efficacy in animal models of autoimmune disease. Using ponesimod and the natural ligand S1P, we investigated the molecular mechanisms leading to different signaling, desensitization and trafficking behavior of S1P1 receptors. In recombinant S1P1 receptor-expressing cells, ponesimod and S1P triggered Gαi protein-mediated signaling and β-arrestin recruitment with comparable potency and efficiency, but only ponesimod efficiently induced intracellular receptor accumulation. In human umbilical vein endothelial cells (HUVEC), ponesimod and S1P triggered translocation of the endogenous S1P1 receptor to the Golgi compartment. However, only ponesimod treatment caused efficient surface receptor depletion, receptor accumulation in the Golgi and degradation. Impedance measurements in HUVEC showed that ponesimod induced only short-lived Gαi protein-mediated signaling followed by resistance to further stimulation, whereas S1P induced sustained Gαi protein-mediated signaling without desensitization. Inhibition of S1P lyase activity in HUVEC rendered S1P an efficient S1P1 receptor internalizing compound and abrogated S1P-mediated sustained signaling. This suggests that S1P lyase - by facilitating S1P1 receptor recycling - is essential for S1P-mediated sustained signaling, and that synthetic agonists are functional antagonists because they are not S1P lyase substrates. Copyright © 2014 Elsevier Inc. All rights reserved.

Theoretical investigations of the structures and electronic spectra of 8-hydroxylquinoline derivatives

Science.gov (United States)

Ning, Pan; Ren, Tiegang; Zhang, Yanxin; Zhang, Jinglai

2013-11-01

The spectroscopic properties of 8-hydroxyquinoline derivatives are theoretically investigated by means of density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. The target molecules are divided into two groups: group (I): (E)-2-(2-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)vinyl)quinolin-8-ol (A), together with corresponding potential reaction products of A with acetic acid, i.e., (E)-2-(2-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)vinyl)quinolin-8-yl acetate (AR1), and (E)-2-(2-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)vinyl)-8-hydroxyquinolinium (AR2); group (II): (E)-2-(2-(1-(4-chlorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl)vinyl)quinolin-8-ol (B), as well as potential reaction products of B with acetic acid, i.e., (E)-2-(2-(1-(4-chlorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl)vinyl)quinolin-8-yl acetate (BR1), and (E)-2-(2-(1-(4-chlorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl)vinyl)-8-hydroxyquinolinium (BR2). The geometries are optimized by B3LYP and M06 methods. The results indicate that product molecules tend to be effectively planar compared with reactants. Subsequently, UV absorption spectra are simulated through TD-DFT method with PCM model to further confirm the reasonable products of two reactions. AR2 and BR2 are identified as the target molecules through the experimental spectra for the real products. It is worth noting that the maximum absorption wavelengths of compounds AR2 and BR2 present prominent red shift compared the initial reactants A and B, respectively, which should be ascribed to the enhancive planarity of products that mentioned above and the decreased HOMO-LUMO energy gap. Geometric structures and optical properties for corresponding compounds are discussed in detail.

Identification of Active Compounds in the Root of Merung (Coptosapelta tomentosa Valeton K. Heyne)

Science.gov (United States)

Fitriyana

2018-04-01

The roots of Merung (Coptosapelta tomentosa Valeton K. Heyne) are a group of shrubs usually found on the margins of secondary dryland forest. Empirically, local people have been using the roots of Merung for medical treatment. However, some researches show that the plant extract is used as a poisonous material applied on the tip of the arrow (dart). Based on the online literature study, there are less than 5 articles that provide information about the active compound of this root extract. This study aimed to give additional information more deeply about the content of active compound of Merung root extract in three fractions, n-hexane (nonpolar), ethyl acetate (semi polar) and methanol (polar). The extract was then analysed using Gas Chromatography-Mass Spectrometry (GC-MS). GC-MS analysis of root extract in n-hexane showed there were 56 compounds, with the main compound being decanoic acid, methyl ester (peak 5, 10.13%), 11-Octadecenoic acid, methyl ester (peak 15, 10.43%) and 1H-Pyrazole, 3- (4-chlorophenyl) -4, 5-dihydro-1-phenyl (peak 43, 11.25%). Extracts in ethyl acetate fraction obtained 81 compounds. The largest component is Benzoic acid (peak 19, 22.40%), whereas in methanol there are 38 compounds, of which the main component is 2-Furancarboxaldehyde, 5-(hydroxyl methyl) (peak 29, 30.46%).

Carbon-14 radiolabelling and tissue distribution evaluation of a potential anti-TB compound.

Science.gov (United States)

Sonopo, Molahlehi S; Venter, Kobus; Winks, Susan; Marjanovic-Painter, Biljana; Morgans, Garreth L; Zeevaart, Jan R

2016-06-15

This paper describes a five-step synthesis of a carbon-14-labelled pyrazole compound (11). A total of 2.96 MBq of 11 was obtained with the specific activity of 2242.4 MBq/mmol. The radiochemical purity was >99%, and the overall radiochemical yield was 60% based on the [(14) C6 ] 4-bromoaniline starting material. Biodistribution results showed that the radiotracer (administrated orally) has a high accumulation in the small intestine, large intestine and liver of both non-infected and tuberculosis (TB)-infected mice. Therefore, this suggests that compound 11 undergoes hepatobiliary clearance. The compound under investigation has been found to be slowly released from the liver between 2 and 8 h. The study revealed that 11 has no affinity for TB cells. Copyright © 2016 John Wiley & Sons, Ltd.

Identification of Two Novel Anti-Fibrotic Benzopyran Compounds Produced by Engineered Strains Derived from Streptomyces xiamenensis M1-94P that Originated from Deep-Sea Sediments

Directory of Open Access Journals (Sweden)

Lei Feng

2013-10-01

Full Text Available The benzopyran compound obtained by cultivating a mangrove-derived strain, Streptomyces xiamenensis strain 318, shows multiple biological effects, including anti-fibrotic and anti-hypertrophic scar properties. To increase the diversity in the structures of the available benzopyrans, by means of biosynthesis, the strain was screened for spontaneous rifampicin resistance (Rif, and a mutated rpsL gene to confer streptomycin resistance (Str, was introduced into the S. xiamenensis strain M1-94P that originated from deep-sea sediments. Two new benzopyran derivatives, named xiamenmycin C (1 and D (2, were isolated from the crude extracts of a selected Str-Rif double mutant (M6 of M1-94P. The structures of 1 and 2 were identified by analyzing extensive spectroscopic data. Compounds 1 and 2 both inhibit the proliferation of human lung fibroblasts (WI26, and 1 exhibits better anti-fibrotic activity than xiamenmycin. Our study presents the novel bioactive compounds isolated from S. xiamenensis mutant strain M6 constructed by ribosome engineering, which could be a useful approach in the discovery of new anti-fibrotic compounds.

Secondary metabolites from the sponge Tedania anhelans: Isolation and characterization of two novel pyrazole acids and other metabolites

Digital Repository Service at National Institute of Oceanography (India)

Parameswaran, P.S.; Naik, C.G.; Hegde, V.R.

Chemical investigation of the methanol extract of the sponge Tedania anhelans yielded the two unusual heteroaromatic acids, pyrazole-3(5)-carboxylic acid (2) and 4-methylpyrazole-3(5)-carboxylic acid (3), which are reported for the first time...

Tris(2-(1 H -pyrazol-1-yl)pyridine)cobalt(III) as p-Type Dopant for Organic Semiconductors and Its Application in Highly Efficient Solid-State Dye-Sensitized Solar Cells

KAUST Repository

Burschka, Julian

2011-11-16

Chemical doping is an important strategy to alter the charge-transport properties of both molecular and polymeric organic semiconductors that find widespread application in organic electronic devices. We report on the use of a new class of Co(III) complexes as p-type dopants for triarylamine-based hole conductors such as spiro-MeOTAD and their application in solid-state dye-sensitized solar cells (ssDSCs). We show that the proposed compounds fulfill the requirements for this application and that the discussed strategy is promising for tuning the conductivity of spiro-MeOTAD in ssDSCs, without having to rely on the commonly employed photo-doping. By using a recently developed high molar extinction coefficient organic D-π-A sensitizer and p-doped spiro-MeOTAD as hole conductor, we achieved a record power conversion efficiency of 7.2%, measured under standard solar conditions (AM1.5G, 100 mW cm -2). We expect these promising new dopants to find widespread applications in organic electronics in general and photovoltaics in particular. © 2011 American Chemical Society.

Department of Defense Costing References Web. Phase 1. Establishing the Foundation

National Research Council Canada - National Science Library

Medlock, Michael

1997-01-01

...) Business Process Reengineering (BPR) Program's "toolbox," feedback from BPR practitioners regarding experiences with functional economic analysis and Major Automated Information Systems Review Council requirements, and the Government...

Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.

Science.gov (United States)

Yang, Weibo; Ye, Shengqing; Schmidt, Yvonne; Stamos, Dean; Yu, Jin-Quan

2016-05-17

A Pd-catalyzed/N-heterocycle-directed C(sp(3) )-H olefination has been developed. The monoprotected amino acid ligand (MPAA) is found to significantly promote Pd-catalyzed C(sp(3) )-H olefination for the first time. Cu(OAc)2 instead of Ag(+) salts are used as the terminal oxidant. This reaction provides a useful method for the synthesis of alkylated pyrazoles. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

EFSA CEF Panel (EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids), 2016. Scientific opinion on Flavouring Group Evaluation 400 (FGE.400): 3-(1- ((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)imidazolidine-2,4-dione

DEFF Research Database (Denmark)

Beltoft, Vibe Meister; Nørby, Karin Kristiane

modifier in specific categories of food. There is no safety concern with respect to genotoxicity. A 90-day dietary administration study in rats showed no adverse effects for doses up to 100 mg/kg body weight (bw) per day, providing an adequate margin of safety. Developmental toxicity was not observed...... for various foods in different food categories.......The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) of EFSA was requested to deliver a scientific opinion on the implications for human health of the flavouring substance 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)imidazolidine-2...

Vibrational spectroscopic and theoretical study of 3,5-dimethyl-1-thiocarboxamide pyrazole (L) and the complexes Co2L2Cl4, Cu2L2Cl4 and Cu2L2Br2

International Nuclear Information System (INIS)

Nemcsok, Denes; Kovacs, Attila; Szecsenyi, Katalin Meszaros; Leovac, Vukadin M.

2006-01-01

In the present paper we report a joint experimental and theoretical study of 3,5-dimethyl-1-thiocarboxamide pyrazole (L) and its complexes Co 2 L 2 Cl 4 , Cu 2 L 2 Cl 4 and Cu 2 L 2 Br 2 . DFT computations were used to model the structural and bonding properties of the title compounds as well as to derive a reliable force field for the normal coordinate analysis of L. The computations indicated the importance of hydrogen bonding interactions in stabilising the global minimum structures on the potential energy surfaces. In contrast to the S-bridged binuclear Cu 2 L 2 Br 2 complex found in the crystal, our computations predicted the formation of (CuLBr) 2 dimers in the isolated state stabilized by very strong (53 kJ/mol) N-H...Br hydrogen bonding interactions. On the basis of FT-IR and FT-Raman experiments and the DFT-derived scaled quantum mechanical force field we carried out a complete normal coordinate analysis of L. The FT-IR spectra of the three complexes were interpreted using the present assignment of L, literature data and computed results

Synthesis, Photophysical and Computational Study of Novel Coumarin-based Organic Dyes.

Science.gov (United States)

Kumbar, Mahadev N; Sannaikar, Madivalagouda S; Shaikh, Saba Kauser J; Kamble, Atulkumar A; Wari, Manjunath N; Inamdar, Sanjeev R; Qiao, Qiquan; Revanna, Bhavya N; Madegowda, Mahendra; Dasappa, Jagadeesh P; Kamble, Ravindra R

2018-03-01

A series of novel coumarin pyrazoline moieties combined with tetrazoles, 3-(1-phenyl-4-(1H-tetrazol-5-yl)-1H-pyrazol-3-yl)-2H-chromen-2-one, 6-chloro-3-(1-phenyl-4-(1H-tetrazol-5-yl)-1H-pyrazol-3-yl)-2H-chromen-2-one, 6-bromo-3-(1-phenyl-4-(1H-tetrazol-5-yl)-1H-pyrazol-3-yl)-2H-chromen-2-one and 6-bromo-3-(1-(4-bromophenyl)-4-(1H-tetrazol-5-yl)-1H pyrazol-3-yl)-2H-chromen-2-one7(a-d), were designed and synthesized. Single crystal X-ray diffraction and their interactions were studied by Hirshfeld surface analysis. Thermal stabilities and electrochemical properties of these compounds were examined from differential scanning calorimetry (DSC), thermogravimetric (TGA) and cyclic voltammetric (CV) studies. Their spectroscopic properties were analyzed in various alcohols and general solvents by UV-Vis absorption, fluorescence and time-resolved spectroscopy. In addition, the ground and excited state electronic properties were investigated using density functional theory (DFT). The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and energy band gap (E g ) values have revealed the effect of substitution of halogens. The substitution has equally affected the ground and excited states of 7(a-d) compounds. The solvatochromism on absorption, fluorescence spectra and fluorescence lifetimes of these compounds was investigated. All these results showed the chromen-2-one of pyrazoline tetrazole derivatives could play an important role in photonic and electronic devices. © 2017 The American Society of Photobiology.

Synthesis and Characterization of Celecoxib Derivatives as Possible Anti-Inflammatory, Analgesic, Antioxidant, Anticancer and Anti-HCV Agents

Directory of Open Access Journals (Sweden)

Amartya Basu

2013-03-01

Full Text Available A series of novel N-(3-substituted aryl/alkyl-4-oxo-1,3-thiazolidin-2-ylidene-4-[5-(4-methylphenyl-3-(trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamides 2a–e were synthesized by the addition of ethyl a-bromoacetate and anhydrous sodium acetate in dry ethanol to N-(substituted aryl/alkylcarbamothioyl-4-[5-(4-methylphenyl-3-(trifluoro-methyl-1H-pyrazol-1-yl]benzene sulfonamides 1a–e, which were synthesized by the reaction of alkyl/aryl isothiocyanates with celecoxib. The structures of the isolated products were determined by spectral methods and their anti-inflammatory, analgesic, antioxidant, anticancer and anti-HCV NS5B RNA-dependent RNA polymerase (RdRp activities evaluated. The compounds were also tested for gastric toxicity and selected compound 1a was screened for its anticancer activity against 60 human tumor cell lines. These investigations revealed that compound 1a exhibited anti-inflammatory and analgesic activities and further did not cause tissue damage in liver, kidney, colon and brain compared to untreated controls or celecoxib. Compounds 1c and 1d displayed modest inhibition of HCV NS5B RdRp activity. In conclusion, N-(ethylcarbamothioyl-4-[5-(4-methylphenyl-3-(trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide (1a may have the potential to be developed into a therapeutic agent.

Fabrication and electrical characterization of Al/diazo compound containing polyoxy chain/p-Si device structure

Science.gov (United States)

Birel, Ozgul; Kavasoglu, Nese; Kavasoglu, A. Sertap; Dincalp, Haluk; Metin, Bengul

2013-03-01

Diazo-compounds are important class of chemical compounds in terms of optical and electronic properties which make them potentially attractive for device applications. Diazo compound containing polyoxy chain has been deposited on p-Si. Current-voltage characteristics of Al/diazo compound containing polyoxy chain/p-Si structure present rectifying behaviour. The Schottky barrier height (SBH), diode factor (n), reverse saturation current (Io), interface state density (Nss) of Al/diazo compound containing polyoxy chain/p-Si structure have been calculated from experimental forward bias current-voltage data measured in the temperature range 100-320 K and capacitance-voltage data measured at room temperature and 1 MHz. The calculated values of SBH have ranged from 0.041 and 0.151 eV for the high and low temperature regions. Diode factor values fluctuate between the values 14 and 18 with temperature. Such a high diode factors stem from disordered interface layer in a junction structure as stated by Brötzmann et al. [M. Brötzmann, U. Vetter, H. Hofsäss, J. Appl. Phys. 106 (2009) 063704]. The calculated values of saturation current have ranged from 3×10-11 A to 2.79×10-7 A and interface state density have ranged from 5×1011 eV-1 cm-2 and 4×1013 eV-1 cm-2 as temperature increases. Results show that Al/diazo compound containing polyoxy chain/p-Si structure is a valuable candidate for device applications in terms of low reverse saturation current and low interface state density.

Synthesis, spectral, crystallography and thermal investigations of novel Schiff base complexes of manganese (III) derived from heterocyclic β-diketone with aromatic and aliphatic diamine

Science.gov (United States)

Surati, Kiran R.; Thaker, B. T.

2010-01-01

The Schiff base tetradentate ligands N,N-bis-(3,5-dimethyl-1-p-tolyl-1H-pyrazol-4-ylmethylene)-ethane-1,2-diamine (H 2L 1), N,N-bis-(3,5-dimethyl-1-p-sulfonyl-1H-pyrazol-4-ylmethylene)-ethane-1,2-diamine (H 2L 2), N,N-bis-(3,5-dimethyl-1-p-tolyl-1H-pyrazol-4-ylmethylene)-benzene-1,2-diamine (H 2L 3) and N,N-bis-(3,5-dimethyl-1-p-sulfonyl-1H-pyrazol-4-ylmethylene)-benzene-1,2-diamine (H 2L 4) were prepared from the reaction between 5-oxo-3-methyl-1-p-tolyl-1H-pyrazole-4-carbaldehyde or 4-(4-formyl-5-oxo-3-methyl-pyrazol-1-yl)-benzenesulfonic acid and o-phenylenediamine or ethylenediamine. And these are characterized by elemental analysis, FT-IR, 1H NMR and GC-MS. The corresponding Schiff base complexes of Mn(III) were prepared by condensation of [Mn 3(μ 3-O)(OAc) 6(H 2O) 3]·3H 2O with ligands H 2L 1, H 2L 2, H 2L 3 and H 2L 4. All these complexes have been characterized by elemental analysis, magnetic susceptibility, X-ray crystallography, conductometry measurement, FT-IR, electronic spectra and mass (FAB) spectrometry. Thermal behaviour of the complexes has been studied by TGA, DTA and DSC. Electronic spectra and magnetic susceptibility measurements indicate octahedral stereochemistry of manganese (III) complexes, while non-electrolytic behaviour complexes indicate the absence of counter ion.

Synthesis, spectral, crystallography and thermal investigations of novel Schiff base complexes of manganese (III) derived from heterocyclic beta-diketone with aromatic and aliphatic diamine.

Science.gov (United States)

Surati, Kiran R; Thaker, B T

2010-01-01

The Schiff base tetradentate ligands N,N-bis-(3,5-dimethyl-1-p-tolyl-1H-pyrazol-4-ylmethylene)-ethane-1,2-diamine (H(2)L(1)), N,N-bis-(3,5-dimethyl-1-p-sulfonyl-1H-pyrazol-4-ylmethylene)-ethane-1,2-diamine (H(2)L(2)), N,N-bis-(3,5-dimethyl-1-p-tolyl-1H-pyrazol-4-ylmethylene)-benzene-1,2-diamine (H(2)L(3)) and N,N-bis-(3,5-dimethyl-1-p-sulfonyl-1H-pyrazol-4-ylmethylene)-benzene-1,2-diamine (H(2)L(4)) were prepared from the reaction between 5-oxo-3-methyl-1-p-tolyl-1H-pyrazole-4-carbaldehyde or 4-(4-formyl-5-oxo-3-methyl-pyrazol-1-yl)-benzenesulfonic acid and o-phenylenediamine or ethylenediamine. And these are characterized by elemental analysis, FT-IR, (1)H NMR and GC-MS. The corresponding Schiff base complexes of Mn(III) were prepared by condensation of [Mn(3)(mu(3)-O)(OAc)(6)(H(2)O)(3)].3H(2)O with ligands H(2)L(1), H(2)L(2), H(2)L(3) and H(2)L(4). All these complexes have been characterized by elemental analysis, magnetic susceptibility, X-ray crystallography, conductometry measurement, FT-IR, electronic spectra and mass (FAB) spectrometry. Thermal behaviour of the complexes has been studied by TGA, DTA and DSC. Electronic spectra and magnetic susceptibility measurements indicate octahedral stereochemistry of manganese (III) complexes, while non-electrolytic behaviour complexes indicate the absence of counter ion. Copyright 2009. Published by Elsevier B.V.

FAKTOR-FAKTOR YANG MEMENGARUHI TINGKAT PENYALURAN KREDIT PADA BPR KONVENSIONAL DI INDONESIA

Directory of Open Access Journals (Sweden)

Novyanti Nora Purba

2016-05-01

Full Text Available The global financial crisis has affected the banking condition in Indonesia, and the impact of this financial crisis has disturbed the banking financial performance. Bank Perkreditan Rakyat is a bank which specializes in serving the middle-lower community levels especially the micro, small and middle scaled entrepreneurships in meeting their capital through the procedures of cheap loan provision and simple loan mechanism. The objective of the research is to analyze factors influencing the level of loan distribution at BPR, and the factors include the variables of the third party fund, Non-Performing Loan (NPL, loan interest, Loan to Deposit Ratio (LDR, Operational Cost on Operational Income (OCOI, and Return on Assets (ROA.The secondary data collection in this research included data time series. The analysis methods used were the descriptive analysis and double linier regression using Minitab 17. The result showed that the variables of the third party fund, and Loan to Deposit Ratio (LDR had a significantly positive influence on the loan distribution rate. The variables of NPL, loan interest rate, and OCOI had a significantly negative influence on loan distribution rate whereas the variable of ROA was not significantly influential toward the load distribution rate. The most important factor that needs to take into account in increasing bank loan distribution is offering a competitive interest rate.Keywords: DPK, NPL, loan interest rate, LDR, OCOI, ROA, loan distribution/disbursement

4D-Qsar Study of Some Pyrazole Pyridine Carboxylic Acid Derivatives by Electron Conformational-Genetic Algorithm Method.

Science.gov (United States)

Tuzun, Burak; Yavuz, Sevtap Caglar; Sabanci, Nazmiye; Saripinar, Emin

2018-05-13

In the present work, pharmacophore identification and biological activity prediction for 86 pyrazole pyridine carboxylic acid derivatives were made using the electron conformational genetic algorithm approach which was introduced as a 4D-QSAR analysis by us in recent years. In the light of the data obtained from quantum chemical calculations at HF/6-311 G** level, the electron conformational matrices of congruity (ECMC) were constructed by EMRE software. Comparing the matrices, electron conformational submatrix of activity (ECSA, Pha) was revealed that are common for these compounds within a minimum tolerance. A parameter pool was generated considering the obtained pharmacophore. To determine the theoretical biological activity of molecules and identify the best subset of variables affecting bioactivities, we used the nonlinear least square regression method and genetic algorithm. The results obtained in this study are in good agreement with the experimental data presented in the literature. The model for training and test sets attained by the optimum 12 parameters gave highly satisfactory results with R2training= 0.889, q2=0.839 and SEtraining=0.066, q2ext1 = 0.770, q2ext2 = 0.750, q2ext3=0.824, ccctr = 0.941, ccctest = 0.869 and cccall = 0.927. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds

Directory of Open Access Journals (Sweden)

Urja D. Nimbalkar

2017-09-01

Full Text Available A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2, hydrazine hydrate (3 and ethyl acetoacetate (4 under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2, breast cancer cell line(MDA-MB-231, leukemia cancer cell line (K-562 and cervical cancer cell line (HeLa. Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.

Fabrication and electrical characterization of Al/diazo compound containing polyoxy chain/p-Si device structure

International Nuclear Information System (INIS)

Birel, Ozgul; Kavasoglu, Nese; Kavasoglu, A. Sertap; Dincalp, Haluk; Metin, Bengul

2013-01-01

Diazo-compounds are important class of chemical compounds in terms of optical and electronic properties which make them potentially attractive for device applications. Diazo compound containing polyoxy chain has been deposited on p-Si. Current–voltage characteristics of Al/diazo compound containing polyoxy chain/p-Si structure present rectifying behaviour. The Schottky barrier height (SBH), diode factor (n), reverse saturation current (I o ), interface state density (N ss ) of Al/diazo compound containing polyoxy chain/p-Si structure have been calculated from experimental forward bias current–voltage data measured in the temperature range 100–320 K and capacitance–voltage data measured at room temperature and 1 MHz. The calculated values of SBH have ranged from 0.041 and 0.151 eV for the high and low temperature regions. Diode factor values fluctuate between the values 14 and 18 with temperature. Such a high diode factors stem from disordered interface layer in a junction structure as stated by Brötzmann et al. [M. Brötzmann, U. Vetter, H. Hofsäss, J. Appl. Phys. 106 (2009) 063704]. The calculated values of saturation current have ranged from 3×10 −11 A to 2.79×10 −7 A and interface state density have ranged from 5×10 11 eV −1 cm −2 and 4×10 13 eV −1 cm −2 as temperature increases. Results show that Al/diazo compound containing polyoxy chain/p-Si structure is a valuable candidate for device applications in terms of low reverse saturation current and low interface state density

Fabrication and electrical characterization of Al/diazo compound containing polyoxy chain/p-Si device structure

Energy Technology Data Exchange (ETDEWEB)

Birel, Ozgul [Mugla Sitki Kocman University, Faculty of Science, Chemistry Department, 48000-Muğla (Turkey); Kavasoglu, Nese, E-mail: knesese@gmail.com [Mugla Sitki Kocman University, Faculty of Science, Physics Department, Photovoltaic Material and Device Laboratory, 48000-Muğla (Turkey); Kavasoglu, A. Sertap [Mugla Sitki Kocman University, Faculty of Science, Physics Department, Photovoltaic Material and Device Laboratory, 48000-Muğla (Turkey); Dincalp, Haluk [Celal Bayar University, Faculty of Arts and Science, Chemistry Department, 45000-Manisa (Turkey); Metin, Bengul [Mugla Sitki Kocman University, Faculty of Science, Physics Department, Photovoltaic Material and Device Laboratory, 48000-Muğla (Turkey)

2013-03-01

Diazo-compounds are important class of chemical compounds in terms of optical and electronic properties which make them potentially attractive for device applications. Diazo compound containing polyoxy chain has been deposited on p-Si. Current–voltage characteristics of Al/diazo compound containing polyoxy chain/p-Si structure present rectifying behaviour. The Schottky barrier height (SBH), diode factor (n), reverse saturation current (I{sub o}), interface state density (N{sub ss}) of Al/diazo compound containing polyoxy chain/p-Si structure have been calculated from experimental forward bias current–voltage data measured in the temperature range 100–320 K and capacitance–voltage data measured at room temperature and 1 MHz. The calculated values of SBH have ranged from 0.041 and 0.151 eV for the high and low temperature regions. Diode factor values fluctuate between the values 14 and 18 with temperature. Such a high diode factors stem from disordered interface layer in a junction structure as stated by Brötzmann et al. [M. Brötzmann, U. Vetter, H. Hofsäss, J. Appl. Phys. 106 (2009) 063704]. The calculated values of saturation current have ranged from 3×10{sup −11} A to 2.79×10{sup −7} A and interface state density have ranged from 5×10{sup 11} eV{sup −1} cm{sup −2} and 4×10{sup 13} eV{sup −1} cm{sup −2} as temperature increases. Results show that Al/diazo compound containing polyoxy chain/p-Si structure is a valuable candidate for device applications in terms of low reverse saturation current and low interface state density.

Cytotoxicity study of pyrazole derivatives

Directory of Open Access Journals (Sweden)

Nusrat Binta Ahasan

2007-06-01

Full Text Available Pyrazolone heterocyclic compound, 3-methyl-1-phenyl-2-pyrazoline-5-one 2(a was synthesized by condensation reaction between ethyl acetoacetate and phenyl hydrazine and was converted into their corresponding heterocyclic derivatives 2(b to 2(f2 . Their cytotoxicity effects were measured by brine shrimp lethality bioassay. Among them the compounds 2(b , 2(f1 , and 2(f2 were highly active according to IC50 values 19.50, 19.50 and 20 ppm respectively. The rest of compounds 2(a , 2(c , 2(d1 , and 2(d2 having IC50 values 38, 33.50, 37.50, 36, 37.50 and 36 ppm in that order, were moderately active.

Cytotoxicity study of pyrazole derivatives

Directory of Open Access Journals (Sweden)

Nusrat Binta Ahasan and Md. Rabiul Islam

2007-12-01

Full Text Available Pyrazolone heterocyclic compound, 3-methyl-1-phenyl-2-pyrazoline-5-one 2(a was synthesized by condensation reaction between ethyl acetoacetate and phenyl hydrazine and was converted into their corresponding heterocyclic derivatives 2(b to 2(f2. Their cytotoxicity effects were measured by brine shrimp lethality bioassay. Among them the compounds 2(b, 2(f1, and 2(f2 were highly active according to IC50 values 19.50, 19.50 and 20 ppm respectively. The rest of compounds 2(a, 2(c, 2(d1, and 2(d2 having IC50 values 38, 33.50, 37.50, 36, 37.50 and 36 ppm in that order, were moderately active.

Ring rearrangements and reactivity of 3-((4-oxo-4H-chromen-3-ylmethylene-4-phenyl-1H-[1,5]benzodiazepin-2(3H-one toward some nucleophiles

Directory of Open Access Journals (Sweden)

Hanan Salah

2017-05-01

Full Text Available Condensation of 4-phenyl-1H-[1,5]benzodiazepin-2(3H-one (1 with 3-formylchromone (2 afforded a mixture of 3-(chromenylmethylene[1,5]benzodiazepinone 3 and 14-chromenylbenzodiazepino[2,3:6,5]pyrano[2,3-b]benzodiazepine 4. Ring rearrangements of compound 3 with different nucleophilic reagents, such as potassium hydroxide and/or ammonium acetate led to rearrangement into pyranobenzodiazepine 5 and pyridobenzodiazepine 6, respectively. Treatment of compound 3 with hydrazine hydrate, hydroxylamine hydrochloride, malononitrile, cyanothioacetamide, 2-cyano-3,3-disufanylacrylonitrile, and/or 2-cyano-3-phenylamino-3-sufanylacrylonitrile, has been carried out at different conditions, leading to versatile heterocyclic substituted benzodiazepines at position 3, viz. pyrazole 8, isoxazole 9, pyridines 10 and 11, 1,3-dithiine 12, and 1,3-thiazine 13 derivatives.

Regulation of the cytochrome P450 2A genes

International Nuclear Information System (INIS)

Su Ting; Ding Xinxin

2004-01-01

Cytochrome P450 monooxygenases of the CYP2A subfamily play important roles in xenobiotic disposition in the liver and in metabolic activation in extrahepatic tissues. Many of the CYP2A transcripts and enzymes are inducible by xenobiotic compounds, and the expression of at least some of the CYP2A genes is influenced by physiological status, such as circadian rhythm, and pathological conditions, such as inflammation, microbial infection, and tumorigenesis. Variability in the expression of the CYP2A genes, which differs by species, animal strain, gender, and organ, may alter the risks of chemical toxicity for numerous compounds that are CYP2A substrates. The mechanistic bases of these variabilities are generally not well understood. However, recent studies have yielded interesting findings in several areas, such as the role of nuclear factor 1 in the tissue-selective expression of CYP2A genes in the olfactory mucosa (OM); the roles of constitutive androstane receptor, pregnane X receptor (PXR), and possibly, peroxisome proliferator-activated receptors in transcriptional regulation of the Cyp2a5 gene; and the involvement of heterogeneous nuclear ribonucleoprotein A1 in pyrazole-induced stabilization of CYP2A5 mRNA. The aims of this minireview are to summarize current knowledge of the regulation of the CYP2A genes in rodents and humans, and to stimulate further mechanistic studies that will ultimately improve our ability to determine, and to understand, these variabilities in humans

Schiff bases derived from 1-aminoanthraquinone: a new class of analgesic compounds

International Nuclear Information System (INIS)

Fareed, G.; Rizwan, G.H.; Fareed, N.

2017-01-01

A series of Schiff bases 1-17 were synthesised by way of a facile condensation between 1-amino-anthraquinone with a variety of carbonyl compounds in the presence of a catalytic amount of dodeca-tungstosilicic acid/P 2O5 under solvent free conditions at room temperature. These were charachterised by1H- and 13C-NMR, LCMS, FTIR and elemental analyses. All the compounds were screened for their analgesic activity using hot plate thermal stimuli method at dose of 10 and 30 mg/kg. Diclofenac sodium was used as a reference drug. All the compounds at dose of 10 and 30 mg/kg body weight showed the significant (p<0.05) increase in latency time as compared to control (normal saline). Compound 5 showed excellent activity after 120 min of drug administration (10 mg/kg) of body weight. Compound 10 was found to be potent (10.48+-1.19s, 11.27+-1.2s and 10.24+-1.9s) at dose of 30 mg/kg at 30, 60 and 120 min, respectively when compared to the standard drug. Compound 6 (10.13+-0.4s) was also found to be an excellent analgesic compound at a dose of 30 mg/kg at 120 min. However, the studies on analgesic activity revealed that some of the target compounds may be strong candidates as an analgesic drug. (author)

MDR1 P-glycoprotein transports endogenous opioid peptides

NARCIS (Netherlands)

Oude Elferink, R. P.; Zadina, J.

2001-01-01

MDR1 P-glycoprotein is generally regarded as an efflux pump for amphipathic toxic compounds. The question remains, however, whether certain endogenous compounds are also substrates for this transporter. Certain peptides have been shown to interact with MDR1 Pgp as well and we have therefore

Gene Expression Profiling Identifies Important Genes Affected by R2 Compound Disrupting FAK and P53 Complex

International Nuclear Information System (INIS)

Golubovskaya, Vita M.; Ho, Baotran; Conroy, Jeffrey; Liu, Song; Wang, Dan; Cance, William G.

2014-01-01

Focal Adhesion Kinase (FAK) is a non-receptor kinase that plays an important role in many cellular processes: adhesion, proliferation, invasion, angiogenesis, metastasis and survival. Recently, we have shown that Roslin 2 or R2 (1-benzyl-15,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane) compound disrupts FAK and p53 proteins, activates p53 transcriptional activity, and blocks tumor growth. In this report we performed a microarray gene expression analysis of R2-treated HCT116 p53 +/+ and p53 −/− cells and detected 1484 genes that were significantly up- or down-regulated (p < 0.05) in HCT116 p53 +/+ cells but not in p53 −/− cells. Among up-regulated genes in HCT p53 +/+ cells we detected critical p53 targets: Mdm-2, Noxa-1, and RIP1. Among down-regulated genes, Met, PLK2, KIF14, BIRC2 and other genes were identified. In addition, a combination of R2 compound with M13 compound that disrupts FAK and Mmd-2 complex or R2 and Nutlin-1 that disrupts Mdm-2 and p53 decreased clonogenicity of HCT116 p53 +/+ colon cancer cells more significantly than each agent alone in a p53-dependent manner. Thus, the report detects gene expression profile in response to R2 treatment and demonstrates that the combination of drugs targeting FAK, Mdm-2, and p53 can be a novel therapy approach

The importance of pKa in an analysis of the interaction of compounds with DNA.

Science.gov (United States)

Saha, Mouli; Nandy, Promita; Chakraborty, Mousumi; Das, Piyal; Das, Saurabh

2018-05-01

pK a of a compound is crucial for determining the contributions of different forms of it towards overall binding with DNA. Hence it is important to use correct pK a values in DNA interaction studies. This study takes a look at the importance of pK a values to realize binding of compounds with DNA. Since pK a of a compound determined in the presence of DNA is quite different from that determined in its absence hence, presence of different forms of a compound during interaction with DNA is different from that realized if the determination of pK a is done in normal aqueous solution in absence of DNA. Hence, calculations determining contributions of different forms of a compound interacting with DNA are affected accordingly. Two simple analogues of anthracyclines, alizarin and purpurin, were used to investigate the influence DNA has on pK a values. Indeed, they were different in presence of DNA than when determined in normal aqueous solution. pK a1 for alizarin and purpurin determined in the absence and presence of calf thymus DNA were used in equations that determine contributions of two forms (neutral and anionic) towards overall binding with DNA. The study concludes that correct pK a values, determined correctly i.e. under appropriate conditions, must be used for DNA binding experiments to evaluate contributions of individual forms. Copyright © 2018 Elsevier B.V. All rights reserved.

Congener-specific metabolism and sequestration of dioxin-like compounds by cytochrome P450 1A induced in the liver of crows from Tokyo, Japan

Energy Technology Data Exchange (ETDEWEB)

Watanabe, M.; Iwata, H.; Tanabe, S. [Ehime Univ., Matsuyama (Japan); Yoneda, K.; Hashimoto, T. [Japan Wildlife Research Center, Tokyo (Japan)

2004-09-15

Jungle crow (JC; Corvus macrorhynchos) is a useful bioindicator for monitoring contaminants in urban areas, because this species is residential, occupies a same habitat as human, and feeds variety of foods including domestic waste and garbage. Therefore, JCs may accumulate environmental contaminants such as polychlorinated dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs) and coplanar polychlorinated biphenyls (Co-PCBs), which are released by human activities. Induction of cytochrome P450 (CYP) 1A is a responsive mechanism elicited by exposure to dioxinlike compounds including PCDDs/DFs and Co-PCBs. Toxicokinetic behavior of dioxin-like compounds in organisms is controlled by excretion, metabolism and absorption. These processes are, at least partly, dependent on CYP1A expression in addition to chemical structure and number of chlorine substitution of each congener. Low chlorinated congeners such as 2378-T{sub 4}CDD, 2378- T{sub 4}CDF, 12378-P{sub 5}CDD and 33'44'-PCB were easily metabolized by CYP1A1/2 in rat liver microsomes. PCDDs/DFs accumulate in hepatic tissue to a greater extent than adipose tissue in rats and mice. Recent study using transgenic CYP1A2 knockout mice demonstrated that CYP1A2 is responsible for the sequestration of 2378-T{sub 4}CDD and 23478-P{sub 5}CDF in hepatic tissue. Therefore, CYP1A is considered as a key factor responsible for toxicokinetics of dioxin-like compounds. However, there's no comprehensive data on the contribution of CYP1A to the toxicokinetics of dioxin-like congeners in wild populations. In this study, we investigated contamination levels of PCDDs/DFs and Co-PCBs in liver and breast muscle of JCs from Tokyo, Japan, and interactions of dioxin-like congeners with hepatic CYP to elucidate congener-specific toxicokinetics related to CYP expression in JC.

p53 modulates the AMPK inhibitor compound C induced apoptosis in human skin cancer cells

Energy Technology Data Exchange (ETDEWEB)

Huang, Shi-Wei [Institute of Biomedical Sciences, National Chung Hsing University, Taichung, Taiwan (China); Wu, Chun-Ying [Division of Gastroenterology and Hepatology, Taichung Veterans General Hospital, Taichung, Taiwan (China); Wang, Yen-Ting [Department of Medical Research and Education, Cheng Hsin General Hospital, Taipei, Taiwan (China); Kao, Jun-Kai [Institute of Biomedical Sciences, National Chung Hsing University, Taichung, Taiwan (China); Department of Pediatrics, Children' s Hospital, Changhua Christian Hospital, Changhua, Taiwan (China); Lin, Chi-Chen; Chang, Chia-Che; Mu, Szu-Wei; Chen, Yu-Yu [Institute of Biomedical Sciences, National Chung Hsing University, Taichung, Taiwan (China); Chiu, Husan-Wen [Institute of Biotechnology, National Cheng-Kung University, Tainan, Taiwan (China); Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan (China); Chang, Chuan-Hsun [Department of Surgical Oncology, Cheng Hsin General Hospital, Taipei, Taiwan (China); Department of Nutrition Therapy, Cheng Hsin General Hospital, Taipei, Taiwan (China); School of Nutrition and Health Sciences, Taipei Medical University, Taipei, Taiwan (China); Liang, Shu-Mei [Institute of Biotechnology, National Cheng-Kung University, Tainan, Taiwan (China); Agricultural Biotechnology Research Center, Academia Sinica, Taipei, Taiwan (China); Chen, Yi-Ju [Department of Dermatology, Taichung Veterans General Hospital, Taichung, Taiwan (China); Huang, Jau-Ling [Department of Bioscience Technology, Chang Jung Christian University, Tainan, Taiwan (China); Shieh, Jeng-Jer, E-mail: shiehjj@vghtc.gov.tw [Institute of Biomedical Sciences, National Chung Hsing University, Taichung, Taiwan (China); Department of Education and Research, Taichung Veterans General Hospital, Taichung, Taiwan (China)

2013-02-15

Compound C, a well-known inhibitor of the intracellular energy sensor AMP-activated protein kinase (AMPK), has been reported to cause apoptotic cell death in myeloma, breast cancer cells and glioma cells. In this study, we have demonstrated that compound C not only induced autophagy in all tested skin cancer cell lines but also caused more apoptosis in p53 wildtype skin cancer cells than in p53-mutant skin cancer cells. Compound C can induce upregulation, phosphorylation and nuclear translocalization of the p53 protein and upregulate expression of p53 target genes in wildtype p53-expressing skin basal cell carcinoma (BCC) cells. The changes of p53 status were dependent on DNA damage which was caused by compound C induced reactive oxygen species (ROS) generation and associated with activated ataxia-telangiectasia mutated (ATM) protein. Using the wildtype p53-expressing BCC cells versus stable p53-knockdown BCC sublines, we present evidence that p53-knockdown cancer cells were much less sensitive to compound C treatment with significant G2/M cell cycle arrest and attenuated the compound C-induced apoptosis but not autophagy. The compound C induced G2/M arrest in p53-knockdown BCC cells was associated with the sustained inactive Tyr15 phosphor-Cdc2 expression. Overall, our results established that compound C-induced apoptosis in skin cancer cells was dependent on the cell's p53 status. - Highlights: ► Compound C caused more apoptosis in p53 wildtype than p53-mutant skin cancer cells. ► Compound C can upregulate p53 expression and induce p53 activation. ► Compound C induced p53 effects were dependent on ROS induced DNA damage pathway. ► p53-knockdown attenuated compound C-induced apoptosis but not autophagy. ► Compound C-induced apoptosis in skin cancer cells was dependent on p53 status.

p53 modulates the AMPK inhibitor compound C induced apoptosis in human skin cancer cells

International Nuclear Information System (INIS)

Huang, Shi-Wei; Wu, Chun-Ying; Wang, Yen-Ting; Kao, Jun-Kai; Lin, Chi-Chen; Chang, Chia-Che; Mu, Szu-Wei; Chen, Yu-Yu; Chiu, Husan-Wen; Chang, Chuan-Hsun; Liang, Shu-Mei; Chen, Yi-Ju; Huang, Jau-Ling; Shieh, Jeng-Jer

2013-01-01

Compound C, a well-known inhibitor of the intracellular energy sensor AMP-activated protein kinase (AMPK), has been reported to cause apoptotic cell death in myeloma, breast cancer cells and glioma cells. In this study, we have demonstrated that compound C not only induced autophagy in all tested skin cancer cell lines but also caused more apoptosis in p53 wildtype skin cancer cells than in p53-mutant skin cancer cells. Compound C can induce upregulation, phosphorylation and nuclear translocalization of the p53 protein and upregulate expression of p53 target genes in wildtype p53-expressing skin basal cell carcinoma (BCC) cells. The changes of p53 status were dependent on DNA damage which was caused by compound C induced reactive oxygen species (ROS) generation and associated with activated ataxia-telangiectasia mutated (ATM) protein. Using the wildtype p53-expressing BCC cells versus stable p53-knockdown BCC sublines, we present evidence that p53-knockdown cancer cells were much less sensitive to compound C treatment with significant G2/M cell cycle arrest and attenuated the compound C-induced apoptosis but not autophagy. The compound C induced G2/M arrest in p53-knockdown BCC cells was associated with the sustained inactive Tyr15 phosphor-Cdc2 expression. Overall, our results established that compound C-induced apoptosis in skin cancer cells was dependent on the cell's p53 status. - Highlights: ► Compound C caused more apoptosis in p53 wildtype than p53-mutant skin cancer cells. ► Compound C can upregulate p53 expression and induce p53 activation. ► Compound C induced p53 effects were dependent on ROS induced DNA damage pathway. ► p53-knockdown attenuated compound C-induced apoptosis but not autophagy. ► Compound C-induced apoptosis in skin cancer cells was dependent on p53 status

Synthesis, biological evaluation and SAR analysis of novel poly-heterocyclic compounds containing pyridylpyrazole group.

Science.gov (United States)

Wang, Bao-Lei; Zhu, Hong-Wei; Li, Zheng-Ming; Wang, Li-Zhong; Zhang, Xiao; Xiong, Li-Xia; Song, Hai-Bin

2018-03-01

In recent years, pyridylpyrazole derivatives, such as pyridylpyrazole-containing anthranilic diamide have attracted much attention by virtue of their useful insecticidal properties and unique action mode. Moreover, some pyridylpyrazole-containing compounds have also been found to possess significant fungicidal activities. With the aim of discovering new bioactive agrochemicals for crop protection, a series of poly-heterocyclic compounds containing pyridylpyrazole and aziridine, or β-lactam, or thiazolinone moieties were synthesized. A series of pyridylpyrazole-containing poly-heterocyclic compounds were obtained, and confirmed through IR, 1 H NMR, 13 C NMR, HRMS and elemental analysis. The crystalline structure of 4-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3-chloro-1-mesitylazetidin-2-one (compound 13f) was determined to further illustrate a trans- configuration of the β-lactam motif. In addition, bioassays showed that most of these new compounds exhibited modest insecticidal activity towards Mythimna separate Walker at 200 µg mL -1 . Some of the compounds displayed excellent fungicidal activity towards some plant fungi, including Cercospora arachidicola (13j: EC 50 = 14.5 µg mL -1 ), Physalospora piricola (12d and 13d: EC 50 = 10.5 and 9.70 µg mL -1 ), Alternaria solani Sorauer (13j: EC 50 = 7.29 µg mL -1 ), Puccinia sorghi Schw. (13d: control efficacy 99.0 ± 2.1% at 200 µg mL -1 ) and Erysiphe graminis (14d: control efficacy 95.0 ± 1.4% at 200 µg mL -1 ). Compounds 12b-12e, 13a, 13d, 13f, 13j, 13 k and 14d could be considered potential fungicidal lead compounds to do further structural optimization. The structure-activity relationship analysis in this study brings some new understanding to the biological activities of N-pyridylpyrazole-containing compounds, and provides important information for the research and development of novel agricultural fungicides with poly-heterocyclic structures. © 2017 Society of Chemical Industry. © 2017 Society

Combined exercise circuit session acutely attenuates stress-induced blood pressure reactivity in healthy adults

Directory of Open Access Journals (Sweden)

Sérgio R. Moreira

2014-03-01

Full Text Available Objective: To investigate the blood pressure (BP responses to cardiovascular stress test after a combined exercise circuit session at moderate intensity. Method: Twenty individuals (10 male/10 fem; 33.4± 6.9 years; 70.2± 15.8 kg; 170.4± 11.5 cm; 22.3± 6.8% body fat were randomized in a different days to control session with no exercise or exercise session consisting of 3 laps of the following circuit: knee extension, bench press, knee flexion, rowing in the prone position, squats, shoulder press, and 5 min of aerobic exercise at 75-85% of age-predicted maximum heart rate and/or 13 on the Borg Rating of Perceived Exertion [scale of 6 to 20]. The sets of resistance exercise consisted of 15 repetitions at ~50% of the estimated 1 repetition maximum test. Systolic blood pressure (SBP and diastolic blood pressure (DBP were measured at rest and during 1h of recovery in both experimental sessions. After that, blood pressure reactivity (BPR was evaluated using the Cold Pressor Test. Results: During 1h of exercise recovery, there was a reduction in SBP (3-6 mmHg and DBP (2-5 mmHg in relation to pre-session rest (p<0.01, while this reduction was not observed in the control session. A decline in BPR (4-7 mmHg; p<0.01 was observed 1h post-exercise session, but not in the control session. Post-exercise reductions in SBP and DBP were significantly correlated with BPR reductions (r=0.50-0.45; p<0.05. Conclusion: A combined exercise circuit session at moderate intensity promoted subsequent post-exercise hypotension and acutely attenuated BPR in response to a cardiovascular stress test. In addition, the post-exercise BP reduction was correlated with BPR attenuation in healthy adults of both genders.

Oxidation reactivity of 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) by Compound I model of cytochrome P450s

Institute of Scientific and Technical Information of China (English)

Zhongyu Wang; Zhiqiang Fu; Qi Yu; Jingwen Chen

2017-01-01

Alternative brominated flame retardants (BFRs) have become prevalent as a consequence of restrictions on the use of polybrominated diphenyl ethers (PBDEs).For risk assessment of these alternatives,knowledge of their metabolism via cytochrome P450 enzymes is needed.We have previously proved that density functional theory (DFT) is able to predict the metabolism of PBDEs by revealing the molecular mechanisms.In the current study,the reactivity of 1,2-bis(2,4,6-tribromophenoxy)ethane and structurally similar chemicals with the Compound I model representing the active site of P450 enzymes was investigated.The DFT calculations delineated reaction pathways which lead to reasonable explanations for products that were detected by wet experiments,meanwhile intermediates which cannot be determined were also proposed.Results showed that alkyl hydrogen abstraction will lead to bis(2,4,6-tribromophenoxy)ethanol,which may undergo hydrolysis yielding 2,4,6-tribromophenol,a neurotoxic compound.In addition,a general pattern of oxidation reactivity regarding the 2,4,6-tribromophenyl moiety was observed among several model compounds.Our study has provided insights for convenient evaluation of the metabolism of other structurally similar BFRs.

Synthesis, studies and in-vitro antibacterial activity of N-substituted 5-(furan-2-yl-phenyl pyrazolines

Directory of Open Access Journals (Sweden)

Mamta Rani

2015-03-01

Full Text Available Novel compounds with antibacterial properties: pyrazoline derivatives were synthesized by the cyclization of various -1-[2-(alkoxyphenyl]-3-(furan-2-yl prop-2-en-1-one 1a–1d with N-substituted phenyl hydrazine in the presence of CH3COOH in ethanol. The structures of these compounds were elucidated by, IR, 1H NMR, 13C NMR, ESI-MS spectral data and their purities were confirmed by elemental analyses. The in vitro antibacterial activity of these compounds was evaluated against two Gram-positive and two Gram-negative bacteria Aeromonas hydrophila, Yersinia enterocolitica, Listeria monocytogenes, and Staphylococcus aureus by microdilution method and then the minimum inhibitory concentration (MIC of compounds were determined. The results showed that compounds (5R-5-(furan-2-yl-1-phenyl-3-[2-(benzyloxyphenyl]-4, 5-dihydro-1H-pyrazole (2b and (5R-5-(furan-2-yl-1-phenyl-3-[2-(naphthalen-2-ylmethoxy prop-2-en-1-yloxyphenyl]-4,5-dihydro-1H-pyrazole (2d showing most promising antibacterial activities as compared to Gentamicin and Tetracycline are given.

Solvent extraction of indium and gallium complexes with bromopyrogallol red by mixed extractants containing chloroform, a polar organic solvent and monocarboxylic acids

International Nuclear Information System (INIS)

Pyatnitskij, I.V.; Lysenko, O.V.; Kolomiets, L.L.

1987-01-01

Solvent extraction of indium and gallium complexes with bromopyragallol red (BPR) has been studied using mixed extractants containing chloroform, capronic acid (HL) and 1-pentanol (S) (extractant 1), and chloroform, HL, S and propionic acid (extractant 2). The latter is more selectie and extracts only the indium complex. Optimal conditions have been found for the extraction of In-BRP complex (pH 6.3-6.5; C BPR 1.5x10 -4 M) its composition has been estimated and discussed

Development of a canine model to enable the preclinical assessment of pH-dependent absorption of test compounds.

Science.gov (United States)

Fancher, R Marcus; Zhang, Hongjian; Sleczka, Bogdan; Derbin, George; Rockar, Richard; Marathe, Punit

2011-07-01

A preclinical canine model capable of predicting a compound's potential for pH-dependent absorption in humans was developed. This involved the surgical insertion of a gastrostomy feeding tube into the stomach of a beagle dog. The tube was sutured in position to allow frequent withdrawal of gastric fluid for pH measurement. Therefore, it was possible to measure pH in the stomach and assess the effect of gastric pH-modifying agents on the absorption of various test compounds. Fasted gastric pH in the dog showed considerable inter- and intra-animal variability. Pretreatment of pentagastrin (6 µg/kg intramuscularly) 20 min prior to test compound administration was determined to be adequate for simulating fasting stomach pH in humans. Pretreatment with famotidine [40 mg orally] 1 h prior to test compound administration was determined to be adequate for simulating human gastric pH when acid-reducing agents are coadministered. Pentagastrin and famotidine pretreatments were used to test two discovery compounds and distinct differences in their potential for pH-dependent absorption were observed. The model described herein can be used preclinically to screen out compounds, differentiate compounds, and support the assessment of various formulation- and prodrug-based strategies to mitigate the pH effect. Copyright © 2011 Wiley-Liss, Inc. and the American Pharmacists Association

Phase transitions and magnetocaloric effects in intermetallic compounds MnFeX (X=P, As, Si, Ge)

International Nuclear Information System (INIS)

Tegus, O.; Bao Li-Hong; Song Lin

2013-01-01

Since the discovery of giant magnetocaloric effect in MnFeP 1−x As x compounds, much valuable work has been performed to develop and improve Fe 2 P-type transition-metal-based magnetic refrigerants. In this article, the recent progress of our studies on fundamental aspects of theoretical considerations and experimental techniques, effects of atomic substitution on the magnetism and magnetocalorics of Fe 2 P-type intermetallic compounds MnFeX (X=P, As, Ge, Si) is reviewed. Substituting Si (or Ge) for As leads to an As-free new magnetic material MnFeP 1−x Si(Ge) x . These new materials show large magnetocaloric effects resembling MnFe(P, As) near room temperature. Some new physical phenomena, such as huge thermal hysteresis and ‘virgin’ effect, were found in new materials. On the basis of Landau theory, a theoretical model was developed for studying the mechanism of phase transition in these materials. Our studies reveal that MnFe(P, Si) compound is a very promising material for room-temperature magnetic refrigeration and thermo-magnetic power generation. (topical review - magnetism, magnetic materials, and interdisciplinary research)

Inteligência emocional e desempenho no trabalho: um estudo com MSCEIT, BPR-5 e 16PF

Directory of Open Access Journals (Sweden)

Cláudia Cobêro

2006-12-01

Full Text Available O presente trabalho teve como objetivo investigar a validade de uma medida de inteligência emocional correlacionando-a com medidas de inteligência, personalidade e desempenho profissional. Participaram do estudo 119 sujeitos, com idade entre 17 e 64 anos, de ambos os sexos e que trabalham em empresas situadas em municípios do interior do estado de São Paulo. Os instrumentos utilizados foram: Versão em Português do Mayer-Salovey-Caruso-Emotional Intelligence Test (MSCEIT, o Questionário Dezesseis Fatores da Personalidade (16PF, Bateria de Provas de Raciocínio (BPR-5, Avaliação de Desempenho respondido por duas pessoas (um supervisor e um colega. Os resultados apontam baixa correlação entre inteligência emocional e personalidade, bem como com inteligência. Indicam também que a faceta regulação das emoções se correlaciona com o desempenho profissional e apresenta validade incremental em relação à inteligência. Em suma conclui-se que a inteligência emocional constitui um tipo diferenciado de inteligência útil na avaliação psicológica no contexto organizacional.

EXAFS study of Mn{sub 1.28}Fe{sub 0.67}P{sub 0.46}Si{sub 0.54} compound with first-order phase transition

Energy Technology Data Exchange (ETDEWEB)

L, Yingjie; Huliyageqi, B; Haschaolu, W; Song, Zhiqiang [Inner Mongolia Key Laboratory for Physics and Chemistry of Functional Materials, Physics and Electronic Information College, Inner Mongolia Normal University, Hohhot 010022 (China); Tegus, O, E-mail: tegusph@imnu.edu.cn [Inner Mongolia Key Laboratory for Physics and Chemistry of Functional Materials, Physics and Electronic Information College, Inner Mongolia Normal University, Hohhot 010022 (China); Nakai, Ikuo [Department of Electrical and Electronic Engineering, Tottori University, Tottori 680-8552 (Japan)

2014-10-15

Highlights: • We have investigated the Fe and Mn K edge XAFS spectra of the Mn{sub 1.28}Fe{sub 0.67}P{sub 0.46}Si{sub 0.54} compound at 25 K and 295 K. • The site occupation of the Fe and Mn atoms and local structure of Mn{sub 1.28}Fe{sub 0.67}P{sub 0.46}Si{sub 0.54} are determined. • The atomic distances between Fe–Fe in c-plane for the ferromagnetic state are larger than those in the paramagnetic state. - Abstract: The Fe{sub 2}P-type MnFe(P,Si) compounds are investigated by means of magnetic measurements and X-ray absorption fine structure spectroscopy. Magnetic measurements show that the Mn{sub 1.28}Fe{sub 0.67}P{sub 0.46}Si{sub 0.54} compound undergoes a first-order phase transition at the Curie temperature of 254 K. The Fe K-edge and Mn K-edge X-ray absorption fine structure spectra show that Mn atom mainly located at the 3g sites, while the 3f sites are occupied by Fe atoms and Mn atom randomly. The distances between the Fe atom and its nearest neighbor atoms in a triangle Fe–Mn–Fe change from 2.80 Å at 25 K to 2.74 Å at 300 K. On the other hand, the distances between Fe atom and its second neighbor atoms change from 4.06 Å at 25 K to 4.02 Å at 300 K.

p53-independent structure-activity relationships of 3-ring mesogenic compounds' activity as cytotoxic effects against human non-small cell lung cancer lines.

Science.gov (United States)

Fukushi, Saori; Yoshino, Hironori; Yoshizawa, Atsushi; Kashiwakura, Ikuo

2016-07-25

We recently demonstrated the cytotoxicity of liquid crystal precursors (hereafter referred to as "mesogenic compounds") in the human non-small cell lung cancer (NSCLC) cell line A549 which carry wild-type p53. p53 mutations are observed in 50 % of NSCLC and contribute to their resistance to chemotherapy. To develop more effective and cancer-specific agents, in this study, we investigated the structure-activity relationships of mesogenic compounds with cytotoxic effects against multiple NSCLC cells. The pharmacological effects of mesogenic compounds were examined in human NSCLC cells (A549, LU99, EBC-1, and H1299) and normal WI-38 human fibroblast. Analyses of the cell cycle, cell-death induction, and capsases expression were performed. The 3-ring compounds possessing terminal alkyl and hydroxyl groups (compounds C1-C5) showed cytotoxicity in NSCLC cells regardless of the p53 status. The compounds C1 and C3, which possess a pyrimidine at the center of the core, induced G2/M arrest, while the compounds without a pyrimidine (C2, C4, and C5) caused G1 arrest; all compounds produced caspase-mediated cell death. These events occurred in a p53-independent manner. Furthermore, it was suggested that compounds induced cell death through p53-independent DNA damage-signaling pathway. Compounds C2, C4, and C5 did not show strong cytotoxicity in WI-38 cells, whereas C1 and C3 did. However, the cytotoxicity of compound C1 against WI-38 cells was improved by modulating the terminal alkyl chain lengths of the compound. We showed the p53-indepdent structure-activity relationships of mesogenic compounds related to the cytotoxic effects. These structure-activity relationships will be helpful in the development of more effective and cancer-specific agents.

Metabolism of chlorofluorocarbons and polybrominated compounds by Pseudomonas putida G786(pHG-2) via an engineered metabolic pathway.

Science.gov (United States)

Hur, H G; Sadowsky, M J; Wackett, L P

1994-11-01

The recombinant bacterium Pseudomonas putida G786(pHG-2) metabolizes pentachloroethane to glyoxylate and carbon dioxide, using cytochrome P-450CAM and toluene dioxygenase to catalyze consecutive reductive and oxidative dehalogenation reactions (L.P. Wackett, M.J. Sadowsky, L.N. Newman, H.-G. Hur, and S. Li, Nature [London] 368:627-629, 1994). The present study investigated metabolism of brominated and chlorofluorocarbon compounds by the recombinant strain. Under anaerobic conditions, P. putida G786(pHG-2) reduced 1,1,2,2-tetrabromoethane, 1,2-dibromo-1,2-dichloroethane, and 1,1,1,2-tetrachloro-2,2-difluoroethane to products bearing fewer halogen substituents. Under aerobic conditions, P. putida G786(pHG-2) oxidized cis- and trans-1,2-dibromoethenes, 1,1-dichloro-2,2-difluoroethene, and 1,2-dichloro-1-fluoroethene. Several compounds were metabolized by sequential reductive and oxidative reactions via the constructed metabolic pathway. For example, 1,1,2,2-tetrabromoethane was reduced by cytochrome P-450CAM to 1,2-dibromoethenes, which were subsequently oxidized by toluene dioxygenase. The same pathway metabolized 1,1,1,2-tetrachloro-2,2-difluoroethane to oxalic acid as one of the final products. The results obtained in this study indicate that P. putida G786(pHG-2) metabolizes polyfluorinated, chlorinated, and brominated compounds and further demonstrates the value of using a knowledge of catabolic enzymes and recombinant DNA technology to construct useful metabolic pathways.

SUN family proteins Sun4p, Uth1p and Sim1p are secreted from Saccharomyces cerevisiae and produced dependently on oxygen level.

Directory of Open Access Journals (Sweden)

Evgeny Kuznetsov

Full Text Available The SUN family is comprised of proteins that are conserved among various yeasts and fungi, but that are absent in mammals and plants. Although the function(s of these proteins are mostly unknown, they have been linked to various, often unrelated cellular processes such as those connected to mitochondrial and cell wall functions. Here we show that three of the four Saccharomyces cerevisiae SUN family proteins, Uth1p, Sim1p and Sun4p, are efficiently secreted out of the cells in different growth phases and their production is affected by the level of oxygen. The Uth1p, Sim1p, Sun4p and Nca3p are mostly synthesized during the growth phase of both yeast liquid cultures and colonies. Culture transition to slow-growing or stationary phases is linked with a decreased cellular concentration of Sim1p and Sun4p and with their efficient release from the cells. In contrast, Uth1p is released mainly from growing cells. The synthesis of Uth1p and Sim1p, but not of Sun4p, is repressed by anoxia. All four proteins confer cell sensitivity to zymolyase. In addition, Uth1p affects cell sensitivity to compounds influencing cell wall composition and integrity (such as Calcofluor white and Congo red differently when growing on fermentative versus respiratory carbon sources. In contrast, Uth1p is essential for cell resistance to boric acids irrespective of carbon source. In summary, our novel findings support the hypothesis that SUN family proteins are involved in the remodeling of the yeast cell wall during the various phases of yeast culture development and under various environmental conditions. The finding that Uth1p is involved in cell sensitivity to boric acid, i.e. to a compound that is commonly used as an important antifungal in mycoses, opens up new possibilities of investigating the mechanisms of boric acid's action.

Synthesis and Evaluation of Curcuminoid Analogues as Antioxidant and Antibacterial Agents

Directory of Open Access Journals (Sweden)

Dalia R. Emam

2017-06-01

Full Text Available Diazocoupling reaction of curcumin with different diazonium salts of p-toluidine, 2-aminopyridine, and 4-aminoantipyrine in pyridine yielded the arylhydrazones 2a–c. Arylhydrazone of p-toluidine reacted with urea, thiourea, and guanidine nitrate to produce 5,6-dihydropyrimidines. Further reaction of 2a with 2,3-diaminopyrdine in sodium ethoxide solution yielded 1H-pyrido[2,3-b][1,4]diazepine derivative. Bis(2,5-dihydroisoxazole is obtained from the reaction of 2a with hydroxylamine hydrochloride, while its reactions with hydrazines afforded the respective 4,5-dihydro-1H-pyrazoles. The target compounds were evaluated as antioxidant and antibacterial agents. The tested compounds showed good to moderate activities compared to ascorbic acid and chloramphenicol, respectively.

Microstructure, mechanical properties, and thermoelectric properties of hot-extruded p-type Te-doped Bi{sub 0.5}Sb{sub 1.5}Te{sub 3} compounds

Energy Technology Data Exchange (ETDEWEB)

Park, K; Seo, J; Lee, C

1997-07-01

The p-type Bi{sub 0.5}Sb{sub 1.5}Te{sub 3} compounds with Te dopant (4.0 and 6.0 wt%) and without dopant were fabricated by hot extrusion in the temperature range of 300 to 510 C under an extrusion ratio of 20:1. The undoped and Te doped compounds were highly dense and showed high crystalline quality. The grains contained many dislocations and were fine equiaxed ({approximately}1.0 {micro}m) owing to the dynamic recrystallization during the extrusion. The hot extrusion gave rise to the preferred orientation of grains. The bending strength and the figure of merit of the undoped and Te doped compounds were increased with increasing the extrusion temperature. The Te dopant significantly increased the figure of merit. The values of the figure of merit of the undoped and 4.0 wt% Te-doped compounds hot extruded at 440 C were 2.11 x 10{sup {minus}3}/K and 2.94 x 10{sup {minus}3}/K, respectively.

Molecular screening of compounds to the predicted Protein-Protein Interaction site of Rb1-E7 with p53- E6 in HPV

Science.gov (United States)

Shaikh, Faraz; Sanehi, Parvish; Rawal, Rakesh

2012-01-01

Cervical cancer is malignant neoplasm of the cervix uteri or cervical area. Human Papillomaviruses (HPVs) which are heterogeneous groups of small double stranded DNA viruses are considered as the primary cause of cervical cancer, involved in 90% of all Cervical Cancers. Two early HPV genes, E6 and E7, are known to play crucial role in tumor formation. E6 binds with p53 and prevents its translocation and thereby inhibit the ability of p53 to activate or repress target genes. E7 binds to hypophosphorylated Rb and thereby induces cells to enter into premature S-phase by disrupting Rb-E2F complexes. The strategy of the research work was to target the site of interaction of Rb1 -E7 & p53-E6. A total of 88 compounds were selected for molecular screening, based on comprehensive literature survey for natural compounds with anti-cancer activity. Molecular docking analysis was carried out with Molegro Virtual Docker, to screen the 88 chosen compounds and rank them according to their binding affinity towards the site of interaction of the viral oncoproteins and human tumor suppressor proteins. The docking result revealed that Nicandrenone a member of Withanolides family of chemical compounds as the most likely molecule that can be used as a candidate drug against HPV induced cervical cancer. Abbreviations HPV - Human Papiloma Virus, HTSP - Human Tumor Suppressor Proteins, VOP - Viral oncoproteins. PMID:22829740

Temperature-controlled formation of Anderson-type compounds and their conversion to [γ-Mo{sub 8}O{sub 26}]{sup 4-}-based variants using pendent ligands

Energy Technology Data Exchange (ETDEWEB)

Tian, Ai-xiang; Li, Ting-ting; Tian, Yan; Ni, Huai-ping; Ji, Xue-bin; Liu, Jia-ni; Liu, Guo-cheng; Ying, Jun [Bohai Univ., Jinzhou (China). Dept. of Chemistry

2017-10-01

By tuning the reaction temperature, two Anderson- and two [γ-Mo{sub 8}O{sub 26}]{sup 4-}-based compounds decorated by pendent organic ligands, [Cu{sup II}{sub 9}(bpz){sub 2}(pz){sub 2}(H{sub 2}O){sub 24}]-[H{sub 2}(Cr(OH){sub 5}Mo{sub 6}O{sub 19}){sub 4}].11H{sub 2}O (1), [Cu{sup II}(bpz){sub 2}(H{sub 2}O){sub 2}(γ-H{sub 4}-Mo{sub 8}O{sub 26})].2H{sub 2}O (2), [Cu{sup II}{sub 2}(tea){sub 2}(H{sub 2}O){sub 6}(HCr(OH){sub 6}Mo{sub 6}O{sub 18}){sub 2}]. 6H{sub 2}O (3) and [Ag{sup I}(bpz)(H{sub 2}O)(γ-H{sub 4}Mo{sub 8}O{sub 26}){sub 0.5}] (4) (bpz=4-butyl-1H-pyrazole, pz=1H-pyrazole, tea=2-[1,2,4]triazol-4-yl-ethylamine), have been hydrothermally synthesized and characterized by single-crystal X-ray diffraction analysis, IR spectra and elemental analyses. In compound 1, there are two kinds of tri-nuclear Cu{sup II} clusters induced by bpz and pz ligands, respectively. Four Anderson-type anions are linked by these tri-nuclear clusters to form a ''W''-type subunit. In compound 2, the [Cu(bpz){sub 2}(H{sub 2}O){sub 2}]{sup 2+} subunits connect the γ-Mo{sub 8} anions to construct a chain. The remaining two non-coordinated N donors in [Cu(bpz){sub 2}(H{sub 2}O){sub 2}]{sup 2+} further link two adjacent γ-Mo{sub 8} anions through Mo-N bonds. In compound 3, there exists a bi-nuclear Cu{sup II} cluster [Cu{sub 2}(tea){sub 2}(H{sub 2}O){sub 6}]{sup 4+}. The discrete bi-nuclear Cu{sup II} clusters and the CrMo{sub 6} anions link each other through abundant hydrogen bonding interactions. In compound 4, the [Ag(bpz)(H{sub 2}O)]{sup +} subunits connect γ-Mo{sub 8} anions to build a zigzag chain. The chains are further fused by other [Ag(bpz)(H{sub 2}O)]{sup +} cations to form a grid-like layer. There still exist Mo-N bonds in 4. We also have investigated the electrochemical and photocatalytic properties of 1-4.

Synthesis and Antiplasmodial Activity of 2-(4-Methoxyphenyl-4-Phenyl-1,10-Phenanthroline Derivative Compounds

Directory of Open Access Journals (Sweden)

Nazudin

2012-08-01

Full Text Available A unique of synthetic methods was employed to prepare 2-(4-methoxyphenyl-4-phenyl-1,10-phenanthroline (5 derivatives from 4-methoxy-benzaldehyde (1, acetophenone (2, and 8-aminoquinoline (4 with aldol condensation and cyclization reactions. The derivatives were tested through antiplasmodial test. The synthesis of derivatives compound 5 was conducted in three steps. The 3-(4-methoxyphenyl-1-phenylpropenone 3 was synthesized through aldol condensation of 1 and 2 which has a yield of 96.42%. The compound 5 was synthesized through cyclization of compound 4 and 3 with 84.55% yield. The derivative of compound 5 was synthesized from compound 5 using DMS and DES reagents which refluxed for 21 and 22 h, to produce (1-N-methyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (6 and (1-N-ethyl-9-(4-methoxyphenyl-7-phenyl-1,10-phenanthrolinium sulfate (7 with 91.42 and 86.36% yields, respectively. Results of in vitro testing of antiplasmodial activity of compound 5 derivatives (i.e., compound 6 and 7 against chloroquine-resistant P. falciparum FCR3 strain showed that compound 7 had higher antimalarial activity than compounds 5 and 6. Whereas, results of in vitro testing against chloroquine-sensitive P. falciparum D10 strain showed that compound 6 has higher antimalarial activity than compounds 5 and 7.

Ru-bis(pyridine)pyrazolate (bpp)-Based Water-Oxidation Catalysts Anchored on TiO2: The Importance of the Nature and Position of the Anchoring Group.

Science.gov (United States)

Francàs, Laia; Richmond, Craig; Garrido-Barros, Pablo; Planas, Nora; Roeser, Stephan; Benet-Buchholz, Jordi; Escriche, Lluís; Sala, Xavier; Llobet, Antoni

2016-04-04

Three distinct functionalisation strategies have been applied to the in,in-[{Ru(II)(trpy)}2(μ-bpp)(H2O)2](3+) (trpy=2,2':6',2''-terpyridine, bpp=bis(pyridine)pyrazolate) water-oxidation catalyst framework to form new derivatives that can adsorb onto titania substrates. Modifications included the addition of sulfonate, carboxylate, and phosphonate anchoring groups to the terpyridine and bis(pyridyl)pyrazolate ligands. The complexes were characterised in solution by using 1D NMR, 2D NMR, and UV/Vis spectroscopic analysis and electrochemical techniques. The complexes were then anchored on TiO2-coated fluorinated tin oxide (FTO) films, and the reactivity of these new materials as water-oxidation catalysts was tested electrochemically through controlled-potential electrolysis (CPE) with oxygen evolution detected by headspace analysis with a Clark electrode. The results obtained highlight the importance of the catalyst orientation with respect to the titania surface in regard to its capacity to catalytically oxidize water to dioxygen. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Compound K, a Ginsenoside Metabolite, Inhibits Colon Cancer Growth via Multiple Pathways Including p53-p21 Interactions

Directory of Open Access Journals (Sweden)

Eugene B. Chang

2013-01-01

Full Text Available Compound K (20-O-beta-D-glucopyranosyl-20(S-protopanaxadiol, CK, an intestinal bacterial metabolite of ginseng protopanaxadiol saponins, has been shown to inhibit cell growth in a variety of cancers. However, the mechanisms are not completely understood, especially in colorectal cancer (CRC. A xenograft tumor model was used first to examine the anti-CRC effect of CK in vivo. Then, multiple in vitro assays were applied to investigate the anticancer effects of CK including antiproliferation, apoptosis and cell cycle distribution. In addition, a qPCR array and western blot analysis were executed to screen and validate the molecules and pathways involved. We observed that CK significantly inhibited the growth of HCT-116 tumors in an athymic nude mouse xenograft model. CK significantly inhibited the proliferation of human CRC cell lines HCT-116, SW-480, and HT-29 in a dose- and time-dependent manner. We also observed that CK induced cell apoptosis and arrested the cell cycle in the G1 phase in HCT-116 cells. The processes were related to the upregulation of p53/p21, FoxO3a-p27/p15 and Smad3, and downregulation of cdc25A, CDK4/6 and cyclin D1/3. The major regulated targets of CK were cyclin dependent inhibitors, including p21, p27, and p15. These results indicate that CK inhibits transcriptional activation of multiple tumor-promoting pathways in CRC, suggesting that CK could be an active compound in the prevention or treatment of CRC.

P-matrix in the quark compound bag model

International Nuclear Information System (INIS)

Kalashnikova, Yu.S.; Narodetskij, I.M.; Veselov, A.I.

1983-01-01

Meaning of the P-matrix analysis is discussed within the quark compound bag (QCB) model. The most general version of this model is considered including the arbitrary coupling between quark and hadronic channels and the arbitrary smearipg of the surface interection region. The behaviour of P-matrix poles as functions of matching radius r,L0 is discussed for r 0 > + . In conclusion are presented the parameters of an illustrative set of NN potentials that has been obtained from the P-matrix fit to experimental data

Cytotoxicity and utility of 1-indanone in the synthesis of some new heterocycles.

Science.gov (United States)

Hegazi, Bahira; Mohamed, Hanan Ahmed; Dawood, Kamal Mohamed; Badria, Farid Abdel-Rahem

2010-04-01

Benzo[d]imidazole 3 and 1,2,4-triazin-5(2H)-one 6 were prepared by the reaction of starting ethyl (3-hydroxy-1H-inden-2-yl)(oxo)-acetate 2 with o-phenylenediamine and thiosemicarbazide respectively. Reaction of 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide 8 with phenylisothiocyanate gave thiosemicarbazide 9, and its reaction with chloroacetic acid or phenacylbromides led to the formation of thiazolidinone-4-one 10 or 1,3-thiazoles 12a, b. The reactivity of hydrazide 8 towards fluorinated aldehyde, phthalic anhydride, and hydrazonoyl chlorides 15a, b was studied to give fluorinated hydrazones, imide bis-hydrazones 13-16. The newly synthesized compounds were screened for their cytotoxic activities and compounds 6, 8, 9 and 10 were found the most potentially cytotoxic. The detailed synthesis, spectroscopic and biological data are reported.

Magnetic structure and phase formation of magnetocaloric Mn-Fe-P-X compounds

NARCIS (Netherlands)

Ou, Z.Q.

2013-01-01

This thesis presents a study of the crystal and magnetic structure, the magnetocaloric effect and related physical properties in Mn-Fe-P-X compounds. The influences of boron addition in (Mn,Fe)2(P,As) compounds have been studied. It is found that boron atoms occupy interstitial sites within the

Preparation of iodine-123 labeled AM251: a potential SPECT radioligand for the brain cannabinoid CB1 receptor

International Nuclear Information System (INIS)

Lan, Ruoxi; Makriyannis, Alexandros; Gatley, S.J.

1996-01-01

We report the synthesis and labeling with iodine-123 of N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2, 4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM251). This compound is an analog of the recently described cannabinoid receptor antagonist, SR141716A, in which a 4-chlorophenyl group is replaced by 4-iodophenyl. Labeling in good yield (62%) and radiochemical purity (> 95%), and high specific activity (> 2500 Ci/mmol) was achieved by an iododestannylation reaction using the tributyltin precursor, no carrier added I-123 iodide, and chloramine-T. (author)

Preparation of iodine-123 labeled AM251: a potential SPECT radioligand for the brain cannabinoid CB1 receptor

Energy Technology Data Exchange (ETDEWEB)

Lan, Ruoxi; Makriyannis, Alexandros [Connecticut Univ., Molecular and Cell Biology Dept., Storrs, CT (United States); Gatley, S.J. [Brookhaven National Lab., Medical Dept., Upton, NY (United States)

1996-10-01

We report the synthesis and labeling with iodine-123 of N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2, 4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM251). This compound is an analog of the recently described cannabinoid receptor antagonist, SR141716A, in which a 4-chlorophenyl group is replaced by 4-iodophenyl. Labeling in good yield (62%) and radiochemical purity (> 95%), and high specific activity (> 2500 Ci/mmol) was achieved by an iododestannylation reaction using the tributyltin precursor, no carrier added I-123 iodide, and chloramine-T. (author).

Synthesis, physical-chemical and biological properties of 1.8-disubstituted of theobromine. V. 8-Benzylidenhydrazino-1-p-methylbenzyltheobromines

Directory of Open Access Journals (Sweden)

D. G. Ivanchenko

2015-10-01

Full Text Available The problem of searching biologically active compounds amidst xanthine derivatives is a crucial one and is an issue for long-term investigation. Aim. In order to find new biologically active compounds among xanthine derivatives, undescribed earlier 8-benzylidenhydrazino-1-p-methylbenzyltheobromines have been synthesized. Methods and results. Reaction of 1-p-methylbenzyl-8-bromoxanthine with the excess of hydrazine hydrate in the aqueous dioxane is implemented through formation of 8-hydrazine-1(4-methylbenzyltheobromine. Through the interaction of 8-hydrazinetheobromine with aldehydes in aqueous propan-2-ol respective 8-benzylidenhydrazino-1-p-methylbenzyltheobromines have been obtained. Structure of synthesized compounds has been definitely proved by NMR-spectroscopy. Conclusions. Molecular and pharmacological descriptors of obtained substances have been calculated. The antioxidant activity of the obtained compounds has been explored. Priorities for further search of biologically active compounds in a range of xanthine derivatives have been set out.

Anti-Pseudomonas aeruginosa compound, 1,2,3,4-tetrahydro-1,3,5-triazine derivative, exerts its action by primarily targeting MreB.

Science.gov (United States)

Yamachika, Shinichiro; Sugihara, Chika; Tsuji, Hayato; Muramatsu, Yasunori; Kamai, Yasuki; Yamashita, Makoto

2012-01-01

In order to find new anti-Pseudomonas agents, we carried out whole-cell based P. aeruginosa growth assay, and identified 1,2,3,4-tetrahydro-1,3,5-triazine (Compound A). This compound showed anti-Pseudomonas activity against wild as well as pumpless strain equally at a same concentration. Also, this compound was structurally very similar to A22, which is known to inhibit the bacterial actin-like protein MreB. By the analysis of resistant strains, the primary target of this compound in P. aeruginosa was definitely confirmed to be MreB. In addition, these compounds showed a bacteriostatic effect, and induced the morphology changes in P. aeruginosa from rod shape to sphere shape, which leads to be clinically favorable in terms of susceptibility to phagocytosis and release of endotoxin. These results display that Compound A is a very attractive compound which shows anti-P. aeruginosa activity based on inhibition of MreB without being affected by efflux pumps, and could provide a new step toward development of new promising anti-Pseudomonas agents, MreB inhibitors.

Hyphenation of ultra high performance supercritical fluid chromatography with atmospheric pressure chemical ionisation high resolution mass spectrometry: Part 1. Study of the coupling parameters for the analysis of natural non-polar compounds.

Science.gov (United States)

Duval, Johanna; Colas, Cyril; Pecher, Virginie; Poujol, Marion; Tranchant, Jean-François; Lesellier, Eric

2017-08-04

An analytical method based on Ultra-High-Performance Supercritical Fluid Chromatography (UHPSFC) coupled with Atmospheric Pressure Chemical Ionization - High-resolution mass spectrometry (APCI-Q-TOF-HRMS) was developed for compounds screening from oily samples. The hyphenation was made using a commercial UHPLC device coupled to a CO 2 pump in order to perform the chromatographic analysis. An adaptation of the injection system for compressible fluids was accomplished for this coupling: this modification of the injection sequence was achieved to prevent unusual variations of the injected volume related to the use of a compressible fluid. UHPSFC-HRMS hyphenation was optimized to enhance the response of the varied compounds from a seed extract (anthraquinones, free fatty acids, diacylglycerols, hydroxylated triacylglycerols and triacylglycerols). No split was used prior to the APCI ionization source, allowing introducing all the compounds in the spectrometer, ensuring a better sensitivity for minor compounds. The effects of a mechanical make-up (T-piece) added before this ionization source was discussed in terms of standard deviation of response, response intensity and fragmentation percentage. The location of the T-piece with regards to the backpressure regulator (BPR), the flow rate and the nature of the make-up solvent were studied. Results show that the effects of the studied parameters depend on the nature of the compounds, whereas the make-up addition favours the robustness of the mass response (quantitative aspect). Copyright © 2017 Elsevier B.V. All rights reserved.

Chemistry of the Enaminone of 1-Acetylnaphthalene under Microwave Irradiation Using Chitosan as a Green Catalyst

Directory of Open Access Journals (Sweden)

Huwaida M. E. Hassaneen

2011-01-01

Full Text Available Enaminone 1 was reacted with hydrazonoyl halides 2a-d to yield 3,4-disubstituted pyrazoles 6a-d. Coupling with arenediazonium chlorides afforded the 2-(arylhydrazono-3-(1-naphthalenyl-3-oxopropionaldehydes 13a-c. Compounds 13 could be utilized for the synthesis of a variety of arylpyrazoles, arylazolopyrimidines, and pyridazinones via reaction with hydrazines, aminoazoles, and active methylene derivatives, respectively. A comparative study of aforementioned reactions was carried out with chitosan as a basic ecofriendly catalyst under conventional heating as well as under pressurized microwave irradiation conditions.

Synthesis and antitumor evaluation of thiophene based azo dyes incorporating pyrazolone moiety

Directory of Open Access Journals (Sweden)

Moustafa A. Gouda

2016-03-01

Full Text Available A series of thiophene incorporating pyrazolone moieties 5a–f and 6a–c were synthesized via diazo coupling of diazonium salt of 3-substituted-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophenes 1a–c with 3-methyl-1H-pyrazol-5(4H-one, 3-methyl-1-phenyl-1H-pyrazol-5(4H-one or 3-amino-1H-pyrazol-5(4H-one, respectively. Newly synthesized dyes were applied to polyester fabric as disperse dyes in which their color measurements and fastness properties were evaluated. These dyes showed generally red to blue shifted color with high extinction coefficient in comparison with aniline-based azo dyes. The antitumor activity of the synthesized dyes was evaluated. The results showed clearly that most of them exhibited good activity and compounds 5c and 5d exhibited moderate activity.

Facile synthesis and antimicrobial evaluation of some new heterocyclic compounds incorporating a biologically active sulfamoyl moiety.

Science.gov (United States)

Darwish, Elham S

2014-01-01

A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reacted in situ with chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, ketene N,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.

0034suppl.docx

Indian Academy of Sciences (India)

Arken

Mo3—O11, 2.3081 (19), 2.304, C4—C5, 1.541 (12), 1.535. Mo3—O12, 1.714 (2), 1.686, C5—C6, 1.519 (7), 1.534. Mo3—O13, 1.694 (2), 1.729, C7—C8, 1.508 (5), 1.537. Mo3—O14, 1.921 (2), 2.039, C7—C12, 1.518 (4), 1.539. Mo3—O15, 2.401 (2), 2.365, C8—C9, 1.548 (6), 1.535. Mo4—O14, 1.938 (2), 1.951, C9—C10 ...

31P-edited diffusion-ordered 1H NMR spectroscopy for the spectral isolation and identification of organophosphorus compounds related to chemical weapons agents and their degradation products.

Science.gov (United States)

Mayer, Brian P; Valdez, Carlos A; Hok, Saphon; Chinn, Sarah C; Hart, Bradley R

2012-12-04

Organophosphorus compounds represent a large class of molecules that include pesticides, flame-retardants, biologically relevant molecules, and chemical weapons agents (CWAs). The detection and identification of organophosphorus molecules, particularly in the cases of pesticides and CWAs, are paramount to the verification of international treaties by various organizations. To that end, novel analytical methodologies that can provide additional support to traditional analyses are important for unambiguous identification of these compounds. We have developed an NMR method that selectively edits for organophosphorus compounds via (31)P-(1)H heteronuclear single quantum correlation (HSQC) and provides an additional chromatographic-like separation based on self-diffusivities of the individual species via (1)H diffusion-ordered spectroscopy (DOSY): (1)H-(31)P HSQC-DOSY. The technique is first validated using the CWA VX (O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothioate) by traditional two-dimensional DOSY spectra. We then extend this technique to a complex mixture of VX degradation products and identify all the main phosphorus-containing byproducts generated after exposure to a zinc-cyclen organometallic homogeneous catalyst.

Five-membered heterocycles. Part I. Application of the HOMA index to 1,2,4-trizoles

Science.gov (United States)

Mrozek, A.; Karolak-Wojciechowska, J.; Amiel, P.; Barbe, J.

2000-06-01

Aromaticity of the heterorings containing nitrogen, sulphur, and/or oxygen was studied on the basis of crystallographic data (CSD). The HOMA index, quantitative estimation of heteroring aromaticity, was calculated for pyrroles, thiophenes, furanes, pyrazoles, oksazoles, and imidazoles. For triazoles, used as a training set of molecules, correlation between heteroring aromaticity and number of substituents was indicated. At the same time, molecular structure of 3-amino-5-[2‧-diethylamino)ethylthio]-1,2,4-triazole hydrochloride was determined as a reference compound using X-ray crystallography.

[5-(1,3-Diphenyl-1H-pyrazol-4-yl-3-phenyl-4,5-dihydropyrazol-1-yl](pyridin-4-ylmethanone

Directory of Open Access Journals (Sweden)

Tarawanti Verma

2011-01-01

Full Text Available A novel pyrazoline derivative 2 was synthesized by reaction of an α,β-unsaturated ketone 1 with isonicotinic acid hydrazide (INH in glacial acetic acid. The structure of the title compound 2 was established on basis of IR, 1H-NMR, 13C-NMR and mass spectral data.

Interpretation of some (p,n), (n,p), and (3He, p) reactions by means of the statistical multistep compound emission theory

International Nuclear Information System (INIS)

Bonetti, R.; Milazzo, L.C.; Melanotte, M.

1983-01-01

A number of (p,n), (n,p), and ( 3 He, p) reactions have been interpreted on the basis of the statistical multistep compound emission mechanism. Good agreement with experiment is found both in spectrum shape and in the value of the coherence widths

Synthesis, physical-chemical and biological properties of 1,8-disubstituted of theobromine. ІV. 8-R-thioderivatives of 1-p-methylbenzyltheobronine

Directory of Open Access Journals (Sweden)

D. G. Ivanchenko

2015-12-01

Full Text Available The problem of biologically active compounds searching amidst xanthine derivatives is a crucial one and is an issue for long-term investigation. Aim. In order to search for new biologically active compounds among xanthine derivatives, 8-R-thioderivatives of 1-p-methylbenzyltheobronine, undescribed earlier have been synthesized. Methods and results. Heating of 1-p-methylbenzyl-8-thiotheobromine with 2-bromo-4’-chloroacetophenone in aqueous ethanol leads to the formation of 1-p-methylbenzyl-8-[2-(4-chlorophenyl-2-oxoethyl]thiotheobromine. Interaction of 8-thiotheobromine with chloroacetic acid methyl ester has lead to formation of (1-p-methylbenzyltheobromine-8-ylthioacetic acid methyl ester. Structure of synthesized compounds has been definitely proved by NMR-spectroscopy. The acute toxicity, diuretic and antimicrobial activities of the obtained compounds have been explored. Conclusion. Priorities for further search of biologically active compounds in a range of xanthine derivatives have been set out.

Generation of Polar Semi-Saturated Bicyclic Pyrazoles for Fragment-Based Drug Discovery Campaigns.

Science.gov (United States)

Luise, Nicola; Wyatt, Paul

2018-05-07

Synthesising polar semi-saturated bicyclic heterocycles can lead to better starting points for fragment-based drug discovery (FBDD) programs. This communication highlights the application of diverse chemistry to construct bicyclic systems from a common intermediate, where pyrazole, a privileged heteroaromatic able to bind effectively to biological targets, is fused to diverse saturated counterparts. The generated fragments can be further developed either after confirmation of their binding pose or early in the process, as their synthetic intermediates. Essential quality control (QC) for selection of small molecules to add to a fragment library is discussed. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Spin correlations in (Mn,Fe)2(P,Si) magnetocaloric compounds above Curie temperature

NARCIS (Netherlands)

Miao, X.F.; Caron, L.; Gubbens, P.C.M.; Yaouanc, A; Dalmas de Réotier, P; Luetkens, H.; Amato, A; van Dijk, N.H.; Brück, E.H.

2016-01-01

The longitudinal-field muon-spin relaxation (LF-μSR) technique was employed to study the spin correlations in (Mn,Fe)2(P,Si) compounds above the ferromagnetic transition temperature (TC). The (Mn,Fe)2(P,Si) compound under study is found to show itinerant magnetism. The standard deviation of the

Synthesis and Characterization of Some New Bis-Pyrazolyl-Thiazoles Incorporating the Thiophene Moiety as Potent Anti-Tumor Agents

Directory of Open Access Journals (Sweden)

Sobhi M. Gomha

2016-09-01

Full Text Available A new series of 1,4-bis(1-(5-(aryldiazenylthiazol-2-yl-5-(thiophen-2-yl-4,5-dihydro-1H-pyrazol-3-ylbenzenes 3a–i were synthesized via reaction of 5,5′-(1,4-phenylenebis(3-(thiophen-2-yl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1 with hydrazonoyl halides 2a–i. In addition, reaction of 1 with ethyl chloroacetate afforded bis-thiazolone derivative 8 as the end product. Reaction of compound 8 with methyl glyoxalate gave bis-thiazolone derivative 10. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. All the synthesized compounds were evaluated for their anti-tumor activities against hepatocellular carcinoma (HepG2 cell lines, and the results revealed promising activities of compounds 3g, 5e, 3e, 10, 5f, 3i, and 3f with IC50 equal 1.37 ± 0.15, 1.41 ± 0.17, 1.62 ± 0.20, 1.86 ± 0.20, 1.93 ± 0.08, 2.03 ± 0.25, and 2.09 ± 0.19 μM, respectively.

[1,3-Bis(diphenyl-phosphino)pentane-κP,P']tetra-carbonyl-chromium(0).

Science.gov (United States)

Shawkataly, Omar Bin; Thangadurai, Daniel T; Pankhi, Mohd Aslam A; Shahinoor Dulal Islam, S M; Fun, Hoong-Kun

2009-02-04

In the title compound, [Cr(C(29)H(30)P(2))(CO)(4)], the Cr atom is octa-hedrally coordinated by four carbonyl ligands and one bidentate phosphine ligand, which is bounded as a chelate in a cis position. The average Cr-P and Cr-C bond lengths are 2.377 and 1.865 Å, respectively.

Structural, crystallographic, Hirshfeld surface, thermal and antimicrobial evaluation of new sulfonyl hydrazones

Science.gov (United States)

Bhat, Mahima; Poojary, Boja; Kumar, S. Madan; Hussain, Mumtaz M.; Pai, Nikhila; Revanasiddappa, B. C.; Kullaiah, Byrappa

2018-05-01

This context explains the condensation of various arylsulfonohydrazides with two pyrazole aldehydes to get corresponding hydrazones (6a-f). The hydrazones synthesized were confirmed with the help of IR, NMR, Mass and single crystal X-ray diffraction techniques. From the X-ray analysis it was observed that, all the three compounds 6a, 6c and 6f crystallizes in monoclinic crystal system with P21/c, P21/n and P21/n space group respectively. The intermolecular hydrogen bond interactions of the type Nsbnd H⋯O, Csbnd H⋯O, Csbnd H….C, Osbnd H ⋯O, Osbnd H⋯N and Csbnd H⋯N plays a significant role in the stability of the molecules. The 3D Hirshfeld analyses and 2D fingerprint plots were helpful in decoding the behavior of the interactions and their quantitative contributions towards the packing structure of the crystals. In addition to this, TGA and DTA curves were helpful in explaining the thermal stability of the compounds. Additionally, the antibacterial effectiveness of the molecules synthesized (6a-f) was analyzed against Gram-negative and Gram-positive strains. Interestingly, the compounds with fluorinated pyrazoles (6a and 6c) emerged as good bacterial inhibitors, having scope to produce potent therapeutics in future.

Proposal of how to update the standard information requirements in REACH, PPPR and BPR – a testing strategy for identification of endocrine disruptors

DEFF Research Database (Denmark)

Holbech, Henrik; Bjerregaard, Poul; Hass, Ulla

to these, new test methods that include endocrine sensitive endpoints have been included with regard to human health and the environment. Similar data requirements and new test methods that include endocrine sensitive endpoints are included in the guidance on Regulation (EU) No 528/2012 on how to fulfil...... review on EDs and the revised strategy for the future work on endocrine disruptors, focusing on adequate detection of substances with endocrine disrupting properties under various legislative frameworks, including REACH (EC No 1907/2006), the Plant Protection Products Regulation (PPPR) (EC No 1107....../2009) and the Biocidal Products Regulation (BPR) (EC No 528/2012). There are currently no specific information requirements or testing strategies with regard to endocrine disruption in REACH and other relevant legislations. However, in relation to biocides and recently also to plant protection products, indications...

Synthesis, basicity and complex properties from A ZN (II) of a acyclic purazol and pyridine proton-ionizable new receptor; Sintesis, basicidad y propiedades complejantes frente a Zn(II) de un nuevo receptor aciclico de pirazol y piridina prton-ionizable

Energy Technology Data Exchange (ETDEWEB)

Bueno, J.M.; Campayo, L.; Navarro, P.; Acerete, C. [Instituto de Quimica Medica CSIC, Madrid (Spain)

1995-12-01

The synthesis of bis (2`-pyridylmethil) N{sub 1}-H pyrazole 3,5-dicarboxylate 1[L] is reported. The formation of its sodium pyrazolate salt 1` [L] has been studied by ``13 CNMR, and the deprotonation pKa value of the pyrazole ring of 1 and those corresponding to the protonation of their pyridine rings have been measured using potentiometric methods in H{sub 2}O-MeOH (v/v 9:1) Starting from 1[L] or 1`[L-], the formation of mono- and di-nuclear complexes 2Zn[L] and 3[Zn{sub 2}[L-

Survivin counteracts the therapeutic effect of microtubule de-stabilizers by stabilizing tubulin polymers

Directory of Open Access Journals (Sweden)

Hsieh Hsing-Pang

2009-07-01

Full Text Available Abstract Background Survivin is a dual function protein. It inhibits the apoptosis of cells by inhibiting caspases, and also promotes cell growth by stabilizing microtubules during mitosis. Over-expression of survivin has been demonstrated to induce drug-resistance to various chemo-therapeutic agents such as cisplatin (DNA damaging agent and paclitaxel (microtubule stabilizer in cancers. However, survivin-induced resistance to microtubule de-stabilizers such as Vinca alkaloids and Combretastatin A-4 (CA-4-related compounds were seldom demonstrated in the past. Furthermore, the question remains as to whether survivin plays a dominant role in processing cytokinesis or inhibiting caspases activity in cells treated with anti-mitotic compounds. The purpose of this study is to evaluate the effect of survivin on the resistance and susceptibility of human cancer cells to microtubule de-stabilizer-induced cell death. Results BPR0L075 is a CA-4 analog that induces microtubule de-polymerization and subsequent caspase-dependent apoptosis. To study the relationship between the expression of survivin and the resistance to microtubule de-stabilizers, a KB-derived BPR0L075-resistant cancer cell line, KB-L30, was generated for this study. Here, we found that survivin was over-expressed in the KB-L30 cells. Down-regulation of survivin by siRNA induced hyper-sensitivity to BPR0L075 in KB cells and partially re-stored sensitivity to BPR0L075 in KB-L30 cells. Western blot analysis revealed that down-regulation of survivin induced microtubule de-stabilization in both KB and KB-L30 cells. However, the same treatment did not enhance the down-stream caspase-3/-7 activities in BPR0L075-treated KB cells. Translocation of a caspase-independent apoptosis-related molecule, apoptosis-inducing factor (AIF, from cytoplasm to the nucleus was observed in survivin-targeted KB cells under BPR0L075 treatment. Conclusion In this study, survivin plays an important role in the

Study of the behaviour of P-oxides produced in the combustion of phosphorus-bearing organic compounds and their absorption on suitable substances by means of compounds labelled with 32P. I

International Nuclear Information System (INIS)

Binkowski, J.; Gizinski, S.; Kaminski, R.; Reimschuessel, W.

1976-01-01

During the pyrolytic reaction of phosphorus-bearing compounds in an atmosphere of oxygen, there are produced P-oxides, which interfere in the determination of carbon and hydrogen. The behaviour of these P-oxides was studied intensively in the empty combustion tube in dependence on temperature, velocity of the carrier gas, the nature of the combustion and the positioning of the tube. The P-oxides were determined by the employment of 32 P-labelled aniline phosphate and by activation measurement of the 32 P directly through the tube walls as well as in the finely divided material. In conventional combustions the P-oxides separate abundantly on the walls of the tube provided that the gas velocity is low, especially in those zones of the tube where there is marked temperature lowering, or where very high temperature prevail. Deposited P-oxides are swept out of the tube only in the course of a very long time. Consequently a tube in which the P-bearing compounds have been burned will interfere because of the eluted P-oxides and hence will interfere also if P-free compounds are burned in this same tube

Synthesis of Some Novel Heterocyclic and Schiff Base Derivatives as Antimicrobial Agents

Directory of Open Access Journals (Sweden)

Mohamed E. Azab

2015-10-01

Full Text Available Treatment of 2,3-diaryloxirane-2,3-dicarbonitriles 1a–c with different nitrogen nucleophiles, e.g., hydrazine, methyl hydrazine, phenyl hydrazine, hydroxylamine, thiosemicarbazide, and/or 2-amino-5-phenyl-1,3,4-thiadiazole, afforded pyrazole, isoxazole, pyrrolotriazine, imidazolothiadiazole derivatives 2–5, respectively. Reacting pyrazoles 2a–c with aromatic aldehydes and/or methyl glycinate produced Schiff’s bases 7a–d and pyrazolo[3,4-b]-pyrazinone derivative 8, respectively. Treating 7 with ammonium acetate and/or hydrazine hydrate, furnished the imidazolopyrazole and pyrazolotriazine derivatives 9 and 10, respectively. Reaction of 8 with chloroacetic acid and/or diethyl malonate gave tricyclic compound 11 and triketone 12, respectively. On the other hand, compound 1 was reacted with active methylene precursors, e.g., acetylacetone and/or cyclopentanone producing adducts 14a,b which upon fusion with ammonium acetate furnished the 3-pyridone derivatives 15a,b, respectively. Some of newly synthesized compounds were screened for activity against bacterial and fungal strains and most of the newly synthesized compounds showed high antimicrobial activities. The structures of the new compounds were elucidated using IR, 1H-NMR, 13C-NMR and mass spectroscopy.

Magnetic properties and magnetocaloric effect of MnFeP0.5Ge0.5-xSix compounds

International Nuclear Information System (INIS)

Song, L.; Wang, G.F.; Ou, Z.Q.; Haschaolu, O.; Tegus, O.; Brueck, E.; Buschow, K.H.J.

2009-01-01

We have studied the magnetic properties and magnetic-entropy changes of the MnFeP 0.5 Ge 0.5-x Si x compounds with x = 0.1, 0.2, 0.3, 0.4 and 0.45. X-ray diffraction shows that the compounds crystallize in the Fe 2 P-type hexagonal structure. The lattice parameter a and the Curie temperature decreases with increasing x. The maximal magnetic-entropy changes for x = 0.4 and 0.45 derived from the magnetization data are about 6.0 J/kg K and 5.8 J/kg K, respectively, for a field change from 0 to 1.5 T

Synthesis, structure, and electronic properties of a dimer of Ru(bpy)2 doubly bridged by methoxide and pyrazolate.

Science.gov (United States)

Jude, Hershel; Rein, Francisca N; White, Peter S; Dattelbaum, Dana M; Rocha, Reginaldo C

2008-09-01

The heterobridged dinuclear complex cis,cis-[(bpy) 2Ru(mu-OCH 3)(mu-pyz)Ru(bpy) 2] (2+) ( 1; bpy = 2,2'-bipyridine; pyz = pyrazolate) was synthesized and isolated as a hexafluorophosphate salt. Its molecular structure was fully characterized by X-ray crystallography, (1)H NMR spectroscopy, and ESI mass spectrometry. The compound 1.(PF 6) 2 (C 44H 38F 12N 10OP 2Ru 2) crystallizes in the monoclinic space group P2 1/ c with a = 13.3312(4) A, b = 22.5379(6) A, c = 17.2818(4) A, beta = 99.497(2) degrees , V = 5121.3(2) A (3), and Z = 4. The meso diastereoisomeric form was exclusively found in the crystal structure, although the NMR spectra clearly demonstrated the presence of two stereoisomers in solution (rac and meso forms at approximately 1:1 ratio). The electronic properties of the complex in acetonitrile were investigated by cyclic voltammetry and UV-vis and NIR-IR spectroelectrochemistries. The stepwise oxidation of the Ru (II)-Ru (II) complex into the mixed-valent Ru (II)-Ru (III) and fully oxidized Ru (III)-Ru (III) states is fully reversible on the time scale of the in situ (spectro)electrochemical measurements. The mixed-valent species displays strong electronic coupling, as evidenced by the large splitting between the redox potentials for the Ru(III)/Ru(II) couples (Delta E 1/2 = 0.62 V; K c = 3 x 10 (10)) and the appearance of an intervalence transfer (IT) band at 1490 nm that is intense, narrow, and independent of solvent. Whereas this salient band in the NIR region originates primarily from highest-energy of the three IT transitions predicted for Ru(II)-Ru(III) systems, a weaker absorption band corresponding to the lowest-energy IT transition was clearly evidenced in the IR region ( approximately 3200 cm (-1)). The observation of totally coalesced vibrational peaks in the 1400-1650 cm (-1) range for a set of five bpy spectator vibrations in Ru (II)-Ru (III) relative to Ru (II)-Ru (II) and Ru (III)-Ru (III) provided evidence for rapid electron transfer and

Disruption of focal adhesion kinase and p53 interaction with small molecule compound R2 reactivated p53 and blocked tumor growth

International Nuclear Information System (INIS)

Golubovskaya, Vita M; Ho, Baotran; Zheng, Min; Magis, Andrew; Ostrov, David; Morrison, Carl; Cance, William G

2013-01-01

Focal Adhesion Kinase (FAK) is a 125 kDa non-receptor kinase that plays a major role in cancer cell survival and metastasis. We performed computer modeling of the p53 peptide containing the site of interaction with FAK, predicted the peptide structure and docked it into the three-dimensional structure of the N-terminal domain of FAK involved in the complex with p53. We screened small molecule compounds that targeted the site of the FAK-p53 interaction and identified compounds (called Roslins, or R compounds) docked in silico to this site. By different assays in isogenic HCT116p53 + / + and HCT116 p53 - / - cells we identified a small molecule compound called Roslin 2 (R2) that bound FAK, disrupted the binding of FAK and p53 and decreased cancer cell viability and clonogenicity in a p53-dependent manner. In addition, dual-luciferase assays demonstrated that the R2 compound increased p53 transcriptional activity that was inhibited by FAK using p21, Mdm-2, and Bax-promoter targets. R2 also caused increased expression of p53 targets: p21, Mdm-2 and Bax proteins. Furthermore, R2 significantly decreased tumor growth, disrupted the complex of FAK and p53, and up-regulated p21 in HCT116 p53 + / + but not in HCT116 p53 - / - xenografts in vivo. In addition, R2 sensitized HCT116p53 + / + cells to doxorubicin and 5-fluorouracil. Thus, disruption of the FAK and p53 interaction with a novel small molecule reactivated p53 in cancer cells in vitro and in vivo and can be effectively used for development of FAK-p53 targeted cancer therapy approaches

Bis(1,3-dithiole) Compounds

DEFF Research Database (Denmark)

Andersen, Jan Rud; Engler, E. M.; Green, D. C.

1977-01-01

There is described the preparation of bis-1,3-dithiole compounds (I) which are key synthetic precursors for the preparation of new polymeric metal bis(dithiolene) (i.e., II) and tetrathiafulvalene compounds (i.e., III): (Image Omitted)...

Insight into π-hole interactions containing the inorganic heterocyclic compounds S2N2/SN2P2.

Science.gov (United States)

Lu, Bo; Zhang, Xueying; Meng, Lingpeng; Zeng, Yanli