Sample records for quinolines

  1. Wet oxidation of quinoline

    DEFF Research Database (Denmark)

    Thomsen, A.B.; Kilen, H.H.


    The influence of oxygen pressure (0.4 and 2 MPa). reaction time (30 and 60 min) and temperature (260 and 280 degrees C) on the wet oxidation of quinoline has been studied. The dominant parameters for the decomposition of quinoline were oxygen pressure and reaction temperature. whereas the reaction...... time was less important within the range studied. Nitrifying bacteria were used to measure the inhibition from wet oxidative-treated samples to study the effect of the (wet oxidation) reaction conditions. Wet oxidation made quinoline more toxic to Nitrosomonas. This was observed for Nitrobacter as well....... The combined wet oxidation and biological treatment of reaction products resulted in 91% oxidation of the parent compound to CO2 and water. Following combined wet oxidation and biological treatment the sample showed low toxicity towards Nitrosomonas and no toxicity towards Nitrobacter. (C) 1998 Elsevier...

  2. Hydrodenitrogenation of quinoline and acridine

    Energy Technology Data Exchange (ETDEWEB)

    Reiff, Jr., E. K.


    The hydrodenitrogenation of quinoline and of acridine was studied in a batch autoclave reactor between 342 and 353/sup 0/C and between 500 and 2000 psig. The several commercial hydrotreating catalysts examined decreased in activity in the following order for quinoline hydrodenitrogenation: Ni--Mo/Al/sub 2/O/sub 3/, Ni--W/Al/sub 2/O/sub 3/, Ni--W/SiO/sub 2/--Al/sub 2/O/sub 3/, and Co--Mo/Al/sub 2/O/sub 3/. The total nitrogen removal rate for quinoline was slightly greater than that for acridine and both followed pseudo first-order kinetics over a conversion range of 0 to 50%. Hydrogenation and cracking steps were both kinetically limiting. Nitrogen-containing reaction products for quinoline hydrodenitrogenation were 1,2,3,4-tetrahydroquinoline, 5,6,7,8-tetrahydroquinoline, decahydroquinoline and o-propylaniline. At 342/sup 0/C and 500 psig quinoline and 1,2,3,4-tetrahydroquinoline were in thermodynamic equilibrium, and the disappearance of the lumped group of quinoline plus 1,2,3,4-tetrahydroquinoline followed pseudo first-order kinetics. Sixteen nitrogen-containing reaction products were found for acridine hydrodenitrogenation, including 1,2,3,4-tetrahydroacridine, 1,2,3,4,9,10,13,14-octahydroacridine, sym-octahydroacridine, perhydroacridine, and o-(methylenecyclohexane)aniline. The hydrogenolysis step for both quinoline and acridine appears to be through hydrogenated forms of these compounds. This is supported by bond strength arguments.

  3. Glycoconjugates of Quinolines: Application in Medicinal Chemistry. (United States)

    Oliveri, Valentina; Vecchio, Graziella


    Compounds with the quinoline scaffold are widely investigated and offer a variety of therapeutical properties. A number of quinoline derivatives have been synthesized and among these there are glycoconjugated derivatives. Based on the interest for this family of compounds, we reviewed the different biological activities (molecular probes, antiinfective, antiproliferative, antiaggregant and antioxidant) and the potential applications in medicinal chemistry of quinoline glycoconjugates. This review wants to show an example of the glycoconjugation strategy which arose not only to modify the water solubility of the quinolines but also to influence their activity and targeting properties.

  4. Difluoro[2-(quinolin-2-ylphenolato]borane

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    Xi Yang


    Full Text Available The title compound, C15H10BF2NO, was synthesized by the reaction of 2-(quinolin-2-ylphenol and boron trifluoride etherate. The quinoline ring system and the benzene ring are twisted, making a dihedral angle of 8.3 (2°. In the crystal, π–π interactions between the aromatic rings [centroid–centroid distance = 3.638 (9 Å] link the molecules into chains propagating in [100].

  5. Benzylchloridobis(quinolin-8-olatotin(IV

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    Qibao Wang


    Full Text Available In the title compound, [Sn(C7H7(C9H6NO2Cl], the SnIV ion is in a distorted octahedral coordination environment formed by the O and N atoms of two bis-chelating quinolin-8-olate ligands, a Cl atom and a C atom from a benzyl ligand. The axial sites are occupied by an N atom of a quinolinate ligand and the C atom of the benzyl ligand. The axial Sn—N bond is slightly shorter than the equatorial Sn—N bond.

  6. Dissociative photoionization of quinoline and isoquinoline

    NARCIS (Netherlands)

    Bouwman, J.; Sztáray, B.; Oomens, J.; Hemberger, P.; Bodi, A.


    Two nitrogen-containing polycyclic aromatic hydrocarbon isomers of C9H7N composition, quinoline, and isoquinoline have been studied by imaging photoelectron photoion coincidence spectroscopy at the VUV beamline of the Swiss Light Source. High resolution threshold photoelectron spectra have been

  7. trans-Dichloridobis(quinoline-κNplatinum(II

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    Kwang Ha


    Full Text Available In the title complex, trans-[PtCl2(C9H7N2], the PtII ion is four-coordinated in an essentially square-planar coordination environment defined by two N atoms from two quinoline (qu ligands and two Cl− anions. The Pt atom is located on an inversion centre and thus the asymmetric unit contains one half of the complex; the PtN2Cl2 unit is exactly planar. The dihedral angle between the PtN2Cl2 unit and the quinoline ligand is 85.1 (1°. In the crystal, the complex molecules are stacked into columns along the b axis. In the columns, several intermolecular π–π interactions between the six-membered rings are present, the shortest ring centroid–centroid distance being 3.733 (5 Å between pyridine rings.

  8. Transformation of indole and quinoline by Desulfobacterium indolicum (DSM 3383)

    DEFF Research Database (Denmark)

    Licht, D.; Johansen, S.S.; Arvin, E.


    Degradation of indole and quinoline by Desulfobacterium indolicum was studied in batch cultures. The first step in the degradation pathway of indole and quinoline was a hydroxylation at the 2 position to oxindole and 2-hydroxyquinoline respectively. These hydroxylation reactions followed saturati...

  9. Hydrotalcite-quinolinate composites as catalysts in a coupling reaction. (United States)

    Ríos, Eloisa; Hernández, Magali; Ibarra, Ilich A; Guzmán, Ariel; Lima, Enrique


    Samples of layered double hydroxides were prepared by a sol-gel procedure. Quinolinate Al(C9H6NO)3 units were added during the synthesis, leading to composite quinolinate hydrotalcite-like compounds. The amount of quinolinate was varied, showing that the number of organic building blocks determines the physicochemical properties of materials, which differ significantly from those commonly reported for hydrotalcites without any quinolinate. The order of layers, specific surface area and coordination of aluminium were the parameters most significantly influenced by the presence of the quinolinate as a part of the brucite-like layers. The composite quinolinate-hydrotalcite materials were tested to catalyse the Kabachnik-Fields reaction.Graphical abstractAdding of quinolinate Al(C9H6NO)3 to hydrotalcite-like compounds creates disorder in the stack of brucite-like layers, leading to a significant modification of structural, textural and catalytic properties. The presence of quinolinate inhibits the enchainment of octahedral blocks in hydrotalcite but develop specific surface areas as high as 600 m(2)g(-1).

  10. Transformation of indole and quinoline by Desulfobacterium indolicum (DSM 3383)

    DEFF Research Database (Denmark)

    Licht, D.; Johansen, S.S.; Arvin, E.


    Degradation of indole and quinoline by Desulfobacterium indolicum was studied in batch cultures. The first step in the degradation pathway of indole and quinoline was a hydroxylation at the 2 position to oxindole and 2-hydroxyquinoline respectively. These hydroxylation reactions followed saturati...

  11. Dual activity of quinolinate synthase: triose phosphate isomerase and dehydration activities play together to form quinolinate. (United States)

    Reichmann, Debora; Couté, Yohann; Ollagnier de Choudens, Sandrine


    Quinolinate synthase (NadA) is an Fe4S4 cluster-containing dehydrating enzyme involved in the synthesis of quinolinic acid (QA), the universal precursor of the essential coenzyme nicotinamide adenine dinucleotide. The reaction catalyzed by NadA is not well understood, and two mechanisms have been proposed in the literature that differ in the nature of the molecule (DHAP or G-3P) that condenses with iminoaspartate (IA) to form QA. In this article, using biochemical approaches, we demonstrate that DHAP is the triose that condenses with IA to form QA. The capacity of NadA to use G-3P is due to its previously unknown triose phosphate isomerase activity.

  12. Thermodynamics of organic mixtures containing amines. VIII. Systems with quinoline

    Energy Technology Data Exchange (ETDEWEB)

    Gonzalez, Juan Antonio [G.E.T.E.F., Grupo Especializado en Termodinamica de Equilibrio entre Fases, Departamento de Fisica Aplicada, Facultad de Ciencias, Universidad de Valladolid, E-47071 Valladolid (Spain)], E-mail:; Domanska, Urszula; Zawadzki, Maciej [Physical Chemistry Division, Faculty of Chemistry, Warsaw University of Technology, 00-664 Warsaw (Poland)


    (Solid + liquid) equilibrium temperatures for mixtures containing quinoline and 1-dodecanol, 1-hexadecanol, or 1-octadecanol have been measured using a dynamic method. (Quinoline + benzene, +alkane, or +1-alkanol) systems were investigated using DISQUAC. The corresponding interaction parameters are reported. The model yields a good representation of molar excess Gibbs free energies, G{sup E}, molar excess enthalpies, H{sup E}, and of the (solid + liquid) equilibria, SLE. Interactional and structural effects were analysed comparing H{sup E} and the molar excess internal energy at constant volume, U{sub V}{sup E}. It was encountered that structural effects are very important in systems involving alkanes or 1-alkanols. Interactions between amine molecules are stronger in mixtures with quinoline than in those containing pyridine, which was ascribed to the higher polarizability of quinoline.

  13. Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation. (United States)

    Chen, Xuan; Zhu, Chongwei; Cui, Xiuling; Wu, Yangjie


    An efficient and direct 2-acetoxylation of quinoline N-oxides via copper(I) catalyzed C-H bond activation has been developed. This transformation was achieved using TBHP as an oxidant in the cross-dehydrogenative coupling (CDC) reaction of quinoline N-oxides with aldehydes, and provided a practical pathway to 2-acyloxyl quinolines.

  14. The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil. (United States)

    Dutta, Uttam; Deb, Arghya; Lupton, David W; Maiti, Debabrata


    A radical based direct C-H iodination protocol for quinolines, quinolones, pyridones, pyridines, and uracil has been developed. The iodination occurs in a C3 selective manner for quinolines and quinolones. Pyridones and pyridines undergo C3 and C5 iodination, while dimethyl uracil undergoes C5 iodination. Scope of the method was demonstrated through the rapid synthesis of both electron rich as well as electron poor heteroaromatic iodides. The protocol was found to be scalable and general, while a mechanism has been proposed.

  15. Benzylchloridobis(quinolin-8-olato)tin(IV)


    Qibao Wang


    In the title compound, [Sn(C7H7)(C9H6NO)2Cl], the SnIV ion is in a distorted octahedral coordination environment formed by the O and N atoms of two bis-chelating quinolin-8-olate ligands, a Cl atom and a C atom from a benzyl ligand. The axial sites are occupied by an N atom of a quinolinate ligand and the C atom of the benzyl ligand. The axial Sn—N bond is slightly shorter than the equatorial Sn—N bond.

  16. Benzyl-chloridobis(quinolin-8-olato)tin(IV). (United States)

    Wang, Qibao


    In the title compound, [Sn(C(7)H(7))(C(9)H(6)NO)(2)Cl], the Sn(IV) ion is in a distorted octa-hedral coordination environment formed by the O and N atoms of two bis-chelating quinolin-8-olate ligands, a Cl atom and a C atom from a benzyl ligand. The axial sites are occupied by an N atom of a quinolinate ligand and the C atom of the benzyl ligand. The axial Sn-N bond is slightly shorter than the equatorial Sn-N bond.

  17. Benzyl­chloridobis(quinolin-8-olato)tin(IV)


    Wang, Qibao


    In the title compound, [Sn(C7H7)(C9H6NO)2Cl], the SnIV ion is in a distorted octa­hedral coordination environment formed by the O and N atoms of two bis-chelating quinolin-8-olate ligands, a Cl atom and a C atom from a benzyl ligand. The axial sites are occupied by an N atom of a quinolinate ligand and the C atom of the benzyl ligand. The axial Sn—N bond is slightly shorter than the equatorial Sn—N bond.

  18. N'-(4-Bromo-benzyl-idene)quinoline-8-sulfonohydrazide. (United States)

    de Oliveira, Kely Navakoski; Nunes, Ricardo José; Foro, Sabine


    In the title compound, C(16)H(12)BrN(3)O(2)S, the dihedral angle between the planes of the almost planar (r.m.s. deviation = 0.0263 Å) quinoline group and the bromo-phenyl group is 87.4 (1)°. The torsion angle of the central S-N-N-C bridge is 144.8 (2)°. The amino group has an intra-molecular contact to the quinoline N atom. The structure is stabilized by one N-H⋯O and two C-H⋯O inter-molecular hydrogen bonds.

  19. Bioremediation of Quinoline-contaminated Soil Using Bioaugmentation in Slurry-phase Reactor

    Institute of Scientific and Technical Information of China (English)



    Objective To investigate the possibility of using bioaugmentation as a strategy for remediating quinoline-contaminated soil. Methods Microorganisms were introduced to the soil to assess the feasibility of enhancing the removal of quinoline from quinoline-contaminated soil. Slurry-phase reactor was used to investigate the bioremediation of quinoline-contaminated soil. HPLC (Hewlett-Packard model 5050 with an UV detector) was used for analysis of quinoline concentration. Results The biodegradation rate of quinoline was increased through the introduction of Burkholderia pickettii. Quinoline, at a concentration of 1 mg/g soil, could be removed completely within 6 and 8 hours with and without combined effect of indigenous microbes, respectively. Although the indigenous microbes alone had no quinoline-degrading ability, they cooperated with the introduced quinoline-degrader to remove quinoline more quickly than the introduced microbes alone. Bioaugmentaion process was accelerated by the increase of inoculum size and bio-stimulation. The ratio of water to soil in slurry had no significant impact on bioremediation results. Conclusion Bioaugmetation is an effective way for bioremediation of quinoline-contaminated soil.

  20. An efficient synthesis of quinolines under solvent-free conditions

    Indian Academy of Sciences (India)

    Mihir K Chaudhuri; Sahid Hussain


    An efficient synthesis of substituted quinolines has been achieved in a one-pot reaction from -nitrobenzaldehyde and enolizable ketones using SnCl2.2H2O as the reductant under microwave irradiation without any solvent or catalyst.

  1. Dasycarine, a New Quinoline Alkaloid from Dictamnus dasycarpus

    Institute of Scientific and Technical Information of China (English)


    Dasycarine, a new quinoline alkaloid along with five known compounds, dictamine, dihydroobacunone, obacunone, fraxinellone and b -sitosterol, were isolated from Dictamnus dasycarpus. The structure of dasycarine was identified as 4, 5, 8- trimethoxyl -3- (3- methyl -2- butenyl)- 2- quinone by 1D and 2D NMR techniques.

  2. Synthesis, photochemistry, DNA cleavage/binding and cytotoxic properties of fluorescent quinoxaline and quinoline hydroperoxides. (United States)

    Chowdhury, Nilanjana; Gangopadhyay, Moumita; Karthik, S; Pradeep Singh, N D; Baidya, Mithu; Ghosh, S K


    Novel fluorescent quinoxaline and quinoline hydroperoxides were shown to perform dual role as both fluorophores for cell imaging and photoinduced DNA cleaving agents. Photophysical studies of newly synthesized quinoxaline and quinoline hydroperoxides showed that they all exhibited moderate to good fluorescence. Photolysis of quinoxaline and quinoline hydroperoxides in acetonitrile using UV light above 350nm resulted in the formation of corresponding ester compounds via γ-hydrogen abstraction by excited carbonyl chromophore. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroperoxides by UV light (⩾350nm). Both hydroxyl radicals and singlet oxygen were identified as reactive oxygen species (ROS) responsible for the DNA cleavage. Further, we showed quinoline hydroperoxide binds to ct-DNA via intercalative mode. In vitro biological studies revealed that quinoline hydroperoxide has good biocompatibility, cellular uptake property and cell imaging ability. Finally, we showed that quinoline hydroperoxide can permeate into cells efficiently and may cause cytotoxicity upon irradiation by UV light.

  3. Quinoline-2-thiol Derivatives as Fluorescent Sensors for Metals, pH and HNO

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    Naphtali A. O’Connor


    Full Text Available A tautomeric equilibrium exists for quinoline-2-thiol and quinoline-2(1H-thione. Quantum mechanical calculations predict the thione is the major tautomer and this is confirmed by the absorption spectra. The utility of quinolone-2-thiol/quinoline-2(1H-thione as a chromophore for developing fluorescent sensors is explored. No fluorescence is observed when excited at absorption maxima, however a fluorescence increase is observed when exposed to HNO, a molecule of import as a cardiovascular therapeutic. Alkylated quinoline-2-thiol derivatives are found to be fluorescent and show a reduction in fluorescence when exposed to metals and changes in pH.

  4. Quinoline based receptor in fluorometric discrimination of carboxylic acids

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    Full Text Available Quinoline and naphthalene-based fluororeceptors 1 and 2 have been designed and synthesized for detection of hydroxy carboxylic acids in less polar solvents. The receptor 1 shows monomer emission quenching followed by excimer emission upon hydrogen bond-mediated complexation of carboxylic acids. The excimer emission distinguishes aromatic dicarboxylic acids from aliphatic dicarboxylic acids and even long chain aliphatic dicarboxylic acids from short chain aliphatic dicarboxylic acids. The receptor 1 is found to be selective for citric acid with a strong excimer emission in CHCl3. On the contrary, the receptor 2 exhibited less binding constant value and did not form any excimer upon complexation with the same acids under similar conditions. This established the role of quinoline ring nitrogen in binding with the acids.

  5. Novel Synthesis of Quinoline-7,8-diol Derivative

    Institute of Scientific and Technical Information of China (English)

    HE,Juan; WANG,Xue-Bin; WAN,Zheng-Kai


    @@ Quinoline 7,8-diol derivatives can be expected to form metal complexes, and are the moiety of marine alkaloid,which exhibits strong cytotoxic activity against several human tumor. Our synthesis of 6 commences from L-dopa (1)(Scheme 1). Esterification of 2 with methanol and treatment of the resulting ester 3 with trichloroethoxycarbonyl (Troc)chloride yielded the N-protected amino acid ester 4. Treatment of 4 with acrolein in 1.3 mol/L methanolic HCl for 4 d at room temperature yielded the quinoline derivative 5, which was dissolved in 25% aq. HBr and the resulting solution was heated at reflux for 6 h to afford compound 6.

  6. Gold-catalyzed oxidative cycloadditions to activate a quinoline framework. (United States)

    Huple, Deepak B; Ghorpade, Satish; Liu, Rai-Shung


    Going for gold! Gold-catalyzed reactions of 3,5- and 3,6-dienynes with 8-alkylquinoline oxides results in an oxidative cycloaddition with high stereospecificity (see scheme; EWG = electron-withdrawing group); this process involves a catalytic activation of a quinoline framework. The reaction mechanism involves the intermediacy of α-carbonyl pyridinium ylides (I) in a concerted [3+2]-cycloaddition with a tethered alkene.

  7. Synthesis, Crystal and Molecular Structure Studies and DFT Calculations of Phenyl Quinoline-2-Carboxylate and 2-Methoxyphenyl Quinoline-2-Carboxylate; Two New Quinoline-2 Carboxylic Derivatives

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    Edakot Fazal


    Full Text Available The crystal and molecular structures of the title compounds, phenyl quinoline-2-carboxylate and 2-methoxyphenyl quinoline-2-carboxylate, two new derivatives of quinolone-2-carboxylic acid, are reported and confirmed by single crystal X-ray diffraction and spectroscopic data. Compound (I, C16H11NO2, crystallizes in the monoclinic space group P21/c, with 8 molecules in the unit cell. The unit cell parameters are a = 14.7910(3 Å; b = 5.76446(12 Å; c = 28.4012(6 Å; β = 99.043(2°; V = 2391.45(9 Å3. Compound (II, C17H13NO5, crystallizes in the monoclinic space group P21/n with 4 molecules in the unit cell. The unit cell parameters are a = 9.6095(3 Å; b = 10.8040(3 Å; c = 13.2427(4 Å; β = 102.012(3°; V = 1344.76(7 Å3. Density functional theory (DFT geometry optimized molecular orbital calculations were performed and frontier molecular orbitals of each compound are displayed. Correlation between the calculated molecular orbital energies (eV for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound has been proposed. Additionally, similar correlations observed among six closely related compounds examining small structural differences to their frontier molecular orbital surfaces and from their DFT molecular orbital energies, provide further support for the suggested assignments of the title compounds.

  8. A correlation study of quinoline derivatives and their pharmaceutical behavior by ab initio calculated NQR parameters. (United States)

    Rafiee, Marjan A; Hadipour, Nasser L; Naderi-manesh, Hossein


    In this paper, ab initio calculated NQR parameters for some quinoline-containing derivatives are presented. The calculations are carried out in a search for the relationships between the charge distribution of these compounds and their ability to interact with haematin. On the basis of NQR parameters, pi-electron density on the nitrogen atom of the quinoline ring plays a dominant role in determining the ability of quinolines to interact with haematin. This point was confirmed with investigation of Fe+3 cation-pi quinoline ring interactions in 2- and 4-aminoquinoline. However, our results do not show any preference for those carbon atoms of the quinoline ring which previous reports have noted. In order to calculate the NQR parameters, the electric field gradient (EFG) should be evaluated at the site of a quadrupolar nucleus in each compound. EFGs are calculated by the Gaussian 98 program using the B3LYP/6-31 G* level of theory.

  9. UV action spectroscopy of protonated PAH derivatives. Methyl substituted quinolines

    DEFF Research Database (Denmark)

    Klærke, Benedikte; Holm, Anne; Andersen, Lars Henrik


    Aims. We investigate the production of molecular photofragments upon UV excitation of PAH derivatives, relevant for the interstellar medium. Methods. The action absorption spectra of protonated gas-phase methyl-substituted quinolines (CH3−C9H7NH+) have been recorded in the 215–338 nm spectral ran...... the estimated IR relaxation time. Photophysical properties of both nitrogen containing and methyl-substituted PAHs are interesting in an astrophysical context in connection with identifying the aromatic component of the interstellar medium....

  10. Neurotoxicity of Quinolinic Acid to Spiral Ganglion Cells in Rats

    Institute of Scientific and Technical Information of China (English)

    肖红俊; 杨琛; 何圆圆; 郑娜


    Our study investigated the neurotoxicity of quinolinic acid(QA) to spiral ganglion cells(SGCs),observed the protective effects of N-methyl-D-aspartate(NMDA) receptor antagonist MK-801 and magnesium ions on the QA-induced injury to SGCs,and analyzed the role of QA in otitis media with effusion(OME)-induced sensorineural hearing loss(SNHL).After culture in vitro for 72 h,SGCs were exposed to different media and divided into 4 groups:the blank control group,the QA injury group,the MK-801 treatment group,and th...

  11. Genotoxicity risk assessment of diversely substituted quinolines using the SOS chromotest. (United States)

    Duran, Leidy Tatiana Díaz; Rincón, Nathalia Olivar; Galvis, Carlos Eduardo Puerto; Kouznetsov, Vladimir V; Lorenzo, Jorge Luis Fuentes


    Quinolines are aromatic nitrogen compounds with wide therapeutic potential to treat parasitic and microbial diseases. In this study, the genotoxicity of quinoline, 4-methylquinoline, 4-nitroquinoline-1-oxide (4-NQO), and diversely functionalized quinoline derivatives and the influence of the substituents (functional groups and/or atoms) on their genotoxicity were tested using the SOS chromotest. Quinoline derivatives that induce genotoxicity by the formation of an enamine epoxide structure did not induce the SOS response in Escherichia coli PQ37 cells, with the exception of 4-methylquinoline that was weakly genotoxic. The chemical nature of the substitution (C-5 to C-8: hydroxyl, nitro, methyl, isopropyl, chlorine, fluorine, and iodine atoms; C-2: phenyl and 3,4-methylenedioxyphenyl rings) of quinoline skeleton did not significantly modify compound genotoxicities; however, C-2 substitution with α-, β-, or γ-pyridinyl groups removed 4-methylquinoline genotoxicity. On the other hand, 4-NQO derivatives whose genotoxic mechanism involves reduction of the C-4 nitro group were strong inducers of the SOS response. Methyl and nitrophenyl substituents at C-2 of 4-NQO core affected the genotoxic potency of this molecule. The relevance of these results is discussed in relation to the potential use of the substituted quinolines. The work showed the sensitivity of SOS chromotest for studying structure-genotoxicity relationships and bioassay-guided quinoline synthesis.

  12. Comparative theoretical and experimental study on novel tri-quinoline system and its anticancer studies (United States)

    Gayathri, Kasirajan; Radhika, Ramachandran; Shankar, Ramasamy; Malathi, Mahalingam; Savithiri, Krishnaswamy; Sparkes, Hazel A.; Howard, Judith A. K.; Mohan, Palathurai Subramaniam


    A novel compound 2-chloro-3,6-bis-(quinolin-8-yloxymethyl)-quinoline 3 bearing a tri-quinoline moiety has been synthesized from 2-chloro-3,6-dimethyl quinoline 1 and 8-hydroxy quinoline 2 using dry acetone and K2CO3 as a base. 3 has been characterized by using FT-IR, FT-Raman, UV-Vis, 1H NMR, 13C NMR spectra and single crystal X-ray diffraction methods. We have also made a combined experimental and theoretical study on the molecular structure, vibrational spectra, NMR, FT-IR, FT-Raman and UV-Vis spectra of 2-chloro-3,6-bis-(quinolin-8-yloxymethyl)-quinoline. The theoretical studies of the title compound have been evaluated by using density functional theory calculations using B3LYP/6-31+G(d,p) and M06-2X/6-31+G(d,p) level of theories. The calculated theoretical values were found to be in good agreement with the experimental findings. The single crystal structure 3 crystallized in the orthorhombic space group Pna21. The compound 3 exhibits higher cytotoxicity in human cervical cancer cell lines (HeLa) than human breast cancer cell lines (MCF7).

  13. True Niacin Deficiency in Quinolinic Acid Phosphoribosyltransferase (QPRT) Knockout Mice. (United States)

    Shibata, Katsumi


    Pyridine nucleotide coenzymes (PNCs) are involved in over 500 enzyme reactions. PNCs are biosynthesized from the amino acid L-tryptophan (L-Trp), as well as the vitamin niacin. Hence, "true" niacin-deficient animals cannot be "created" using nutritional techniques. We wanted to establish a truly niacin-deficient model animal using a protocol that did not involve manipulating dietary L-Trp. We generated mice that are missing the quinolinic acid phosphoribosyltransferase (QPRT) gene. QPRT activity was not detected in qprt(-/-)mice. The qprt(+/+), qprt(+/-) or qprt(-/-) mice (8 wk old) were fed a complete diet containing 30 mg nicotinic acid (NiA) and 2.3 g L-Trp/kg diet or an NiA-free diet containing 2.3 g L-Trp/kg diet for 23 d. When qprt(-/-)mice were fed a complete diet, food intake and body weight gain did not differ from those of the qprt(+/+) and the qprt(+/-) mice. On the other hand, in the qprt(-/-) mice fed the NiA-free diet, food intake and body weight were reduced to 60% (pniacin such as blood and liver NAD concentrations were also lower in the qprt(-/-) mice than in the qprt(+/+) and the qprt(+/-) mice. Urinary excretion of quinolinic acid was greater in the qprt(-/-) mice than in the qprt(+/+) and the qprt(+/-) mice (pniacin-deficient mice.

  14. (E-2-[(Pyren-1-yliminomethyl]quinolin-8-ol

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    Soma Mukherjee


    Full Text Available In the title compound, C26H16N2O, the pyrene ring system (r.m.s. deviation = 0.021 Å is inclined to the planar quinoline ring system (r.m.s. deviation = 0.017 Å by 30.62 (5°, and the conformation about the bridging N=C bond is E. There is an intramolecular O—H...N hydrogen bond with an S(5 ring motif present. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds, forming inversion dimers with an R22(14 ring motif, flanked by two R21(7 ring motifs. The dimers stack along the b axis with slipped parallel π–π interactions involving neighbouring molecules; the shortest π–π interaction involves aromatic rings of the quinoline ring system [inter-centroid distance = 3.6267 (11 Å].

  15. (Quinoline-2-carboxyl-ato-κO)(quinoline-2-carb-oxy-lic acid-κO)bis-(quinoline-2-carb-oxy-lic acid-κN,O)potassium. (United States)

    Ng, Seik Weng


    The K atom in the title complex, [K(C(10)H(6)NO(2))(C(10)H(7)NO(2))(3)], lies on a twofold rotation axis that relates one N,O-chelating quinoline-2-carb-oxy-lic acid to the other; their N and O atoms are cis to each other in the distorted octa-hedral coordination geometry. The K atom is also coordinated by another monodentate quinoline-2-carb-oxy-lic acid; the acid is disordered with respect to a monodentate quinoline-2-carboxyl-ate anion; the acid and anion are linked by an O-H⋯O hydrogen bond. An O-H⋯N hydrogen bond links adjacent mol-ecules into a linear chain structure along the a axis.

  16. Coordination chemistry and biological activity of 5'-OH modified quinoline-B12 derivatives. (United States)

    Zelenka, Karel; Brandl, Helmut; Spingler, Bernhard; Zelder, Felix


    The consequences of structural modifications at the 5'-OH ribofuranotide moiety of quinoline modified B12 derivatives are discussed in regard of the coordination chemistry, the electrochemical properties and the biological behaviour of the compound.

  17. Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines. (United States)

    Rueping, Magnus; Theissmann, Thomas; Stoeckel, Mirjam; Antonchick, Andrey P


    A convenient protocol for the enantioselective synthesis of 4-substituted tetrahydroquinolines has been developed. Chiral BINOL phosphoric acids promote the reduction of a wide range of 4-substituted quinolines with Hantzsch esters with good to high levels of enantioselectivity.

  18. Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation

    Institute of Scientific and Technical Information of China (English)


    A facile and efficient method for the preparation of 2-non-substituted quinoline-4-carboxylic acids is described via the Pfitzinger reaction of isatins with sodium pyruvate following consequent decarboxylation under microwave irradiation.

  19. A quinoline based pH sensitive ratiometric fluorescent sensor: Structure and spectroscopy

    Indian Academy of Sciences (India)

    Soma Mukherjee; Amit Kumar Paul; Helen Stoeckli-Evans


    A new quinoline based hydrazone was synthesized via a condensation reaction and characterized by NMR, mass and single crystal X-ray diffraction studies. It was investigated for suitability as a reversible ratiometric fluorescent pH sensor in acidic pH region. The sensor exhibits intramolecular charge transfer (ICT) type photophysical changes upon protonation of the quinoline ring. No significant interference on emission behavior was observed in the presence of various metal ions.

  20. 4-Hy-droxy-1-methyl-3-phenyl-quinolin-2(1H)-one. (United States)

    Kafka, Stanislav; Pevec, Andrej; Proisl, Karel; Kimmel, Roman; Košmrlj, Janez


    In the title compound, C(16)H(13)NO(2), the quinoline system is approximately planar with a maximum deviation from the least-squares plane of 0.059 (1) Å for the N atom. The phenyl ring is rotated by 62.16 (4)° with respect to the plane of the quinoline system. In the crystal, O-H⋯O hydrogen bonds link mol-ecules into infinite chains running along the b-axis direction.

  1. Quinolinic Acid: An Endogenous Neurotoxin with Multiple Targets

    Directory of Open Access Journals (Sweden)

    Rafael Lugo-Huitrón


    Full Text Available Quinolinic acid (QUIN, a neuroactive metabolite of the kynurenine pathway, is normally presented in nanomolar concentrations in human brain and cerebrospinal fluid (CSF and is often implicated in the pathogenesis of a variety of human neurological diseases. QUIN is an agonist of N-methyl-D-aspartate (NMDA receptor, and it has a high in vivo potency as an excitotoxin. In fact, although QUIN has an uptake system, its neuronal degradation enzyme is rapidly saturated, and the rest of extracellular QUIN can continue stimulating the NMDA receptor. However, its toxicity cannot be fully explained by its activation of NMDA receptors it is likely that additional mechanisms may also be involved. In this review we describe some of the most relevant targets of QUIN neurotoxicity which involves presynaptic receptors, energetic dysfunction, oxidative stress, transcription factors, cytoskeletal disruption, behavior alterations, and cell death.

  2. Determination of aniline and quinoline compounds in textiles. (United States)

    Luongo, Giovanna; Iadaresta, Francesco; Moccia, Emanuele; Östman, Conny; Crescenzi, Carlo


    A simple method for simultaneous determination of twenty-one analytes, belonging to two classes of compounds, aromatic amines and quinolines, is presented. Several of the analytes considered in this study frequently occur in textiles goods on the open market and have been related to allergic contact dermatitis and/or are proven or suspected carcinogens. The method includes an efficient clean-up step using graphitized carbon black (GCB) that simplifies and improves the robustness of the subsequent GC-MS analysis. Briefly, after solvent extraction of the textile sample, the extract is passed through a GCB SPE cartridge that selectively retain dyes and other interfering compounds present in the matrix, producing a clean extract, suitable for GC-MS analysis, is obtained. The method was evaluated by spiking blank textiles with the selected analytes. Method quantification limits (MQL) ranged from 5 to 720ng/g depending on the analyte. The linear range of the calibration curves ranged over two order magnitude with coefficients of determination (R(2)) higher than 0.99. Recoveries ranged from 70 to 92% with RSDs 1.7-14%. The effectiveness of the method was tested on a variety of textile materials samples from different origin. In a pilot explorative survey, 2,6-dichloro-4-nitroaniline was detected in all the analysed clothing samples in concentrations ranging from 1.0 to 576μg/g. 2,4-dinitroaniline was detected in four of the seven samples with a highest concentration of 305μg/g. Quinoline was detected in all samples in concentrations ranging from 0.06 to 6.2μg/g. Copyright © 2016 Elsevier B.V. All rights reserved.

  3. Quinolines in clothing textiles--a source of human exposure and wastewater pollution? (United States)

    Luongo, Giovanna; Thorsén, Gunnar; Ostman, Conny


    A production process in which the use of various types of chemicals seems to be ubiquitous makes the textile industry a growing problem regarding both public health as well as the environment. Among several substances used at each stage, the present study focuses on the quinolines, a class of compounds involved in the manufacture of dyes, some of which are skin irritants and/or classified as probable human carcinogens. A method was developed for the determination of quinoline derivatives in textile materials comprising ultrasound-assisted solvent extraction, solid phase extraction cleanup, and final analysis by gas chromatography/mass spectrometry. Quinoline and ten quinoline derivatives were determined in 31 textile samples. The clothing samples, diverse in color, material, brand, country of manufacture, and price, and intended for a broad market, were purchased from different shops in Stockholm, Sweden. Quinoline, a possible human carcinogen, was found to be the most abundant compound present in almost all of the samples investigated, reaching a level of 1.9 mg in a single garment, and it was found that quinoline and its derivatives were mainly correlated to polyester material. This study points out the importance of screening textiles with nontarget analysis to investigate the presence of chemicals in an unbiased manner. Focus should be primarily on clothing worn close to the body.

  4. CO{sub 2} binding in the (quinoline-CO{sub 2}){sup −} anionic complex

    Energy Technology Data Exchange (ETDEWEB)

    Graham, Jacob D.; Buytendyk, Allyson M.; Wang, Yi; Bowen, Kit H., E-mail: [Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218 (United States); Kim, Seong K. [Department of Chemistry, Seoul National University, Seoul 151-747 (Korea, Republic of)


    We have studied the (quinoline-CO{sub 2}){sup −} anionic complex by a combination of mass spectrometry, anion photoelectron spectroscopy, and density functional theory calculations. The (quinoline-CO{sub 2}){sup −} anionic complex has much in common with previously studied (N-heterocycle-CO{sub 2}){sup −} anionic complexes both in terms of geometric structure and covalent bonding character. Unlike the previously studied N-heterocycles, however, quinoline has a positive electron affinity, and this provided a pathway for determining the binding energy of CO{sub 2} in the (quinoline-CO{sub 2}){sup −} anionic complex. From the theoretical calculations, we found CO{sub 2} to be bound within the (quinoline-CO{sub 2}){sup −} anionic complex by 0.6 eV. We also showed that the excess electron is delocalized over the entire molecular framework. It is likely that the CO{sub 2} binding energies and excess electron delocalization profiles of the previously studied (N-heterocycle-CO{sub 2}){sup −} anionic complexes are quite similar to that of the (quinoline-CO{sub 2}){sup −} anionic complex. This class of complexes may have a role to play in CO{sub 2} activation and/or sequestration.

  5. Crystal Structures of the Iron–Sulfur Cluster-Dependent Quinolinate Synthase in Complex with Dihydroxyacetone Phosphate, Iminoaspartate Analogues, and Quinolinate

    Energy Technology Data Exchange (ETDEWEB)

    Fenwick, Michael K. [Cornell Univ., Ithaca, NY (United States); Ealick, Steven E. [Cornell Univ., Ithaca, NY (United States)


    The quinolinate synthase of prokaryotes and photosynthetic eukaryotes, NadA, contains a [4Fe-4S] cluster with unknown function. We report crystal structures of Pyrococcus horikoshii NadA in complex with dihydroxyacetone phosphate (DHAP), iminoaspartate analogues, and quinolinate. DHAP adopts a nearly planar conformation and chelates the [4Fe-4S] cluster via its keto and hydroxyl groups. The active site architecture suggests that the cluster acts as a Lewis acid in enediolate formation, like zinc in class II aldolases. The DHAP and putative iminoaspartate structures suggest a model for a condensed intermediate. The ensemble of structures suggests a two-state system, which may be exploited in early steps.

  6. 40 CFR 180.426 - 2-[4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinoline carboxylic acid... (United States)


    ... 40 Protection of Environment 23 2010-07-01 2010-07-01 false 2- -3-quinoline carboxylic acid... Tolerances § 180.426 2- -3-quinoline carboxylic acid; tolerance for residues. A tolerance is established for residues of the herbicide 2- -3-quinoline carboxylic acid, in or on the raw agricultural commodity...

  7. A Novel Preparation of 2,4-Disubstituted Quinolines Catalyzed by FeCl3 ·6H2O in Ionic Liquids

    Institute of Scientific and Technical Information of China (English)

    FAN Xue-Sen; ZHANG Xin-Ying


    @@ Quinolines and their derivatives occur in numerous natural products. Many quinolines display interesting physi ological activities and have found attractive applications as pharmaceuticals and agrochemicals as well as being general synthetic building blocks. [1] Many synthetic methods have been developed for quinolines, [2] but due to their great importance, the development of novel synthetic methods remains an active research area. [3

  8. Comparative neuroprotective profile of statins in quinolinic acid induced neurotoxicity in rats. (United States)

    Kalonia, Harikesh; Kumar, Puneet; Kumar, Anil


    A possible neuroprotective role has been recently suggested for 3H3MGCoA reductase inhibitors (statins). Here, we sought to determine neuroprotective effect of statins in quinolinic acid induced neurotoxicity in rats. Rats were surgically administered quinolinic acid and treated with Atorvastatin (10, 20 mg/kg), simvastatin (15, 30 mg/kg) and fluvastatin (5, 10 mg/kg) once daily up to 3 weeks. Atorvastatin (10, 20 mg/kg), simvastatin (30 mg/kg) and fluvastatin (10 mg/kg) treatment significantly attenuated the quinolinic acid induced behavioral (locomotor activity, rotarod performance and beam walk test), biochemical (lipid peroxidation, nitrite concentration, SOD and catalase), mitochondrial enzyme complex alterations in rats suggesting their free radical scavenging potential. Additionally, atorvastatin (10, 20 mg/kg), simvastatin (30 mg/kg) and fluvastatin (10 mg/kg) significantly decrease the TNF-α level and striatal lesion volume in quinolinic acid treated animals indicating their anti-inflammatory effects. In comparing the protective effect of different statins, atorvastatin is effective at both the doses while simvastatin and fluvastatins at respective lower doses were not able to produce the protective effect in quinolinic acid treated animals. These modulations can account, at least partly, for the beneficial effect of statins in our rodent model of striatal degeneration. Our findings show that statins could be explored as possible neuroprotective agents for neurodegenerative disorders such as HD.

  9. Mineralization of Quinoline by BDD Anodes: Variable Effects and Its Effluent Characteristics

    Directory of Open Access Journals (Sweden)

    C. R. Wang


    Full Text Available BDD anodes were selected for quinoline mineralization and influence of operating parameters, such as current density, initial quinoline concentration, supporting electrolyte, and initial pH was investigated. Based on the consideration of quinoline removal efficiency and average current efficiency, at initial quinoline concentration of 50 mg L−1 and pH of 7, the optimal condition was confirmed as current density of 75 mA cm−2, electrolysis time of 1.5 h, and Na2SO4 concentration of 0.05 mol L−1 by orthogonal test. At different electrolysis time, its effluent characteristics were focused on. The biodegradability (the ratio between BOD5 and COD was enhanced from initial 0.02 to 0.57 at 90 min. The specific oxygen uptake rate was used to assess effluent toxicity, and the value gradually reduced with decreasing effluent organic concentration with mean value of 5.51, 4.19, and 2.20 mgO2 g−1MLSS at electrolysis time of 15, 30, and 45 min, respectively. Compared with control sample (prepared with glucose, the effluent of quinoline mineralization showed obvious inhibition effect on microorganisms at electrolysis time of 15 min, and then it was significantly faded at 30 min and 45 min.

  10. Characterization of Strain Pseudomonas sp.Q1 in Microbial Fuel Cell for Treatment of Quinoline-Contaminated Water

    Institute of Scientific and Technical Information of China (English)

    ZHANG Cui-Ping; CHEN Shan-Shan; LIU Guang-Li; ZHANG Ren-Duo; XIE Jian


    To find new strain in the microbial fuel cell (MFC) for quinoline removal from wastewater and soil,a facultative anaerobic bacterium strain was isolated from the anode of MFC,utilizing quinoline as the carbon source and electron donor.Based on the 16S rRNA sequence analysis,the bacterium strain was Gram-negative and identified as Pseudomonas sp.Q1 according to its morphology and physiochemical properties.The strain was inoculated into a double-chambered MFC using various quinoline concentratious (0,50,75,86,100,150,200 and 300 mg L-1) combining with 300 mg L-1 glucose as the fuel.Results showed that electricity was generated from the MFC,in which quinoline was degraded simultaneously.The values of Coulombic efficiency (CE) increased with the increase of quinoline concentrations from 0 to 100 mg L-1 then decreased with the increase of quinoline concentration from 100 to 300 mg L-1,and the maximum CE 36.7% was obtained at the quinoline concentration of 100 mg L-1.The cyclic voltammetry analysis suggested that the mechanism of electron transfer was through excreting mediators produced by the strain Q1.The MFC should be a potential method for the treatment of quinoline-contaminated water and soil.

  11. Quinolinic acid induces oxidative stress in rat brain synaptosomes. (United States)

    Santamaría, A; Galván-Arzate, S; Lisý, V; Ali, S F; Duhart, H M; Osorio-Rico, L; Ríos, C; St'astný, F


    The oxidative action of quinolinic acid (QUIN), and the protective effects of glutathione (GSH), and 2-amino-5-phosphonovaleric acid (APV), were tested in rat brain synaptosomes, Reactive oxygen species (ROS) formation was quantified after the exposure of synaptosomes to increasing concentrations of QUIN (25-500 microM). The potency of QUIN to induce lipid peroxidation (LP) was tested as a regional index of thiobarbituric acid-reactive substances (TBARS) production, and the antioxidant actions of both GSH (50 microM) and APV (250 microM) on QUIN-induced LP were evaluated in synaptosomes prepared from different brain regions. QUIN induced concentration-dependent increases in ROS formation and TBARS in all regions analyzed, but increased production of fluorescent peroxidized lipids only in the striatum and the hippocampus, whereas both GSH and APV decreased this index. These results suggest that the excitotoxic action of QUIN involves regional selectivity in the oxidative status of brain synaptosomes, and may be prevented by substances exhibiting antagonism at the NMDA receptor.

  12. Anion- interactions in layered structures of salts of 5-(hydroxyimino) quinolin-8-one and related salts

    Indian Academy of Sciences (India)

    Prithiviraj Khakhlary; Jubaraj B Baruah


    Relevance of anion- interactions in chloride, bromide, nitrate and perchlorate salts of 5-(hydroxyimino)quinolin-8-one are discussed. Structures of nitrate salt of 5-aminoquinoline as well as nitrate salt of 4-hydroxyquinazoline are compared with the structure of nitrate salt of 5-(hydroxyimino)quinolin-8-one. From such a comparison, two different arrangements of nitrate ions with respect to the respective cations are discerned. Nitrate ions are sandwiched between aromatic planes of cations in nitrate salts of 5-(hydroxyimino)quinolin-8-one or 4-hydroxyquinazoline; whereas, nitrate ions are in oblique positions with respect to aromatic planes of counter cations in nitrate salt of 5-aminoquinoline. Binding constants of different nitrate salts in solution are determined by UV-visible spectroscopic titrations. Solution study shows formation of ion-pairs of these salts in solution.

  13. Bis(quinolin-8-olsilver(I 2-hydroxy-3,5-dinitrobenzoate

    Directory of Open Access Journals (Sweden)

    Fang-Fang Jian


    Full Text Available The title compound, [Ag(C9H7NO2](C7H3N2O7, was prepared from 3,5-dinitrosalicylic acid (DNS, quinolin-8-ol and AgNO3. The AgI atom is coordinated by two N atoms and two O atoms from two quinolin-8-ols in a roughly planar [maximum deviation = 0.223 (2 Å] environment. The two quinolin-8-ol ligands are bent slightly with respect to each other, making a dihedral angle of 9.55 (9°. The DNS anion interacts with the silver complex through O—H...O hydrogen bonds

  14. Chemical consequences of pyrazole orientation in Ru(II) complexes of unsymmetric quinoline-pyrazole ligands. (United States)

    Hedberg Wallenstein, Joachim; Fredin, Lisa A; Jarenmark, Martin; Abrahamsson, Maria; Persson, Petter


    A series of homoleptic Ru(II) complexes including the tris-bidentate complexes of a new bidentate ligand 8-(1-pyrazol)-quinoline (Q1Pz) and bidentate 8-(3-pyrazol)-quinoline (Q3PzH), as well as the bis-tridentate complex of bis(quinolinyl)-1,3-pyrazole (DQPz) was studied. Together these complexes explore the orientation of the pyrazole relative to the quinoline. By examining the complexes structurally, photophysically, photochemically, electrochemically, and computationally by DFT and TD-DFT, it is shown that the pyrazole orientation has a significant influence on key properties. In particular, its orientation has noticeable effects on oxidation and reduction potentials, photostability and proton sensitivity, indicating that [Ru(Q3PzH)3](2+) is a particularly good local environment acidity-probe candidate.

  15. Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents

    Directory of Open Access Journals (Sweden)

    Ghorab Mostafa M.


    Full Text Available As a part of ongoing studies in developing new anticancer agents, novel 1,2-dihydropyridine 4, thienopyridine 5, isoquinolines 6–20, acrylamide 21, thiazolidine 22, thiazoles 23–29 and thiophenes 33–35 bearing a biologically active quinoline nucleus were synthesized. The structure of newly synthesized compounds was confirmed on the basis of elemental analyses and spectral data. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. 2,3-Dihydrothiazole-5-carboxamides 27, 25, 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (34, 1,2-dihydroisoquinoline-7-carbonitrile (7, 5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide (35, 1,2-dihydroisoquinoline-7-carbonitrile (6, 2-cyano-3-(dimethylamino-N-(quinolin-3-ylacrylamide (21, 1,2-dihydroisoquinoline-7-carbonitriles (11 and (8 exhibited higher activity (IC50 values of 27–45 μmol L–1 compared to doxorubicin (IC50 47.9 μmol L–1. LQ quinolin-3-yl-1,2-dihydroisoquinoline-7-carbonitrile (12, 2-thioxo-2,3-dihydrothiazole-5-carboxamide (28 and quinolin-3-yl-1,2-dihydroisoquinoline-7-carbonitrile (15 show activity comparable to doxorubicin, while (quinolin-3-yl-1,2-dihydroisoquinoline-7-carbonitrile (9, 2,3-dihydrothiazole-5-carboxamide (24, thieno [3,4-c] pyridine-4(5H-one (5, cyclopenta[b]thiophene-3-carboxamide (33 and (quinolin-3-yl-6-stryl-1,2-dihydroisoquinoline-7-carbonitrile (10 exhibited moderate activity, lower than doxorubicin.

  16. The Ayurvedic drug, Ksheerabala, ameliorates quinolinic acid-induced oxidative stress in rat brain. (United States)

    Swathy, S S; Indira, M


    One of the mechanisms of neurotoxicity is the induction of oxidative stress. There is hardly any cure for neurotoxicity in modern medicine, whereas many drugs in Ayurveda possess neuroprotective effects; however, there is no scientific validation for these drugs. Ksheerabala is an ayurvedic drug which is used to treat central nervous system disorders, arthritis, and insomnia. The aim of our study was to evaluate the effect of Ksheerabala on quinolinic acid-induced toxicity in rat brain. The optimal dose of Ksheerabala was found from a dose escalation study, wherein it was found that Ksheerabala showed maximum protection against quinolinic acid-induced neurotoxicity at a dose of 15 microL/100 g body weight/day, which was selected for further experiments. Four groups of female albino rats were maintained for 21 days as follows: 1. Control group, 2. Quinolinic acid (55 microg/100 g body weight), 3. Ksheerabala (15 microL/100 g body weight), 4. Ksheerabala (15 microL/100 g body weight) + Quinolinic acid (55 microg/100 g body weight). At the end of the experimental period, levels of lipid peroxidation products, protein carbonyls, and activities of scavenging enzymes were analyzed. The results revealed that quinolinic acid intake caused enhanced lipid and protein peroxidation as evidenced by increased levels of peroxidation products such as malondialdehyde, hydroperoxide, conjugated dienes, and protein carbonyls. On the other hand, the activities of scavenging enzymes such as catalase, superoxide dismutase (SOD), glutathione peroxidase, and glutathione reductase as well as the concentration of glutathione were reduced. On coadminstration of Ksheerabala along with quinolinic acid, the levels of all the biochemical parameters were restored to near-normal levels, indicating the protective effect of the drug. These results were reinforced by histopathological studies.

  17. Structural study on few co-crystals and a salt of quinoline derivatives having amide bond (United States)

    Karmakar, Anirban; Kalita, Dipjyoti; Baruah, Jubaraj B.


    The N-[2-(4-Methoxy-phenyl)-ethyl]-2-(quinolin-8-yloxy)-acetamide forms 1:1 co-crystals with aromatic diols namely 1,4-dihydroxybenzene, 1,5-dihydroxynaphthalene. In the later case co-crystal is formed in hydrated form. The hydrated form of co-crystal with 1,5-naphthalenediol has two symmetry independent host molecules in its unit cell, whereas such phenomenon in the co-crystal 1,4-dihydroxybenzene is not observed. The crystal structure of perchloric acid salt of (Quinolin-8-ylamino)-acetic acid is determined and this salt also shows two symmetry independent parent molecules in unit cell.

  18. Jusbetonin, the first indolo[3,2-b]quinoline alkaloid glycoside, from Justicia betonica. (United States)

    Subbaraju, Gottumukkala V; Kavitha, Jakka; Rajasekhar, Dodda; Jimenez, Jorge I


    A new indolo[3,2-b]quinoline alkaloid glycoside, jusbetonin (1), and three known alkaloids, namely, 10H-quindoline (2), 6H-quinindoline (3), and 5H,6H-quinindolin-11-one (4), have been isolated from the leaves of Justicia betonica. The structure of 1 was established on the basis of 1D and 2D NMR ((1)H-(1)H COSY, HMQC, and HMBC) and HRFABMS data. Compound 1 is the first example of a glycosylated indolo[3,2-b]quinoline alkaloid, while compound 4 was isolated for the first time from a natural source.

  19. Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines. (United States)

    Saunthwal, Rakesh K; Patel, Monika; Verma, Akhilesh K


    A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups which has been successfully extended with diynes, (2-aminopyridin-3-yl)methanol, and 1,4-bis(phenylethynyl)benzene to afford (Z)-phenyl-2-styrylquinolines, phenylnaphthyridine, and alkyne-substituted quinolines, respectively. The proposed mechanism and significant role of the solvent were well supported by isolating the azadiene intermediate and deuterium-labeling studies.

  20. Vibronic Spectroscopy of a Structural Isomer of Quinoline: - (United States)

    Mehta-Hurt, Deepali N.; Korn, Joseph A.; Zwier, Timothy S.


    This talk will present results of a gas phase, jet-cooled vibronic spectroscopy study of (Z)-phenylvinylnitrile ((Z)-C_6H_5-CH=CH-C=N, (Z)-PVN). With a substituent locked into a cis conformation with respect to the aromatic ring, (Z)-PVN is postulated to be a molecule with an ideal functionality to isomerize to quinoline upon photoexcitation. As such, (Z)-PVN is particularly relevant to Titan's nitrile-containing atmosphere, where much of the chemistry is photochemically driven. As a first step towards such photochemical studies, a fluorescence excitation spectrum of a mixture of (E)- and (Z)-PVN was collected spanning the range 33,300-35,580 cm^{-1} (300.0-281.0 nm). Previous investigations in the Zwier group pertaining to the vibronic spectroscopy of (E)-PVN allowed for the identification of peaks in the (E)- and (Z)-PVN composite spectrum that were solely due to (Z)-PVN, and the S_0-S_1 origin of (Z)-PVN was identified as a dominant band that occurs at 33,706 cm^{-1}. For additional confirmation, ultraviolet depletion spectroscopy (UVD) was used to obtain an isomer specific spectrum of (Z)-PVN as well as search for non-radiative transitions. Dispersed fluorescence spectra that characterize the vibronic activity have also been acquired. A comparison between the vibronic spectroscopy of (Z)-PVN with both (E)-PVN and (Z)-phenylvinylacetylene ((Z)-PVA), the hydrocarbon analog of (Z)-PVN, will be made in this talk.

  1. Synthesis and structure of interaction products of quinoline-2(1H)-thione with molecular iodine. (United States)

    Chernov'yants, Margarita S; Starikova, Zoya A; Kolesnikova, Tatiana S; Karginova, Anastasia O; Lyanguzov, Nikolay V


    The behavior of quinoline-2(1H)-thione, which is a potential antithyroid drug toward molecular iodine, was investigated. The ability of quinoline-2(1H)-thione to form the outer-sphere charge-transfer complex C9H7NS·I2 with iodine molecular in dilute chloroform solution has been studied by UV-vis spectroscopy (lgβ=3.85). The crystal structure of the new salt 2-(quinoline-2-yldisulfanyl)quinolinium triiodide - product of irreversible oxidation of quinoline-2(1H)-thione was determined by X-ray diffraction. The 2-(quinoline-2-yldisulfanyl)quinolinium cations form dimers through π-π-stacking interaction between quinoline rings. Strong intramolecular interactions are observed between iodine - sulfur atoms and iodine - hydrogen atoms with shortened contacts (less of sum of van der Waals contacts). It is noteworthy that two perfectly centrosymmetrical anions I3(-) form a very short contact I(3)⋯I(3') 3.7550(5) so we can state the formation of the dianion I(6)(2-). Therefore the formation and topology of polyiodide species depend on the characteristics, such as shape, size and charge, etc., of the counter cation, 2-(quinoline-2-yldisulfanyl)quinolinium, which is considered as templating agent.

  2. Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of monodentate BINOL-derived phosphoramidites

    NARCIS (Netherlands)

    Mrsic, Natasa; Lefort, Laurent; Boogers, Jeroen A. F.; Minnaard, Adriaan J.; Feringa, Ben L.; de Vries, Johannes G.; Mršić, Nataša

    The monodentate BINOL-derived phosphoramidite PipPhos is used as ligand for the iridium-catalyzed asymmetric hydrogenation of 2- and 2,6-substituted quinolines. If tri-ortho-tolylphosphine and/or chloride salts are used as additives enantioselectivities are strongly enhanced up to 89%. NMR indicates

  3. Degradation of quinoline by wet oxidation - kinetic aspects and reaction mechanisms

    DEFF Research Database (Denmark)

    Thomsen, A.B.


    of succinic acid is suggested to be a result of a coupling reaction of the acetic acid radical A reaction mechanism is suggested for the degradation of quinoline: it involves hydroxyl radicals and the possible interaction with autoclave walls is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved....

  4. Copper(II)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines. (United States)

    Li, Gang; Jia, Chunqi; Sun, Kai; Lv, Yunhe; Zhao, Feng; Zhou, Kexiao; Wu, Hankui


    Copper acetate-catalyzed C-H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields. Electrophilic amination can also be performed in good yield on a gram scale.

  5. Metabolic pathways of quinoline, indole and their methylated analogs by Desulfobacterium indolicum (DSM 3383)

    DEFF Research Database (Denmark)

    Johansen, S.S.; Licht, D.; Arvin, E.


    The transformation of quinoline, isoquinoline and 3-, 4-, 6- and 8-methylquinoline by Desulfobacterium indolicum was compared with that of the N-containing analogues indole and 1-, 2-, 3- and 7-methylindole. The metabolites were identified using high-performance liquid chromatography with UV dete...

  6. Chiral pyrrolo[1,2-a]quinolines as second-order nonlinear optical materials

    NARCIS (Netherlands)

    Kelderman, E.; Kelderman, E.; Verboom, Willem; Engbersen, Johannes F.J.; Harkema, Sybolt; Heesink, G.J.T.; Heesink, G.J.T.; Lehmusvaara, E.; van Hulst, N.F.; Reinhoudt, David; Derhaeg, L.; Persoons, A.


    The synthesis and nonlinear optical properties of a series of chiral pyrrolo[1,2-a]quinolines la-e is presented. The microscopic hyperpolarizabilities (beta(z)) were determined by EFISH measurements and the macroscopic susceptibilities (X2) were estimated by the Kurtz powder test. A small fixed

  7. An experimental screen for quinoline/fumaric acid salts and co-crystals

    DEFF Research Database (Denmark)

    Beko, S. L.; Schmidt, M. U.; Bond, A. D.


    An experimental screen has been carried out for salts and co-crystals of quinoline (C9H7N) and fumaric acid (C4H4O4), including solution-based co-crystallisation from a variety of solvents, solvent-assisted and solvent-free co-grinding, and direct co-crystallisation of the starting materials...

  8. Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety

    Directory of Open Access Journals (Sweden)

    Murat Bingul


    Full Text Available Identification of the novel (E-N′-((2-chloro-7-methoxyquinolin-3-ylmethylene-3-(phenylthiopropanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19–26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved by replacement of the quinoline moiety with other aromatic systems. All the newly synthesized compounds were evaluated for their anti-cancer activity against the SH-SY5Y and Kelly neuroblastoma cell lines, as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Analogues 19 and 22 significantly reduced the cell viability of neuroblastoma cancer cells with micromolar potency and significant selectivity over normal cells. The quinoline hydrazide 22 also induced G1 cell cycle arrest, as well as upregulation of the p27kip1 cell cycle regulating protein.

  9. Synthesis, Characterization and Antibacterial Activity of a New Series of s-Triazines Derived with Quinolines

    Directory of Open Access Journals (Sweden)

    J. J. Vora


    Full Text Available 8-Hydroxy quinoline was synthesized using Skraup reaction. This was condensed with trichloro-s-triazine. The product of the above reaction was allowed to react with triazole derivative. Finally, urea derivatives were allowed to react and the products were characterized by conventional and instrumental methods. Their structures were determined and important biochemical properties were studied

  10. Anxiogenic activity of quinolinic acid and kynurenine in the social interaction test in mice. (United States)

    Lapin, I P; Mutovkina, L G; Ryzov, I V; Mirzaev, S


    Quinolinic acid, a metabolite of tryptophan on the kynurenine pathway, shortened the duration of social contacts (sniffings) in C57BL/6 mice which had been previously isolated for 24 h. This effect was observed at the following time intervals after i.c.v. administration: 2-6, 22-26 and 32-36 min. Locomotion was significantly less inhibited and only during the first interval. L-Kynurenine sulphate was less active. It shortened the duration of contacts only during the 32-36 min interval after i.c.v. administration. Grooming was significantly reduced by quinolinic acid at 7-11, 12-16 and 17-21 min after administration. These effects of quinolinic acid in the social interaction test are similar to those of standard anxiogens and suggest that quinolinic acid belongs to the putative endogenous anxiogens (and not only to the endogenous convulsants). The same assumption about L-kynurenine based on data in other models of anxiety has been made previously.

  11. Synthesis and cytotoxic activity of 2,5-disubstituted pyrimido [5,4-c] quinoline derivatives

    Institute of Scientific and Technical Information of China (English)

    Fan Zhang; Xin Zhai; Li Juan Chen; Jian Guo Qi; Bo Cui; Yu Cheng Gu; Ping Gong


    A series of 2,5-disubstituted pyrimido[5,4-c]quinoline derivatives were synthesized and their cytotoxic activity against H460, HT-29 and MDA-MB-231 cell lines was evaluated in vitro. It was found that most of the tested compounds especially compound 17, shown stronger activity to the selected three cell lines than ZM447439.

  12. Bis(quinolin-8-ol)silver(I) 2-hydr­oxy-3,5-dinitro­benzoate


    Fang-Fang Jian; Chun-Lan Zhang


    The title compound, [Ag(C9H7NO)2](C7H3N2O7), was prepared from 3,5-dinitrosalicylic acid (DNS), quinolin-8-ol and AgNO3. The AgI atom is coordinated by two N atoms and two O atoms from two quinolin-8-ols in a roughly planar [maximum deviation = 0.223 (2) Å] environment. The two quinolin-8-ol ligands are bent slightly with respect to each other, making a dihedral angle of 9.55 (9)°. The DNS anion interacts with the silver complex through O...


    Directory of Open Access Journals (Sweden)

    Hildebrando Ayala


    Full Text Available The aquatic ecotoxicological determination of phytonematicide products using the zooplanktonic cladoceran Daphnia magna is important for environmental risk assessment. Evaluations were made of the acute median lethal concentration (LC50 of phenyl quinoline on D. magna, that was 4.12 ug i.a. L-1 at 48 h of exposure. The chronic effects of phenyl quinoline in the mortality rate of the cladoceran D. magna at 17 d of exposure, with 0.18 ug ai L-1 of LOEC (Lowest Observed Effect Concentration and 0.072 ug ai L-1 of NOEC (No Observed Effect Concentration were determined. Evaluations of the chronic effect of phenyl quinoline on three parameters of growth of D. magna (total length, antenna length and caudal length to 17 d of exposure, only showed significant differences in length of the antenna between the control and 0.072 ug ai L-1 been this the value of LOEC and thus the lower concentration 0.0288 ug ai L-1, the NOEC value for phenyl quinoline. The ratio between acute and chronic toxicity (RAC for the relationship showed acute 48 h exposure on mortality NOEC 17 d a value of 57.22, and for the ratio of acute NOEC on of the length of the antenna to 17 d was a value of 143. The environmental risk assessment (ERA shows that the PEC (Probable Effect Concentration / PNEC (Predicted No-Effect Concentration for acute assay was 582 524 and for the PEC / PNEC for chronic test was 83 333 333. These results demonstrate that phenyl quinoline has a high impact on aquatic biota represented by the trophic level that belongs to D. magna, and therefore shows that the substance is a candidate for a comprehensive ecotoxicological assessment.

  14. The washout effect during laundry on benzothiazole, benzotriazole, quinoline, and their derivatives in clothing textiles. (United States)

    Luongo, Giovanna; Avagyan, Rozanna; Hongyu, Ren; Östman, Conny


    In two previous papers, the authors have shown that benzothiazole, benzotriazole, quinoline, and several of their derivatives are widespread in clothing textile articles. A number of these compounds exhibit allergenic and irritating properties and, due to their octanol-water partition coefficient, are prone to be absorbed by the skin. Moreover, they are slightly soluble in water, which could make washing of clothes a route of emission into the environment. In the present study, the washout effect of benzothiazole, benzotriazole, quinoline, and some of their derivatives has been investigated. Twenty-seven textile samples were analyzed before, as well as after five and ten times of washing. The most abundant analyte was found to be benzothiazole, which was detected in 85 % of the samples with an average concentration of 0.53 μg/g (median 0.44 μg/g), followed by quinoline, detected in 81 % of the samples with an average concentration of 2.42 μg/g (median 0.21 μg/g). The average decrease in concentration for benzothiazoles was 50 % after ten times washing, while it was around 20 % for quinolines. The average emission to household wastewater of benzothiazoles and quinolines during one washing (5 kg of clothes made from polyester materials) was calculated to 0.5 and 0.24 g, respectively. These results strongly indicate that laundering of clothing textiles can be an important source of release of these compounds to household wastewater and in the end to aquatic environments. It also demonstrates a potential source of human exposure to these chemicals since considerable amounts of the compounds remain in the clothes even after ten times of washing.

  15. [Absorption spectra analysis in the degradation process of quinoline in aqueous solution by VUV lights]. (United States)

    Zhu, Da-Zhang; Sun, Dong-Mei; Wang, Shi-Long; Sun, Xiao-Yu; Ni, Ya-Ming


    The feasibility of monitoring the degradation progress on line by UV-Vis absorption spectra in the degradation process of quinoline in aqueous solution using the low-pressure quartz mercury lamp as vacuum ultraviolet source was evaluated by the monitoring and protracting of the UV-Vis absorption spectra at different time. The characteristic and mechanism of the change in the UV absorption spectra were analyzed by monitoring the concentration of the substrate, COD (chemical oxygen demand), TOC (total organic carbon) and pH value of the solution. It was showed that quinoline occurs in different forms under different pH conditions and consequently causes different UV-Vis absorption spectra due to the N atom in the pyridine ring. In the degradation progress, the UV-Vis absorption spectra were impacted by the degradation rate of the substrates, the production rate of the intermediates and the pH value of the solution. Proton acids were produced as intermediates and make quinoline occur in the form of its conjugated acid. When the increase in the absorption produced by the protonation was equal to the decrease induced by the degradation, the curve of the absorption at 313 nm, the characteristic absorption peak of quinoline, showed a flat in the duration of 1-3 min and then decayed continuously. In addition, the absorption at 254 nm reached a maximum at 5 min and then decayed continuously to nearly 0 at 30 min, when the absorption of the system only occurred in the region of wavelength shorter than 220 nm, indicating that the substrate was degraded completely. The research revealed that UV absorption spectra could be used to monitor the degradation process of quinoline in aqueous solution by VUV lights.

  16. Design and Synthesis of Some New Quinoline Based 1,2,3-Triazoles as Antimicrobial and Antimalarial Agents

    Directory of Open Access Journals (Sweden)

    Parthasaradhi Y.


    Full Text Available A series of novel 6-bromo-2-chloro-3-(4-phenyl-[1,2,3]triazol-1-ylmethyl-quinoline and its derivatives (5a-j were synthesized in good yields from the intermediates (6-bromo-2-chloro-quinolin-3-yl-methanol (2, methanesulfonic acid (6-bromo-2-chloroquinolin-3-ylmethyl methanesulfonate (3 and 3-azidomethyl-6-bromo-2-chloro-quinoline (4. The synthetic route leading to the title compounds is commenced from commercially available 6-bromo-2-chloro-quinolin-3-carbaldehyde (1. The chemical structures of the newly synthesized compounds were elucidated by their IR, 1H and 13C NMR, mass spectral data and elemental analysis. Further, all the target compounds were screened for their antimicrobial activity against various microorganisms and antimalarial activity towards P. falciparum. DOI: 

  17. Studies on adsorption and corrosion inhibitive properties of quinoline derivatives on N80 steel in 15% hydrochloric acid

    Directory of Open Access Journals (Sweden)

    K.R. Ansari


    Full Text Available This paper deals with the N80 steel corrosion protection study in 15% HCl which was carried by three quinoline derivatives namely 3-acetyl-1-(4-methylbenzylideneamino quinolin-2-one (AQ-1, 3-acetyl-1-(4 hydroxy benzylideneamino quinolin-2-one (AQ-2, 3-acetyl-1-(3-nitrobenzylideneamino quinolin-2(1H-one (AQ-3 using gravimetric, electrochemical, and quantum chemical studies. Tafel polarization showed that AQs are mixed type inhibitors but dominantly affect cathodic reaction more. The observed results reveal that AQ-1 is the best inhibitor. All the three inhibitors were found to obey the Langmuir adsorption isotherm. Scanning electron microscopy (SEM micrographs supports the protection of the N80 steel by AQs. Quantum chemical study reveals that the inhibitors have a tendency to get protonated and this protonated form has greater tendency to get adsorbed onto the N80 steel surface.

  18. Genetic relationship of organic bases of the quinoline and isoquinoline series from lignite semicoking tars with the initial biological material

    Energy Technology Data Exchange (ETDEWEB)

    Platonov, V.V.; Proskuryakov, V.A.; Podshibyakin, S.I.; Domogatskii, V.V.; Shvykin, A.Y.; Shavyrina, O.A.; Chilachava, K.B. [Leo Tolstoy State Pedagog University, Tula (Russian Federation)


    The genetic relationship of quinoline and isoquinoline compounds present in semicoking tars of Kimovsk lignites (near-Moscow fields) with the initial vegetable material is discussed. Transformation pathways of the native compounds in the course of lignite formation are suggested.

  19. Design, synthesis and evaluation of 3-quinoline carboxylic acids as new inhibitors of protein kinase CK2. (United States)

    Syniugin, Anatolii R; Ostrynska, Olga V; Chekanov, Maksym O; Volynets, Galyna P; Starosyla, Sergiy A; Bdzhola, Volodymyr G; Yarmoluk, Sergiy M


    In this article, the derivatives of 3-quinoline carboxylic acid were studied as inhibitors of protein kinase CK2. Forty-three new compounds were synthesized. Among them 22 compounds inhibiting CK2 with IC50 in the range from 0.65 to 18.2 μM were identified. The most active inhibitors were found among tetrazolo-quinoline-4-carboxylic acid and 2-aminoquinoline-3-carboxylic acid derivatives.

  20. PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives

    Indian Academy of Sciences (India)

    M A Nasseri; S A Alavi; B Zakerinasab


    A convenient and efficient method was developed for the synthesis of quinolines, an important class of potentially bioactive compounds. The quinoline derivatives were prepared in water, an excellent solvent in terms of environmental impact and with reduced waste production. PEG-SO3H effectively catalysed the one-pot synthesis of quinolines by the condensation of -aminoaryl ketones and carbonyl compound with high yields (75-95%). The compounds were isolated by simple filtration in a high purity form.

  1. Synthesis, crystal structure, optical and electrochemical properties of 9,10-dihydroxybenzo[ℎ]quinoline

    Indian Academy of Sciences (India)

    Kew-Yu Chen; Hsing-Yang Tsai; Wei-Chi Lin; Hou-Hsein Chu; Yu-Ching Weng; Chih-Chieh Chan


    9,10-Dihydroxybenzo[ℎ]quinoline (1), a 10-hydroxybenzo[ℎ]quinoline (2) derivative, was synthesized and characterized by 1H NMR, 13C NMR, UV-vis and fluorescence spectra, and single-crystal X-ray diffraction. Compound 1 possesses an intramolecular six-membered-ring hydrogen bond, from which excitedstate intramolecular proton transfer (ESIPT) takes place from the phenolic proton to the pyridinic nitrogen, resulting in a proton-transfer tautomer emission of 650 nm in dichloromethane. Its molecular geometry in the ground state has also been calculated using density functional theory (DFT) at the B3LYP/6-31G∗∗ level and compared with its crystal structure. Results show that the optimized geometry can well reproduce the crystal structure. Furthermore, both absorption and emission spectra of 1 and 2 were calculated using time-dependent DFT (TD-DFT) calculations, and were in good agreement with the experimental results.

  2. Tetrakis(quinolin-8-olato-κ2N,Ohafnium(IV toluene disolvate

    Directory of Open Access Journals (Sweden)

    Maryke Steyn


    Full Text Available In the title compound, [Hf(C9H6NO4]·2C7H8, the hafnium metal centre is coordinated by four N,O-donating bidentate quinolin-8-olate ligands arranged to give a square-antiprismatic coordination polyhedron with a slightly distorted dodecahedral geometry. The average Hf—O and Hf—N distances are 2.096 (3 and 2.398 (3 Å, respectively, and the average O—Hf—N bite angle is 70.99 (11°. The crystal packing is controlled by π–π interactions between quinoline ligands of neighbouring molecules and hydrogen-bonding interactions. The interplanar distances vary between 3.138 (1 and 3.208 (2 Å, while the centroid–centroid distances range from 3.576 (1 to 4.074 (1 Å.

  3. Syntheses and anti-microbial evaluation of new quinoline scaffold derived pyrimidine derivatives

    Directory of Open Access Journals (Sweden)

    Shikha S. Dave


    Full Text Available A series of diversely substituted chalcones derived from a quinoline scaffold, e.g. (E-3-(2-chloroquinolin-3-yl-1-(2-hydroxyphenyl prop-2-en-1-one and its pyrimidine analogues e.g. 2-[2-amino-6-(2-chloroquinolin-3-yl-5,6-dihydropyrimidin-4-yl]phenols have been prepared by condensation of 2-chloro-3-formyl quinoline with differently substituted 2-hydroxy acetophenones and further treatment with guanidine carbonate. All the newly synthesized compounds have been evaluated for their in vitro growth inhibitory activity against Escherichia coli, Pseudomonas vulgaris, Bacillus subtilis, Staphylococcus aureus, Staphylococcus typhi, Candida albicans, Aspergillus niger and Pseudomonas chrysogenum.

  4. Optimization of the Separation of Quinolines in Micellar Liquid Chromatography by Experimental Design and Regression Models

    Institute of Scientific and Technical Information of China (English)



    The chemometrics approach was applied to the optimization of separation of quinolines in micellar liquid tigated by means of multivariate analysis. The factors considered were the concentration of sodium dodecyl sulfate (SDS), the organic modifier concentration and the length of its alkyl chain, and pH of the mobile phase. The ex-periments were performed according to a face centered cube response surface experimental design. In order to op-timize the separation a Pareto-optimality method was employed. The models were verified, because a good agree-ment was observed between the predicted and experimental values of the chromatographic response function in the optimal condition. The obtained regression models were characterized by both descriptive and predictive ability (R2≥0.97 and R2cv≥0.92) and allowed the chromatographic separation of the quinolines with a good resolution and a total analysis time of 50 min.

  5. Ionic liquid catalyzed convenient synthesis of imidazo[1,2-a]quinoline under sonic condition

    Energy Technology Data Exchange (ETDEWEB)

    Patel, Devji S.; Avalani, Jemin R.; Raval, Dipak K., E-mail: [Department of Chemistry, Sardar Patel University Gujarat (India)


    An efficient protocol for the synthesis of imidazo[1,2-a]quinoline from aldehydes, enaminones, and malononitrile using 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate ([DBU][Ac]) as a catalyst under ultrasound irradiation is described. Compared with other methods, this new method has the advantages of easier work-up, milder reaction conditions, high yields and environmentally benign procedure. (author)



    M.P.Santhi, G.Bupesh* , V.SenthilKumar*, K.Meenakumari, K.Prabhu, S.Sugunthan, E.Manikandan, K.Saravanan


    The oncogenic protein receptors were key molecular targets for cancers. Especially in tumor cells, they were frequently transformed or mutated at abnormal states. The normal cells encounter a programmed cell death (apoptosis). It is an imperative and striking focus for anticancer medication advancement and disclosure. Biophytum sensitivum is a medicinal plant rich in quinoline and amentoflavone.  The aqueous extract of plant was still administered for various ailments in naturopathy medicines...

  7. Diiodido[methyl 2-(quinolin-8-yloxyacetate-κN]mercury(II

    Directory of Open Access Journals (Sweden)

    Yu-Hong Wang


    Full Text Available In the title mononuclear complex, [HgI2(C12H11NO3], the HgII ion has a distorted trigonal–planar coordination sphere defined by two I− anions and the N atom of a methyl 2-(quinolin-8-yloxyacetate ligand. In the crystal, face-to-face π–π stacking interactions, with a centroid–centroid distance of 3.563 (9 Å, are observed.

  8. The Ayurvedic drug, Ksheerabala, ameliorates quinolinic acid-induced oxidative stress in rat brain


    Swathy, S. S.; Indira, M.


    One of the mechanisms of neurotoxicity is the induction of oxidative stress. There is hardly any cure for neurotoxicity in modern medicine, whereas many drugs in Ayurveda possess neuroprotective effects; however, there is no scientific validation for these drugs. Ksheerabala is an ayurvedic drug which is used to treat central nervous system disorders, arthritis, and insomnia. The aim of our study was to evaluate the effect of Ksheerabala on quinolinic acid-induced toxicity in rat brain. The o...

  9. A tetranuclear cadmium(II) complex based on the 2-(quinolin-8-yloxy)acetonitrile ligand. (United States)

    Liu, Ming-Liang; Ye, Qiong


    The hydrothermal reaction of 2-(quinolin-8-yloxy)acetonitrile and Cd(ClO(4))(2) yielded the noncentrosymmetric coordination complex tetrakis[μ-2-(quinolin-8-yloxy)acetato]tetrakis[μ-2-(quinolin-8-yloxy)acetonitrile]tetracadmium tetrakis(perchlorate) dihydrate, [Cd(4)(C(11)H(8)NO(3))(4)(C(11)H(8)N(2)O)(4)](ClO(4))(4)·2H(2)O. The local coordination environment around the Cd(II) cation can be best described as a capped octahedron defined by two N atoms and five O atoms from three ligands. The Cd(II) cations are linked by the ligands with Cd-O-Cd and Cd-O-C-C-O-Cd bridges, forming tetranuclear units, there being two independent tertranuclear units in the structure. The fourfold rotoinversion centre sits at the centre of each Cd(4) core. The two perchlorate anions in the asymmetric unit are linked by the water molecule through O-H...O hydrogen bonds.

  10. Active-site models for complexes of quinolinate synthase with substrates and intermediates

    Energy Technology Data Exchange (ETDEWEB)

    Soriano, Erika V.; Zhang, Yang; Colabroy, Keri L.; Sanders, Jennie M.; Settembre, Ethan C.; Dorrestein, Pieter C.; Begley, Tadhg P.; Ealick, Steven E., E-mail: [Cornell University, Ithaca, NY 14853-1301 (United States)


    Structural studies of quinolinate synthase suggest a model for the enzyme–substrate complex and an enzyme–intermediate complex with a [4Fe–4S] cluster. Quinolinate synthase (QS) catalyzes the condensation of iminoaspartate and dihydroxyacetone phosphate to form quinolinate, the universal precursor for the de novo biosynthesis of nicotinamide adenine dinucleotide. QS has been difficult to characterize owing either to instability or lack of activity when it is overexpressed and purified. Here, the structure of QS from Pyrococcus furiosus has been determined at 2.8 Å resolution. The structure is a homodimer consisting of three domains per protomer. Each domain shows the same topology with a four-stranded parallel β-sheet flanked by four α-helices, suggesting that the domains are the result of gene triplication. Biochemical studies of QS indicate that the enzyme requires a [4Fe–4S] cluster, which is lacking in this crystal structure, for full activity. The organization of domains in the protomer is distinctly different from that of a monomeric structure of QS from P. horikoshii [Sakuraba et al. (2005 ▶), J. Biol. Chem.280, 26645–26648]. The domain arrangement in P. furiosus QS may be related to protection of cysteine side chains, which are required to chelate the [4Fe–4S] cluster, prior to cluster assembly.

  11. Excited-state intramolecular proton transfer (ESIPT) inspired azole-quinoline based fluorophores: Synthesis and photophysical properties study

    Energy Technology Data Exchange (ETDEWEB)

    Padalkar, Vikas S.; Sekar, Nagaiyan, E-mail:


    7-Hydroxy-3-(4-nitrophenyl)quinoline-6-carboxylic acid was obtained by the condensation reaction of p-amino salicylic acid and 4-nitrophenylmalonadialdehyde which was obtained from phenylacetonitrile through nitration, hydrolysis and Vilsmeier reaction. 7-Hydroxy-3-(4-nitrophenyl) quinoline-6-carboxylic acid was condensed with different o-aminophenols or o-aminothiophenol in ethanol in the presence of phosphorustrichloride. Synthesized quinoline contained benzimidazole and benzothiazole moieties. Photophysical behaviors of these compounds in solvents of different polarities were studied using UV–vis and fluorescence spectroscopy. The compounds showed single absorption in all the studied solvents. The dual emissions (normal emission and ESIPT emission) as well as large Stokes' shift emission pattern were observed for the synthesized fluorophores. The photophysical study shows that the emission properties of the compounds depend on the solvent polarity. The photophysical properties of the compounds were compared with structurally analogous ESIPT quinoline. Thermal stability of the compounds was studied using thermogravimetric analysis and results show that compounds are thermally stable up to 300 °C. The synthesized quinoline derivatives were characterized using elemental analysis, FT-IR and {sup 1}H –NMR, {sup 13}C –NMR spectroscopy and mass spectral analysis. - Highlights: • First and unique study of quinoline derivatives contain ESIPT azole unit at 6-position and hydroxyl group at 7-position. • Compounds are fluorescent with considerable quantum yields. • All compounds showed absorption in ultraviolet region and emission in visible region with large Stokes' shift. • The photophysical properties of new compounds were compared with reported ESIPT quinoline analogous.

  12. Synthesis of 5-iodopyrrolo[1,2-a]quinolines and indolo[1,2-a]quinolines via iodine-mediated electrophilic and regioselective 6-endo-dig ring closure. (United States)

    Verma, Akhilesh Kumar; Shukla, Satya Prakash; Singh, Jaspal; Rustagi, Vineeta


    The endo-cyclic ring closure of 1-(2-(substituted ethynyl)phenyl)-1H-pyrroles 3a-t and 1-(2-(substituted ethynyl)phenyl)-H-indole 4a-o mediated by Lewis acid (I(2)) under mild conditions afforded substituted 5-iodopyrrolo[1,2-a]quinolines 5a-t and 5-iodoindolo[1,2-a]quinolines 6a-o in good to excellent yields. The reaction shows selective C-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized product. Iodo derivatives of pyrrolo- and indoloquinolines allow functional group diversification on the quinoline nucleus, which proves to be highly advantageous for structural and biological activity assessments.

  13. Quinoline alkaloids and friedelane-type triterpenes isolated from leaves and wood of Esenbeckia alata kunt (Rutaceae

    Directory of Open Access Journals (Sweden)

    Luis Enrique Cuca-Suarez


    Full Text Available This work describes the phytochemical exploration of the ethanol extract from leaves and wood of Esenbeckia alata, leading to the isolation and identification of quinoline alkaloids 4-methoxy-3-(3'-methyl-but-2'-enyl-N-methyl-quinolin-2(1 H-one, N-methylflindersine, dictamine, kokusaginine, Γ-fagarine, flindersiamine, as well as the fridelane-type triterpenes, frideline, fridelanol and its acetate derivative. Identification of these compounds was based on full analyses of spectroscopic data (¹H, 13C, 1D, 2D, IR, MS and comparison with data reported in literature. Compound 4-methoxy-3-(3'-methyl-but-2'-enyl-N-methyl-quinolin-2(1 H-one is reported for the first time for the genus Esenbeckia.

  14. Zanthoxoaporphines A–C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae

    Directory of Open Access Journals (Sweden)

    Fidelis N. Samita


    Full Text Available The bioassay-guided purification of Zanthoxylum paracanthum (Rutaceae extracts led to the isolation of three new alkaloids, namely 1-hydroxy-10-methoxy-7H-dibenzo[de,g]quinolin-7-one (zanthoxoaporphine A, 2, 1-hydroxy-7H-dibenzo[de,g]quinolin-7-one (zanthoxoaporphine B, 3 and 1,8-dihydroxy-9-methoxy-7H-dibenzo[de,g]quinolin-7-one (zanthoxaporphine C, 4, and a known lignan identified as sesamin (1. Isolation and purification of the constituent compounds was achieved through conventional chromatographic methods. The chemical structures of the isolated compounds were determined on the basis of UV, IR, NMR and MS data, and confirmed by comparison with those reported in the literature. The larvicidal activity of some of the isolated compounds was investigated by using third-instar Anopheles gambiae larvae.

  15. Analysis of denitrifier community in a bioaugmented sequencing batch reactor for the treatment of coking wastewater containing pyridine and quinoline

    Energy Technology Data Exchange (ETDEWEB)

    Bai, Yaohui; Xing, Rui; Wen, Donghui; Tang, Xiaoyan [Peking Univ., Beijing (CN). Key Lab. of Water and Sediment Sciences (Ministry of Education); Sun, Qinghua [Peking Univ., Beijing (CN). Key Lab. of Water and Sediment Sciences (Ministry of Education); Chinese Center for Disease Control and Prevention, Beijing (China). Inst. of Environmental Health and Related Product Safety


    The denitrifier community and associated nitrate and nitrite reduction in the bioaugmented and general sequencing batch reactors (SBRs) during the treatment of coking wastewater containing pyridine and quinoline were investigated. The efficiency and stability of nitrate and nitrite reduction in SBR was considerably improved after inoculation with four pyridine- or quinoline-degrading bacterial strains (including three denitrifying strains). Terminal restriction fragment length polymorphism (T-RFLP) based on the nosZ gene revealed that the structures of the denitrifier communities in bioaugmented and non-bioaugmented reactors were distinct and varied during the course of the experiment. Bioaugmentation protected indigenous denitrifiers from disruptions caused by pyridine and quinoline. Clone library analysis showed that one of the added denitrifiers comprised approximately 6% of the denitrifier population in the bioaugmented sludge. (orig.)

  16. Polyamine quinoline rhodium complexes: synthesis and pharmacological evaluation as antiparasitic agents against Plasmodium falciparum and Trichomonas vaginalis. (United States)

    Stringer, Tameryn; Taylor, Dale; Guzgay, Hajira; Shokar, Ajit; Au, Aaron; Smith, Peter J; Hendricks, Denver T; Land, Kirkwood M; Egan, Timothy J; Smith, Gregory S


    A series of mono- and bis-salicylaldimine ligands and their corresponding Rh(i) complexes were prepared. The compounds were characterised using standard spectroscopic techniques including NMR, IR spectroscopy and mass spectrometry. The salicylaldimine ligands and complexes were screened for antiparasitic activity against two strains of Plasmodium falciparum i.e. the NF54 CQ-sensitive and K1 CQ-resistant strain as well as against the G3 isolate of Trichomonas vaginalis. The monomeric salicylaldimine quinolines exhibited good activity against the NF54 strain and the dimeric salicylaldimine quinolines exhibited no cross resistance across the two strains. The binuclear 5-chloro Rh(i) complex displayed the best activity against the Trichomonas vaginalis parasite, possibly a consequence of its enhanced lipophilicity. The compounds were also screened for cytotoxicity in vitro against WHCO1 oesophageal cancer cells. The monomeric salicylaldimine quinolines exhibited high selectivity towards malaria parasites compared to cancer cells, while the dimeric compounds were less selective.

  17. Bis(quinolin-8-ol)silver(I) 2-hydr-oxy-3,5-dinitro-benzoate. (United States)

    Zhang, Chun-Lan; Jian, Fang-Fang


    The title compound, [Ag(C(9)H(7)NO)(2)](C(7)H(3)N(2)O(7)), was prepared from 3,5-dinitro-salicylic acid (DNS), quinolin-8-ol and AgNO(3). The Ag(I) atom is coordinated by two N atoms and two O atoms from two quinolin-8-ols in a roughly planar [maximum deviation = 0.223 (2) Å] environment. The two quinolin-8-ol ligands are bent slightly with respect to each other, making a dihedral angle of 9.55 (9)°. The DNS anion inter-acts with the silver complex through O-H⋯O hydrogen bonds.


    Energy Technology Data Exchange (ETDEWEB)

    Parker, Dorian S. N.; Kaiser, Ralf I. [Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822 (United States); Kostko, Oleg; Troy, Tyler P.; Ahmed, Musahid [Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (United States); Mebel, Alexander M. [Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199 (United States); Tielens, Alexander G. G. M. [Leiden Observatory, University of Leiden, Leiden (Netherlands)


    Nitrogen-substituted polycyclic aromatic hydrocarbons (NPAHs) have been proposed to play a key role in the astrochemical evolution of the interstellar medium, yet the formation mechanisms of even their simplest prototypes—quinoline and isoquinoline—remain elusive. Here, we reveal a novel concept that under high temperature conditions representing circumstellar envelopes of carbon stars, (iso)quinoline can be synthesized via the reaction of pyridyl radicals with two acetylene molecules. The facile gas phase formation of (iso)quinoline in circumstellar envelopes defines a hitherto elusive reaction class synthesizing aromatic structures with embedded nitrogen atoms that are essential building blocks in contemporary biological-structural motifs. Once ejected from circumstellar shells and incorporated into icy interstellar grains in cold molecular clouds, these NPAHs can be functionalized by photo processing forming nucleobase-type structures as sampled in the Murchison meteorite.

  19. Experimental and quantum chemical studies on corrosion inhibition performance of quinoline derivatives for MS in 1N HCl

    Indian Academy of Sciences (India)

    B M Mistry; N S Patel; S Sahoo; S Jauhari


    The corrosion inhibition effect of two quinoline derivatives, viz. 2-chloro quinoline 3-carbaldehyde (CQC) and (2-chloro-quinoline-3ylmethyl)--tolyl-amine (CQA) have been investigated against mild steel (MS) in 1N HCl solution using conventional weight loss, potentiodynamic polarization, linear polarization and electrochemical impedance spectroscopy. The losses in weights of MS samples have proved that both CQC and CQA are efficient inhibitors of corrosion. The mixed mode of inhibition was confirmed by electrochemical polarizations. The results of electrochemical impedance spectroscopy have showed changes in the impedance parameters like charge transfer resistance and double-layer capacitance that confirmed strong adsorption of inhibitors on the MS surface. The inhibition action of these compounds was assumed to occur via adsorption on the steel surface through the active centres contained in the molecules. Furthermore, quantum chemical calculations have been performed at B3LYP/6-31G( , ) level to complement the experimental evidence.

  20. Quinoline alkaloids and friedelane-type triterpenes isolated from leaves and wood of Esenbeckia alata Kunt (Rutaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Cuca-Suarez, Luis Enrique; Barrera, Ericsson David Coy [Universidad Nacional de Colombia, Bogota (Colombia). Dept. de Quimica; Alvarez Caballero, Juan Manuel [Universidad del Magdalena, Santa Marta DTCH (Colombia). Facultad de Ciencias Basicas


    This work describes the phytochemical exploration of the ethanol extract from leaves and wood of Esenbeckia alata, leading to the isolation and identification of quinoline alkaloids 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1 H)-one, N-methylflindersine, dictamine, kokusaginine, G-fagarine, flindersiamine, as well as the fridelane-type triterpenes, frideline, fridelanol and its acetate derivative. Identification of these compounds was based on full analyses of spectroscopic data ({sup 1}H, {sup 13}C, {sup 1}D, {sup 2}D, IR, MS) and comparison with data reported in literature. Compound 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1 H)-one is reported for the first time for the genus Esenbeckia. (author)

  1. Efficient example of cross-linked polymeric catalysed synthesis of 7-benzo[ℎ]indeno[1,2-]quinolin-8-one and 8-naphtho[2,3-ℎ]indeno[1,2-]quinolin-9-one

    Indian Academy of Sciences (India)

    Reza Sandaroos; Mehdi Vadi; Saman Damavandi


    Cross-linked poly(2-acrylamido-2-methyl propane sulphonic acid) (AMPS) was found to be an efficient heterogeneous catalyst for direct synthesis of 7-benzo[ℎ]indeno[1, 2-]quinolin-8-one and 8-naphtho[2, 3-ℎ]indeno[1, 2-]quinolin-9-one derivatives through one-pot condensation of aromatic aldehydes, 1, 3-indandione and 1-naphthylamine or 1-antharacylamine. The catalyst could be recovered conveniently and reused without any loss of activity. Mild conditions, short reaction times, simplicity, easy workup, and good to excellent yields can be mentioned as the advantages of this research.

  2. Synthesis of C-glycosyl triazolyl quinoline-based fluorescent sensors for the detection of mercury ions. (United States)

    Wang, Linfang; Jin, Jianzhong; Zhao, Linwei; Shen, Hongyun; Shen, Chao; Zhang, Pengfei


    A series of novel C-glycosyl triazolyl quinoline-based fluorescent sensors have been synthesized via click chemistry. It was found that novel sensors exhibited good selectivity for Hg(2+) over many other metal ions. The glucose framework was introduced to increase the water-solubility of the fluorescent sensors and broaden its application for the detection of Hg(II) in the water-solubility biological systems. The mechanism of the chemodosimetric behavior of the sensors has been attributed to a binding mode of triazolyl quinoline with Hg(2+) which has been characterized by a number of spectroscopic techniques.

  3. Thermo-optical properties of 1H[3,4-b] quinoline films used in electroluminescent devices (United States)

    Jaglarz, Janusz; Kępińska, Mirosława; Sanetra, Jerzy


    Electroluminescence cells with H[3,4-b] quinoline layers are promising devices for a blue light emitting EL diode. This work measured the optical reflectance as a function of temperature in copolymers PAQ layers deposited on Si crystalline substrate. Using the extended Cauchy dispersion model of the film refractive index we determined the thermo-optical coefficients for quinoline layers in the temperature range of 76-333 K from combined ellipsometric and spectrofotometric studies. The obtained values of thermo-optical coefficients of thin PAQ film, were negative and ranged in 5-10 × 10-4 [1/K].

  4. Naphthalene/quinoline amides and sulfonylureas as potent and selective antagonists of the EP4 receptor. (United States)

    Burch, Jason D; Farand, Julie; Colucci, John; Sturino, Claudio; Ducharme, Yves; Friesen, Richard W; Lévesque, Jean-François; Gagné, Sébastien; Wrona, Mark; Therien, Alex G; Mathieu, Marie-Claude; Denis, Danielle; Vigneault, Erika; Xu, Daigen; Clark, Patsy; Rowland, Steve; Han, Yongxin


    Two new series of EP(4) antagonists based on naphthalene/quinoline scaffolds have been identified as part of our on-going efforts to develop treatments for inflammatory pain. One series contains an acidic sulfonylurea pharmacophore, whereas the other is a neutral amide. Both series show subnanomolar intrinsic binding potency towards the EP(4) receptor, and excellent selectivity towards other prostanoid receptors. While the amide series generally displays poor pharmacokinetic parameters, the sulfonylureas exhibit greatly improved profile. MF-592, the optimal compound from the sulfonylurea series, has a desirable overall preclinical profile that suggests it is suitable for further development.

  5. Metabolic pathways of quinoline, indole and their methylated analogs by Desulfobacterium indolicum (DSM 3383)

    DEFF Research Database (Denmark)

    Johansen, S.S.; Licht, D.; Arvin, E.


    The transformation of quinoline, isoquinoline and 3-, 4-, 6- and 8-methylquinoline by Desulfobacterium indolicum was compared with that of the N-containing analogues indole and 1-, 2-, 3- and 7-methylindole. The metabolites were identified using high-performance liquid chromatography with UV dete...... inhibited. An incomplete transformation of some methylated compounds was observed, e.g. for 3- and 6-methylquinoline and 3- and 7-methylindole, with residual concentrations of 0.5-4 mg/l in relation to initial concentrations of 10-15 mg/l....

  6. Synthesis of (iso)quinoline, (iso)coumarin and (iso)chromene derivatives from acetylene compounds (United States)

    Ryabukhin, D. S.; Vasilyev, A. V.


    Published data on the methods of synthesis of quinoline, isoquinoline, coumarin, isocoumarin, chromene and isochromene derivatives from acetylene compounds are summarized. The reactions catalyzed by metal complexes (Pd, Pt, Ru, Rh, Au, Ag, Ni, Cu, etc.) and transformations induced by various electrophilic reagents (Brynsted and Lewis acids) are considered. Moieties of the mentioned heterocyclic systems are present in many biologically active natural products and pharmaceutical agents. Besides, derivatives of these heterocycles are used in the manufacture of catalysts, dyes, perfumery and cosmetic products, corrosion inhibitors and so on. The bibliography includes 211 references.

  7. The discovery of quinoline based single-ligand human H1 and H3 receptor antagonists. (United States)

    Procopiou, Panayiotis A; Ancliff, Rachael A; Gore, Paul M; Hancock, Ashley P; Hodgson, Simon T; Holmes, Duncan S; Keeling, Steven P; Looker, Brian E; Parr, Nigel A; Rowedder, James E; Slack, Robert J


    A novel series of potent quinoline-based human H1 and H3 bivalent histamine receptor antagonists, suitable for intranasal administration for the potential treatment of allergic rhinitis associated nasal congestion, were identified. Compound 18b had slightly lower H1 potency (pA2 8.8 vs 9.7 for the clinical goldstandard azelastine), and H3 potency (pKi 9.1vs 6.8 for azelastine), better selectivity over α1A, α1B and hERG, similar duration of action, making 18b a good back-up compound to our previous candidate, but with a more desirable profile.

  8. Solvent-dependent enthalpic versus entropic anion binding by biaryl substituted quinoline based anion receptors. (United States)

    Sun, Zhan-Hu; Albrecht, Markus; Raabe, Gerhard; Pan, Fang-Fang; Räuber, Christoph


    Anion receptors based on an 8-thiourea substituted quinoline with pentafluorinated (1a) or nonfluorinated (1b) biarylamide groups in the 2-position show similar binding of halide anions with somewhat higher association constants for the more acidic fluorinated derivative. Surprisingly, binding affinities for the halides in the case of the nonfluorinated 1b are similar in nonpolar chloroform or polar DMSO as solvent. Thorough thermodynamic investigations based on NMR van't Hoff analysis show that anion binding in chloroform is mainly enthalpically driven. In DMSO, entropy is the driving force for the binding of the ions with replacement of attached solvent.

  9. (Methoxo-κO)oxidobis(quinolin-8-olato-κ2N,O)vanadium(V)


    Zhenghua Guo; Lianzhi Li; Chengyuan Wang; Tao Xu; Jinghong Li


    In the title complex, [V(C9H6NO)2(CH3O)O], the central VV atom is coordinated by the O atoms from the oxido and methoxo ligands and the N and O atoms of two bis-chelating quinolin-8-olate ligands, forming a distorted octahedral environment. In the crystal structure, weak intermolecular C—H...O hydrogen bonds connect molecules into centrosymmetric dimers which are, in turn, linked by weak C—H...π interactions into chains along the b axis.

  10. (Methoxo-κO)oxidobis(quinolin-8-olato-κN,O)vanadium(V). (United States)

    Guo, Zhenghua; Li, Lianzhi; Wang, Chengyuan; Xu, Tao; Li, Jinghong


    In the title complex, [V(C(9)H(6)NO)(2)(CH(3)O)O], the central V(V) atom is coordinated by the O atoms from the oxido and methoxo ligands and the N and O atoms of two bis-chelating quinolin-8-olate ligands, forming a distorted octa-hedral environment. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect mol-ecules into centrosymmetric dimers which are, in turn, linked by weak C-H⋯π inter-actions into chains along the b axis.

  11. (Methoxo-κOoxidobis(quinolin-8-olato-κ2N,Ovanadium(V

    Directory of Open Access Journals (Sweden)

    Zhenghua Guo


    Full Text Available In the title complex, [V(C9H6NO2(CH3OO], the central VV atom is coordinated by the O atoms from the oxido and methoxo ligands and the N and O atoms of two bis-chelating quinolin-8-olate ligands, forming a distorted octahedral environment. In the crystal structure, weak intermolecular C—H...O hydrogen bonds connect molecules into centrosymmetric dimers which are, in turn, linked by weak C—H...π interactions into chains along the b axis.

  12. (Methoxo-κO)oxidobis(quinolin-8-olato-κ2 N,O)vanadium(V)


    Guo, Zhenghua; Li, Lianzhi; Wang, Chengyuan; Xu, Tao; Li, Jinghong


    In the title complex, [V(C9H6NO)2(CH3O)O], the central VV atom is coordinated by the O atoms from the oxido and methoxo ligands and the N and O atoms of two bis-chelating quinolin-8-olate ligands, forming a distorted octa­hedral environment. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds connect mol­ecules into centrosymmetric dimers which are, in turn, linked by weak C—H⋯π inter­actions into chains along the b axis.

  13. Alteration of kainic acid and quinolinic acid toxicity by neostriatal transplants in vitro. (United States)

    Whetsell, W O; Allen, G S; Tulipan, N B


    Mature (greater than 21 days in vitro) organotypic corticostriatal cultures prepared from newborn rat brain were incubated in either kainic acid (KA) 10(-3) M or quinolinic acid (QUIN) 10(-3) M for up to 48 h. Other identical cultures were similarly incubated immediately after they had received one or two additional explants of neonatal striatal tissue placed beside each corticostriatal culture. The cultures incubated with either KA or QUIN in the presence of the neonatal striatal tissue showed better preservation than cultures incubated with KA or QUIN alone. Results suggest that the neonatal striatal explants or 'transplants' afford some protective effect against the toxicity or either KA or QUIN.

  14. Synthesis of new biphenyl-substituted quinoline derivatives, preliminary screening and docking studies

    Indian Academy of Sciences (India)

    Nellisara D Shashikumar; Ganganaika Krishnamurthy; Halehatti S Bhojyanaik; Mayasandra R Lokesh; Kaginalli S Jithendrakumara


    New quinoline derivatives containing biphenyl ring were synthesized and characterized by IR, 1H NMR and mass spectral studies. The synthesized compounds were screened for antimicrobial, anthelmintic activities as well as free radical scavenging property against the DPPH radical. The minimum inhibition concentration values showed promising inhibiting activity and are potent biological agents. The compounds showed minimum binding energy towards -tubulin. The compounds 11a, 11c, 13c and 13d have good affinity towards the active pocket and may be considered as a good inhibitor of -tubulin.

  15. Interleukin-1beta but not tumor necrosis factor-alpha potentiates neuronal damage by quinolinic acid: protection by an adenosine A2A receptor antagonist. (United States)

    Stone, Trevor W; Behan, Wilhelmina M H


    Quinolinic acid is an agonist at glutamate receptors sensitive to N-methyl-D-aspartate (NMDA). It has been implicated in neural dysfunction associated with infections, trauma, and ischemia, although its neurotoxic potency is relatively low. This study was designed to examine the effects of a combination of quinolinic acid and the proinflammatory cytokines interleukin-1beta (IL-1beta) and tumor necrosis factor-alpha (TNF-alpha). Compounds were administered to the hippocampus of anesthetized male rats, animals being allowed to recover for 7 days before histological analysis of the hippocampus for neuronal damage estimated by counting of intact, healthy neurons. A low dose of quinolinic acid or IL-1beta produced no damage by itself, but the two together induced a significant loss of pyramidal neurons in the hippocampus. Higher doses produced almost total loss of pyramidal cells. Intrahippocampal TNF-alpha produced no effect alone but significantly reduced the neuronal loss produced by quinolinic acid. The adenosine A(2A) receptor antagonist ZM241385 reduced neuronal loss produced by the combinations of quinolinic acid and IL-1beta. The results suggest that simultaneous quinolinic acid and IL-1beta, both being induced by cerebral infection or injury, are synergistic in the production of neuronal damage and could together contribute substantially to traumatic, infective, or ischemic cerebral damage. Antagonism of adenosine A(2A) receptors protects neurons against the combination of quinolinic acid and IL-1beta.

  16. Application of Porous Nickel-Coated TiO2 for the Photocatalytic Degradation of Aqueous Quinoline in an Internal Airlift Loop Reactor

    Directory of Open Access Journals (Sweden)

    Mingxin Huo


    Full Text Available P25 film, prepared by a facile dip-coating method without any binder, was further developed in a recirculating reactor for quinoline removal from synthetic wastewater. Macroporous foam Ni, which has an open three-dimensional network structure, was utilized as a substrate to make good use of UV rays. Field emission scanning electron microscopy and X-ray diffraction analysis showed that the coated/calcinated P25 films consisted of two crystal phases, and had a number of uniform microcracks on the surface. The effects of initial quinoline concentration, light intensity, reaction temperature, aeration, and initial pH were studied. Increased reaction time, light intensity, environmental temperature, and gas aeration were found to significantly improve the quinoline removal efficiency. The aeration effect of oxygen dependency on the quinoline degradation had the trend pure oxygen > air > no gas > pure nitrogen with free O2. The solution pH crucially affected quinoline photodegradation; the high electrostatic adsorption of quinoline molecules on the TiO2 surface was strongly pH dependent. 2-Pyridine-carboxaldehyde, 3-pyridinecarboxaldehyde, and 2(1H-quinolinone were identified as the major intermediates of quinoline degradation. Based on these intermediates, a primary degradation mechanism was proposed. This reusable P25 film benefits the photodegradation of water contaminants and has potential in other various applications.

  17. Dipodal quinoline-tethered fluorescent probe synthesis and investigation of spectroscopic properties (United States)

    Obalı, Aslıhan Yılmaz; Yilmaz, Menzeher Serkan; Uçan, Halil İsmet


    Novel quinoline-tethered fluorescent probe was designed and synthesized as multidentate ligand. Their sensing actions were confirmed by UV-Vis absorbance and emission spectroscopic studies in presence of perchlorate salts of Co2+, Li+, Fe2+, K+, Pb2+, Cu2+, Zn2+, Ni2+, Hg2+, Ag+ cations in acetonitrile (1 × 10-5 M for absorption studies, 1 × 10-7 M for fluorescence studies). It was found that the dipodal compounds can selectively bind to Cu2+ and Ag+ metal ions with a significant quenching in their emissions. The capture of Cu2+ and Ag+ by the probe resulted in deprotonation of the secondary amine conjugated to the quinoline-tethered probe, so that the electron-donation ability of the 'N' atom would be greatly enhanced and the probe (2) showed blue-shift in emission and exhibited an on-off fluorescent response. The binding study was explored by using fluorescence spectroscopy with Job plot method.

  18. An environmentally benign one pot synthesis of substituted quinolines catalysed by fluoroboric acid based ionic liquid

    Indian Academy of Sciences (India)

    A Rajendran; C Karthikeyan; K Rajathi; D Ragupathy


    Organic synthesis generally required large amount of solvent, avoiding the use of organic solvents in synthesis is a paradigm shift directed at developing more benign chemistry, and with ionic liquids surprisingly can lead to access to new compounds. An elegant one-pot synthesis of quinoline derivatives has been achieved by reaction of substituted anilines with -ketoester at 60°C in ethanol using an ionic liquid [Et3NH]+[BF4]−as catalyst. All the reactions gave products with high degree of purity and excellent yield (78-93%) within the shorter span of time (20-65 min) than those reactions with conventional methods. The screening of solvents as well as the reuse of ionic liquid has been evaluated. The structure of the products has been elucidated by spectral and analytical data. The present scope and potential economic impact of the reaction are demonstrated by the synthesis of substituted quinolines. Remaining challenges and future perspectives of the new transformation are discussed.

  19. Grafting polyethylenimine with quinoline derivatives for targeted imaging of intracellular Zn(2+) and logic gate operations. (United States)

    Pan, Yi; Shi, Yupeng; Chen, Junying; Wong, Chap-Mo; Zhang, Heng; Li, Mei-Jin; Li, Cheuk-Wing; Yi, Changqing


    In this study, a highly sensitive and selective fluorescent Zn(2+) probe which exhibited excellent biocompatibility, water solubility, and cell-membrane permeability, was facilely synthesized in a single step by grafting polyethyleneimine (PEI) with quinoline derivatives. The primary amino groups in the branched PEI can increase water solubility and cell permeability of the probe PEIQ, while quinoline derivatives can specifically recognize Zn(2+) and reduce the potential cytotoxicity of PEI. Basing on fluorescence off-on mechanism, PEIQ demonstrated excellent sensing capability towards Zn(2+) in absolute aqueous solution, where a high sensitivity with a detection limit as low as 38.1nM, and a high selectivity over competing metal ions and potential interfering amino acids, were achieved. Inspired by these results, elementary logic operations (YES, NOT and INHIBIT) have been constructed by employing PEIQ as the gate while Zn(2+) and EDTA as chemical inputs. Together with the low cytotoxicity and good cell-permeability, the practical application of PEIQ in living cell imaging was satisfactorily demonstrated, emphasizing its wide application in fundamental biology research. Copyright © 2016. Published by Elsevier B.V.

  20. A computational study on corrosion inhibition performances of novel quinoline derivatives against the corrosion of iron (United States)

    Erdoğan, Şaban; Safi, Zaki S.; Kaya, Savaş; Işın, Dilara Özbakır; Guo, Lei; Kaya, Cemal


    In this computational study, the adsorption and corrosion inhibition properties of some novel quinoline derivatives namely, 2-amino-7-hydroxy-4-phenyl-1,4-dihydroquinoline-3-carbonitrile (Q1), 2-amino-7-hydroxy-4-(p-tolyl)-1,4-dihydroquinoline-3-carbonitrile (Q2), 2-amino-7-hydroxy-4-(4-methoxyphenyl)-1,4-dihydroquinoline-3-carbonitrile) (Q3) and 2-amino-4-(4-(dimethylamino)phenyl)-7-hydroxy-1,4-dihydroquinoline-3-carbonitrile (Q4) on the corrosion of iron were investigated using quantum chemical and molecular dynamics simulation approaches. Quantum chemical calculations section of the study provides enough calculation and discussion on the relationship between corrosion inhibition and global reactivity descriptors such as EHOMO, ELUMO, HOMO-LUMO energy gap (ΔE), chemical hardness (η), softness (σ), electronegativity (χ), chemical potential (μ), electrophilicity (ω), nucleophilicity (ɛ), electrons transferred from inhibitors to metal surface (ΔN), initial molecule-metal interaction energy (Δψ), total electronic energy (E), the energy change during electronic back-donation process (ΔEb-d). The adsorption behaviors of studied compounds on Fe (110) surface were investigated with the help of molecular dynamics simulation approach. The binding energies calculated on Fe (110) surface of mentioned quinoline derivatives followed the order: Q4 > Q3 > Q2 > Q1. It should be noted that the results obtained in the study are in good agreement with experimental inhibition efficiency results earlier reported.

  1. New quinoline alkaloid from Ruta graveolens aerial parts and evaluation of the antifertility activity. (United States)

    Salib, Josline Y; El-Toumy, Sayed A; Hassan, Emad M; Shafik, Nabila H; Abdel-Latif, Sally M; Brouard, Ignacio


    Bioassay-guided isolation of methanol extract of Ruta graveolens L. leaves yielded a new quinoline alkaloid, (4S) 1,4-dihydro-4-methoxy-1,4-dimethyl-3-(3-methylbut-2-enyl)quinoline 2,7-diol, and nine phenolic compounds including rutin as a major compound. Structures of the isolated compounds were determined by using chromatography, UV, HR-ESI-MS and 1D/2D (1)H/(13)C NMR spectroscopy. The uterotonic activity of methanol extract fractions (ethyl acetate, n-butanol and aqueous fraction) as well as the isolated major compounds was tested in the isolated mouse uterus in vitro. The n-butanol-soluble fraction was found to demonstrate the most potent uterotonic activity in a dose-dependent manner, also the major isolated compound rutin revealed the occurrence of an uterotonic response, which was maximum at a concentration level of 0.25 mg/mL, accounting for 68.7% of that exhibited by the chosen concentration of oxytocin.

  2. The sensitivity and selectivity properties of a fluorescence sensor based on quinoline-Bodipy

    Energy Technology Data Exchange (ETDEWEB)

    Nuri Kursunlu, Ahmed, E-mail:; Guler, Ersin


    A novel florescence sensor (Q-BODIPY) based on quinoline-Bodipy (quinoline-boradiazaindacene) was prepared by ‘click chemistry’ in several stages. The sensing actions of Q-BODIPY were confirmed by UV–vis titration, emission and excitation spectroscopic studies in presence of Mn{sup 2+}, Co{sup 2+}, Ni{sup 2+}, Cu{sup 2+}, Zn{sup 2+}, Cd{sup 2+}, Sn{sup 2+}, Hg{sup 2+}, Pb{sup 2+}, La{sup 3+}, Ga{sup 3+}, Er{sup 3+} and Yb{sup 3+} ions in methanol:H{sub 2}O (1:1) medium. Whereas some metal ions can only cause quenching effect on the fluorescence intensity of Q-BODIPY, some of them show an increase in fluorescence intensity. The stoichiometry of host–guest complexes formed was determined by Job′s plot method. The binding constants were calculated by Stern–Volmer method. As a fluorescence sensor, Q-BODIPY shows the best selectivity performance against Zn{sup 2+} ions in according to all spectroscopic data. -- Highlights: • Q-BODIPY prepared by several techniques shows a fluorescent behavior toward p, d and f block metal ions. • Q-BODIPY has both a more sensitivity and more effective ability for the detection of Zn(II) ion. • The synthesis strategies to produce Bodipy′s with metal coordinating offer a new approach for the design of novel fluorescence sensors.

  3. Novel Triazole-Quinoline Derivatives as Selective Dual Binding Site Acetylcholinesterase Inhibitors

    Directory of Open Access Journals (Sweden)

    Susimaire P. Mantoani


    Full Text Available Alzheimer’s disease (AD is the most prevalent neurodegenerative disorder worldwide. Currently, the only strategy for palliative treatment of AD is to inhibit acetylcholinesterase (AChE in order to increase the concentration of acetylcholine in the synaptic cleft. Evidence indicates that AChE also interacts with the β-amyloid (Aβ protein, acting as a chaperone and increasing the number and neurotoxicity of Aβ fibrils. It is known that AChE has two binding sites: the peripheral site, responsible for the interactions with Aβ, and the catalytic site, related with acetylcholine hydrolysis. In this work, we reported the synthesis and biological evaluation of a library of new tacrine-donepezil hybrids, as a potential dual binding site AChE inhibitor, containing a triazole-quinoline system. The synthesis of hybrids was performed in four steps using the click chemistry strategy. These compounds were evaluated as hAChE and hBChE inhibitors, and some derivatives showed IC50 values in the micro-molar range and were remarkably selective towards hAChE. Kinetic assays and molecular modeling studies confirm that these compounds block both catalytic and peripheral AChE sites. These results are quite interesting since the triazole-quinoline system is a new structural scaffold for AChE inhibitors. Furthermore, the synthetic approach is very efficient for the preparation of target compounds, allowing a further fruitful new chemical library optimization.

  4. Striatal grafts provide sustained protection from kainic and quinolinic acid-induced damage. (United States)

    Tulipan, N; Luo, S Q; Allen, G S; Whetsell, W O


    Grafts of neonatal striatal tissue were placed into the striata of adult rats. When challenged immediately with intrastriatal injections of either kainic or quinolinic acid, excitotoxic damage was prevented. Thirty days later these same graft recipients received another injection of excitotoxin. The intrastriatal grafts continued to mitigate toxin-induced damage. It is hypothesized that the grafted cells not only survive, but that they may continue to elaborate some substance or substances that prevent excitotoxin-induced injury for at least 30 days. Previous investigations indicated that grafts of neonatal striatal tissue can protect the recipient striatum from kainic acid toxicity. In the following study it is demonstrated that such grafts also protect the striatum from quinolinic acid, an endogenous excitotoxin which induces kainate-like neuronal degeneration and has been implicated in the pathogenesis of Huntington's disease. It is postulated that the salutary effect of striatal grafting may be sufficiently long lasting to mitigate a chronic toxic insult. Such grafting may therefore represent a therapy for Huntington's disease and other neurodegenerative disorders in which an endogenous or exogenous toxin has been implicated as the pathogenetic agent.

  5. Substituent influence on the spectra of some benzo[f]quinoline derivatives (United States)

    Oanca, Gabriel; Stare, Jernej; Todirascu, Antonina Gritco; Creanga, Dorina; Dorohoi, Dana Ortansa


    The aim of this study was to investigate the relations between the properties of some organic compounds that are cycloaddition derivatives of benzo[f]quinoline, namely benzo[f]pyrrolo[1,2-a]quinolines (BQCDs) and the structure of variable substituent in the addition cycle. The work was focused on the differences in the molecular parameters like frontier orbitals and dipole moment as well as electronic absorption spectra of substituted BQCDs. The optimized molecular structures of BQCDs were calculated using Gaussian 09, with DFT method, the frontier orbitals and electronic absorption spectra being modeled with restricted Hartree Fock method also implemented in Gaussian 09. Influence of substituted radical on the dipole moments and frontier orbital energies of the BQCDs was evidenced from calculated values. Substituent effect on the BQCDs recorded electronic absorption spectra in diluted solution and protonated diluted solution was also emphasized: different types of the transitions underlying absorption bands in the visible range were presumed based on the quantum chemical and experimental investigation.

  6. Synthesis, characterization and emission properties of quinolin-8-olato chelated ruthenium organometallics

    Indian Academy of Sciences (India)

    Bikash Kumar Panda


    The reaction of Ru(RL1)(PPh3)2(CO)Cl, 1, with quinolin-8-ol (HQ) has afforded complexes of the type [Ru(RL2)(PPh3)2(CO)(Q)], 3, in excellent yield (RL1 is C6H2O-2-CHNHC6H4R()-3-Me-5, RL2 is C6H2OH-2-CHNC6H4R()-3-Me-5 and R is Me, OMe, Cl). In this process, quinolin-8-olato (Q) undergoes five-membered chelation, the iminium-phenolato function tautomerizing to the imine-phenol function. In dichloromethane solution, 3 displays a quasireversible 3+/3 couple near 0×50 V vs SCE (3+ is the ruthenium (III) analogue of 3). Coulometrically generated solutions of 3+ display a strong absorption near 395 nm associated with a shoulder near 475 nm and rhombic EPR spectra with values near 2.55, 2.13, 1.89. Solutions of 3 absorb near 415 nm and emit near 510 nm at 298 K and 585 nm at 77 K. The fluorescence is believed to originate from the 3MLCT state.

  7. Experimental and theoretical studies on IR, Raman, and UV-Vis spectra of quinoline-7-carboxaldehyde. (United States)

    Kumru, M; Küçük, V; Kocademir, M; Alfanda, H M; Altun, A; Sarı, L


    Spectroscopic properties of quinoline-7-carboxaldehyde (Q7C) have been studied in detail both experimentally and theoretically. The FT-IR (4000-50 cm(-1)), FT-Raman (4000-50 cm(-1)), dispersive-Raman (3500-50 cm(-1)), and UV-Vis (200-400 nm) spectra of Q7C were recorded at room temperature (25 °C). Geometry parameters, potential energy surface about CCH(O) bond, harmonic vibrational frequencies, IR and Raman intensities, UV-Vis spectrum, and thermodynamic characteristics (at 298.15K) of Q7C were computed at Hartree-Fock (HF) and density functional B3LYP levels employing the 6-311++G(d,p) basis set. Frontier molecular orbitals, molecular electrostatic potential, and Mulliken charge analyses of Q7C have also been performed. Q7C has two stable conformers that are energetically very close to each other with slight preference to the conformer that has oxygen atom of the aldehyde away from the nitrogen atom of the quinoline.

  8. Synthetically simple, click-generated quinoline-based Fe3+ sensors (United States)

    Wang, Zhaoyun; Wang, Hua; Meng, Ting; Hao, Erhong; Jiao, Lijuan


    Simple quinoline-based fluorescent probes for Fe3+ have been efficiently synthesized through ‘click’ reaction. Both probes gave intense fluorescence compared to 8-hydroquinoline in various organic solvents due to the inhibition of the excited state intramolecular photon transfer process, while showing dramatically quenched and red-shifted fluorescence in an aqueous solution, which can be attributed to the hydrogen bond-induced intermolecular excited state proton transfer process. In the presence of Fe3+ or in an acidic condition (pH less than 4.0), both probes showed similar quenching of the emission and over 100 nm red-shifts of their emission maxima. The binding mode between the probes and Fe3+ has been found to be 1:1 based on Job’s plot. A highly sensitive and selective response in their absorption and emission towards Fe3+ over many other metal ions, including Cr3+ and Cu2+, was observed and may be the result of the ground state metal to ligand charge transfer effect from Fe3+ to quinoline ligands.

  9. Hydrogen bonding in asphaltenes and coal. Progress report, July 1, 1976--December 31, 1976. [Between quinoline and o-phenylphenol

    Energy Technology Data Exchange (ETDEWEB)

    Li, N.C.


    Calorimetric studies of hydrogen bonding between quinoline and o-phenylphenol were carried out because they represent the nitrogenous heteronuclear aromatic bases and aromatic bases, respectively, found in the liquefaction products from coal. Further experiments are planned to try to resolve discrepancies observed between experimental and calculated values. (EJH)

  10. 10-hydroxybenzo[h]quinoline: Switching between single and double-well proton transfer through structural modifications

    DEFF Research Database (Denmark)

    Hristova, S; Dobrikov, G; Kamounah, F. S.;


    Proton transfer in 10-hydroxybenzo[h]quinoline (HBQ) and structurally modified compounds was investigated experimentally (steady state UV-Vis absorption and emission spectroscopy, NMR and advanced chemometric techniques) and theoretically (DFT and TD-DFT M06-2X/TZVP calculations) in the ground...

  11. B(HSO43: An efficient and recyclable catalyst for the preparation of substituted Friedländer quinoline synthesis

    Directory of Open Access Journals (Sweden)

    Saghanezhad Seyyed Jafar


    Full Text Available Substituted quinolines have been synthesized in the presence of catalytic amounts of boron sulfonic acid (BSA in solvent-free conditions. This methodology offers some advantages including high yield, short reaction time, low cost of the catalyst, green conditions by avoiding toxic solvents and recoverable catalyst.

  12. Solvent effect on copper-catalyzed azide-alkyne cycloaddition (CuAAC): synthesis of novel triazolyl substituted quinolines as potential anticancer agents. (United States)

    Ellanki, Amarender Reddy; Islam, Aminul; Rama, Veera Swamy; Pulipati, Ranga Prasad; Rambabu, D; Krishna, G Rama; Reddy, C Malla; Mukkanti, K; Vanaja, G R; Kalle, Arunasree M; Kumar, K Shiva; Pal, Manojit


    A regioselective route to novel mono triazolyl substituted quinolines has been developed via copper-catalyzed azide-alkyne cycloaddition (CuAAC) of 2,4-diazidoquinoline with terminal alkynes in DMF. The reaction provided bis triazolyl substituted quinolines when performed in water in the presence of Et(3)N. A number of the compounds synthesized showed promising anti-proliferative properties when tested in vitro especially against breast cancer cells. Copyright © 2012 Elsevier Ltd. All rights reserved.

  13. Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]-quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents

    Institute of Scientific and Technical Information of China (English)

    Divyesh C. Mungra; Harshad G. Kathrotiya; Niraj K. Ladani; Manish P. Patel; Ranjan G. Patel


    A series of some new tetrazolo[1,5-a]quinoline based tetrasubstituted imidazole derivatives 6a-I have been synthesized by a reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde 3a-d,benzil 4,aromatic amine 5a-c and ammonium acetate in the presence of iodine through one-pot multi-component reaction (MCR) approach.All the derivatives were screened for antimicrobial and antituberculosis activities and results worth further investigations.

  14. Involvement of quinolinic acid in the neuropathogenesis of amyotrophic lateral sclerosis. (United States)

    Lee, Jong-Min; Tan, Vanessa; Lovejoy, David; Braidy, Nady; Rowe, Dominic B; Brew, Bruce J; Guillemin, Gilles J


    Amyotrophic lateral sclerosis (ALS) is the most common adult-onset motor neuron disease characterized by a progressive degeneration of central and peripheral motor neurons, leading to the atrophy of voluntary muscles. It has been previously demonstrated that the kynurenine pathway (KP), the major biochemical pathway for tryptophan metabolism, is dysregulated in ALS. In particular, the neuroactive intermediate, quinolinic acid (QUIN) has been shown to accumulate with a concomitant decrease in other neuroprotective and immunomodulatory KP metabolites. Furthermore, multiple biochemical phenomena associated with QUIN cytotoxicity are present in ALS, suggesting that QUIN may play a substantial role in the pathogenesis of ALS. This review highlights the potential roles of QUIN in ALS, and explores KP modulation as a therapeutic candidate in ALS. This article is part of the Special Issue entitled 'The Kynurenine Pathway in Health and Disease'. Copyright © 2016 Elsevier Ltd. All rights reserved.

  15. New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

    Energy Technology Data Exchange (ETDEWEB)

    Ambrozin, Alessandra R.P.; Mafezoli, Jair; Vieira, Paulo C.; Fernandes, Joao B.; Silva, M. Fatima das G.F. da [Sao Carlos Univ., SP (Brazil). Dept. de Quimica]. E-mail:; Ellena, Javier A. [Sao Paulo Univ., Sao Carlos, SP (Brazil). Inst. de Fisica; Albuquerque, Sergio de [Sao Paulo Univ., Ribeirao Preto, SP (Brazil). Faculdade de Ciencias Farmaceuticas. Dept. de Analises Clinicas, Toxicologicas, Bromatologicas


    The investigation of the ethyl acetate fraction of methanol extract from leaves of Almeidea rubra A. St.-Hil. (Rutaceae) afforded two new compounds 4-methoxy-6-[2-(methylamino)phenyl]-2Hpyran- 2-one and rel-(7R,8R)-8-[(E)-3-hydroxy-3-methyl-1-butenyl]-4,8-dimethoxy-5,6,7,8- tetrahydrofuro[2,3-b]quinoline-7-yl acetate, along with the known compounds arborinine, N-methyl- 1-hydroxy-3-methoxyacridone, skimmianine, kokusagine, isodutaduprine, isoskimmianine, and isokokusagine. Their structures were established based on their spectral data, and for the new compounds these data are described herein. Additionally, these compounds were assayed on the tripomastigote forms of Trypanosoma cruzi showing moderate trypanocidal activity. (author)

  16. A fluorescence turn-on chemosensor for hydrogen sulfate anion based on quinoline and naphthalimide (United States)

    Luo, Zaoli; Yin, Kai; Yu, Zhu; Chen, Mengxue; Li, Yan; Ren, Jun


    A new fluorescence turn-on chemosensor 1 based on quinoline and naphthalimide was prepared and its anion sensing toward various anions behavior was explored in this paper. Sensor 1 exhibited a highly selective fluorescent response toward HSO4- with an 8-fold fluorescence intensity enhancement in the presence of 10 equiv. of HSO4- in DMSO-H2O (1/1, v/v) solution. The sensor also displayed high sensitivity to hydrogen sulfate and the detection limit was calculated to be 7.79 × 10- 7 M. The sensing mechanism has been suggested to proceed via a hydrolysis process of the Schiff base group. The hydrolysis product has been isolated and further identified by 1H NMR and MS.

  17. Pyrazolo[3,4-h]quinolines promising photosensitizing agents in the treatment of cancer. (United States)

    Spanò, Virginia; Parrino, Barbara; Carbone, Anna; Montalbano, Alessandra; Salvador, Alessia; Brun, Paola; Vedaldi, Daniela; Diana, Patrizia; Cirrincione, Girolamo; Barraja, Paola


    A new series of pyrazolo[3,4-h]quinolines, heteroanalogues of angelicin was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular photocytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI50 values reaching the nanomolar level (14.52-0.04 μM). Selected compounds were able to photoinduce a massive cell death with the involvement of mitochondria. Their photodamage cellular targets were proteins and lipids and they did not cause any kind of DNA photodamage. This latter event is of considerable importance in the modulation of long term side effects, generally associated with the use of classical furocoumarins.

  18. Deuterium isotope effects on 13C chemical shifts of 10-Hydroxybenzo[h]quinolines

    DEFF Research Database (Denmark)

    Hansen, Poul Erik; Kamounah, Fadhil S.; Gryko, Daniel T.


    to be negative, indicating transmission via the hydrogen bond. In addition unusual long-range effects are seen. Structures, NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using DFT methods. Two-bond deuterium isotope effects on 13C chemical shifts are correlated......Deuterium isotope effects on 13C-NMR chemical shifts are investigated in a series of 10-hydroxybenzo[h]quinolines (HBQ’s) The OH proton is deuteriated. The isotope effects on 13C chemical shifts in these hydrogen bonded systems are rather unusual. The formal four-bond effects are found...... with calculated OH stretching frequencies. Isotope effects on chemical shifts are calculated for systems with OH exchanged by OD. Hydrogen bond potentials are discussed. New and more soluble nitro derivatives are synthesized....

  19. Quinolin-6-Yloxyacetamides Are Microtubule Destabilizing Agents That Bind to the Colchicine Site of Tubulin

    Directory of Open Access Journals (Sweden)

    Ashwani Sharma


    Full Text Available Quinolin-6-yloxyacetamides (QAs are a chemical class of tubulin polymerization inhibitors that were initially identified as fungicides. Here, we report that QAs are potent anti-proliferative agents against human cancer cells including ones that are drug-resistant. QAs act by disrupting the microtubule cytoskeleton and by causing severe mitotic defects. We further demonstrate that QAs inhibit tubulin polymerization in vitro. The high resolution crystal structure of the tubulin-QA complex revealed that QAs bind to the colchicine site on tubulin, which is targeted by microtubule-destabilizing agents such as colchicine and nocodazole. Together, our data establish QAs as colchicine-site ligands and explain the molecular mechanism of microtubule destabilization by this class of compounds. They further extend our structural knowledge on antitubulin agents and thus should aid in the development of new strategies for the rational design of ligands against multidrug-resistant cancer cells.

  20. Excess Transport Properties of Binary Mixtures of Quinoline with Xylenes at Different Temperatures

    Directory of Open Access Journals (Sweden)

    Sk. Fakruddin


    Full Text Available The ultrasonic velocity and density of binary liquid mixtures of quinoline with o-xylene, m-xylene, and p-xylene have been measured over the entire range of composition at = 303.15, 308.15, 313.15, and 318.15 K. Using these data, various parameters like adiabatic compressibility (β, intermolecular free length (, and acoustic impedance ( and some excess parameters like excess adiabatic compressibility (, excess intermolecular free length (, excess acoustic impedance (, and excess ultrasonic velocity ( have been calculated for all the three mixtures. The calculated deviations and excess functions have been fitted to Redlich-Kister polynomial equation. The observed deviations have been explained on the basis of the intermolecular interactions present in these mixtures.

  1. Separation and preconcentration of U(VI) on XAD-4 modified with 8-hydroxy quinoline. (United States)

    Singh, B N; Maiti, B


    Amberlite XAD-4 adsorber resin was modified with 8-hydroxy quinoline (Oxine) by equilibrating with methanol solution of the reagent and the modified resin was used as a support material for the solid phase extraction and preconcentration of UO(2)(2+) from aqueous solution at pH between 4 and 5.5. Ten micrograms of uranium from 300 ml of aqueous phase could be quantitatively extracted in to 1g of the modified resin giving an enrichment of 200. Uranium collected in the column could be eluted out with methanol-HCl mixture and determined spectrophotometrically using arsenazo(III) as the chromogenic reagent. The preconcentration could be made selective to uranium by using EDTA as a masking agent for transition metal ions and Th(IV).

  2. Second-order optical effects in several pyrazolo-quinoline derivatives (United States)

    Makowska-Janusik, M.; Gondek, E.; Kityk, I. V.; Wisła, J.; Sanetra, J.; Danel, A.


    Using optical poling of several pyazolo-quinoline (PAQ) derivatives we have found an existence of sufficiently high second order optical susceptibility at wavelength 1.76 μm varying in the range 0.9-2.8 pm/V. The performed quantum chemical simulations of the UV-absorption for isolated, solvated and incorporated into the polymethacrylate (PMMA) polymer films have shown that the PM3 method is the best among the semi-empirical ones to simulate the optical properties. The calculations of the hyperpolarizabilites have shown a good correlation with experimentally measured susceptibilities obtained from the optical poling. We have found that experimental susceptibility depends on linear molecular polarizability and photoinducing changes of the molecular dipole moment. It is clearly seen for the PAQ4-PAQ6 molecules possessing halogen atoms with relatively large polarizabilities.

  3. Second-order optical effects in several pyrazolo-quinoline derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Makowska-Janusik, M. [Solid State Department, Institute of Physics, WSP Czestochowa, Al. Armii Krajowej 13/15, Czestochowa PL42201 (Poland); Gondek, E. [Institute of Physics, Cracow University of Technology, ul. Podchorazych 1, 30-084 (Poland); Kityk, I.V. [Department of Biology and Biophysics, Technical University of Czestochowa, Al. Armii Krajowej 36, Czestochowa PL-42210 (Poland)]. E-mail:; WisIa, J. [Departament of Chemistry, Hugon Kollataj Agricultural University, Al. Mickiewicza 24/28, 30-059 Cracow (Poland); Sanetra, J. [Institute of Physics, Cracow University of Technology, ul. Podchorazych 1, 30-084 (Poland); Danel, A. [Department of Chemistry, Hugon Kollataj Agricultural University, Al. Mickiewicza 24/28, 30-059 Cracow (Poland)


    Using optical poling of several pyazolo-quinoline (PAQ) derivatives we have found an existence of sufficiently high second order optical susceptibility at wavelength 1.76 {mu}m varying in the range 0.9-2.8 pm/V. The performed quantum chemical simulations of the UV-absorption for isolated, solvated and incorporated into the polymethacrylate (PMMA) polymer films have shown that the PM3 method is the best among the semi-empirical ones to simulate the optical properties. The calculations of the hyperpolarizabilites have shown a good correlation with experimentally measured susceptibilities obtained from the optical poling. We have found that experimental susceptibility depends on linear molecular polarizability and photoinducing changes of the molecular dipole moment. It is clearly seen for the PAQ4-PAQ6 molecules possessing halogen atoms with relatively large polarizabilities.

  4. Photocytotoxicity of a 5-nitrofuran-ethenyl-quinoline antiseptic (Quinifuryl to P388 mouse leukemia cells

    Directory of Open Access Journals (Sweden)

    Daghastanli N.A.


    Full Text Available Quinifuryl (MW 449.52, 2-(5'-nitro-2'-furanylethenyl-4-{N-[4'-(N,N-diethylamino-1'-methylbutyl]carbamoyl} quinoline, is a water soluble representative of a family of 5-nitrofuran-ethenyl-quinoline drugs which has been shown to be highly toxic to various lines of transformed cells in the dark. In the present study, the toxicity of Quinifuryl to P388 mouse leukemia cells was compared in the dark and under illumination with visible light (390-500 nm. Illumination of water solutions of Quinifuryl (at concentrations ranging from 0.09 to 9.0 µg/ml in the presence of P388 cells resulted in its photodecomposition and was accompanied by elevated cytotoxicity. A significant capacity to kill P388 cells was detected at a drug concentration as low as 0.09 µg/ml. The toxic effect detected at this drug concentration under illumination exceeded the effect observed in the dark by more than three times. Moreover, the general toxic effect of Quinifuryl, which included cell proliferation arrest, was nearly 100%. Both dose- and time-dependent toxic effects were measured under illumination. The LC50 value of Quinifuryl during incubation with P388 cells was ~0.45 µg/ml under illumination for 60 min and >12 µg/ml in the dark. We have demonstrated that the final products of the Quinifuryl photolysis are not toxic, which means that the short-lived intermediates of Quinifuryl photodecomposition are responsible for the phototoxicity of this compound. The data obtained in the present study are the first to indicate photocytotoxicity of a nitroheterocyclic compound and demonstrate the possibility of its application as a photosensitizer drug for photochemotherapy.

  5. Effect of 8-hydroxy-, 8-mercapto- and 5-chloro-7-iodo-8-hydroxy-quinoline on the uptake and distribution of nickel in mice

    Energy Technology Data Exchange (ETDEWEB)

    Borg-Neczak, K.; Tjaelve, H. (Department of Pharmacology and Toxicology, Faculty of Veterinary Medicine, Swedish University of Agricultural Sciences, Uppsala Biomedical Centre, Uppsala (Sweden))


    Oral administration of Ni[sup 2+] together with 8-hydroxyquinoline (8-OH-quinoline), 8-mercaptoquinoline (8-SH-quinoline) or 5-chloro-7-iodo-8-hydroxyquinoline (clioquinol) resulted in increased tissue levels of the metal in several tissues of mice in comparison with animals given the Ni[sup 2+] alone. Ni[sup 2+] forms lipophilic complexes with these compounds and it can be assumed that this will facilitate the uptake of Ni[sup 2+] over the walls of the gastrointestinal tract. Our results showed that 8-SH-quinoline, in contrast to 8-OH-quinoline and clioquinol, induces a markedly changed distribution pattern of the Ni[sup 2+] in the body, with uptake of the metal in tissues such as the central nervous system, pigmented tissues, the pancreatic islets and the thyroid. It is probable that the Ni[sup 2+] -complex with 8-SH-quinoline is stable enough to persist for a time period in the tissues and that the obtained pattern partly reflects the distribution of the complexed metal. In contrast, following the absorption from the gastrointestinal tract there may be a dissociation of the complexes between Ni[sup 2+] and 8-OH-quinoline or clioquinol, resulting in increased metal levels in various tissues, but with similar distribution as when the Ni[sup 2+] is given alone. (au) (21 refs.).

  6. CsxH3-xPW12O40 heteropoly salts catalyzed quinoline synthesis via Friedlander reaction

    Institute of Scientific and Technical Information of China (English)

    Ezzat Rafiee; Fereshte Khajooei Nejad; Mohammad Joshaghani


    Various type of cesium partially substituted phosphotungstate, CsxH3-xPW12O40 (x = 1.0, 2.0 and 2.5), were synthesized and their catalytic activities were investigated in the synthesis of quinoline. It was shown that catalytic activities of these catalysts correlated to surface acidity and total number of acidic sites. Finally, a series of quinoline derivatives were synthesized with Cs2.5H0.5PW12O40 via the Friedlander reaction in high to excellent yields and the plausible mechanism was proposed. Simple experiment, catalyst reusability, short reaction time and preclusion of toxic solvent are the advantages of this method.

  7. Ruthenium-catalysed synthesis of 2- and 3-substituted quinolines from anilines and 1,3-diols

    DEFF Research Database (Denmark)

    Monrad, Rune Nygaard; Madsen, Robert


    A straightforward synthesis of substituted quinolines is described by cyclocondensation of anilines with 1,3-diols. The reaction proceeds in mesitylene solution with catalytic amounts of RuCl3·xH 2O, PBu3 and MgBr2·OEt2. The transformation does not require any stoichiometric additives and only...... produces water and dihydrogen as byproducts. Anilines containing methyl, methoxy and chloro substituents as well as naphthylamines were shown to participate in the heterocyclisation. In the 1,3-diol a substituent was allowed in the 1- or the 2-position giving rise to 2- and 3-substituted quinolines......, respectively. The best results were obtained with 2-alkyl substituted 1,3-diols to afford 3-alkylquinolines. The mechanism is believed to involve dehydrogenation of the 1,3-diol to the 3-hydroxyaldehyde which eliminates water to the corresponding α,β-unsaturated aldehyde. The latter then reacts with anilines...

  8. Regioselective Synthesis of C-3-Functionalized Quinolines via Hetero-Diels-Alder Cycloaddition of Azadienes with Terminal Alkynes. (United States)

    Saunthwal, Rakesh K; Patel, Monika; Verma, Akhilesh K


    A highly efficient metal and protection-free approach for the regioselective synthesis of C-3-functionalized quinolines from azadienes (in situ generated from 2-aminobenzyl alcohol) and terminal alkynes through [4 + 2] cycloaddition has been developed. An unprecedented reaction of 2-aminobenzyl alcohol with 1,3- and 1,4-diethynylbenzene provided the C-3 tolylquinolines via [4 + 2] HDA and oxidative decarboxylation. The -NH2 group directed mechanistic approach was well supported by the control experiments and deuterium-labeling studies and by isolating the azadiene intermediate. The reactivity and selectivity of unprotected azadiene in metal-free base-assisted hetero-Diels-Alder reaction is exploited to quickly assemble an important class of C-3-functionalized quinolines, which are difficult to access.

  9. Synthesis of spiro[benzo[ℎ]quinoline-7,3'- indolines] via a three-component condensation reaction

    Indian Academy of Sciences (India)

    Abbas Rahmati; Miranda Eskandari-Vashareh


    An efficient one-pot synthesis of a new series of spiro[benzo[ℎ]quinoline-7,3'-indoline] was accomplished simply by the reaction of an isatin, naphthalen-1-amine and a CH-acid (,-dimethylbarbituric acid, barbituric acid, dimedone or 1,3-indandion) in acetic acid. During this process, the effects of solvent and temperature have been investigated on the yield of reactions.

  10. Copper-catalyzed direct amination of quinoline N-oxides via C-H bond activation under mild conditions. (United States)

    Zhu, Chongwei; Yi, Meiling; Wei, Donghui; Chen, Xuan; Wu, Yangjie; Cui, Xiuling


    A highly efficient and concise one-pot strategy for the direct amination of quinoline N-oxides via copper-catalyzed dehydrogenative C-N coupling has been developed. The desired products were obtained in good to excellent yields for 22 examples starting from the parent aliphatic amines. This methodology provides a practical pathway to 2-aminoquinolines and features a simple system, high efficiency, environmental friendliness, low reaction temperature, and ligand, additives, base, and external oxidant free conditions.

  11. Conformational isomerization of N-(naphthalen-1-yl)-N-(phenyl(quinolin-3-yl)methyl)amide derivatives

    Institute of Scientific and Technical Information of China (English)


    A series of N-(naphthalen-1-yl)-N-(phenyl(quinolin-3-yl)methyl)amide derivatives were designed and synthesized as anti-Mycobacterium tuberculosis drugs. NMR spectra showed that two conformational isomers of these compounds exist in solution,which is not due to cis-trans isomerization of amide bond. We proposed that the spatial interactions between three large aromatic groups caused the conformational isomerization,which was supported by molecular modeling and X-ray diffraction.

  12. Microwave-assisted Synthesis of Pyrazolo[4,3-f]quinolin-7-one Derivatives via Multi-component Reactions

    Institute of Scientific and Technical Information of China (English)

    PENG Juhua; HAO Wenjuan; WANG Xiang; TU Shujiang; MA Ning; ZHANG Ge


    A series of new pyrazolo[4,3-f]quinolin-7-one derivatives were synthesized by multi-component reactions of equimolar amount of aromatic aldehydes with 2,2-dimethyl-1,3-dioxane-4,6-dione and 1H-indazol-5-amine in ethylene glycol without catalyst under microwave irradiation.This one-pot protocol has the advantage of good yields,simple workup procedure and shorter reaction time.

  13. 磷钼酸喹啉重量法测磷%Determination of Phosphorus Content Using Quinoline Phosphomolybdate

    Institute of Scientific and Technical Information of China (English)



    Quinoline phosphomolybdate gravimetric determination of phosphorus ore and phosphorus pentoxide content in the concentrate,the method was accurate,reliable,and was the phosphate arbitration analysis,which corresponded with national standards GB/T 1871-80 and GB/T 1871.1-1995.International standard ISO 6598(Fertilizers-Determination of Phosphorus Content-Quinoline Phosphomolybdate Gravimetric Method) and the national standard GB 10512-89(Nitrate Fertilizer in the Determination of Phosphorus Quinoline Phosphomolybdate Gravimetric Method) were basically the same test procedure.It was used that quinoline molybdenum lemon ketone reagents,the glass filter of crucible type,and maintaining(180±2) ℃ constant temperature oven.Glass crucible-type filter was a special vessel.The feasibility of analysis of phosphorus pentoxide content was discussed by using ordinary filter paper instead of glass crucible filter.Tests showed that the method with an ordinary filter paper for analysis instead of glass crucible-type filter was practical,and its precision and accuracy met the requirements of GB/T 1871.1-1995.%磷钼酸喹啉重量法测定磷矿石和磷精矿中五氧化二磷含量,方法准确可靠,是磷矿的仲裁分析法。本文探讨了用普通滤纸代替玻璃坩埚式滤器分析五氧化二磷含量的可行性。试验表明,用普通滤纸代替玻璃坩埚式滤器切实可行,方法精密度和准确度能满足常规分析要求。

  14. Microwave-assisted synthesis of novel nonperipherally substituted metallophthalocyanines bearing (7-(trifluoromethyl)quinolin-4-yl)oxy groups


    EVREN, Didem; YENİLMEZ, Hacer Yasemin; BURAT, Ayfer KALKAN


    The synthesis, characterization, and spectroscopic properties of novel nonperipherally tetrasubstituted metallophthalocyanines (zinc, cobalt, copper, manganese, and indium) bearing 4 (7-(trifluoromethyl)quinolin-4-yl)oxy units has been reported. The new compounds have been characterized using UV-Vis, IR, 1H NMR, 13C NMR, 19F NMR, and mass spectroscopic data. The absorption properties of these new complexes were compared to those of peripherally substituted phthalocyanine derivatives. Based on...

  15. Synthesis and anticonvulsant activity of 7-benzylamino-4, 5-dihydro- [ 1, 2, 4] triazolo[ 4, 3-a] quinolines

    Institute of Scientific and Technical Information of China (English)


    A series of 7-substituted-benzylamino-4, 5-dihydro-[ 1,2, 4]triazolo[4, 3-a] quinoline derivatives was synthesized and evaluated for their anticonvulsant activity. The subcutaneous pentylenetetrazole test (sc-PTZ) demonstrated that the most effective compound in controlling the sc-PTZ induced seizure was 7-(3-bromine-benzylamino)-4, 5-dihydro-[ 1,2, 4]triazolo[4, 3-a]quinoline (4j) with an ED50 of 5.0 mg/kg and the PI of 20.7, which was also safer than the reference drugs. And the maximal electroshock test (MES)demonstrated that among these derivatives, 7-(3-fluorobenzylamino) -4, 5-dihydro-[ 1,2, 4]trizolo[4, 3-a]quinoline (4i), with an ED50 of 15.3 mg/kg and the PI of 7.2, was the safest in MES test. Furthermore, their neurotoxicities were measured by the rotarod neurotoxicity test, and the results showed that all derivatives possessed lower neurotoxicity.

  16. The phosphorylation status and cytoskeletal remodeling of striatal astrocytes treated with quinolinic acid

    Energy Technology Data Exchange (ETDEWEB)

    Pierozan, Paula; Ferreira, Fernanda; Ortiz de Lima, Bárbara; Gonçalves Fernandes, Carolina [Departamento de Bioquímica, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90035-003 (Brazil); Totarelli Monteforte, Priscila; Castro Medaglia, Natalia de; Bincoletto, Claudia; Soubhi Smaili, Soraya [Departamento de Farmacologia, Universidade Federal de São Paulo (UNIFESP/EPM), São Paulo, SP (Brazil); Pessoa-Pureur, Regina, E-mail: [Departamento de Bioquímica, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90035-003 (Brazil)


    Quinolinic acid (QUIN) is a glutamate agonist which markedly enhances the vulnerability of neural cells to excitotoxicity. QUIN is produced from the amino acid tryptophan through the kynurenine pathway (KP). Dysregulation of this pathway is associated with neurodegenerative conditions. In this study we treated striatal astrocytes in culture with QUIN and assayed the endogenous phosphorylating system associated with glial fibrillary acidic protein (GFAP) and vimentin as well as cytoskeletal remodeling. After 24 h incubation with 100 µM QUIN, cells were exposed to {sup 32}P-orthophosphate and/or protein kinase A (PKA), protein kinase dependent of Ca{sup 2+}/calmodulin II (PKCaMII) or protein kinase C (PKC) inhibitors, H89 (20 μM), KN93 (10 μM) and staurosporin (10 nM), respectively. Results showed that hyperphosphorylation was abrogated by PKA and PKC inhibitors but not by the PKCaMII inhibitor. The specific antagonists to ionotropic NMDA and non-NMDA (50 µM DL-AP5 and CNQX, respectively) glutamate receptors as well as to metabotropic glutamate receptor (mGLUR; 50 µM MCPG), mGLUR1 (100 µM MPEP) and mGLUR5 (10 µM 4C3HPG) prevented the hyperphosphorylation provoked by QUIN. Also, intra and extracellular Ca{sup 2+} quelators (1 mM EGTA; 10 µM BAPTA-AM, respectively) prevented QUIN-mediated effect, while Ca{sup 2+} influx through voltage-dependent Ca{sup 2+} channel type L (L-VDCC) (blocker: 10 µM verapamil) is not implicated in this effect. Morphological analysis showed dramatically altered actin cytoskeleton with concomitant change of morphology to fusiform and/or flattened cells with retracted cytoplasm and disruption of the GFAP meshwork, supporting misregulation of actin cytoskeleton. Both hyperphosphorylation and cytoskeletal remodeling were reversed 24 h after QUIN removal. Astrocytes are highly plastic cells and the vulnerability of astrocyte cytoskeleton may have important implications for understanding the neurotoxicity of QUIN in neurodegenerative

  17. Studies on laser flash photolysis and pulse radiolysis of quinoline and some of its derivatives%喹啉及其衍生物的脉冲辐解和激光光解研究

    Institute of Scientific and Technical Information of China (English)

    ZHU Dazhang; WANG Shilong; SUN Xiaoyu; LI Wenzhe; ZENG Kailing; NI Yaming; WANG Wenfeng; YAO Side


    Quinoline and some of its derivatives were reported to be carcinogenic, toxic and mutagenic[1-3]. The widespread use of quinoline and its derivatives entails that these compounds are distributed in the environment, polluting soil and water together with many other environmental chemicals.Time-resolved laser flash photolysis and pulse radiolysis have been used to study the reaction of quinoline (Q), 2, 6-dimethyl-quinoline (DMQ) and isoquinoline (IQ) with hydrated electrons, hydroxyl radicals and hydrogen radicals. Transient absorption spectra were obtained and reaction rate constants to the reactions were determined, as showed in Table 1. Rossible mechanisms of the reactions were suggested.In addition, oxidization reactions of SO4·-, Br2·- and N3·- with isoquinoline, quinoline and its derivatives were studied. It showed that SO4- could oxidize quinoline, 2, 6-dimethylquinoline and isoquinoline; Br2·-could oxidize isoquinoline to its cation radicals, but it could not oxidize quinoline or 2, 6-diemethylquinoline; N3·- could oxidize none of them.With a better understandings on photolysis and radiolysis of isoquinoline, quinoline and its derivates, the study is of help for degradation of the chemicals and for environment protection.

  18. Effects of impregnation methods and drying conditions on quinoline hydrodenitrogenation over Ni-W based catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Guo, Fang; Qiu, Zegang; Zhao, Liangfu; Xiang, Hongwei [Institute of Coal Chemistry, Chinese Academy of Sciences (China); Guo, Shaoqing [Taiyuan University of Science and Technology (China)


    The effects of impregnation methods (co-impregnation and sequential impregnation) and drying conditions (air and vacuum) on the structure and catalytic behavior of MCM-41 supported Ni-W catalysts were investigated. The catalysts were characterized by powder X-ray diffraction (XRD) analysis, Fourier-transform infrared spectroscopy (FT-IR), diffuse reflectance UV-Vis absorbance spectroscopy (DRS), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS) and pyridine adsorbed infrared spectroscopy (Py-IR) techniques. They were tested for hydrodenitrogenation (HDN) of quinoline at temperatures of 300-400 deg C. The HDN results showed that the catalysts prepared by co-impregnation were more active than the catalysts prepared by sequential impregnation and the catalysts prepared by drying under vacuum were more active than the catalysts dried in air. Characterization revealed that the co-impregnation method and drying under vacuum promoted the dispersion of W, the formation of the active phases, and the formation of acidic sites on the catalysts. (author)

  19. Of mice, rats and men: Revisiting the quinolinic acid hypothesis of Huntington's disease. (United States)

    Schwarcz, Robert; Guidetti, Paolo; Sathyasaikumar, Korrapati V; Muchowski, Paul J


    The neurodegenerative disease Huntington's disease (HD) is caused by an expanded polyglutamine (polyQ) tract in the protein huntingtin (htt). Although the gene encoding htt was identified and cloned more than 15 years ago, and in spite of impressive efforts to unravel the mechanism(s) by which mutant htt induces nerve cell death, these studies have so far not led to a good understanding of pathophysiology or an effective therapy. Set against a historical background, we review data supporting the idea that metabolites of the kynurenine pathway (KP) of tryptophan degradation provide a critical link between mutant htt and the pathophysiology of HD. New studies in HD brain and genetic model organisms suggest that the disease may in fact be causally related to early abnormalities in KP metabolism, favoring the formation of two neurotoxic metabolites, 3-hydroxykynurenine and quinolinic acid, over the related neuroprotective agent kynurenic acid. These findings not only link the excitotoxic hypothesis of HD pathology to an impairment of the KP but also define new drug targets and therefore have direct therapeutic implications. Thus, pharmacological normalization of the imbalance in brain KP metabolism may provide clinical benefits, which could be especially effective in early stages of the disease.

  20. Determination of acrolein in urine by liquid chromatography and fluorescence detection of its quinoline derivative. (United States)

    al-Rawithi, S; el-Yazigi, A; Nicholls, P J


    We describe an assay for acrolein in urine, employing derivatization with m-aminophenol in the presence of ferrous sulfate solution in sulfuric acid. The derivative (7-OH quinoline; DER) and the internal standard (quinine-bisulfate; IS) were separated on a 10-micron particle, 8 mm x 10-cm C18 cartridge in conjunction with a radial compression system using a mixture of 0.05 M dibasic ammonium phosphate solution (pH 2.5):acetonitrile:methanol (92:6:2) at a flow rate of 3 mL/min as a mobile phase. The effluent was monitored fluorometrically at excitation and emission wavelengths of 360 and 495 nm, respectively. The retention times of DER and IS under these conditions were 4.3 and 26 min, respectively, and no interference in the assay from any endogenous substance or other concomitantly used drug was observed. The assay was highly linear (r > 0.994) in the range 1-20 micrograms/mL of acrolein in urine (CV at different concentrations, < or = 7.9%). This method can serve to monitor acrolein pharmacokinetics in patients.

  1. Green synthesis of novel quinoline based imidazole derivatives and evaluation of their antimicrobial activity

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    N.C. Desai


    Full Text Available We have described the conventional and microwave method for the synthesis of N-(4-((2-chloroquinolin-3-ylmethylene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl(arylamides 3a–l. It is observed that the solvent-free microwave thermolysis is a convenient, rapid, high-yielding, and environmental friendly protocol for the synthesis of quinoline based imidazole derivatives when compared with conventional reaction in a solution phase. Antimicrobial activity of the newly synthesized compounds is screened in vitro on the following microbial cultures: Escherichia coli (MTCC 443, Pseudomonas aeruginosa (MTCC 1688, Staphylococcus aureus (MTCC 96, Streptococcus pyogenes (MTCC 442, Candida albicans (MTCC 227, Aspergillus niger (MTCC 282, Aspergillus clavatus (MTCC 1323. All the synthesized bio-active molecules are tested for their in vitro antimicrobial activity by bioassay namely serial broth dilution. Among these compounds 3c, 3d, 3f, 3h and 3j show significant potency against different microbial strains. All the compounds have been characterized by IR, 1H NMR, 13C NMR and mass spectral data. On the basis of statistical analysis, it is observed that these compounds give significant co-relation.

  2. Hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives and evaluation of their anticancer and antimycobacterial activity. (United States)

    Mantu, Dorina; Antoci, Vasilichia; Moldoveanu, Costel; Zbancioc, Gheorghita; Mangalagiu, Ionel I


    The design, synthesis, structure, and in vitro anticancer and antimycobacterial activity of new hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives are described. The strategy adopted for synthesis is straight and efficient, involving a three-step setup procedure: N-acylation, N-alkylation, and quaternization of nitrogen heterocycle. The solubility in microbiological medium and anticancer and antimycobacterial activity of a selection of new synthesized compounds were evaluated. The hybrid derivatives have an excellent solubility in microbiological medium, which make them promising from the pharmacological properties point of view. One of the hybrid compounds, 9 (with a benzimidazole and 8-aminoquinoline skeleton), exhibits a very good and selective antitumor activity against Renal Cancer A498 and Breast Cancer MDA-MB-468. Moreover, the anticancer assay suggests that the hybrid Imz (Bimz)/2-AP (8-AQ) compounds present a specific affinity to Renal Cancer A498. Concerning the antimycobacterial activity, only the hybrid compound, 9, has a significant activity. SAR correlations have been performed.

  3. Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres

    Directory of Open Access Journals (Sweden)

    Ales Imramovsky


    Full Text Available In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET in spinach (Spinacia oleracea L. chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial species. N-Cycloheptylquinoline-2-carboxamide, N-cyclohexylquinoline-2-carboxamide and N-(2-phenylethylquinoline-2-carboxamide showed higher activity against M. tuberculosis than the standards isoniazid or pyrazinamide and 2-(pyrrolidin-1-ylcarbonylquinoline and 1-(2-naphthoylpyrrolidine expressed higher activity against M. kansasii and M. avium paratuberculosis than the standards isoniazid or pyrazinamide. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound N-benzyl-2-naphthamide was 7.5 μmol/L. For all compounds, the structure-activity relationships are discussed.

  4. Establishment of true niacin deficiency in quinolinic acid phosphoribosyltransferase knockout mice. (United States)

    Terakata, Miki; Fukuwatari, Tsutomu; Sano, Mitsue; Nakao, Natsuki; Sasaki, Ryuzo; Fukuoka, Shin-Ichi; Shibata, Katsumi


    Pyridine nucleotide coenzymes are involved in >500 enzyme reactions and are biosynthesized from the amino acid L-tryptophan (L-Trp) as well as the vitamin niacin. Hence, "true" niacin-deficient animals cannot be "created" using nutritional techniques. We wanted to establish a truly niacin-deficient model animal using a protocol that did not involve manipulating dietary L-Trp. We generated mice that are missing the quinolinic acid (QA) phosphoribosyltransferase (QPRT) gene. QPRT activity was not detected in qprt(-/-)mice. The qprt(+/+), qprt(+/-), or qprt(-/-) mice (8 wk old) were fed a complete diet containing 30 mg nicotinic acid (NiA) and 2.3 g L-Trp/kg diet or an NiA-free diet containing 2.3 g L-Trp/kg diet for 23 d. When qprt(-/-)mice were fed a complete diet, food intake and body weight gain did not differ from those of the qprt(+/+) and qprt(+/-) mice. On the contrary, in the qprt(-/-) mice fed the NiA-free diet, food intake and body weight were reduced to 60% (P niacin, such as blood and liver NAD concentrations, were also lower in the qprt(-/-) mice than in the qprt(+/+) and the qprt(+/-) mice. Urinary excretion of QA was greater in the qprt(-/-) mice than in the qprt(+/+) and qprt(+/-) mice (P niacin-deficient mice.

  5. Determination of three physical properties of quinoline ionic liquids with hexafluorophosphate

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    Tang Dan


    Full Text Available Densities of one acidic ionic liquid (IL Quinolinum hexafluorophosphate ([HBpy][PF6], and four neutral dicationic ionic liquids (ILs based on quinoline and hexafluoro-phosphate and linked with poly(ethylene glycol (PEG: ([PEG200-DIL][PF6]2, [PEG400-DIL][PF6]2, [PEG800-DIL][PF6]2 and [PEG1000-DIL][PF6]2 were determined. In addition, the solubilities of six ILs in six lower alcohols, water, acetonitrile and diethyl ether were measured at 288.15 K; and the hydroscopicity of above five ILs were measured at the temperature of 298.15 K and relative humidity of 79% for 24 h. Densities of five ionic liquids were determined between 283.15 and 333.15 K. Then the densities of five binary system (ILs/acetonitrile were explored between 283.15 and 333.15 K, the type of the ionic liquid, the concentration of five ILs in CH3CN, and the effect of temperature on the binary systems, were correlated with the measured data.

  6. Spectral investigation and theoretical study of zwitterionic and neutral forms of quinolinic acid (United States)

    Karabacak, M.; Sinha, L.; Prasad, O.; Bilgili, S.; Sachan, Alok K.; Asiri, A. M.; Atac, A.


    In this study, molecular structure and vibrational analysis of quinolinic acid (2,3-pyridinedicarboxylic acid), in zwitterionic and neutral forms, were presented using FT-IR, FT-Raman, NMR, UV experimental techniques and quantum chemical calculations. FT-IR and FT-Raman spectra of 2,3-pyridinedicarboxylic acid (2,3-PDCA) in the solid phase were recorded in the region 4000-400 cm-1 and 3500-0 cm-1, respectively. The geometrical parameters and energies were obtained for zwitter and neutral forms by using density functional theory (DFT) at B3LYP/6-311++G(d,p) level of theory. 3D potential energy scan was performed by varying the selected dihedral angles using M06-2X and B3LYP functionals at 6-31G(d) level of theory and thus the most stable conformer of the title compound was determined. The most stable conformer was further optimized at higher level and vibrational wavenumbers were calculated. Theoretical vibrational assignment of 2,3-PDCA, using percentage potential energy distribution (PED) was done with MOLVIB program. 13C and 1H NMR spectra were recorded in DMSO. Chemical shifts were calculated at the same level of theory. The UV absorption spectra of the studied compound in ethanol and water were recorded in the range of 200-400 nm. The optimized geometric parameters were compared with experimental data.

  7. Quinoline based polymeric drug for biological applications: synthesis, characterization, antimicrobial, and drug releasing studies. (United States)

    Uma, P; Suresh, J; Selvaraj, Revathy; Karthik, S; Arun, A


    Novel acrylate monomer of quinoline-based chalcone 1-(4-(7-chloroquinolin-4-ylamino)phenyl) acrylate (CPA) was synthesized using (4-(2-chloroquinolin-5-ylamino)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (CPE) and acryloyl chloride. CPA is characterized by different techniques like IR, (1)H NMR and UV-visible spectrometry techniques. Poly(CPA), poly(CPA-co-AA) and poly(CPA-co-HEA) are prepared by solution polymerization technique using CPA, acrylic acid (AA) and hydroxyethylacrylate (HEA), respectively. The antimicrobial activities of the compounds are tested using four different micro-organisms. In vitro cumulative drug release studies are done using UV visible spectroscopic technique. The molecular weights of these polymers are found to be around 5000 g/mol. The synthesized polymers showed two stages of thermal decomposition temperature centred around 220 and 350 °C, respectively. The antimicrobial activity of the polymer sample is found to be very high and especially for gram-negative bacteria with a minimum value of 3.91 μg/mL. The in vitro drug-releasing rate is dependent on the comonomer, pH and temperature of the medium.

  8. Effect of quinolinic acid on human astrocytes morphology and functions: implications in Alzheimer's disease

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    Brew Bruce J


    Full Text Available Abstract The excitotoxin quinolinic acid (QUIN is synthesized through the kynurenine pathway (KP by activated monocyte lineage cells. QUIN is likely to play a role in the pathogenesis of several major neuroinflammatory diseases including Alzheimer's disease (AD. The presence of reactive astrocytes, astrogliosis, increased oxidative stress and inflammatory cytokines are important pathological hallmarks of AD. We assessed the stimulatory effects of QUIN at low physiological to high excitotoxic concentrations in comparison with the cytokines commonly associated with AD including IFN-γ and TNF-α on primary human astrocytes. We found that QUIN induces IL-1β expression, a key mediator in AD pathogenesis, in human astrocytes. We also explored the effect of QUIN on astrocyte morphology and functions. At low concentrations, QUIN treatment induced concomitantly a marked increase in glial fibrillary acid protein levels and reduction in vimentin levels compared to controls; features consistent with astrogliosis. At pathophysiological concentrations QUIN induced a switch between structural protein expressions in a dose dependent manner, increasing VIM and concomitantly decreasing GFAP expression. Glutamine synthetase (GS activity was used as a functional metabolic test for astrocytes. We found a significant dose-dependent reduction in GS activity following QUIN treatment. All together, this study showed that QUIN is an important factor for astroglial activation, dysregulation and cell death with potential relevance to AD and other neuroinflammatory diseases.

  9. Quinolinic acid selectively induces apoptosis of human astrocytes: potential role in AIDS dementia complex

    Directory of Open Access Journals (Sweden)

    Wang Lily


    Full Text Available Abstract There is evidence that the kynurenine pathway (KP and particularly one of its end products, quinolinic acid (QUIN play a role in the pathogenesis of several major neuroinflammatory diseases, and more particularly AIDS dementia complex (ADC. We hypothesized that QUIN may be involved in astrocyte apoptosis because: 1 apoptotic astrocytes have been observed in the brains of ADC patients, 2 ADC patients have elevated cerebrospinal fluid QUIN concentrations, and 3 QUIN can induce astrocyte death. Primary cultures of human fetal astrocytes were treated with three pathophysiological concentrations of QUIN. Numeration of apoptotic cells was assessed using double immunocytochemistry for expression of active caspase 3 and for nucleus condensation. We found that treatment of human astrocytes with QUIN induced morphological (cell body shrinking and biochemical changes (nucleus condensation and over-expression of active caspase 3 of apoptosis. After 24 hours of treatment with QUIN 500 nM and 1200 nM respectively 10 and 14% of astrocytes were undergoing apoptosis. This would be expected to lead to a relative lack of trophic support factors with consequent neuronal dysfunction and possibly death. Astroglial apoptosis induced by QUIN provides another potential mechanism for the neurotoxicity of QUIN during ADC.

  10. Synthesis of 2-Substituted Furo[2,3-b]- and Furo[3,2-c]quinolines via Heterogeneous Palladium-catalyzed Heteroannulation

    Energy Technology Data Exchange (ETDEWEB)

    Park, Hee Jung [Korea Basic Science Institute, Seoul (Korea, Republic of); Yang, Ok-Kyung; Park, Young Chul; Yum, Eul Kgun [Chungnam National University, Daejon (Korea, Republic of)


    As a part of our continuing organometallic studies on diversification of nitrogen-containing biologically active heterocycles, we attempted to synthesize furo[2,3-b]- and furo[3,2-c]quinolines starting from o-halohydroxyquinolines and terminal alkynes with heterogeneous Pd(OAc)2 catalyst, which was supported by nanosized pore carbon ball. 2-substituted furo[2,3-b]quinolines and furo[3,2-c]quinolines were synthesized from the reaction of 3-iodoquinolin-2-ol and 3-iodoquinolin-4-ol, respectively, with diverse alkynes. The heteroannulation reaction proceeds with Sonogashira coupling followed by 5-endo-dig cyclization in good isolated yields under copper and ligand free conditions.

  11. Determination of brilliant blue FCF in the presence and absence of erythrosine and quinoline yellow food colours by cathodic stripping voltammetry. (United States)

    Florian, M; Yamanaka, H; Carneiro, P A; Zanoni, M Valnice Boldrin


    A study of the voltammetric behaviour of the food colours brilliant blue FCF (C.I. 42090), erythrosine (C.I. 45430) and quinoline yellow (C.I. 47005) in the pH range 2-10 have been carried out by cathodic#10; stripping voltammetry. At pH 4.5 (acetate buffer) with an accumulation potential of 0 V and accumulation time of 30s, the voltammograms presented well-defined reduction peaks at potential - 0.76 V for brilliant blue FCF, - 0.85 V for quinoline yellow and - 0.54 V for erythrosine. Linear calibration graphs were obtained from 8 to 80 microg l(-1) brilliant blue, from 4 to 43 microg l(-1) quinoline yellow and from 10 to 70 microg l(-1) erythrosine. The method has been successfully applied to identify and quantify binary mixtures of these dyes and applied for determining brilliant blue FCF in commercial food products.

  12. Differences in anti-malarial activity of 4-aminoalcohol quinoline enantiomers and investigation of the presumed underlying mechanism of action

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    Mullié Catherine


    Full Text Available Abstract Background A better anti-malarial efficiency and lower neurotoxicity have been reported for mefloquine (MQ (+- enantiomer. However, the importance of stereoselectivity remains poorly understood as the anti-malarial activity of pure enantiomer MQ analogues has never been described. Building on these observations, a series of enantiopure 4-aminoalcohol quinoline derivatives has previously been synthesized to optimize the efficiency and reduce possible adverse effects. Their in vitro activity on Plasmodium falciparum W2 and 3D7 strains is reported here along with their inhibition of β-haematin formation and peroxidative degradation of haemin, two possible mechanisms of action of anti-malarial drugs. Results The (S-enantiomers of this series of 4-aminoalcohol quinoline derivatives were found to be at least as effective as both chloroquine (CQ and MQ. The derivative with a 5-carbon side-chain length was the more efficient on both P. falciparum strains. (R -enantiomers displayed an activity decreased by 2 to 15-fold as compared to their (S counterparts. The inhibition of β-haematin formation was significantly stronger with all tested compounds than with MQ, irrespective of the stereochemistry. Similarly, the inhibition of haemin peroxidation was significantly higher for both (S and (R-enantiomers of derivatives with a side-chain length of five or six carbons than for MQ and CQ. Conclusions The prominence of stereochemistry in the anti-malarial activity of 4-aminoalcohol quinoline derivatives is confirmed. The inhibition of β-haematin formation and haemin peroxidation can be put forward as presumed mechanisms of action but do not account for the stereoselectivity of action witnessed in vitro.

  13. Central nervous system exposure of next generation quinoline methanols is reduced relative to mefloquine after intravenous dosing in mice

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    Shackleford David M


    Full Text Available Abstract Background The clinical use of mefloquine (MQ has declined due to dose-related neurological events. Next generation quinoline methanols (NGQMs that do not accumulate in the central nervous system (CNS to the same extent may have utility. In this study, CNS levels of NGQMs relative to MQ were measured and an early lead chemotype was identified for further optimization. Experimental design The plasma and brain levels of MQ and twenty five, 4-position modified NGQMs were determined using LCMS/MS at 5 min, 1, 6 and 24 h after IV administration (5 mg/kg to male FVB mice. Fraction unbound in brain tissue homogenate was assessed in vitro using equilibrium dialysis and this was then used to calculate brain-unbound concentration from the measured brain total concentration. A five-fold reduction CNS levels relative to mefloquine was considered acceptable. Additional pharmacological properties such as permeability and potency were determined. Results The maximum brain (whole/free concentrations of MQ were 1807/4.9 ng/g. Maximum whole brain concentrations of NGQMs were 23 - 21546 ng/g. Maximum free brain concentrations were 0.5 to 267 ng/g. Seven (28% and two (8% compounds exhibited acceptable whole and free brain concentrations, respectively. Optimization of maximum free brain levels, IC90s (as a measure or potency and residual plasma concentrations at 24 h (as a surrogate for half-life in the same molecule may be feasible since they were not correlated. Diamine quinoline methanols were the most promising lead compounds. Conclusion Reduction of CNS levels of NGQMs relative to mefloquine may be feasible. Optimization of this property together with potency and long half-life may be feasible amongst diamine quinoline methanols.

  14. Cannizzaro reaction of 2-chloro-3-formylquinolines and its synthetic utility for 2-acetylfuro[2,3-]quinolines: The alkaloid analogues

    Indian Academy of Sciences (India)

    Devadoss Karthik Kumar; Rajakandhan Shankar; Subramaniam Parameswaran Rajendran


    Cannizzaro reaction of 2-chloro-3-formylquinolines was investigated under two different conditions. Under both conditions, redox and methoxylation proceeded simultaneously and gave 2-methoxy- 3-formylquinolines, 2-methoxyquinolin-3-yl-methanols and 2-methoxyquinoline-3-carboxylic acids. The synthesized 2-methoxy-3-formylquinolines were then condensed with acetone in the presence of sulphuric acid to give 4-(2-methoxy-quinolin-3-yl)-but-3-en-2-ones which in turn were bromocyclized and dehydrobrominated to get 2-acetylfuro[2,3-]quinolines.

  15. Synthesis, characterization, crystal structure, in-vitro anti-inflammatory and molecular docking studies of 5-mercapto-1-substituted tetrazole incorporated quinoline derivative (United States)

    Sureshkumar, K.; Maheshwaran, V.; Dharma Rao, T.; Themmila, Khamrang; Ponnuswamy, M. N.; Kadhirvel, Saraboji; Dhandayutham, Saravanan


    A novel 5-mercapto-1-substituted tetrazole incorporated quinoline analog was synthesized. The compound 2-Cyclopropyl-4-(4-fluorophenyl)-3-{1-[2-(4-methoxybenzyloxy)ethyl]1H-tetrazol-5-ylsulfanylmethyl}quinoline was characterized by IR, Mass, 1H and 13C NMR spectroscopic techniques. Molecular structure was confirmed by using single crystal X-ray diffraction technique. Thermal behavior was studied by using TGA and DSC techniques. Further, in vitro anti-inflammatory and in silico docking analysis has been carried out to study the activity of the compound.

  16. Rh-Catalyzed, Regioselective, C-H Bond Functionalization: Access to Quinoline-Branched Amines and Dimers. (United States)

    Reddy, M Damoder; Fronczek, Frank R; Watkins, E Blake


    Rh-catalyzed, chelation-induced, C-5 regioselective C-H functionalization of 8-amidoquinolines with a range of N-Boc aminals is reported for the first time. The addition of in situ generated imines to C(sp(2))-H bonds afforded branched amines in good to excellent yields. Moreover, this transformation features good functional group compatibility, broad substrate scope, and mild reaction conditions and is suitable for gram-scale synthesis. In addition, an unprecedented, chelation-induced, site-selective, remote dimerization of quinolines led to the formation of dimer frameworks in moderate yields under Rh-catalyzed conditions.

  17. Investigation of prototypal MOFs consisting of polyhedral cages with accessible Lewis-acid sites for quinoline synthesis. (United States)

    Gao, Wen-Yang; Leng, Kunyue; Cash, Lindsay; Chrzanowski, Matthew; Stackhouse, Chavis A; Sun, Yinyong; Ma, Shengqian


    A series of prototypal metal-organic frameworks (MOFs) consisting of polyhedral cages with accessible Lewis-acid sites, have been systematically investigated for Friedländer annulation reaction, a straightforward approach to synthesizing quinoline and its derivatives. Amongst them MMCF-2 demonstrates significantly enhanced catalytic activity compared with the benchmark MOFs, HKUST-1 and MOF-505, as a result of a high-density of accessible Cu(II) Lewis acid sites and large window size in the cuboctahedral cage-based nanoreactor of MMCF-2.

  18. 3-Ethyl-4-hy-droxy-8-meth-oxy-quinolin-2(1H)-one. (United States)

    Kafka, Stanislav; Pevec, Andrej; Proisl, Karel; Kimmel, Roman; Košmrlj, Janez


    In the title compound, C(12)H(13)NO(3), the quinoline ring system is approximately planar with a maximum deviation from the least-squares plane of 0.058 (2) Å. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into chains running along the b-axis direction. The chains also feature π-π inter-actions between pyridine and benzene rings of inversion-related mol-ecules [centroid-centroid distance = 3.609 (2) Å].

  19. 4-(2-aminooxyethoxy)-2-(ethylureido)quinoline-oligonucleotide conjugates: synthesis, binding interactions, and derivatization with peptides. (United States)

    Hamma, Tomoko; Miller, Paul S


    Oligo-2'-O-methylribonucleotides conjugated with 4-(2-aminooxyethoxy)-2-(ethylureido)quinoline (AOQ) and 4-ethoxy-2-(ethylureido)quinoline (EOQ) were prepared by reaction of the AOQ or EOQ phosphoramidite with the protected oligonucleotide on a controlled pore glass support. Deprotection with ethylenediamine enabled successful isolation and purification of the highly reactive AOQ-conjugated oligomer. Polyacrylamide gel electrophoresis mobility shift experiments showed that the dissociation constants of complexes formed between an AOQ- or EOQ-conjugated 8-mer and complementary RNA or 2'-O-methyl-RNA targets (9- and 10-mers) were in the low nM concentration range at 37 degrees C, whereas no binding was observed for the corresponding nonconjugated oligomer, even at a concentration of 500 nM. Fluorescence studies suggested that this enhanced affinity is most likely due to the ability of the quinoline ring of the AOQ or EOQ group to stack on the last base pair formed between the oligomer and target, thus stabilizing the duplex. The binding affinity of a 2'-O-methyl RNA 15-mer, which contained an alternating methylphosphonate/phosphodiester backbone, for a 59-nucleotide stem-loop HIV TAR RNA target, increased 2.3 times as a consequence of conjugation with EOQ. The aminooxy group of AOQ-conjugated oligomers is a highly reactive nucleophile, which reacts readily with aldehydes and ketones to form stable oxime derivatives. This feature was used to couple an AOQ-oligomer with leupeptin, a tripeptide that contains a C-terminus aldehyde group. A simple method was developed to introduce a ketone functionality into peptides that contain a cysteine residue by reacting the peptide with bromoacetone. The resulting keto-peptide was then coupled to the AOQ-oligomer. This procedure was used to prepare oligonucleotide conjugates of a tetrapeptide, RGDC, and a derivative of HIV tat peptide having a C-terminus cysteine. The combination of the unique reactivity of the aminooxy group and

  20. Dichlorido[methyl 2-(quinolin-8-yloxy-κ2N,Oacetate-κO]mercury(II

    Directory of Open Access Journals (Sweden)

    Yu-Hong Wang


    Full Text Available In the neutral title complex, [HgCl2(C12H11NO3], the HgII ion is pentacoordinated by two Cl atoms, one N atom and two weakly coordinating O atoms from the methyl 2-(quinolin-8-yloxyacetate ligand. The coordination around the HgII ion may be described as highly distorted trigonal–bipyramidal. Centrosymmetric dimers are formed by an additional weak Hg...Cl interaction, leading to a distorted octahedral coordination geometry around the HgII ion.

  1. Crystal structure of chlorido(piperidine-κN(quinoline-2-carboxylato-κ2N,Oplatinum(II

    Directory of Open Access Journals (Sweden)

    Chi Nguyen Thi Thanh


    Full Text Available The title compound, [Pt(C10H6NO2Cl(C5H11N], crystallizes with one molecule in the asymmetric unit. The PtII cation has a slightly distorted square-planar coordination environment defined by a chloride anion, the quinoline N atom and a carboxylate O atom of the bidentate quinaldate ligand and a piperidine N atom. An intramolecular C—H...Cl hydrogen bond occurs. In the crystal, molecules are stacked into columns along the c axis by the formation of N—H...Cl and C—H...O hydrogen bonds.

  2. Specific reactions of different striatal neuron types in morphology induced by quinolinic acid in rats.

    Directory of Open Access Journals (Sweden)

    Qiqi Feng

    Full Text Available Huntington's disease (HD is a neurological degenerative disease and quinolinic acid (QA has been used to establish HD model in animals through the mechanism of excitotoxicity. Yet the specific pathological changes and the underlying mechanisms are not fully elucidated. We aimed to reveal the specific morphological changes of different striatal neurons in the HD model. Sprague-Dawley (SD rats were subjected to unilaterally intrastriatal injections of QA to mimic the HD model. Behavioral tests, histochemical and immunhistochemical stainings as well as Western blots were applied in the present study. The results showed that QA-treated rats had obvious motor and cognitive impairments when compared with the control group. Immunohistochemical detection showed a great loss of NeuN+ neurons and Darpp32+ projection neurons in the transition zone in the QA group when compared with the control group. The numbers of parvalbumin (Parv+ and neuropeptide Y (NPY+ interneurons were both significantly reduced while those of calretinin (Cr+ and choline acetyltransferase (ChAT+ were not changed notably in the transition zone in the QA group when compared to the controls. Parv+, NPY+ and ChAT+ interneurons were not significantly increased in fiber density while Cr+ neurons displayed an obvious increase in fiber density in the transition zone in QA-treated rats. The varicosity densities of Parv+, Cr+ and NPY+ interneurons were all raised in the transition zone after QA treatment. In conclusion, the present study revealed that QA induced obvious behavioral changes as well as a general loss of striatal projection neurons and specific morphological changes in different striatal interneurons, which may help further explain the underlying mechanisms and the specific functions of various striatal neurons in the pathological process of HD.

  3. Quinoline based furanones and their nitrogen analogues: Docking, synthesis and biological evaluation

    Directory of Open Access Journals (Sweden)

    Sukhbir Lal Khokra


    Full Text Available A small library of twenty-four quinoline based butenolides also known as furanones and their nitrogen analogues was prepared by using two different aroylpropionic acids, viz. 3-(2-naphthoylpropionic acid (3 and 3-(biphenyl-4-ylpropionic acid (4, as starting materials. The 3-aroylpropionic acids were reacted with different 6-substituted-2-chloroquinolin-3-carbaldehydes (2a–d to obtain the corresponding furan-2(3H-ones (5a–h. The purified and characterized furanones were then converted into their corresponding 2(3H-pyrrolones (6a–h and N-benzyl-pyrrol-2(3H-ones (7a–h. The antimicrobial activities of the title compounds were evaluated against two strains of each Gram +ve (Staphylococcus aureus and Bacillus subtilis, Gram −ve bacteria (Escherichia coli and Pseudomonas aeruginosa and against fungal strains of Aspergillus niger and Aspergillus flavus. In vivo anti-inflammatory potential of the title compounds was investigated by standard method. Majority of the compounds showed significant antibacterial activity against both the Gram +ve strains. Eight most potent anti-inflammatory compounds (5b, 5d, 5h, 6b, 7b, 7d, 7f, 7h which exhibited >53% inhibition in edema, were also screened for their in vivo analgesic activity. All the tested compounds were found to have significant reduction in ulcerogenic action but only three compounds (5d, 5h and 7h showed comparable analgesic activity to standard drug, diclofenac. The results were also validated using in silico approach and maximum mol doc score was obtained for compounds 7a–h. On comparing the in vivo and in silico anti-inflammatory results of synthesized compounds, N-benzyl pyrrolones (7a–h emerged as the potent anti-inflammatory agents. It was also observed that compounds that possess electron withdrawing group such as Cl or NO2 are more biologically active.

  4. Studies on cluster, salt and molecular complex of zinc-quinolinate

    Indian Academy of Sciences (India)

    Prithiviraj Khakhlary; Jubaraj B Baruah


    Reactions of zinc halides with 8-hydroxyquinoline (hydroxQ) in equimolar ratio were carried out in different solvents. Respective solvates of tetranuclear clusters, namely [Zn4(oxyQ)6X2].(solvent)2, (when X=Cl, Solvent=dimethylformamide (1), dimethylacetamide (2) and dimethysulphoxide (3); X = Br, solvent = dimethylformamide (4), oxyQ=quinolinate anion) were obtained. Bond parameters of these isostructural clusteres 1–4 are compared from their single crystal structures. Anhydrous form of the cluster have porous packing and is thermally stable below 250° C. Surface area of the clusters 1 and 4 are 8.933 and 6.172 m2/g, respectively. Complexes 1 and 4 can be reversibly hydrated, which is reflected in colour changes. The reaction of zinc chloride with 8-hydroxyquinoline in equimolar ratio followed by crystallization from water gave salt (HhydroxQ)2 [ZnCl4] (5) and a similar reaction followed by crystallization from 3-methylpyridine (3mepy) resulted in the molecular complex [Zn(oxyQ)2(3mepy)]. [Zn(oxyQ)2(3mepy)2].3H2O (6). Complex 5 is formed from a hydrolytic equilibrium of water with zinc chloride yielding tetrachloro zinc anion and zinc hydroxide. Taking advantage of this reaction, a composite material of ZnO@complex 5 exhibiting dual fluorescence at 450 and 575 nm on excitation at 390 nm was prepared. Fluorescence emission properties of all the complexes in solid state are compared with fluorescence emission of the ligand

  5. Antiperoxidative and antiinflammatory effect of Sida cordifolia Linn. on quinolinic acid induced neurotoxicity. (United States)

    Swathy, S S; Panicker, Seema; Nithya, R S; Anuja, M M; Rejitha, S; Indira, M


    Sida cordifolia is a plant belonging to the Malvaceae family used in many ayurvedic preparations. This study aimed at assessing the effects of ethanolic extract of Sida cordifolia root on quinolinic acid (QUIN) induced neurotoxicity and to compare its effect with the standard drug deprenyl in rat brain. Rats were divided into six groups: (1) control group (2) QUIN (55 microg/100 g bwt/day) (3) 50% ethanolic plant extract treated group (50 mg/100 g bwt/day) (4) Deprenyl (100 microg/100 g bwt/day) (5) QUIN (55 microg/100 g bwt/day) + 50% ethanolic plant extract treated group (50 mg/100 g bwt/day) (6) QUIN (55 microg/100 g bwt/day) + Deprenyl (100 microg/100 g bwt/day). At the end of the experimental period a status of lipid peroxidation products, protein peroxidation product, activities of the scavenging enzymes and the activities of the inflammatory markers were analyzed. Results revealed that the lipid peroxidation products decreased and the activities of the scavenging enzymes increased significantly in the brain of the plant extract treated group, deprenyl treated group and also in the coadminstered groups. The activities of markers of inflammatory responses such as cyclooxygenase and lipoxygenase were found to be significantly increased in the QUIN treated rats and this was decreased upon the administration of plant extract and deprenyl. In short, the study revealed that 50% ethanolic extract of Sida cordifolia has got potent antioxidant and antiinflammatory activity and the activity is comparable with the standard drug deprenyl.

  6. Quinolinic acid induces disrupts cytoskeletal homeostasis in striatal neurons. Protective role of astrocyte-neuron interaction. (United States)

    Pierozan, Paula; Ferreira, Fernanda; de Lima, Bárbara Ortiz; Pessoa-Pureur, Regina


    Quinolinic acid (QUIN) is an endogenous metabolite of the kynurenine pathway involved in several neurological disorders. Among the several mechanisms involved in QUIN-mediated toxicity, disruption of the cytoskeleton has been demonstrated in striatally injected rats and in striatal slices. The present work searched for the actions of QUIN in primary striatal neurons. Neurons exposed to 10 µM QUIN presented hyperphosphorylated neurofilament (NF) subunits (NFL, NFM, and NFH). Hyperphosphorylation was abrogated in the presence of protein kinase A and protein kinase C inhibitors H89 (20 μM) and staurosporine (10 nM), respectively, as well as by specific antagonists to N-methyl-D-aspartate (50 µM DL-AP5) and metabotropic glutamate receptor 1 (100 µM MPEP). Also, intra- and extracellular Ca(2+) chelators (10 µM BAPTA-AM and 1 mM EGTA, respectively) and Ca(2+) influx through L-type voltage-dependent Ca(2+) channel (10 µM verapamil) are implicated in QUIN-mediated effects. Cells immunostained for the neuronal markers βIII-tubulin and microtubule-associated protein 2 showed altered neurite/neuron ratios and neurite outgrowth. NF hyperphosphorylation and morphological alterations were totally prevented by conditioned medium from QUIN-treated astrocytes. Cocultured astrocytes and neurons interacted with one another reciprocally, protecting them against QUIN injury. Cocultured cells preserved their cytoskeletal organization and cell morphology together with unaltered activity of the phosphorylating system associated with the cytoskeleton. This article describes cytoskeletal disruption as one of the most relevant actions of QUIN toxicity in striatal neurons in culture with soluble factors secreted by astrocytes, with neuron-astrocyte interaction playing a role in neuroprotection.

  7. Design and synthesis of new RAF kinase-inhibiting antiproliferative quinoline derivatives. Part 2: Diarylurea derivatives. (United States)

    El-Gamal, Mohammed I; Khan, Mohammad Ashrafuddin; Tarazi, Hamadeh; Abdel-Maksoud, Mohammed S; Gamal El-Din, Mahmoud M; Yoo, Kyung Ho; Oh, Chang-Hyun


    This article describes the design, synthesis, and biological screening of a new series of diarylurea derivatives possessing quinoline nucleus. Nine target compounds were selected by the National Cancer Institute (NCI, Bethesda, Maryland, USA) for in vitro antiproliferative screening against a panel of 58 cancer cell lines of nine cancer types. Following one-dose initial screening, compounds 1d-g and 2b were selected for 5-dose screening in order to calculate their IC50 and total growth inhibition (TGI) values against the cell lines. Compounds 1e and 1g were the most promising analogues. Both compounds showed strong potency and broad-spectrum antiproliferative activity against the different tested cancer types. Their IC50 and TGI values were less than those of the reference drug, sorafenib, against most of the tested cell lines of the nine different cancer types. Furthermore, the most potent compounds 1d-g were tested against C-RAF kinase as a potential molecular target of this series of compounds. All of them showed high potency, and the most potent derivative was compound 1e (IC50 = 0.10 μM). It was further tested against a panel of another twelve kinases, and it showed selectivity against C-RAF kinase. This could be, at least in part, the possible mechanism of antiproliferative action of this series of compounds at molecular level. The binding modes of compounds 1e and 1g were studied by docking studies, which highlighted the importance of the urea linker compared with the amide linker.

  8. Tetra­kis(quinolin-8-olato-κ2 N,O)hafnium(IV) toluene disolvate (United States)

    Viljoen, J. Augustinus; Visser, Hendrik G.; Roodt, Andreas; Steyn, Maryke


    In the title compound, [Hf(C9H6NO)4]·2C7H8, the hafnium metal centre is coordinated by four N,O-donating bidentate quinolin-8-olate ligands arranged to give a square-anti­prismatic coordination polyhedron with a slightly distorted dodeca­hedral geometry. The average Hf—O and Hf—N distances are 2.096 (3) and 2.398 (3) Å, respectively, and the average O—Hf—N bite angle is 70.99 (11)°. The crystal packing is controlled by π–π inter­actions between quinoline ligands of neighbouring mol­ecules and hydrogen-bonding inter­actions. The inter­planar distances vary between 3.138 (1) and 3.208 (2) Å, while the centroid–centroid distances range from 3.576 (1) to 4.074 (1) Å. PMID:21578562

  9. Determination of mercury(II) in aquatic plants using quinoline-thiourea conjugates as a fluorescent probe. (United States)

    Feng, Guodong; Ding, Yuanyuan; Gong, Zhiyong; Dai, Yanna; Fei, Qiang


    In this study, a quinoline-thiourea conjugate (1-phenyl-3-(quinoline-8-yl) thiourea, PQT) was synthesized and used as a fluorescence sensor to detect mercury ion. The observation is coincident with the well-documented phenomenon that a thiocarbonyl-containing group on a fluorochrome quenches the fluorescence due to the heavy atom effect of the S atom. The large fluorescence enhancement of PQT in the buffered MeCN-water mixture (1/1 v/v; HEPES 100 mM; pH 8.0) was caused by the Hg(2+) induced transformation of the thiourea function into a urea group. As such, protic solvents can be ascribed to hydrogen bond formation on the carbonyl oxygen to reduce the internal conversion rate. The fluorescence intensity of PQT was enhanced quantitatively with an increase in the concentration of mercury ion. The limit of detection of Hg(2+) was 7.5 nM. The coexistence of other metal ions with mercury had no obvious influence on the detection of mercury. A quinolone-thiourea conjugate was used as a fluorescent probe to detect Hg(2+) in aquatic plants and the experimental results were satisfactory.

  10. Laboratory Infrared Spectra of Polycyclic Aromatic Nitrogen Heterocycles: Quinoline, and Phenanthridine in Solid Argon and H2O (United States)

    Bernstein, M. P.; Mattioda, A. L.; Sandford, S. A.; Hudgins, D. M.


    Polycyclic aromatic hydrocarbons (PAHs) are common throughout the universe. Their detection and identification are based on telescopic infrared (IR) spectra compared with laboratory data. Polycyclic Aromatic Nitrogen Heterocycles (PANHs) are heterocyclic aromatics i.e., PAHs with carbon atoms replaced by a nitrogen atom. These molecules should be present in the interstellar medium, but have received relatively little attention. We present mid-IR spectra of two PANHs, quinoline (C9H7N), and phenanthridine (C13H9N) isolated in solid argon and frozen in solid H2O at 12 K, conditions yielding data directly comparable to astronomical observations. In contrast to simple PAHs, that do not interact strongly with solid H2O, the nitrogen atoms in PANHs are potentially capable of hydrogen bonding with H2O. Whereas the IR spectrum of phenanthridine in H2O is similar to that of the same compound isolated in an argon matrix, quinoline absorptions shift up to 16 cm(sup -1) (0.072 mm) between argon and H2O. Thus, astronomers will not always be able to rely on IR band positions of matrix isolated PANHs to correctly interpret the absorptions of PANHs frozen in H2O ice grains. Furthermore, our data suggest that relative band areas also vary, so determining column densities to better than a factor of 3 will require knowledge of the matrix in which the PANH is embedded and laboratory studies of relevant samples.

  11. Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. (United States)

    Lilienkampf, Annamaria; Mao, Jialin; Wan, Baojie; Wang, Yuehong; Franzblau, Scott G; Kozikowski, Alan P


    Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 microM, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 microM concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

  12. Novel Polycarbo-Substituted Alkyl (Thieno[3,2-c]quinoline-2-Carboxylates: Synthesis and Cytotoxicity Studies

    Directory of Open Access Journals (Sweden)

    Malose Jack Mphahlele


    Full Text Available Direct one-pot base-promoted conjugate addition–elimination of 6,8-dibromo-4-chloroquinoline-3-carbaldehyde with methyl mercaptoacetate and subsequent cyclization afforded methyl [(6,8-dibromothieno[3,2-c]quinoline]-2-carboxylate. The latter undergoes Suzuki-Miyaura cross-coupling with arylboronic acids to yield exclusively the corresponding alkyl [(6,8-diarylthieno[3,2-c]quinoline]-2-carboxylates,. The cytotoxicity of the prepared compounds was evaluated against the human breast cancer cell line MCF-7 using the MTT assay. The effects of compounds 2, 3c and 4d on cell kinetics were further determined using the xCELLigence Real Time Cell Analysis (RTCA system. In both the MTT assay and Real Time Cell Analysis, the compounds inhibited cancer cell growth in a dose- and time-dependent manner. Furthermore, on the basis of the calculated LC50 values, the compounds compared favourably with nocodazole, a well-established anticancer drug.

  13. Effect of substitution group on dielectric properties of 4H-pyrano [3, 2-c] quinoline derivatives thin films (United States)

    H, M. Zeyada; F, M. El-Taweel; M, M. El-Nahass; M, M. El-Shabaan


    The AC electrical conductivity and dielectrical properties of 2-amino-6-ethyl-5-oxo-4-(3-phenoxyphenyl)-5,6-dihydro-4H-pyrano[3, 2-c]quinoline-3-carbonitrile (Ph-HPQ) and 2-amino-4-(2-chlorophenyl)-6-ethyl-5-oxo-5,6-dihydro-4H-pyrano [3, 2-c] quinoline-3-carbonitrile (Ch-HPQ) thin films were determined in the frequency range of 0.5 kHz-5 MHz and the temperature range of 290-443 K. The AC electrical conduction of both compounds in thin film form is governed by the correlated barrier hopping (CBH) mechanism. Some parameters such as the barrier height, the maximum barrier height, the density of charges, and the hopping distance were determined as functions of temperature and frequency. The phenoxyphenyl group has a greater influence on those parameters than the chlorophenyl group. The AC activation energies were determined at different frequencies and temperatures. The dielectric behaviors of Ph-HPQ and Ch-HPQ were investigated using the impedance spectroscopy technique. The impedance data are presented in Nyquist diagrams for different temperatures. The Ch-HPQ films have higher impedance than the Ph-HPQ films. The real dielectric constant and dielectric loss show a remarkable dependence on the frequency and temperature. The Ph-HPQ has higher dielectric constants than the Ch-HPQ.

  14. Convenient synthesis of 2,2-Dimethyl-3,4-dihydro-2 H-pyrano[2,3- b]quinolines

    Digital Repository Service at National Institute of Oceanography (India)

    Parsekar, S.B.; Amonkar, C; Parameswaran, P.S.; Tilve, S.G.

    A convenient general synthesis of 2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]quinolines using the Wittig reaction is described. The o-nitrobenzaldehydes (1a-d) on reaction with phosphorane 2 provided (E)-ethyl-a-(2,2-dimethylprop-2-ene)-2...

  15. Visible light photoredox catalysis: synthesis of indazolo[2,3-a]quinolines from 2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinolines. (United States)

    Lin, Wen-Chung; Yang, Ding-Yah


    The synthesis of indazolo[2,3-a]quinoline derivatives in moderate to good yields from 2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinolines via visible light photoredox catalysis is reported. The reaction involves a novel ruthenium-catalyzed intramolecular formation of the N-N bond of the indazole ring.

  16. Discovery of Quinoline-Derived Trifluoromethyl Alcohols, Determination of Their in vivo Toxicity and Anticancer Activity in a Zebrafish Embryo Model. (United States)

    Sittaramane, Vinoth; Padgett, Jihan; Salter, Philip; Williams, Ashley; Luke, Shauntelle; McCall, Rebecca; Arambula, Jonathan F; Graves, Vincent B; Blocker, Mark; Van Leuven, David; Bowe, Keturah; Heimberger, Julia; Cade, Hannah C; Immaneni, Supriya; Shaikh, Abid


    In this study the rational design, synthesis, and anticancer activity of quinoline-derived trifluoromethyl alcohols were evaluated. Members of this novel class of trifluoromethyl alcohols were identified as potent growth inhibitors in a zebrafish embryo model. Synthesis of these compounds was carried out with an sp(3) -C-H functionalization strategy of methyl quinolines with trifluoromethyl ketones. A zebrafish embryo model was also used to explore the toxicity of ethyl 4,4,4-trifluoro-3-hydroxy-3-(quinolin-2-ylmethyl)butanoate (1), 2-benzyl-1,1,1-trifluoro-3-(quinolin-2-yl)propan-2-ol (2), and trifluoro-3-(isoquinolin-1-yl)-2-(thiophen-2-yl)propan-2-ol (3). Compounds 2 and 3 were found to be more toxic than compound 1; apoptotic staining assays indicated that compound 3 causes increased cell death. In vitro cell proliferation assays showed that compound 2, with an LC50 value of 14.14 μm, has more potent anticancer activity than cisplatin. This novel class of inhibitors provides a new direction in the discovery of effective anticancer agents.

  17. An efficient ultrasound promoted catalyst-free protocol for the synthesis of chromeno[4,3-b]quinolin-6-ones

    Indian Academy of Sciences (India)

    J Venkata Prasad; J Satyanarayana Reddy; N Ravi Kumar; K Anand Solomon; G Gopikrishna


    A convenient, catalyst-free protocol for the quantitative synthesis of fused chromeno[4,3-b]quinolin-6-ones has been developed by simple one-pot reaction of substituted anilines with 4-chloro-3-formylcoumarin using ultrasound irradiation. The protocol offers the advantages of mild reaction conditions, short reaction times and high yields.

  18. Synthesis of furo[3,2-c ]- and pyrano[ 3,2-c ] quinolines by lanthanide triflate catalyzed imino-Diels-Alder reaction

    Institute of Scientific and Technical Information of China (English)

    MA, Yun(马云); QIAN, Chang-Tao(钱长涛); SUN, Jie(孙杰); XIE, Mei-Hua(谢美华)


    Imino Diels-Alder reaction of imines witth 2,3-dihydrofuran or 3,4-dihydro-2H-pyran proceeded smothly in the presence of a catalytic amount (0.5 mol %) of ytterbium triflate to afford furo[3,2-c]- and pyrano[3,2-c] quinolines conveniently in high yield.

  19. Combined experimental and quantum chemical studies on spectroscopic (FT-IR, FT-Raman, UV-Vis, and NMR) and structural characteristics of quinoline-5-carboxaldehyde (United States)

    Kumru, Mustafa; Altun, Ahmet; Kocademir, Mustafa; Küçük, Vesile; Bardakçı, Tayyibe; Şaşmaz, İbrahim


    Comparative experimental and theoretical studies have been performed on the structure and spectral (FT-IR, FT-Raman, UV-Vis and NMR) features of quinoline-5-carboxaldehyde. Quantum chemical calculations have been carried out at Hartree-Fock and density functional B3LYP levels with the triple-zeta 6-311++G** basis set. Two stable conformers of quinoline-5-carboxaldehyde arising from the orientation of the carboxaldehyde moiety have been located at the room temperature. The energetic separation of these conformers is as small as 2.5 kcal/mol with a low transition barrier (around 9 kcal/mol). Therefore, these conformers are expected to coexist at the room temperature. Several molecular characteristics of quinoline-5-carboxaldehyde obtained through B3LYP and time-dependent B3LYP calculations, such as conformational stability, key geometry parameters, vibrational frequencies, IR and Raman intensities, UV-Vis vertical excitation energies and the corresponding oscillator strengths have been analyzed. The 1H and 13C NMR chemical shifts of quinoline-5-carboxaldehyde were also investigated.

  20. Dermal Sensitization Potential of Insect Repellents: Methyl N,N’-Dihexylethylenediaminemonocarbamate (CHR4), (E)-1,2,3,4-Tetrahydro-6-Methyl-1-(2-Methyl-1-Oxo-2-Butenyl) Quinoline (CHR5), and 1,2,3,4-Tetrahydro-6-Methyl-1-(3-Methyl-1-Oxo-2-Butenyl) Quinoline (CHR6). (United States)


    Chemical name: Methyl-N,N’-Dihexylethylenediamine- monocarbamate (CHR4) Chemical Abstract Service Registry No.: None Structural formula: CH3 (C11 2 )sNH...Quinoline (CRj5) Chemical Abstract Service Registry No.: None Structural formula: CH I C=O CH 3 ’CH 3 Empirical formula: C H NO- 3. Chemical Name...l,2,3,4-Tetralhydro-6-Me thyl-l-(3-Methiyi- l-Oxo-2-Sutenyl) Quinoline (CdiR6) Chemical Abstract Service Registry No.: None Ieia

  1. Primary Eye Irritation Potential of Insect Repellents. Methyl N,N’-Dihexylethylenediaminemonocarbamate (CHR4), (E)-1,2,3,4-Tetrahydro-6-Methyl-1-(2-Methyl-1-Oxo-2-Butenyl) Quinoline (CHR5) and 1,2,3,4-Tetrahydro-6-Methyl-1-(3-Methyl-1-Oxo-2-Butenyl) Quinoline (CHR6). (United States)


    Chemical name: 1,2,3,4-Tetrahydro-6-Methyl-1-(2- Methyl-l-Oxo-2-Butenyl) Quinoline (CHR5) Chemical Abstract Service Registry No.: None Structural formula: CH...Quinoline (CHR6) Chemical Abstract Service Registry No.: None Structural formula: CH I CH3 0 "tCH3 Empirical formula: C 15H 19NO Appendix A provides...aminemonocarbomate Chemical Abstract Service Registry No.: None Structural formula: CH3 (CH 2 ) 5NH(CH2 ) 2 N(CH2 )5 CH3 c02CH 3 Empirical formula: C16H34lN202

  2. Discovery and optimization of novel 4-phenoxy-6,7-disubstituted quinolines possessing semicarbazones as c-Met kinase inhibitors. (United States)

    Qi, Baohui; Mi, Bin; Zhai, Xin; Xu, Ziyi; Zhang, Xiaolong; Tian, Zeru; Gong, Ping


    A novel series of N(1)-(3-fluoro-4-(6,7-disubstituted-quinolin-4-yloxy)phenyl)-N(4)-arylidenesemicarbazide derivatives were synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against A549, HT-29, MKN-45 and MDA-MB-231 cancer cell lines in vitro. Several potent compounds were further evaluated against three other cancer cell lines (U87MG, NCI-H460 and SMMC7721). Most of compounds tested exhibited moderate to excellent activity. The studies of SARs identified the most promising compound 28 (c-Met IC50=1.4nM) as a c-Met kinase inhibitor. In this study, a promising compound 28 was identified, which displayed 2.1-, 3.3-, 48.4- and 3.6-fold increase against A549, HT-29, U87MG and NCI-H460 cell lines, respectively, compared with that of Foretinib.

  3. Comparative molecular field analysis of quinoline derivatives as selective and noncompetitive mGluR1 antagonists. (United States)

    Sekhar, Y Nataraja; Nayana, M Ravi Shashi; Ravikumar, Muttineni; Mahmood, S K


    A 3D- QSAR model os Comparative Molecular Field Analysib (CoMFA) of 45 quinoline derivatives as metaborropic glutamate receptor subtype 1 (mGluR1) inhibitors wew investigated. The CoMFA analysis provided a model with q(2) value of 0.827 and r(2) value of 0.990, in which q(2) value of 0.827 and an r(2) value of 0.990, in which the good correlation between the inhibitory activities and the steric and electrostatic molecular field around the analoques was observed. The predictive ability of the models was validated using the set of 12 compounds that were not included in the training set of 33 compounds. These results provided further understanding of the relationship between the structural features of quinolone derivatives and its activities, which should be applicable to design and find new potential mGluR1 inhibitors.

  4. A new series of diarylamides possessing quinoline nucleus: Synthesis, in vitro anticancer activities, and kinase inhibitory effect. (United States)

    El-Gamal, Mohammed I; Khan, Mohammad Ashrafuddin; Abdel-Maksoud, Mohammed S; Gamal El-Din, Mahmoud M; Oh, Chang-Hyun


    Synthesis of a new series of diarylamides possessing 6,7-dimethoxy(dihydroxy)quinoline scaffold is described. Their in vitro antiproliferative activities against NCI-58 human cancer cell lines of nine different cancer types were tested. Compounds 1a and 1d-g showed the highest mean %inhibition values over the 58 cell line panel at 10 μM, and they were further tested in 5-dose testing mode to determine their IC50 values. The five compounds were more potent than Imatinib against all the cell lines of nine different cancer types. Compound 1g showed the highest potencies. It showed inhibitory effect against C-RAF kinase (76.65% at 10 μM concentration).

  5. Bis[μ-N,N'-bis(quinolin-8-yl)pyridine-2,6-dicarboxamido]dizinc(II) dichloromethane disolvate. (United States)

    Xu, Hui-Hua; Tao, Xian; Li, Yue-Qin; Shen, Ying-Zhong; Wei, Yan-Hong


    The title compound, [Zn(2)(C(25)H(15)N(5)O(2))(2)]·2CH(2)Cl(2), is a dinuclear double-helical complex which lies on a crystallographic twofold axis. In the complex, both ligands are partitioned into two tridentate domains which allow each ligand to bridge both metal centres. Each Zn(II) atom is six-coordinated in a distorted octahedral environment formed by two amide N atoms, two quinoline N atoms and two pyridine N atoms from two different ligand molecules, with the central pyridine ring, unusually, bridging two Zn(II) atoms. The deprotonated ligand is not planar, the amide side chains being considerably twisted out from the plane of the central pyridine ring.

  6. A one-dimensional carboxylate-bridged helical copper(II) complex containing (quinolin-8-yloxy)acetate. (United States)

    Wang, Yu-Hong; Lu, Fang


    The title compound, catena-poly[[bromocopper(II)]-mu-(quinolin-8-yloxy)acetato-kappa(4)N,O,O':O''], [CuBr(C(11)H(8)NO(3))](n), is a novel carboxylate-bridged one-dimensional helical copper(II) polymer. The metal ion exhibits an approximately square-pyramidal CuBrNO(3) coordination environment, with the three donor atoms of the ligand and the bromide ion occupying the basal positions, and an O atom belonging to the carboxylate group of an adjacent molecule in the apical site. Carboxylate groups are mutually cis oriented, and each anti-anti carboxylate group bridges two copper(II) ions via one apical and one basal position [Cu...Cu = 5.677 (1) A], resulting in the formation of a helical chain along the crystallographic b axis.

  7. 2-Oxo-4-(thiophen-2-yl-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile

    Directory of Open Access Journals (Sweden)

    Abdullah M. Asiri


    Full Text Available In the molecule of the title compound, C18H12N2OS, the tetrahydrobenzo[h]quinoline fused-ring system is buckled owing to the ethylene –CH2CH2– fragment, the benzene ring and the pyridine ring being twisted by 16.0 (1°. The 4-substituted aromatic ring is bent away from the pyridine ring by 59.5 (2° (for the major disordered thienyl component in order to avoid crowding the cyanide substituent. In the crystal, two molecules are linked by a pair of N—H...O hydrogen bonds to form a centrosymmetric dimer. The thienyl ring is disordered over two sites in a 72.7 (2:27.3 ratio.

  8. 1-Phenyl-3-(quinolin-5-yl)urea as a host for distinction of phthalic acid and terephthalic ac

    Indian Academy of Sciences (India)

    Dipjyoti Kalita; Jubaraj B Baruah


    Co-crystals of 1-phenyl-3-(quinolin-5-yl)urea (1) with terephthalic acid, adipic acid; and salts of 1 with phthalic acid, -toluenesulphonic acids are prepared and structurally characterized. The reaction of phthalic acid and -toluenesulphonic acid resulted in protonation of the host 1, whereas the terephthalic acid and adipic acid interact with 1, led to cocrystals with the host 1 through hydrogen bond interactions. The hydrogen bonds that appears in the urea taps of the host molecules 1 are lost while formation of salts; in such cases anions interacts with the urea portion of the host, while in the co-crystals the hydrogen bonded urea taps are retained. The salts are yellow in colour while the co-crystals are colourless; thereby the positional isomer phthalic acid can be distinguished from the terephthalic acid.

  9. A simple ratiometric fluorescent sensor for fructose based on complexation of 10-hydroxybenzo[h]quinoline with boronic acid (United States)

    Li, Huihui; Yang, Cailing; Zhu, Xinyue; Zhang, Haixia


    A simple ratiometric fluorescent sensor for fructose was presented. It consisted of 10-hydroxybenzo[h]quinoline (HBQ) which showed emission at 572 nm and 3-pyridylboronic acid (PDBA) whose complex with HBQ gave emission at 500 nm. The reaction of fructose with PDBA inhibited the complexation of HBQ with PDBA, resulting in the change of dual-emission intensity ratio. The sensor well quantified fructose in the range of 0.015-2.5 mM with detection limit of 0.005 mM. Besides, this sensor exhibited excellent selectivity and was successfully applied to fructose detection in food. This work provides a simple ratiometric sensing platform for sensitive and selective detection of fructose.


    Institute of Scientific and Technical Information of China (English)

    Qi-song Shi; Xiang Hao; Carl Redshaw; Wen-hua Sun


    A series of nickel halides bearing 2,4-di-t-butyl-6-(quinolin-8-yliminomethyl) phenolate ligands was synthesized and characterized by IR spectroscopy and elemental analysis.Molecular structures of C1 (R =H,X =Br) and C2 (R =H,X =Cl) were further confirmed by single-crystal X-ray crystallographic studies,and revealed a distorted square planar geometry at nickel.Upon activation with diethylaluminum chloride (Et2AlCl),all nickel pre-catalysts displayed good catalytic activity [up to 9.3 × 105 g mol-1(Ni) h-1] for ethylene oligomerization with major dimerization.In the presence of methylaluminoxane (MAO),the nickel complex C1 was capable of ethylene polymerization under 3 MPa,and produced polyethylene products with narrow polydispersity (1.16-1.73) and molecular weights in the range of 2.6-4.95 kg/mol.

  11. Rotation-vibration interactions in the spectra of polycyclic aromatic hydrocarbons: Quinoline as a test-case species

    Energy Technology Data Exchange (ETDEWEB)

    Pirali, O.; Gruet, S. [AILES Beamline, Synchrotron SOLEIL, l’Orme des Merisiers, Saint-Aubin, 91192 Gif-sur-Yvette cedex (France); Institut des Sciences Moléculaires d’Orsay, UMR8214 CNRS – Université Paris-Sud, Bât. 210, 91405 Orsay cedex (France); Kisiel, Z. [Institute of Physics, Polish Academy of Sciences, Al. Lotników 32/46, 02-668 Warsaw (Poland); Goubet, M. [Laboratoire de Physique des Lasers, Atomes et Molécules, UMR 8523 CNRS - Université Lille 1, Bâtiment P5, F-59655 Villeneuve d’Ascq Cedex (France); Martin-Drumel, M. A.; Cuisset, A.; Hindle, F.; Mouret, G. [Laboratoire de Physico-Chimie de l’Atmosphère, EA-4493, Université du Littoral – Côte d’Opale, 59140 Dunkerque (France)


    Polycyclic aromatic hydrocarbons (PAHs) are highly relevant for astrophysics as possible, though controversial, carriers of the unidentified infrared emission bands that are observed in a number of different astronomical objects. In support of radio-astronomical observations, high resolution laboratory spectroscopy has already provided the rotational spectra in the vibrational ground state of several molecules of this type, although the rotational study of their dense infrared (IR) bands has only recently become possible using a limited number of experimental set-ups. To date, all of the rotationally resolved data have concerned unperturbed spectra. We presently report the results of a high resolution study of the three lowest vibrational states of quinoline C{sub 9}H{sub 7}N, an N-bearing naphthalene derivative. While the pure rotational ground state spectrum of quinoline is unperturbed, severe complications appear in the spectra of the ν{sub 45} and ν{sub 44} vibrational modes (located at about 168 cm{sup −1} and 178 cm{sup −1}, respectively). In order to study these effects in detail, we employed three different and complementary experimental techniques: Fourier-transform microwave spectroscopy, millimeter-wave spectroscopy, and Fourier-transform far-infrared spectroscopy with a synchrotron radiation source. Due to the high density of states in the IR spectra of molecules as large as PAHs, perturbations in the rotational spectra of excited states should be ubiquitous. Our study identifies for the first time this effect and provides some insights into an appropriate treatment of such perturbations.

  12. Synthesis of Diethyl Pyridin-2-ylphosphonates and Quinolin-2-ylphosphonates by Deoxygenative Phosphorylation of the Corresponding N-Oxides

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Sangjin; Kim, Hyunsoo; Yang, Haewon; Yoo, Byungwoo; Yoon, Cheol Min [Korea Univ., Seoul (Korea, Republic of)


    The reaction of pyridine N-oxide and quinoline N-oxide activated by ethyl chloroformate with triethyl phosphites at rt gave the corresponding diethyl pyridin-2-ylphosphonate and diethyl quinolin-2-ylphosphonate regio-selectively in good to excellent yield through oxygenative phosphorylation. The reaction condition is mild and efficient compared to the reported methods. All chemicals including commercially available pyridine N-oxides were purchased from specialized suppliers with analytical purity and used without further purification. Non commercially available pyridine N-oxide for the reaction were prepared by known method. IR spectra of products were recorded on a Perkin-Elmer FT-IR 240-c spectrometer using KBr disks. {sup 1}H NMR (300 MHz) and {sup 13}C NMR (75 MHz) spectra were recorded on a Bruker 300 spectrometer in CDCl{sub 3}. High-resolution ESI-MS spectra were obtained on an IT-TOF (Shimadzu, Japan) at Korea Basic Science Institute (KBSI). Column chromatography was performed using Merck silica gel (230-400 mesh). Some known products have physical, spectroscopic, and analytic data identical to those (shown as a CAS registry number) given in the literature. Dialkyl pyridin-2-ylphosphonates widely used as corrosion inhibitors, dispersing and emulsifying agents, antistatics and lubricant additives in various technological fields are known as potent insecticides, fungicides and herbicides. Pyridin-2-ylphosphonates have also been reported to have a promising cytokinin activity, anti-proliferating and antiplatelet activating factor (anti-PAF) activities, and to be used as a chelate ligand to prepare various metal-organic frameworks, such as polymeric material with Zn, Cd and Ag showing luminescence properties, iron complex as a catalyst and copper complex with weak ferromagnetism. Because biological properties of dialkyl pyridin-2-ylphosphonates and physical properties of their complexes depend both on the phosphorus-containing ligand, simple and efficient

  13. Biochemical characterization of quinolinic acid phosphoribosyltransferase from Mycobacterium tuberculosis H37Rv and inhibition of its activity by pyrazinamide.

    Directory of Open Access Journals (Sweden)

    Hyun Kim

    Full Text Available Quinolinic acid phosphoribosyltransferase (QAPRTase, EC is a key enzyme in the de novo pathway of nicotinamide adenine dinucleotide (NAD biosynthesis and a target for the development of new anti-tuberculosis drugs. QAPRTase catalyzes the synthesis of nicotinic acid mononucleotide from quinolinic acid (QA and 5-phosphoribosyl-1-pyrophosphate (PRPP through a phosphoribosyl transfer reaction followed by decarboxylation. The crystal structure of QAPRTase from Mycobacterium tuberculosis H37Rv (MtQAPRTase has been determined; however, a detailed functional analysis of MtQAPRTase has not been published. Here, we analyzed the enzymatic activities of MtQAPRTase and determined the effect on catalysis of the anti-tuberculosis drug pyrazinamide (PZA. The optimum temperature and pH for MtQAPRTase activity were 60°C and pH 9.2. MtQAPRTase required bivalent metal ions and its activity was highest in the presence of Mg2+. Kinetic analyses revealed that the Km values for QA and PRPP were 0.08 and 0.39 mM, respectively, and the kcat values for QA and PRPP were 0.12 and 0.14 [s-1], respectively. When the amino acid residues of MtQAPRTase, which may interact with QA, were substituted with alanine residues, catalytic activity was undetectable. Further, PZA, which is an anti-tuberculosis drug and a structural analog of QA, markedly inhibited the catalytic activity of MtQAPRTase. The structure of PZA may provide the basis for the design of new inhibitors of MtQAPRTase. These findings provide new insights into the catalytic properties of MtQAPRTase.

  14. Distorted octahedral environments in tricarbonylrhenium(I) complexes of 5-[2-(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olate and 5,7-bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-olate. (United States)

    Schutte-Smith, Marietjie; Muller, Theunis J; Visser, Hendrik G; Roodt, Andreas


    The Re(I) centres of two Re(I)-tricarbonyl complexes, viz. tricarbonyl(pyridine-κN){5-[2-(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olato-κ(2)N(1),O}rhenium(I), [Re(C23H21N4O)(CO)3], (I), and {5,7-bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-olato-κ(2)N(1),O}tricarbonyl(pyridine-κN)rhenium(I), [Re(C28H23N6O)(CO)3], (II), are facially surrounded by three carbonyl ligands, a pyridine ligand and either a 5-[2-(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olate [in (I)] or a 5,7-bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-olate [in (II)] ligand, in a slightly distorted octahedral environment. The crystal structure of (I) is stabilized by two intermolecular C-H···O interactions and that of (II) is stabilized by three intermolecular C-H···O hydrogen-bonding interactions.

  15. EFSA CEF Panel (EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids), 2015. Scientific Opinion on Flavouring Group Evaluation 77, Revision 2 (FGE.77Rev2): Consideration of Pyridine, Pyrrole and Quinoline Derivatives evaluated by JECFA (63rd meeting) structurally related, to Pyridine, Pyrrole, Indole and Quinoline Derivatives evaluated by EFSA in FGE.24Rev2 (2013)

    DEFF Research Database (Denmark)

    Beltoft, Vibe Meister; Nørby, Karin Kristiane

    evaluation is necessary, as laid down in Commission Regulation (EC) No 1565/2000. The present consideration concerns a group of 22 pyridine, pyrrole and quinoline derivatives evaluated by JECFA (63rd meeting). The revision of this consideration is made since additional toxicity data have become available...

  16. Indium Titanium Oxide Nanoparticles Induced Hepatic Damage: Hepatoprotective Role of Novel 2-Imino-4-methyl-1, 2-Dihydropyrimido [5, 4C] Quinoline-5(6H-one

    Directory of Open Access Journals (Sweden)

    Dinesh Bheeman


    Full Text Available Protective role of 2-imino-4-methyl-1, 2-dihydropyrimido [5, 4C] quinoline-5(6H-one (IMDHPQ in indium titanium oxide nanoparticles (InTiO NPs induced hepatotoxicity was analyzed. InTiO NPs were synthesized and given orally to albino rats to assess their hepatotoxicity. NPs mediated oxidative stress and liver tissue pathology were analyzed. Altered antioxidants (GSH, GPx, and catalase and, biochemical (SGOT, SGPT, ALP, total protein, and total bilirubin and histopathological changes were observed due to the oxidative stress caused by InTiO NPs. Varying effects of IMDHPQ on each parameter were observed in the present study. The altered parameters of InTiO NPs exposed rats might be due to the oxidative stress caused by NPs and hepatoprotective or ameliorative efficacy of quinoline compound IMDHPQ on signaling and molecular mechanism needs further study.

  17. Crystal structure of bis{μ-(E-2-[(2-oxidophenyliminomethyl]quinolin-8-olato-κ4O,N,N′,O′}bis[dibutyltin(IV

    Directory of Open Access Journals (Sweden)

    Camacho-Camacho Carlos


    Full Text Available Condensation of 8-hydroxyquinoline-2-carbaldehyde with 2-aminophenol gave the (E-2-[(2-hydroxyphenyliminomethyl]quinolin-8-ol derivative that reacted with di-n-butyltin oxide with release of H2O to yield the chelate title complex, [Sn2(C4H94(C16H10N2O22]. The compound crystallizes in the triclinic space group P-1, with two independent centrosymmetric dimers in the unit cell. Each features a typical pincer-type structure where the dianionic ligand is tetradentate, coordinating to the central tin atom through both phenolate oxygen atoms, as well as through the quinoline and imine N atoms. Each metal atom adopts a distorted pentagonal–bipyramidal SnC2N2O3 coordination arising from the N,N′,O,O′-tetradentate deprotonated Schiff base, one bridging phenolate O atom of the neighbouring ligand and two butyl groups in the axial sites.

  18. The interplay of skeletal deformations and ultrafast excited-state intramolecular proton transfer: Experimental and theoretical investigation of 10-hydroxybenzo[h]quinoline

    Energy Technology Data Exchange (ETDEWEB)

    Schriever, Christian [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany)], E-mail:; Barbatti, Mario [Institute for Theoretical Chemistry - University of Vienna, Waehringer Strasse 17, 1090 Vienna (Austria)], E-mail:; Stock, Kai [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany); Aquino, Adelia J.A.; Tunega, Daniel [Institute for Theoretical Chemistry - University of Vienna, Waehringer Strasse 17, 1090 Vienna (Austria); Lochbrunner, Stefan [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany); Riedle, Eberhard [Fakultaet fuer Physik - Ludwig-Maximilians-Universitaet (LMU), Oettingenstrasse 67, 80538 Muenchen (Germany)], E-mail:; Vivie-Riedle, Regina de [Department Chemie - Ludwig-Maximilians-Universitaet (LMU), Butenandt-Strasse 11, 81377 Muenchen (Germany)], E-mail:; Lischka, Hans [Institute for Theoretical Chemistry - University of Vienna, Waehringer Strasse 17, 1090 Vienna (Austria)], E-mail:


    The excited-state intramolecular proton transfer in the aromatic polycycle 10-hydroxybenzo[h]quinoline is investigated by means of transient absorption experiments with 30 fs time resolution, classical dynamics and wavepacket dynamics. The experiments establish the ultrafast transfer after UV excitation and show signatures of coherent vibrational motion in the keto product. To elucidate details of the proton transfer mechanism, the classical dynamics is also performed for 2-(2'-hydroxyphenyl)benzothiazole and the results are compared. For both systems the proton transfer takes place on the ultrafast scale of 30-40 fs, with good agreement between the theoretical investigations and the measurements. The dynamics simulations show that for both molecules the proton is handed over by means of skeletal deformation of the molecule. Due to the more rigid structure of 10-hydroxybenzo[h]quinoline the hydrogen migration mode participates more actively than in 2-(2'-hydroxyphenyl)benzothiazole.

  19. Synthesis and cytotoxicity of thieno[2,3-b]quinoline-2-carboxamide and cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide derivatives. (United States)

    Leung, Euphemia; Pilkington, Lisa I; van Rensburg, Michelle; Jeon, Chae Yeon; Song, Mirae; Arabshahi, Homayon J; De Zoysa, Gayan Heruka; Sarojini, Vijayalekshmi; Denny, William A; Reynisson, Jóhannes; Barker, David


    Seventy nine derivatives of thieno[2,3-b]quinolines, tetrahydrothieno[2,3-b]quinoline, dihydrocyclopenta[b]thieno[3,2-e]pyridine, cyclohepta[b]thieno[3,2-e]pyridine and hexahydrocycloocta[b]thieno[3,2-e]pyridine were either synthesized or obtained commercially and tested for their antiproliferative activity against HCT116, MDA-MB-468 and MDA-MB-231 human cancer cell lines. The most potent eight compounds were active against all cell lines with IC50 values in the 80-250nM range. In general hexahydrocycloocta[b]thieno[3,2-e]pyridines were most active with increasing activity observed as larger cycloalkyl rings were fused to the pyridine ring.

  20. Photophysical properties of 6-N,N-dimethylpyrazolo[3,4-b]quinoline substituted with pyridyl in the 3-position (United States)

    Grabka, Danuta; Danel, Andrzej; Kolbus, Anna; Szary, Karol


    The new electron donor-acceptor dye, 6-N,N-dimethyl-3-pyridyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline (DMA-3PPhPQ) was synthesized. Spectral properties of DMA-3PPhPQ were investigated in a great number of organic solvents with different polarity. The red shifts in absorption and fluorescence maxima with increasing polarity of the solvents was observed for various functions of polarity of the solvents. This compound exhibit a CT fluorescence.

  1. Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety:Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde

    Institute of Scientific and Technical Information of China (English)


    A series of novel N,O-type chiral ligands derived from enantiopure inherently chiral calix[4]arenes containing quinolin-2-yl-methanol moiety in the cone or partialcone conformation have been synthe-sized and characterized. Moreover,they have been applied to the catalytic asymmetric addition of diethylzinc to benzaldehyde,which represents the first example that the inherently chiral calixarene can be used as the chiral ligands for the catalytic asymmetric synthesis.

  2. Enthalpies of hydrogen bonding of quinoline with o-phenylphenol and of hydrogen-bonding reactions involving the acid and base components of a coal-derived asphaltene

    Energy Technology Data Exchange (ETDEWEB)

    Dietz, A.G.; Blaha, C.; Li, N.C.


    Calorimetric studies are reported of hydrogen bonding between quinoline (Qu) and o-phenylphenol (OPP). The enthalpies of hydrogen-bonding of the acid and base components of a coal-derived asphaltene with OPP and Qu are also reported. The results provide strong evidence that the acid and base components of asphaltene function substantially as hydrogen donor and acceptor, respectively. 1 figure, 1 table.

  3. 6-Methyl-2-oxo-N-(quinolin-6-yl)-2H-chromene-3-carboxamide: crystal structure and Hirshfeld surface analysis. (United States)

    Gomes, Lígia R; Low, John Nicolson; Fonseca, André; Matos, Maria João; Borges, Fernanda


    The title coumarin derivative, C20H14N2O3, displays intra-molecular N-H⋯O and weak C-H⋯O hydrogen bonds, which probably contribute to the approximate planarity of the mol-ecule [dihedral angle between the coumarin and quinoline ring systems = 6.08 (6)°]. The supra-molecular structures feature C-H⋯O hydrogen bonds and π-π inter-actions, as confirmed by Hirshfeld surface analyses.

  4. Modulation of Tinospora rumphii and Zinc Salt on DNA Damage in Quinoline-Induced Genotoxicity and Hepatotoxicity in Male Albino Mice


    Roger Salvacion Tan; Lydia M. Bajo


    Tinospora rumphii (T. rumphii) is a folkloric medicinal plant that is widely distributed in Asia and Africa. It has been widely used by locals to treat many diseases including jaundice, which is a manifestation of liver damage. We investigated the action of T. rumphii crude extract together with zinc sulphate, a known tumor modulator, on hepatic injuries induced by intraperitoneal (i.p) injections of quinoline on albino mice. The hepatotoxic effect was assessed by bilirubin concentration in t...

  5. One-pot synthesis of novel pyrimido[4,5-]quinolines and pyrido[2,3-:6,5']dipyrimidines using encapsulated--Fe2O3 nanoparticles

    Indian Academy of Sciences (India)

    Moona Mohsenimehr; Manouchehr Mamaghani; Farhad Shirini; Mehdi Sheykhan; Sima Abbaspour; Leila Shafei Sabet


    Novel pyrimido[4,5-]quinolines and pyrido[2,3-:6,5-']dipyrimidine derivatives were synthe-sized in one-pot, three-component approach using sulfonic acid supported on hydroxyapatite-encapsulated--Fe2O3 [-Fe2O3 @HAp-SO3H] as magnetically recoverable nanocatalyst. The protocol provided a rapid, useful and green method for the preparation of the products in short reaction times and high yields.

  6. Dehydrogenative [2 + 2 + 1] Heteroannulation Using a Methyl Group as a One-Carbon Unit: Access to Pyrazolo[3,4-c]quinolines. (United States)

    Deng, Guo-Bo; Li, Hai-Bing; Yang, Xu-Heng; Song, Ren-Jie; Hu, Ming; Li, Jin-Heng


    A practical and straightforward access to pyrazolo[3,4-c]quinolines by molecular sieve mediated dehydrogenative [2 + 2 + 1] heteroannulation of N-(o-alkenylaryl)imines with aryldiazonium salts is described using a sp(3)-hybrid carbon atom as a one-carbon unit. The reaction enables the formation of three new chemical bonds, a C-C bond and two C-N bonds, in a single reaction and features simple operation and excellent functional group tolerance.

  7. Enhanced treatment of coking wastewater containing phenol, pyridine, and quinoline by integration of an E-Fenton process into biological treatment. (United States)

    Xue, Lanlan; Liu, Jiaxin; Li, Meidi; Tan, Liang; Ji, Xiangyu; Shi, Shengnan; Jiang, Bei


    In this study, the pyridine and quinoline could be cometabolically degraded by phenol-cultivated Comamonas sp. strain JB(strain JB). The integration of magnetically immobilized cells of JB and an E-Fenton process into one entity has been designed to prepare a novel integration system to improve the treatment efficiency of phenol, pyridine, and quinoline in coking wastewater. The optimal pH for the integration system was 3.5. Degradation rates of phenol, pyridine, quinoline, and COD by the integration system were significantly exceeded the sum degradation rates of the single E-Fenton process and magnetically immobilized cells at the optimal voltage of 1 V. During the 6 cycles, the integration system still showed higher degradation rates than that by the single magnetically immobilized cells for all the compounds. These findings demonstrated that a synergistic effect existed between the biological treatment and the E-Fenton process, and the applied voltage in the integration system played the key roles in the synergistic effect, which not only electrogenerated H2O2 but also improved the activity of phenol hydroxylase and strain JB concentration.

  8. Modulation of Tinospora rumphii and Zinc Salt on DNA Damage in Quinoline-Induced Genotoxicity and Hepatotoxicity in Male Albino Mice

    Directory of Open Access Journals (Sweden)

    Roger Salvacion Tan


    Full Text Available Tinospora rumphii (T. rumphii is a folkloric medicinal plant that is widely distributed in Asia and Africa. It has been widely used by locals to treat many diseases including jaundice, which is a manifestation of liver damage. We investigated the action of T. rumphii crude extract together with zinc sulphate, a known tumor modulator, on hepatic injuries induced by intraperitoneal (i.p injections of quinoline on albino mice. The hepatotoxic effect was assessed by bilirubin concentration in the blood serum, while the genotoxic effect was determined by single-cell gel electrophoresis (SCGE. The mice orally fed with the crude extracts, following quinoline exposure, had reduced serum bilirubin concentration and DNA damage. Mice treated with Zinc sulphate, on the other hand, had remarkably reduced DNA damage on hepatocytes. Our findings showed that hepatoprotective potential of T. rumphii extract is dose-dependent and that utilization of the extract as medicinal remedy must be strictly monitored, while zinc was proven to reverse genotoxic effect of quinoline. This study unraveled the potential of T. rumphii extract and zinc as important hepatoprotective agents for future treatment of hepatic damage caused by chemotherapeutic agents used in cancer treatment.

  9. Density functional theory and molecular dynamics simulation study on corrosion inhibition performance of mild steel by mercapto-quinoline Schiff base corrosion inhibitor (United States)

    Saha, Sourav Kr.; Ghosh, Pritam; Hens, Abhiram; Murmu, Naresh Chandra; Banerjee, Priyabrata


    Corrosion inhibition mechanism of two mercapto-quinoline Schiff bases, eg., 3-((phenylimino)methyl)quinoline-2-thiol (PMQ) and 3-((5-methylthiazol-2-ylimino)methyl) quinoline-2-thiol (MMQT) on mild steel surface is investigated by quantum chemical calculation and molecular dynamics simulation. Quantum chemical parameters such as EHOMO, ELUMO, energy gap (ΔE), dipolemoment (μ), electronegativity (χ), global hardness (η) and fraction of electron transfers from the inhibitor molecule to the metallic atom surface (ΔN) have been studied to investigate their relative corrosion inhibition performance. Parameters like local reactive sites of the present molecule have been analyzed through Fukui indices. Moreover, adsorption behavior of the inhibitor molecules on Fe (1 1 0) surface have been analyzed using molecular dynamics simulation. The binding strength of the concerned inhibitor molecules on mild steel surface follows the order MMQT>PMQ, which is in good agreement with the experimentally determined inhibition efficiencies. In view of the above, our approach will be helpful for quick prediction of a potential inhibitor from a lot of similar inhibitors and subsequently in their rational designed synthesis for corrosion inhibition application following a wet chemical synthetic route.

  10. Alkoxide coordination of iron(III) protoporphyrin IX by antimalarial quinoline methanols: a key interaction observed in the solid-state and solution. (United States)

    Gildenhuys, Johandie; Sammy, Chandre J; Müller, Ronel; Streltsov, Victor A; le Roex, Tanya; Kuter, David; de Villiers, Katherine A


    The quinoline methanol antimalarial drug mefloquine is a structural analogue of the Cinchona alkaloids, quinine and quinidine. We have elucidated the single crystal X-ray diffraction structure of the complexes formed between racemic erythro mefloquine and ferriprotoporphyrin IX (Fe(iii)PPIX) and show that alkoxide coordination is a key interaction in the solid-state. Mass spectrometry confirms the existence of coordination complexes of quinine, quinidine and mefloquine to Fe(iii)PPIX in acetonitrile. The length of the iron(iii)-O bond in the quinine and quinidine complexes as determined by Extended X-ray Absorption Fine Structure (EXAFS) spectroscopy unequivocally confirms that coordination of the quinoline methanol compounds to Fe(iii)PPIX occurs in non-aqueous aprotic solution via their benzylic alkoxide functional group. UV-visible spectrophotometric titrations of the low-spin bis-pyridyl-Fe(iii)PPIX complex with each of the quinoline methanol compounds results in the displacement of a single pyridine molecule and subsequent formation of a six-coordinate pyridine-Fe(iii)PPIX-drug complex. We propose that formation of the drug-Fe(iii)PPIX coordination complexes is favoured in a non-aqueous environment, such as that found in lipid bodies or membranes in the malaria parasite, and that their existence may contribute to the mechanism of haemozoin inhibition or other toxicity effects that lead ultimately to parasite death. In either case, coordination is a key interaction to be considered in the design of novel antimalarial drug candidates.

  11. Poly[(μ(4)-3-carb-oxy-benzoato-κO:O,O:O:O)(quinolin-8-olato-κN,O)lead(II)]. (United States)

    Ghaemi, Akbar; Dadkhah, Zohreh; Ng, Seik Weng; Tiekink, Edward R T


    The asymmetric unit of the title complex, [Pb(C(8)H(5)O(4))(C(9)H(6)NO)](n), comprises a Pb(II) cation, a quinolin-8-olate anion and a 3-carb-oxy-benzoate anion. The coordination geometry of the Pb(II) atom is defined by one N and six O atoms, as well as a stereochemically active lone pair of electrons, and is based on a Ψ-dodeca-hedron. The quinolin-8-olate is chelating and the 3-carb-oxy-benzoate anion forms bonds to four different Pb(II) atoms. The benzoate end of the 3-carb-oxy-benzoate ligand chelates one Pb(II) atom and simultaneously bridges two Pb(II) atoms on either side, forming a chain along the b axis. The carboxyl end of the 3-carb-oxy-benzoate connects to a neighbouring chain by employing its carbonyl atom to form a bond to a Pb(II) atom and the hydroxyl group to form a hydrogen bond to a quinolin-8-olate O atom. Thereby, a layer is formed in the bc plane.

  12. Synthesis of quinoline derivatives containing pyrazole group and investigation of their crystal structure and spectroscopic properties in relation to acidity and alkalinity of mediums (United States)

    Ren, Tiegang; Wang, Jie; Li, Guihui; Cheng, Hongbin; Li, Yongzhe


    Two series of quinoline derivatives containing pyrazole group were synthesized and characterized by means of 1H NMR, FT-IR, MS, elemental analysis and X-ray single crystal diffraction, and their UV-vis absorption behavior and fluorescence properties were also measured. Moreover, the effects of acetic acid and triethylamine on the spectroscopic properties of synthesized products were examined with compounds 3a and 5a as examples. It has been found that all synthesized quinoline derivatives show maximum absorption peak at 303 nm and emission peaks around 445 nm. Besides, both acetic acid and triethylamine can change the acidity of the medium, thereby influencing the UV-vis absorption spectra and fluorescence spectra of synthesized products. Moreover, theoretical investigations indicate that the integration of H+ and N atom of quinoline ring favors the formation of a new product in the presence of acetic acid, and the product obtained in this case shows a new UV-vis absorption peak at 400 nm.

  13. Bioremediation of quinolin-contaminated soil by white rot fungi%白腐真菌对受喹啉污染模拟土壤的生物修复研究

    Institute of Scientific and Technical Information of China (English)

    瞿晶晶; 王玲; 王晓书; 沈珊; 任大军


    通过引入白腐真菌对受喹啉污染的模拟土壤进行生物修复.结果表明,白腐真菌对受喹啉污染土壤的生物修复是可行的;土壤含水率升高,喹啉去除率提高;投菌量越大,喹啉的去除效果越显著;不同pH土壤中的白腐真菌对喹啉降解差异不大,添加木屑能为白腐真菌提供额外的营养源,对土壤中喹啉的降解起到了促进作用.%White rot fungi Pleurotus ostreatus was selected to degrade quinoline in simulated soil,and the effect of soil moisture,fungi inoculum size,soil pH and wood dust on degradation efficiency was investigated. Results showed it was feasible to bioremediation quinolin-contaminated soil by white rot fungi. The removal rate of quinoline was increased with'increasing the soil moisture,higher inoculim size of fungi resulted in a higher degradation rate of quinoline,while soil pH had little effect on quinoline degradation. Addition of wood dust could promote quinoline degradation for it provided nutrition source to white rot fungi. The mechanism of quinoline degradation by white rot fungi still needed further exploration and study.

  14. A Redox-Active Fluorescent pH Indicator for Detecting Plasmodium falciparum Strains with Reduced Responsiveness to Quinoline Antimalarial Drugs. (United States)

    Jida, Mouhamad; Sanchez, Cecilia P; Urgin, Karène; Ehrhardt, Katharina; Mounien, Saravanan; Geyer, Aurelia; Elhabiri, Mourad; Lanzer, Michael; Davioud-Charvet, Elisabeth


    Mutational changes in the Plasmodium falciparum chloroquine resistance transporter (PfCRT) have been associated with differential responses to a wide spectrum of biologically active compounds including current and former quinoline and quinoline-like antimalarial drugs. PfCRT confers altered drug responsiveness by acting as a transport system, expelling drugs from the parasite's digestive vacuole where these drugs exert, at least part of, their antiplasmodial activity. To preserve the efficacy of these invaluable drugs, novel functional tools are required for epidemiological surveys of parasite strains carrying mutant PfCRT variants and for drug development programs aimed at inhibiting or circumventing the action of PfCRT. Here we report the synthesis and characterization of a pH-sensitive fluorescent chloroquine analogue consisting of 7-chloro-N-{2-[(propan-2-yl)amino]ethyl}quinolin-4-amine functionalized with the fluorochrome 7-nitrobenzofurazan (NBD) (henceforth termed Fluo-CQ). In the parasite, Fluo-CQ accumulates in the digestive vacuole, giving rise to a strong fluorescence signal but only in parasites carrying the wild type PfCRT. In parasites carrying the mutant PfCRT, Fluo-CQ does not accumulate. The differential handling of the fluorescent probe, combined with live cell imaging, provides a diagnostic tool for quick detection of those P. falciparum strains that carry a PfCRT variant associated with altered responsiveness to quinoline and quinoline-like antimalarial drugs. In contrast to the accumulation studies, chloroquine (CQ)-resistant parasites were observed cross-resistant to Fluo-CQ when the chemical probe was tested in various CQ-sensitive and -resistant parasite strains. NBD derivatives were found to act as redox cyclers of two essential targets, using a coupled assay based on methemoglobin and the NADPH-dependent glutathione reductase (GRs) from P. falciparum. This redox activity is proposed to contribute to the dual action of Fluo-CQ on redox

  15. Quinoline-based clioquinol and nitroxoline exhibit anticancer activity inducing FoxM1 inhibition in cholangiocarcinoma cells

    Directory of Open Access Journals (Sweden)

    Chan-on W


    Full Text Available Waraporn Chan-on,1 Nguyen Thi Bich Huyen,2 Napat Songtawee,3 Wilasinee Suwanjang,1 Supaluk Prachayasittikul,3 Virapong Prachayasittikul2 1Center for Research and Innovation, 2Department of Clinical Microbiology and Applied Technology, 3Center of Data Mining and Biomedical Informatics, Faculty of Medical Technology, Mahidol University, Bangkok, Thailand Purpose: Fork head box M1 (FoxM1 is an oncogenic transcription factor frequently elevated in numerous cancers, including cholangiocarcinoma (CCA. A growing body of evidence documents its diverse functions contributing to tumorigenesis and cancer progression. As such, discovery of agents that can target FoxM1 would be valuable for the treatment of CCA. The quinoline-based compounds, namely clioquinol (CQ and nitroxoline (NQ, represent a new class of anticancer drug. However, their efficacy and underlying mechanisms have not been elucidated in CCA. In this study, anticancer activities and inhibitory effects of CQ and NQ on FoxM1 signaling were explored using CCA cells.Methods: The effects of CQ and NQ on cell viability and proliferation were evaluated using the colorimetric 3-(4,5-dimethylthiazol-2yl-5-(3-carboxymethoxyphenyl-(4-sulfophenyl-2H-tetrazolium (MTS assay. Colony formation and cell migration affected by CQ and NQ were investigated using a clonogenic and a wound healing assay, respectively. To demonstrate the agents’ effects on FoxM1 signaling, expression levels of the target genes were quantitatively determined using real-time polymerase chain reaction.Results: CQ and NQ significantly inhibited cell survival of HuCCT1 and Huh28 in a dose- and a time-dependent fashion. Further investigations using the rapidly proliferating HuCCT1 cells revealed significant suppression of cell proliferation and colony formation induced by low doses of the compounds. Treatment of CQ and NQ repressed expression of cyclin D1 but enhanced expression of p21. Most importantly, upon CQ and NQ treatment

  16. The effect of the nanosize on surface properties of NiO nanoparticles for the adsorption of Quinolin-65. (United States)

    Marei, Nedal N; Nassar, Nashaat N; Vitale, Gerardo


    Using Quinolin-65 (Q-65) as a model-adsorbing compound for polar heavy hydrocarbons, the nanosize effect of NiO nanoparticles on the adsorption of Q-65 was investigated. Different-sized NiO nanoparticles with sizes between 5 and 80 nm were prepared by the controlled thermal dehydroxylation of Ni(OH)2. The properties of the nanoparticles were characterized using XRD, BET, FTIR, HRTEM and TGA. The effects of the nanosize on the textural properties, the shape and the morphology were studied. The adsorption of Q-65 molecules onto different-sized nanoparticles was tested in toluene-based solutions. On a normalized surface area basis, the number of Q-65 molecules adsorbed per nm(2) of the NiO surface was the highest for NiO nanoparticles of size 80 nm, while that for 5 nm sized NiO nanoparticles was the lowest. Excitingly, the adsorption capacity of other NiO sizes varied from loading suggesting different adsorption behavior, which exhibits the significance of textural properties during the adsorption of Q-65. Computational modeling of the interaction between the Q-65 molecule and the NiO nanoparticle surface was carried out to get more understanding of its adsorption behavior. A number of factors contributing to the enhanced adsorption capacity of nanoscale NiO were determined. These include surface reactivity, topology, morphology and textural properties.

  17. Development of a New Radiofluorinated Quinoline Analog for PET Imaging of Phosphodiesterase 5 (PDE5 in Brain

    Directory of Open Access Journals (Sweden)

    Jianrong Liu


    Full Text Available Phosphodiesterases (PDEs are enzymes that play a major role in cell signalling by hydrolysing the secondary messengers cyclic adenosine monophosphate (cAMP and/or cyclic guanosine monophosphate (cGMP throughout the body and brain. Altered cyclic nucleotide-mediated signalling has been associated with a wide array of disorders, including neurodegenerative disorders. Recently, PDE5 has been shown to be involved in neurodegenerative disorders such as Alzheimer’s disease, but its precise role has not been elucidated yet. To visualize and quantify the expression of this enzyme in brain, we developed a radiotracer for specific PET imaging of PDE5. A quinoline-based lead compound has been structurally modified resulting in the fluoroethoxymethyl derivative ICF24027 with high inhibitory activity towards PDE5 (IC50 = 1.86 nM. Radiolabelling with fluorine-18 was performed by a one-step nucleophilic substitution reaction using a tosylate precursor (RCY(EOB = 12.9% ± 1.8%; RCP > 99%; SA(EOS = 70–126 GBq/μmol. In vitro autoradiographic studies of [18F]ICF24027 on different mouse tissue as well as on porcine brain slices demonstrated a moderate specific binding to PDE5. In vivo studies in mice revealed that [18F]ICF24027 was metabolized under formation of brain penetrable radiometabolites making the radiotracer unsuitable for PET imaging of PDE5 in brain.

  18. Quinoline Alkaloids Isolated from Choisya Aztec-Pearl and Their Contribution to the Overall Antinociceptive Activity of This Plant (United States)

    Pinheiro, Mariana Martins; Fernandes, Patricia Dias


    Choisya ‘Aztec-Pearl’, a hybrid of Choisya ternata and Choisya dumosa var. arizonica, had the antinociceptive activity in the ethanol extract (EECA) of its leaves evaluated. Two quinoline alkaloids, anhydroevoxine (A) and choisyine (C), isolated from these leaves were also tested. The results obtained pointed out to a very high antinociceptive activity measured by the hot plate model for EECA (at doses of 10, 30 and 100 mg/kg) as well as for A and C (at doses of 1, 3 and 10 mg/kg). The magnitude of the activity was two-fold higher than the one observed for the morphine treated animals for the higher doses of extracts/compounds (30, 100 mg/kg and 3, 10 mg/kg respectively). The mechanism of action for this activity was also investigated and it seems that for EECA as well as A and C, the opiate system plays an important role. Results have also shown that the nitric oxide (NO) system also play a pivotal role in the case of EECA and A while for C it seems that the cholinergic system have some involvement. The acute toxicity was evaluated for EECA with results showing no important toxic effect. PMID:27768733

  19. Solid phase extractive preconcentration of uranium(VI) using quinoline-8-ol anchored chloromethylated polymeric resin beads. (United States)

    Praveen, R S; Metilda, P; Daniel, S; Rao, T Prasada


    A new chelating polymeric sorbent has been developed using Merrifield chloromethylated resin anchored with quinoline-8-ol (HQ). The modified polymeric resin was characterized by FT-IR spectroscopy and elemental analysis. The HQ anchored resin showed superior binding affinity for U(VI) over Th(IV) and La(III). The influence of various physicochemical parameters on the recovery of U(VI) were optimized by both static and dynamic methods. The phase exchange kinetic studies performed for U(VI) revealed that XAD-16. The developed HQ anchored polymeric resin is highly selective as none of the extraneous species were found to have any deleterious effect. Solid phase extraction (SPE) studies performed using HQ anchored polymeric resin offered enrichment factor of 100 and the lowest concentration below which recoveries become non-quantitative is 5mugl(-1). The accuracy of the developed SPE method in conjunction with Arsenazo III procedure was tested by analyzing marine sediment (MESS-3) and soil (IAEA-Soil 7) reference materials. Furthermore, the above procedure has been successfully employed for the analysis of real soil and sediment samples.

  20. Low-temperature spectra of the analogues of 10-hydroxybenzo[h]quinoline as an indication of barrierless ESIPT. (United States)

    Deperasińska, Irena; Gryko, Daniel T; Karpiuk, Elena; Kozankiewicz, Bolesław; Makarewicz, Artur; Piechowska, Joanna


    The absorption and fluorescence spectra of two analogues of 10-hydroxybenzo[h]quinoline (10-HBQ), namely, 1-hydroxy-7-methylbenzo[c]acridine (HMBA) and 4-hydroxybenzo[c]phenanthridine (HBPA), were studied in n-alkane matrices at 5 K. Considerable energy separation between the onsets of the spectra and broadening of the bands was an indication that intramolecular proton transfer (ESIPT) takes place at such a low temperature. DFT and ab initio methods were used to calculate the electronic transition energies and oscillator strengths and the vibronic structure of the electronic spectra. Shortcomings in our knowledge of the shape of the potential energy surface for ESIPT systems are highlighted in the context of the discussion of the shape of the electronic spectra. The π-expansion of the 10-HBQ chromophore achieved by adding a benzene moiety at various positions adjacent to the pyridine ring led to compounds possessing diverse photophysical properties, ranging from the non-ESIPT strongly fluorescent molecule of 10-hydroxy-1-azaperylene to weakly emitting (or nonemitting) molecules, where ESIPT occurs very efficiently.

  1. Profiling the Interaction Mechanism of Quinoline/Quinazoline Derivatives as MCHR1 Antagonists: An in Silico Method (United States)

    Wu, Mingwei; Li, Yan; Fu, Xinmei; Wang, Jinghui; Zhang, Shuwei; Yang, Ling


    Melanin concentrating hormone receptor 1 (MCHR1), a crucial regulator of energy homeostasis involved in the control of feeding and energy metabolism, is a promising target for treatment of obesity. In the present work, the up-to-date largest set of 181 quinoline/quinazoline derivatives as MCHR1 antagonists was subjected to both ligand- and receptor-based three-dimensional quantitative structure–activity (3D-QSAR) analysis applying comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). The optimal predictable CoMSIA model exhibited significant validity with the cross-validated correlation coefficient (Q2) = 0.509, non-cross-validated correlation coefficient (R2ncv) = 0.841 and the predicted correlation coefficient (R2pred) = 0.745. In addition, docking studies and molecular dynamics (MD) simulations were carried out for further elucidation of the binding modes of MCHR1 antagonists. MD simulations in both water and lipid bilayer systems were performed. We hope that the obtained models and information may help to provide an insight into the interaction mechanism of MCHR1 antagonists and facilitate the design and optimization of novel antagonists as anti-obesity agents. PMID:25257526

  2. A diverse bacterial community in an anoxic quinoline-degrading bioreactor determined by using pyrosequencing and clone library analysis. (United States)

    Zhang, Xiaojun; Yue, Siqing; Zhong, Huihui; Hua, Weiying; Chen, Ruijia; Cao, Youfang; Zhao, Liping


    There is a concern of whether the structure and diversity of a microbial community can be effectively revealed by short-length pyrosequencing reads. In this study, we performed a microbial community analysis on a sample from a high-efficiency denitrifying quinoline-degrading bioreactor and compared the results generated by pyrosequencing with those generated by clone library technology. By both technologies, 16S rRNA gene analysis indicated that the bacteria in the sample were closely related to, for example, Proteobacteria, Actinobacteria, and Bacteroidetes. The sequences belonging to Rhodococcus were the most predominant, and Pseudomonas, Sphingomonas, Acidovorax, and Zoogloea were also abundant. Both methods revealed a similar overall bacterial community structure. However, the 622 pyrosequencing reads of the hypervariable V3 region of the 16S rRNA gene revealed much higher bacterial diversity than the 130 sequences from the full-length 16S rRNA gene clone library. The 92 operational taxonomic unit (OTUs) detected using pyrosequencing belonged to 45 families, whereas the 37 OTUs found in the clone library belonged to 25 families. Most sequences obtained from the clone library had equivalents in the pyrosequencing reads. However, 64 OTUs detected by pyrosequencing were not represented in the clone library. Our results demonstrate that pyrosequencing of the V3 region of the 16S rRNA gene is not only a powerful tool for discovering low-abundance bacterial populations but is also reliable for dissecting the bacterial community structure in a wastewater environment.

  3. Modeling the Interaction between Quinolinate and the Receptor for Advanced Glycation End Products (RAGE): Relevance for Early Neuropathological Processes (United States)

    Serratos, Iris N.; Castellanos, Pilar; Pastor, Nina; Millán-Pacheco, César; Rembao, Daniel; Pérez-Montfort, Ruy; Cabrera, Nallely; Reyes-Espinosa, Francisco; Díaz-Garrido, Paulina; López-Macay, Ambar; Martínez-Flores, Karina; López-Reyes, Alberto; Sánchez-García, Aurora; Cuevas, Elvis; Santamaria, Abel


    The receptor for advanced glycation end products (RAGE) is a pattern-recognition receptor involved in neurodegenerative and inflammatory disorders. RAGE induces cellular signaling upon binding to a variety of ligands. Evidence suggests that RAGE up-regulation is involved in quinolinate (QUIN)-induced toxicity. We investigated the QUIN-induced toxic events associated with early noxious responses, which might be linked to signaling cascades leading to cell death. The extent of early cellular damage caused by this receptor in the rat striatum was characterized by image processing methods. To document the direct interaction between QUIN and RAGE, we determined the binding constant (Kb) of RAGE (VC1 domain) with QUIN through a fluorescence assay. We modeled possible binding sites of QUIN to the VC1 domain for both rat and human RAGE. QUIN was found to bind at multiple sites to the VC1 dimer, each leading to particular mechanistic scenarios for the signaling evoked by QUIN binding, some of which directly alter RAGE oligomerization. This work contributes to the understanding of the phenomenon of RAGE-QUIN recognition, leading to the modulation of RAGE function. PMID:25757085

  4. Synthesis, antiproliferative activity and DNA binding properties of novel 5-aminobenzimidazo[1,2-a]quinoline-6-carbonitriles. (United States)

    Perin, Nataša; Nhili, Raja; Ester, Katja; Laine, William; Karminski-Zamola, Grace; Kralj, Marijeta; David-Cordonnier, Marie-Hélène; Hranjec, Marijana


    The synthesis of 5-amino substituted benzimidazo[1,2-a]quinolines prepared by microwave assisted amination from halogeno substituted precursor was described. The majority of compounds were active at micromolar concentrations against colon, lung and breast carcinoma cell lines in vitro. The N,N-dimethylaminopropyl 9 and piperazinyl substituted derivative 19 showed the most pronounced activity towards all of the three tested tumor cell lines, which could be correlated to the presence of another N heteroatom and its potential interactions with biological targets. The DNA binding studies, consisting of UV/Visible absorbency, melting temperature studies, and fluorescence and circular dichroism titrations, revealed that compounds 9, 19 and 20 bind to DNA as strong intercalators. The cellular distribution analysis, based on compounds' intrinsic fluorescence, showed that compound 20 does not enter the cell, while compounds 9 and 19 do, which is in agreement with their cytotoxic effects. Compound 9 efficiently targets the nucleus whereas 19, which also showed DNA intercalating properties in vitro, was mostly localised in the cytoplasm suggesting that the antitumor mechanism of action is DNA-independent. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  5. Inhibition of corrosion of mild steel in acid media by N′-benzylidene-3-(quinolin-4-ylthio)propanohydrazide

    Indian Academy of Sciences (India)

    V Ramesh Saliyan; Airody Vasudeva Adhikari


    In the present investigation a new corrosion inhibitor, N′-(3,4-dihydroxybenzylidene)-3-{[8-(trifluoromethyl) quinolin-4-yl]thio}propanohydrazide(DHBTPH) was synthesized, characterized and tested as a corrosion inhibitor for mild steel in HCl (1 M, 2 M) and H2SO4 (0.5 M, 1 M) solutions using weight-loss method, electrochemical impedance spectroscopy (EIS) and potentiodynamic polarization methods. The corrosion inhibition efficiency measured by all the above three techniques were in good agreement with each other. The results showed that DHBTPH is a very good inhibitor for mild steel in acidic media. The inhibition efficiency in different acid media was found to be in the decreasing order 0.5 M H2SO4 > 1 M HCl > 1 M H2SO4 > 2 M HCl. The inhibition efficiency increases with increasing inhibitor concentration and with increasing temperature. It acts as an anodic inhibitor. Thermodynamic and activation parameters are discussed. Adsorption of DHBTPH was found to follow the Langmuir’s adsorption isotherm. Chemisorption mechanism is proposed. The mild steel samples were also analysed by scanning electron microscopy (SEM).

  6. Modeling the interaction between quinolinate and the receptor for advanced glycation end products (RAGE: relevance for early neuropathological processes.

    Directory of Open Access Journals (Sweden)

    Iris N Serratos

    Full Text Available The receptor for advanced glycation end products (RAGE is a pattern-recognition receptor involved in neurodegenerative and inflammatory disorders. RAGE induces cellular signaling upon binding to a variety of ligands. Evidence suggests that RAGE up-regulation is involved in quinolinate (QUIN-induced toxicity. We investigated the QUIN-induced toxic events associated with early noxious responses, which might be linked to signaling cascades leading to cell death. The extent of early cellular damage caused by this receptor in the rat striatum was characterized by image processing methods. To document the direct interaction between QUIN and RAGE, we determined the binding constant (Kb of RAGE (VC1 domain with QUIN through a fluorescence assay. We modeled possible binding sites of QUIN to the VC1 domain for both rat and human RAGE. QUIN was found to bind at multiple sites to the VC1 dimer, each leading to particular mechanistic scenarios for the signaling evoked by QUIN binding, some of which directly alter RAGE oligomerization. This work contributes to the understanding of the phenomenon of RAGE-QUIN recognition, leading to the modulation of RAGE function.

  7. Application of N-Quinoline-2-carboxamido-8-aminoquinoline in Fabrication of a Ho(III-PVC Membrane Sensor

    Directory of Open Access Journals (Sweden)

    Hassan Ali Zamani


    Full Text Available The N-quinoline-2-carboxamido-8-aminoquinoline (QCA was used as a suitable ion carrier in the construction of a Ho(III PVC-based membrane sensor. This sensor demonstrated good selectivity and sensitivity towards the holmium ion for a broad variety of cations, including alkali, alkaline earth, transition and heavy metal ions. The proposed electrode exhibits a linear dynamic range between 1.0×10-6 and 1.0×10-2 M, with a near Nernstian slope of 20.4±0.3 mV per decade and a detection limit of 4.2×10-7 M. The best performance was obtained with a membrane composition of 30% poly(vinyl chloride, 56% nitrobenzene, 2% sodium tetraphenyl borate, 10% oleic acid and 2% QCA. The potentiometric response of the constructed electrode is pH independent in the range of 2.4-7.4. The sensor possesses the advantages of short conditioning time, fast response time (∼ 5 s and especially, good selectivity towards transition and heavy metal and some mono, di and trivalent cations. The Ho3+ sensor was successfully applied as an indicator electrode in the potentiometric titration of Ho(III ions with EDTA. The electrode was also used for the determination of Ho3+ ions in mixtures of different ions and the determination of the fluoride ion in mouth wash solutions.

  8. Sharp green electroluminescence from 1H-pyrazolo[3,4-b]quinoline-based light-emitting diodes (United States)

    Tao, Y. T.; Balasubramaniam, E.; Danel, A.; Jarosz, B.; Tomasik, P.


    A multilayer organic light-emitting diode was fabricated using a fluorescent compound {6-N,N-diethylamino-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoline} (PAQ-NEt2) doped into the hole-transporting layer of NPB {4,4'-bis[N-(1-naphthyl-1-)-N-phenyl-amino]-biphenyl}, with the TPBI {2,2',2″-(1,3,5-phenylene)tris[1-phenyl-1H-benzimidazole]} as an electrontransporting material. At 16% PAQ-NEt2 doping concentration, the device gave a sharp, bright, and efficient green electroluminescence (EL) peaked at around 530 nm. The full width at half maximum of the EL is 60 nm, which is 60% of the green emission from typical NPB/AlQ [where AlQ=tris(8-hydroxyquinoline) aluminum] device. For the same concentration, a maximum luminance of 37 000 cd/m2 was obtained at 10.0 V and the maximum power, luminescence, and external quantum efficiencies were obtained 4.2 lm/W, 6.0 cd/A, and 1.6%, respectively, at 5.0 V.

  9. Rapid and Green Analytical Method for the Determination of Quinoline Alkaloids from Cinchona succirubra Based on Microwave-Integrated Extraction and Leaching (MIEL Prior to High Performance Liquid Chromatography

    Directory of Open Access Journals (Sweden)

    Farid Chemat


    Full Text Available Quinas contains several compounds, such as quinoline alkaloids, principally quinine, quinidine, cinchonine and cichonidine. Identified from barks of Cinchona, quinine is still commonly used to treat human malaria. Microwave-Integrated Extraction and Leaching (MIEL is proposed for the extraction of quinoline alkaloids from bark of Cinchona succirubra. The process is performed in four steps, which ensures complete, rapid and accurate extraction of the samples. Optimal conditions for extraction were obtained using a response surface methodology reached from a central composite design. The MIEL extraction has been compared with a conventional technique soxhlet extraction. The extracts of quinoline alkaloids from C. succirubra obtained by these two different methods were compared by HPLC. The extracts obtained by MIEL in 32 min were quantitatively (yield and qualitatively (quinine, quinidine, cinchonine, cinchonidine similar to those obtained by conventional Soxhlet extraction in 3 hours. MIEL is a green technology that serves as a good alternative for the extraction of Cinchona alkaloids.

  10. Rapid and green analytical method for the determination of quinoline alkaloids from Cinchona succirubra based on Microwave-Integrated Extraction and Leaching (MIEL) prior to high performance liquid chromatography. (United States)

    Fabiano-Tixier, Anne-Sylvie; Elomri, Abdelhakim; Blanckaert, Axelle; Seguin, Elisabeth; Petitcolas, Emmanuel; Chemat, Farid


    Quinas contains several compounds, such as quinoline alkaloids, principally quinine, quinidine, cinchonine and cichonidine. Identified from barks of Cinchona, quinine is still commonly used to treat human malaria. Microwave-Integrated Extraction and Leaching (MIEL) is proposed for the extraction of quinoline alkaloids from bark of Cinchona succirubra. The process is performed in four steps, which ensures complete, rapid and accurate extraction of the samples. Optimal conditions for extraction were obtained using a response surface methodology reached from a central composite design. The MIEL extraction has been compared with a conventional technique soxhlet extraction. The extracts of quinoline alkaloids from C. succirubra obtained by these two different methods were compared by HPLC. The extracts obtained by MIEL in 32 min were quantitatively (yield) and qualitatively (quinine, quinidine, cinchonine, cinchonidine) similar to those obtained by conventional Soxhlet extraction in 3 hours. MIEL is a green technology that serves as a good alternative for the extraction of Cinchona alkaloids.

  11. Anti-uropathogenic activity, drug likeness, physicochemical and molecular docking assessment of(E-)-N’-(substituted-benzylidene)-2-(quinolin-8-yloxy) acetohydrazide

    Institute of Scientific and Technical Information of China (English)

    Essa; Ajmi; Alodeani; Mohammad; Arshad; Mohammad; Asrar; Izhari


    Objective: To deal with the anti-uropathogenic and in silico screening of(E-)-N’-(substitutedbenzylidene)-2-(quinolin-8-yloxy)acetohydrazide analogues in order to search the potential anti-uropathogenic agents.Methods: Three(E-)-N’-(substituted-benzylidene)-2-(quinolin-8-yloxy)acetohydrazide analogues were synthesized. Structure elucidation was done using various spectroscopic techniques including infrared radiation, 1hydrogen-nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, etc. Physicochemical score, bioactivity score and molecular docking studies were carried out using Lipinski’s rule of five, Molinspiration(web based software), Autodock 4.2 tools. In vitro anti-uropathogenic activity was carried out against four pathogens named as Staphylococcus aureus(S. aureus), Staphylococcus epidermidis, Proteus mirabilis and Escherichia coli by disc diffusion method and macro-dilution test following their morphological and biochemical characterization.Results: The formation of(E-)-N’-(substituted-benz ylidene)-2-(quinolin-8-yloxy)acetohydrazide is confirmed from the spectroscopic results. All the compounds were found in compliance with Lipinski’s rule of five and exhibited bioactivity score from-0.50 to 0.00. Docking results revealed that compound-1 is forming one hydrogen bond with TYR 576 and two hydrogen bond with GLU 569, while compound-2 is forming one hydrogen bond with ARG 599, and compound-3 forming 0 hydrogen bond. The anti-uropathogenic evaluation exhibited that compound one exhibited better activity against S. aureus, while it was found to possess moderate to good activity against both Gram-positive bacteria and Gram-negative bacteria excluding S. aureus.Conclusions: Our study revealed that compound one exhibited better activity than the standard in case of S. aureus and moderate to good activity against rest of the pathogens. Molecular docking, physicochemical and bioactivity studies strongly supported the experimental results. From

  12. Crystal structure and Hirshfeld surface analysis of ethyl 2-{[4-ethyl-5-(quinolin-8-yloxymeth­yl)-4H-1,2,4-triazol-3-yl]sulfan­yl}acetate (United States)

    Bahoussi, Rawia Imane; Djafri, Ahmed; Djafri, Ayada


    In the title compound, C18H20N4O3S, the 1,2,4-triazole ring is twisted with respect to the mean plane of quinoline moiety at 65.24 (4)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds, forming the three-dimensional supra­molecular packing. π–π stacking between the quinoline ring systems of neighbouring mol­ecules is also observed, the centroid-to-centroid distance being 3.6169 (6) Å. Hirshfeld surface (HS) analyses were performed. PMID:28217336

  13. Rice husk ash supported FeCl2·2H2O:A mild and highly efficient heterogeneous catalyst for the synthesis of polysubstituted quinolines by Friedländer heteroannulation

    Institute of Scientific and Technical Information of China (English)

    Farhad Shirini; Somayeh Akbari-Dadamahaleh; Ali Mohammad-Khah


    Rice husk ash was used as a new, green, and cheap adsorbent for FeCl3. Characterization of the ob-tained reagent showed that rice husk ash supported FeCl2·2H2O was formed. This reagent is effi-cient at catalyzing the synthesis of multisubstituted quinolines by the Friedländer heteroannulation of o-aminoaryl ketones with ketones orβ-diketones under mild reaction conditions. This method-ology allows for the synthesis of a broad range of substituted quinolines in high yields and with excellent regioselectivity in the absence of a solvent.

  14. Microwave assisted synthesis of novel Hantzsch 1,4-dihydropyridines, acridine-l,8-diones and polyhydroquinolines bearing the tetrazolo [1,5-a]quinoline moiety and their antimicrobial activity assess

    Institute of Scientific and Technical Information of China (English)

    Niraj K. Ladani; Divyesh C. Mungra; Manish P. Patel; Ranjan G. Patel


    Microwave assisted efficient Hantzsch reaction via four-component coupling reactions of tetrazolo [l,5-a]quinoline-4-carbal-dehyde, dimedone/cyclohexane-l,3-dione, ethyl/methyl acetoacetate and ammonium acetate was described as the preparation of tetrazolo [l,5-a]quinoline based 1,4-dihydropyridines, acridine-l,8-diones and polyhydroquinolines. The process presented here is simple, rapid, environmentally welcoming and high yielding. All the derivatives were subjected to an in vitro antimicrobial screening against a representative panel of bacteria and fungi and results worth further investigations.

  15. Synthesis and biological study of novel 5-{(4-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-ylsulfonyl)phenylamino)-methyl}-quinolin-8-ol and its metal complexes

    Institute of Scientific and Technical Information of China (English)

    Paresh N. Patel; Khyati D. Patel; Hasmukh S. Patel


    A novel 5-((4-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)phenylamino)methyl)quinolin-8-ol (HTPSMQol) was synthesized by optimized reaction of 4-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)aniline with 5-chloromethyI-8-hydroxy_ quinoline hydrochloride (CMHQ). Also complexes of HTPSMQol were prepared by using various M (II) metal salts. All compounds were analyzed by spectroscopic techniques and screened against various strains of microorganisms. The results showed higher antimicrobial activity of HTPSMQol compared to its metal complexes and comparable with Ciprofloxacin.

  16. Substituted quinolinones. Part 17: Some nucleophilic reactions with 4-hydroxy-1-methyl-3-[(2-oxo-2-chromen-3-yl)carbonyl]quinolin-2(1)-one

    Indian Academy of Sciences (India)

    Mohamed Abass; El-Hussain A Mohamed; Aisha S Mayas; Akram H Ibrahim


    The reactivity of 4-hydroxy-1-methyl-3-[(2-oxo-2-chromen-3-yl)carbonyl]-quinolin-2(1)-one (2), as a new asymmetric diheterocyclic ketone, towards different nucleophilic reagents, was examined. The reaction of the ketone 2 with hydrazine led to pyrazolinone 5, and excess of hydrazine pyrazolinopyrazole 7 was obtained. Treatment of the ketone 2 with 2,2-dimethoxyethanamine gave pyrrolocoumarin 12, while cyanoguanidine afforded pyrimidinone 15. Under PTC conditions, the ketone 2 was reacted with chloroacetonitrile, diethyl malonate, ethyl cyanoacetate, malononitrile, and cyanoacetamide to give coumarinyl furoquinoline 18, pyranoquinolines 20a, 20b, 21, and benzonaphthyridine 22, respectively.

  17. Synthesis of novel precursors of Pfitzinger reaction: A facile one-pot strategy to the synthesis of quinoline carboxylic acid derivatives of pyrazolo-carbazoles and azacarbazoles

    Indian Academy of Sciences (India)

    Ruchi Tyagi; Bhawani Singh; D Kishore


    Interaction of 5-indazolyldiazonium chloride 2 with 2-hydroxymethylidene cyclohexanone 5 and -benzyl-3-hydroxymethylidene-4-piperidone 6 under the conditions of Japp-Klingemann reaction, followed by Fischer-indolization of the resulting hydrazones, formed the 5,7,8,9-tetrahydropyrazolo[4,3-b]carbazol- 6(1)-one 9 and 9-benzyl-5,7,8,9-tetrahydropyrido[2',3':4,5]pyrrolo[2,3-f]indazol-6(1)-one 10, respectively. Pfitzinger reaction of 9 and 10 with isatin in alkali afforded the corresponding quinoline carboxylic acid derivatives 12 and 13, respectively.

  18. Hydrogen bonding study of quinoline and coal-derived asphaltene components with o-phenylphenol by proton magnetic resonance. [9 references

    Energy Technology Data Exchange (ETDEWEB)

    Taylor, S.R.; Galya, L.G.; Brown, B.J.; Li, N.C.


    Proton magnetic resonance (PMR) studies are reported of hydrogen bonding between the OH proton of o-phenylphenol (OPP) and the nitrogen electron donor of quinoline (Qu). Data are also reported on the hydrogen bonding of a coal-derived asphaltene and its acid and base components with OPP. Determination was made of the equilibrium constants of the 1 : 1 complex between OPP and Qu at 39, 32, 1, and -18/sup 0/C from the PMR studies. Qualitative results are reported for the interaction between the base fraction of asphaltene and OPP at 32, 1, and -26/sup 0/C.

  19. Hydrogen bonding study of quinoline and coal-derived asphaltene components with o-phenylphenol by proton magnetic resonance. [9 refs

    Energy Technology Data Exchange (ETDEWEB)

    Taylor, S.C.; Galya, L.G.; Brown, B.J.; Li, N.C.


    Proton magnetic resonance (PMR) studies are reported of hydrogen bonding between the OH proton of o-phenylphenol (OPP) and the nitrogen electron donor of quinoline (Qu). Data are also reported on the hydrogen bonding of a coal-derived asphaltene and its acid and base components with OPP. Determination was made of the equilibrium constants of the 1:1 complex between OPP and Qu at 39, 32, 1, and -18/sup 0/C from the PMR studies. Qualitative results are reported for the interaction between the base fraction of asphaltene and OPP at 32, 1, and -26/sup 0/C.

  20. Synthesis of 4-substituted oxazolo[4,5-c]quinolines by direct reaction at the C-4 position of oxazoles. (United States)

    Akula, Mahesh; Thigulla, Yadagiri; Davis, Connor; Jha, Mukund; Bhattacharya, Anupam


    A facile synthesis of 4-aryl substituted oxazolo[4,5-c]quinolines has been described via a modified Pictet-Spengler method and using Cu(TFA)2 as a catalyst. The developed methodology directly functionalizes the C-4 position of oxazoles without the aid of any prefunctionalization, in the presence of the more reactive C-2 position in good yields. The versatility of the established method has been demonstrated by its application in the synthesis of 4-substituted oxazolo-[1,8]naphthyridine ring systems.

  1. Amberlite-IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo [1,2-a] quinolines and isoquinolines: antibacterial and antifungal evaluation of the products. (United States)

    Hazra, Abhijit; Mondal, Shyamal; Maity, Arindam; Naskar, Subhendu; Saha, Pritam; Paira, Rupankar; Sahu, Krishnendu B; Paira, Priyankar; Ghosh, Soma; Sinha, Chandrima; Samanta, Amalesh; Banerjee, Sukdeb; Mondal, Nirup B


    A number of indolizines and pyrrolo[1,2-a]quinolines/isoquinolines were prepared from phenacyl pyridinium, quinolinium and isoquinolinium salts derived from the reaction of the heterocycles with 2-bromo acetophenone with alkynes and alkenes using amberlite-IRA-402 (OH) ion exchange resin as the base. Antibacterial and antifungal studies were carried out against thirteen bacterial and four fungal strains, which revealed that three derivatives (4a, 4b, 7a) out of fifteen are effective against all the thirteen strains and one derivative, 10, showed dual antibactericidal and antifungal efficacy.

  2. Regulation of quinolinic acid neosynthesis in mouse, rat and human brain by iron and iron chelators in vitro. (United States)

    Stachowski, Erin K; Schwarcz, Robert


    Several lines of evidence indicate that excess iron may play an etiologically significant role in neurodegenerative disorders. This idea is supported, for example, by experimental studies in animals demonstrating significant neuroprotection by iron chelation. Here, we tested whether this effect might be related to a functional link between iron and the endogenous excitotoxin quinolinic acid (QUIN), a presumed pathogen in several neurological disorders. In particular, the present in vitro study was designed to examine the effects of Fe(2+), a known co-factor of oxygenases, on the activity of QUIN's immediate biosynthetic enzyme, 3-hydroxyanthranilic acid dioxygenase (3HAO), in the brain. In crude tissue homogenate, addition of Fe(2+) (2-40 μM) stimulated 3HAO activity 4- to 6-fold in all three species tested (mouse, rat and human). The slope of the iron curve was steepest in rat brain where an increase from 6 to 14 μM resulted in a more than fivefold higher enzyme activity. In all species, the Fe(2+)-induced increase in 3HAO activity was dose-dependently attenuated by the addition of ferritin, the main iron storage protein in the brain. The effect of iron was also readily prevented by N,N'-bis(2-hydroxybenzyl) ethylenediamine-N,N'-diacetic acid (HBED), a synthetic iron chelator with neuroprotective properties in vivo. All these effects were reproduced using neostriatal tissue obtained postmortem from normal individuals and patients with end-stage Huntington's disease. Our results suggest that QUIN levels and function in the mammalian brain might be tightly controlled by endogenous iron and proteins that regulate the bioavailability of iron.

  3. Design, synthesis, physicochemical studies, solvation, and DNA damage of quinoline-appended chalcone derivative: comprehensive spectroscopic approach toward drug discovery. (United States)

    Kumar, Himank; Chattopadhyay, Anjan; Prasath, R; Devaraji, Vinod; Joshi, Ritika; Bhavana, P; Saini, Praveen; Ghosh, Sujit Kumar


    The present study epitomizes the design, synthesis, photophysics, solvation, and interaction with calf-thymus DNA of a potential antitumor, anticancer quinoline-appended chalcone derivative, (E)-3-(anthracen-10-yl)-1-(6,8-dibromo-2-methylquinolin-3-yl)prop-2-en-1-one (ADMQ) using steady state absorption and fluorescence spectroscopy, molecular modeling, molecular docking, Fourier-transform infrared spectroscopy (FTIR), molecular dynamics (MD) simulation, and gel electrophoresis studies. ADMQ shows an unusual photophysical behavior in a variety of solvents of different polarity. The dual emission has been observed along with the formation of twisted intramolecular charge transfer (TICT) excited state. The radiationless deactivation of the TICT state is found to be promoted strongly by hydrogen bonding. Quantum mechanical (DFT, TDDFT, and ZINDO-CI) calculations show that the ADMQ is sort of molecular rotor which undergoes intramolecular twist followed by a complete charge transfer in the optimized excited state. FTIR studies reveals that ADMQ undergoes important structural change from its native structure to a β-hydroxy keto form in water at physiological pH. The concentration-dependent DNA cleavage has been identified in agarose gel DNA electrophoresis experiment and has been further supported by MD simulation. ADMQ forms hydrogen bond with the deoxyribose sugar attached with the nucleobase adenine DA-17 (chain A) and result in significant structural changes which potentially cleave DNA double helix. The compound does not exhibit any deleterious effect or toxicity to the E. coli strain in cytotoxicity studies. The consolidated spectroscopic research described herein can provide enormous information to open up new avenues for designing and synthesizing chalcone derivatives with low systematic toxicity for medicinal chemistry research.

  4. Computational and Experimental Study on Molecular Structure of Benzo[g]pyrimido[4,5-b]quinoline Derivatives: Preference of Linear over the Angular Isomer

    Directory of Open Access Journals (Sweden)

    Jorge Trilleras


    Full Text Available A series of 5-aryl-2-methylthio-5,12-dihydrobenzo[g]pyrimido[4,5-b]quinoline-4,6,11(3H-trione was synthesized through an environmental friendly multicomponent methodology and characterized with FT-IR (Fourier Transform infrared spectroscopy, 1H NMR (Nuclear Magnetic Resonance , 13C NMR and GC-MS (gas chromatography-mass spectrometry. The 5-(4-methoxyphenyl-2-methylthio-5,12-dihydrobenzo[g]pyrimido[4,5-b]quinoline-4,6,11(3H-trione 4c compound was characterized by X-ray single crystal diffraction. The geometry of 4c has been fully optimized using DFT (Density functional theory, B3LYP functional and 6-31G(d,p basis set, thus establishing the ground state energy and thermodynamic features for the mentioned compound, which are in accordance with the experimental data and the crystal structure. The experimental results reveal a strong preference for the regioselective formation of 4c linear four fused rings over the angular four fused and suggest a possible kinetic control in product formation.

  5. Quinolinic acid/tryptophan ratios predict neurological disease in SIV-infected macaques and remain elevated in the brain under cART (United States)

    Drewes, Julia L.; Meulendyke, Kelly A.; Liao, Zhaohao; Witwer, Kenneth W.; Gama, Lucio; Ubaida-Mohien, Ceereena; Li, Ming; Notarangelo, Francesca M.; Tarwater, Patrick M.; Schwarcz, Robert; Graham, David R.; Zink, M. Christine


    Activation of the kynurenine pathway (KP) of tryptophan catabolism likely contributes to HIV-associated neurological disorders. However, KP activation in brain tissue during HIV infection has been understudied, and the effect of combination anti-retroviral therapy (cART) on KP induction in the brain is unknown. To examine these questions, tryptophan, kynurenine, 3-hydroxykynurenine, quinolinic acid, and serotonin levels were measured longitudinally during SIV infection in striatum and CSF from untreated and cART-treated pigtailed macaques. mRNA levels of KP enzymes also were measured in striatum. In untreated macaques, elevations in KP metabolites coincided with transcriptional induction of upstream enzymes in the KP. Striatal KP induction was also temporally associated - but did not directly correlate - with serotonin losses in the brain. CSF quinolinic acid/tryptophan ratios were found to be the earliest predictor of neurological disease in untreated SIV-infected macaques, outperforming other KP metabolites as well as the putative biomarkers Interleukin-6 (IL-6) and Monocyte chemoattractant protein-1 (MCP-1). Finally, cART did not restore KP metabolites to control levels in striatum despite control of virus, though CSF metabolite levels were normalized in most animals. Overall these results demonstrate that cerebral KP activation is only partially resolved with cART, and that CSF QUIN/TRP ratios are an early, predictive biomarker of CNS disease. PMID:25776527

  6. Discovery of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinolin-4-amine derivatives as novel VEGFR-2 kinase inhibitors. (United States)

    Shi, Lei; Wu, Ting-Ting; Wang, Zhi; Xue, Jia-Yu; Xu, Yun-Gen


    Inhibition of the VEGF signaling pathway has become a valuable approach in the treatment of cancers. In this work, a series of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinolin-4-amine derivatives were designed and identified as potent inhibitors of VEGFR-2 (KDR) kinase. These compounds with quinoline scaffold and benzimidazole moiety were synthesized and their biological activities against VEGFR-2 and two human cancer cell lines were evaluated. Among them, compound 7s exhibited the most potent inhibitory activity against VEGFR-2 with IC50 of 0.03 μM and it also showed the highest anticancer activity against the tested cancer cell lines with IC50 of 1.2 μM against MCF-7 and 13.3 μM against Hep-G2. Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of VEGFR-2, which demonstrates that compound 7s is a potential agent for cancer therapy deserving further researching. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

  7. Quinolino[3,4-b]quinoxalines and pyridazino[4,3-c]quinoline derivatives: Synthesis, inhibition of topoisomerase IIα, G-quadruplex binding and cytotoxic properties. (United States)

    Palluotto, Fausta; Sosic, Alice; Pinato, Odra; Zoidis, Grigoris; Catto, Marco; Sissi, Claudia; Gatto, Barbara; Carotti, Angelo


    The quinoline motif fused with other heterocyclic systems plays an important role in the field of anticancer drug development. An extensive series of tetracyclic quinolino[3,4-b]quinoxalines N-5 or C-6 substituted with basic side chain and a limited number of tricyclic pyridazino[4,3-c]quinolines N-6 substituted were designed, synthesized and evaluated for topoisomerase IIα (Topo IIα) inhibitory activity, ability to bind and stabilize G-quadruplex structures and cytotoxic properties against two human cancer cell lines (HeLa and MCF-7). Almost all of the tested agents showed a high activity as Topo IIα inhibitors and G-quadruplex stabilizers. Among all the derivatives studied, the quinolino[3,4-b]quinoxalines 11 and 23, N-5 and C-6 substituted respectively, stand out as the most promising compounds. Derivative 11 resulted a selective binder to selected G-quadruplex sequences, while derivative 23 displayed the most interesting Topo IIα inhibitory activity (IC50 = 5.14 μM); both showed high cytotoxic activity (IC50 HeLa = 2.04 μM and 2.32 μM, respectively).

  8. Synthesis and crystal structure of tetra(quinolin-8-olatothorium ethanol solvate, Th(C9H6NO4*C2H5OH

    Directory of Open Access Journals (Sweden)

    Holger Kohlmann


    Full Text Available Metal quinolinolates (also known as oxinates have been widely used for gravimetric analysis and in recent days as materials for organic light emitting diodes (OLEDs. Recrystallisation of tetra(quinolin-8- olatothorium(IV (ThQ4 yielded yellow, translucent, prismatic crystals of the title compound, ThQ4*C2H5OH, the single-crystal structure of which is described. Only one crystallographically distinct molecule is found, all ligands are crystallographically inequivalent. Thorium is coordinated by four 8-hydroxyquinolinato with average Th-O distances of 233.3 pm and average Th-N distances of 272.4 pm, and one ethanol ligand with a Th-O distance 256.7 pm. O and N surroundings around thorium can be described by a tricapped trigonal prism. In contrast to quinolinates of the trivalent metals, ThQ4*C2H5OH does not fluoresce under UV irradiation, which is in accordance with the lack of π-π overlap in the crystal structure.

  9. Synthesis, antibacterial and anti-MRSA activity, in vivo toxicity and a structure-activity relationship study of a quinoline thiourea. (United States)

    Dolan, Niamh; Gavin, Declan P; Eshwika, Ahmed; Kavanagh, Kevin; McGinley, John; Stephens, John C


    We report the synthesis, antibacterial evaluation of a series of thiourea-containing compounds. 1-(3,5-Bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)-((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea 5, was the most active against a range of Gram-positive and Gram-negative bacteria, and exhibited bacteriostatic activity against methicillin resistant Staphylococcus aureus (MRSA) comparable to that of the well-known antibacterial agent vancomycin. Quinoline thiourea 5 was subjected to a detailed structure-activity relationship study, with 5 and its derivatives evaluated for their bacteriostatic activity against both Gram-negative and Gram-positive bacteria. A number of structural features important for the overall activity of quinoline thiourea 5 have been identified. A selection of compounds, including 5, was also evaluated for their in vivo toxicity using the larvae of the Greater wax moth, Galleria mellonella. Compound 5, and a number of derivatives, were found to be non-toxic to the larvae of Galleria mellonella. A new class of antibiotic can result from the further development of this family of compounds.

  10. Hydrogenation of tetralin in the presence of dibenzothiophene and quinoline on Pt-Pd/SiO{sub 2}-Al{sub 2}O{sub 3}

    Energy Technology Data Exchange (ETDEWEB)

    Gutierrez, O.Y.; Yu, Y.; Jentys, A.; Lercher, J.A. [Technische Univ. Muenchen, Garching (Germany). Dept. of Chemistry and Catalysis Research Center


    Three Pt-Pd catalysts with 0.3 and 0.5 wt.% of Pt and Pd, respectively, were supported on amorphous silica alumina with Al{sub 2}O{sub 3}:SiO{sub 2} wt.% ratios of 20:80, 30:70 and 55:45. The materials were characterized by physisorption of N{sub 2}, TEM, X-ray absorption spectroscopy and adsorption of pyridine and CO followed by IR spectroscopy. The EXAFS fitting and IR characterization showed that bimodal distributions of monometallic Pd and bimetallic Pt-Pd particles. The bimetallic particles in all catalysts have a Pt-rich core and a Pd-rich shell. However, the degree of alloying and proportion of exposed Pt increases with increasing concentration of Lewis acid sites (LAS) in the support, probably because the LAS are good anchoring sites for Pt species. The activity of the catalysts for the hydrogenation of tetralin in the presence of DBT and quinoline, and the corresponding selectivity to cis-decalin increase with the proportion of exposed Pt. Therefore, in the presence of DBT and quinoline the morphology of bimetallic clusters is the parameter determining its hydrogenation performance. (orig.)

  11. Solid-state transition metal chemistry with quinolin-4-yl-methyl-[N-(n-butyl)amino]-diphenylphosphine oxide (4-qmape): Crystal structure of the 4-qmape ligand (United States)

    Żurowska, Bogumiła; Brzuszkiewicz, Anna; Boduszek, Bogdan


    A series of three perchlorate coordination compounds of bioactive diethyl quinolin-4-yl-methyl(N-butylamino)diphenylphosphine oxide (4-qmape) ligand, with the following stoichiometries [M(2-qmape)2](ClO4)2 Mdbnd Cu and Ni and [Co(2-qmape)2](ClO4)2, were obtained and studied. Stoichiometry and stereochemistry of the compounds was confirmed by spectroscopic and magnetic studies as well as by elemental analyses. In particular, the crystal structure of the free ligand was determined. The 4-qmape ligand has a potential capacity to coordinate to metal ions by following atoms: phosphoryl oxygen, amino nitrogen and quinolyl nitrogen. In studied compounds, 4-qmape adopts the didentate N,O-coordination mode, bonding metal centers through the phosphoryl oxygen and amino nitrogen. Quinoline nitrogen atom does not participate in coordination. The all complexes are monomeric with tetrahedral environment of metal ions. Magnetic studies (1.8-300 K) indicate existence of a very weak exchange coupling between metal centers in crystal lattice.

  12. Mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in colon and liver of Big Blue Rats: role of DNA adducts, strand breaks, DNA repair and oxidative stress

    DEFF Research Database (Denmark)

    Møller, Peter; Wallin, Håkan; Vogel, Ulla;


    The contribution of oxidative stress, different types of DNA damage and expression of DNA repair enzymes in colon and liver mutagenesis induced by 2-amino-3-methylimidazo [4,5-f]quinoline (IQ) was investigated in four groups of six Big Blue rats fed diets with 0, 20, 70, and 200 mg IQ/kg for 3...

  13. 4-Hy-droxy-5-meth-oxy-N,1-dimethyl-2-oxo-N-[4-(tri-fluoro-meth-yl)phen-yl]-1,2-di-hydro-quinoline-3-carboxamide. (United States)

    Akinboye, Emmanuel S; Butcher, Ray J; Yildirim, Sema Ozturk; Isaacs, John T


    The title compound, C20H17F3N2O4, named tasquinimod, is a second-generation oral quinoline-3-carboxamide analogue, which is currently in phase III clinical trials for the treatment of metastatic prostate cancer. The quinoline unit is almost planar (r.m.s. deviation of fitted atoms = 0.0075 Å). The carboxamide side chain, substituted at position 3, is tilted by 88.07 (7)° to the quinoline plane. Both the methyl and carbonyl groups of this carboxamide side chain are in a syn conformation. The 4-(tri-fluoro-meth-yl)phenyl plane is inclined at 50.62 (17)° to the plane of the carboxamide side chain, and at 87.14 (4)° to the plane of the quinoline ring system. The 4-hy-droxy H atom acts as a double proton donor in an intra-molecular hydrogen bond to the 5-position meth-oxy O atom and in an inter-molecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.

  14. An Efficient Synthesis of Ethyl 7-Chloro-6-fluoro-1-methyl-4-oxo-1, 4-dihydro-[1, 3]thiazeto[3, 2-a]quinoline-3-carboxylate as Intermediate of the Prulifloxacin Containing Tricyclic Fluoroquinolone

    Institute of Scientific and Technical Information of China (English)

    Shu Tao MA; Hong Xiang LOU


    Novel ethyl 7-chloro-6-fluoro-1-methyl-4-oxo-1, 4-dihydro-[1, 3]thiazeto[3, 2-a]quinoline-3-carboxylate 2 was prepared from 3-chloro-4-fluoroaniline in eight steps. It can be used as a new intermediate for the synthesis of tricyclic fluoroquinolones.

  15. Isolation and Identification a Strain of Pseudomonas sp.QLD-9 and Its Biodegradation of Quinoline%假单胞菌QLD-9的分离鉴定及其对喹啉的生物降解

    Institute of Scientific and Technical Information of China (English)

    朱希坤; 王芳; 李小明; 胥维昌


    [Methods] Quinoline-degrading bacteria were isolated from contaminated soil by using enrichment culture method. [Results] A bacterial strain QLD-9 of utilizing quinoline as its sole nitrogen source and utilizing glucose as the carbon source was obtained. The strain was identified as Pseudomonas sp. according to the results of 16S rDNA sequence analysis. The strain could keep excellent degradation activity to quinoline with a concentration under 600 mg/L, and above 99.9% of quinoline with a concentration of 300 mg/L could be degraded within 48 h. [Conclusions] Strain QLD-9 showed potential of application for bio-remediation to quinoline in environment.%[方法]采用富集培养法从受杂环类污染的土壤中分离喹啉降解菌株.[结果]分离得到1株以喹啉为唯一氮源、葡萄糖为碳源生长的QLD-9菌株,经16S rDNA鉴定为假单胞菌属(Pseudomonas sp.),该菌株能在48 h内将300 mg/L的喹啉降解99.9%以上,对600 mg/L以内喹啉具有良好的降解效果.[结论]QLD-9菌株对环境中喹啉的生物修复具有很好的应用潜力.

  16. Novel iridium(III) complexes based on 2-(2,2’-bithien-5-yl)-quinoline. Synthesis, photophysical, photochemical and DFT studies

    Energy Technology Data Exchange (ETDEWEB)

    Szafraniec-Gorol, Grażyna, E-mail: [Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice (Poland); Słodek, Aneta; Filapek, Michał [Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice (Poland); Boharewicz, Bartosz; Iwan, Agnieszka [Electrotechnical Institute, Division of Electrotechnology and Materials Science, M. Sklodowskiej-Curie 55/61, 50-369 Wroclaw (Poland); Jaworska, Maria; Żur, Lidia; Sołtys, Marta; Pisarska, Joanna; Grudzka-Flak, Iwona [Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice (Poland); Czajkowska, Sylwia [Centre of Polymer and Carbon Materials, Polish Academy of Sciences, M. Curie-Sklodowskiej 34, 41-819 Zabrze (Poland); Sojka, Maciej; Danikiewicz, Witold [Institute of Organic Chemistry, Polish Academy of Science, Kasprzaka 44/52, 01-224 Warsaw (Poland); Krompiec, Stanisław [Institute of Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40-007 Katowice (Poland)


    Four novel cyclometalated iridium(III) complexes: [Ir(q-bt-Ph){sub 2}(phen)]PF{sub 6}, [Ir(q-bt-Ph){sub 2}(acac)], [Ir(q-bt-Me){sub 2}(bpy)]PF{sub 6} and [Ir(q-bt-Me){sub 2}(acac)] (where q-bt-Ph, q-bt-Me correspond to 2-(2,2’-bithien-5-yl)-4-phenylquinoline and 2-(2,2’-bithien-5-yl)-4-methylquinoline), are reported. The complexes were characterized by NMR, FTIR and HRMS. The optical, electrochemical properties and thermal stability of novel iridium(III) complexes were thoroughly investigated. The complexes emit a light in the narrow range of 693–707 nm. The optical study showed that replacement of fragment in the main quinoline ligand did not affect wavelength of the emitted light. On the other hand, the modification of the ancillary ligand and substituent in the quinoline ring caused the increase of the photoluminescence quantum yields. Electrochemical experiments demonstrate that the oxidation process for complexes [Ir(q-bt-Ph){sub 2}(phen)]PF{sub 6} and [Ir(q-bt-Ph){sub 2}(acac)] was reversible (or quasi-reversible) and well detectable whereas for complexes with quinoline substituted by methyl group was irreversible, even at low temperature (−70 °C). The electrochemical and photophysical studies have been well confirmed by density functional theory (DFT) calculations. In addition, bulk heterojunction polymer solar cells based on complexes [Ir(q-bt-Ph){sub 2}(phen)]PF{sub 6} and [Ir(q-bt-Ph){sub 2}(acac)] were fabricated. Only the solar cell incorporating [Ir(q-bt-Ph){sub 2}(acac)] exhibited a photovoltaic effect. The architecture of the cell was ITO/PEDOT:PSS/P3HT:PCBM:[Ir(q-bt-Ph){sub 2}(acac)]/Al. A power conversion efficiency of 0.25% was measured under 1 sun illumination using an AM 1.5G filter to simulate the solar spectrum. - Graphical abstract: Display Omitted - Highlights: • Iridium(III) complexes bearing 2-bithienylquinolines as main ligands were examined. • Optical and electrochemical measurements were compared with DFT calculations.

  17. Adsorption characteristics of quinoline on activated carbon fiber%活性碳纤维对水中喹啉的吸附性能

    Institute of Scientific and Technical Information of China (English)

    张培; 张小平; 方益民; 兰永辉


    The static adsorption of quinoline on activated carbon fiber (ACF) was studied. The factors effecting adsorption efficiency and behaviors such as time, quinoline does, temperature, pH and organic compound were investigated. The results show that quinoline adsorption capacity on ACF was up to 210 mg/g at higher concentration and adsorption efficiency decreased with an increase of temperature. It was found that ACF had good adsorption properties when pH<7. The presence of organic substances inhibits the sorption efficiency. The adsorption isotherms conform to Langmuir adsorption isotherm and the adsorption process fits a pseudo-second-order model. The sorption parameters Δ/f° and ΔG° were both negative, so the adsorption is spontaneous and exothermic. Scientific basis is offered for environment function material ACF using in industrial production. Based on the experimental results, dynamic adsorption experiment and treatment of coke plant wastewater is necessary. In addition, the problem of the respect such as high cost and desorption regeneration of ACF remain to be further studied.%采用活性碳纤维(activated carbon fiber,ACF)静态吸附模拟废水中的喹啉,考察了吸附时间、喹啉初始浓度、温度、pH值、有机物等对吸附速率与吸附行为的影响.结果表明,ACF对喹啉的吸附速率快,30 min内基本达到平衡,初始浓度较高时,最终吸附容量较大,达210 mg/g,低温和pH值小于7时,吸附效果较好,苯酚与喹啉产生竞争吸附,配水中的吸附行为能较好的符合Langmuir等温方程,吸附动力学符合准二级动力学模型,热力学参数△H0、△G0为负值,表明该吸附是一个自发的放热过程.本研究为环境功能材料ACF应用于工业化生产提供了理论依据,有必要在此基础上进行动态吸附实验以及实际焦化废水的吸附处理实验,同时ACF成本高及脱附再生等方面问题还有待进一步深入研究.

  18. IQ (2-amino-3-methylimidazo[4,5-f]quinoline)- induced aberrant crypt foci and colorectal tumour development in rats fed two different carbohydrate diets

    DEFF Research Database (Denmark)

    Mølck, A.M.; Meyer, Otto A.; Kristiansen, E.


    In most aberrant crypt foci (ACF) and colorectal tumour studies, chemical carcinogens not normally found in food have been used as initiators. In the present study the food-related compound, IQ (2-amino-3-methylimidazo[4,5-f]quinoline), has been used. A diet high in refined carbohydrates has been...... on the development of IQ-induced ACF over time and (2) possible correlation between early and late ACF and/or colorectal tumour development. The study showed that a feeding regimen with continuous doses of 0.03% IQ in the diet for 14 weeks, followed by 32 weeks without IQ was able to induce tumours in the rat colon...

  19. Aminothiols linked to quinoline and acridine chromophores efficiently decrease 7,8-dihydro-8-oxo-2'-deoxyguanosine formation in [gamma]-irradiated DNA

    Energy Technology Data Exchange (ETDEWEB)

    Laayoun, A.; Coulombeau, C.; Constant, J.F.; Lhomme, J. (Univ. Joseph Fourier, Grenoble (France). LEDSS); Berger, M.; Cadet, J. (CEA Centre d' Etudes Nucleaires de Grenoble, 38 (France). Dept. de Recherche Fondamentale)


    In a search for more active radioprotective compounds, we have prepared and examined a series of model molecules in which the radioprotective [beta]-aminothiol unit (free or derivatized as acetate or phosphorothioate) is tethered to the DNA-binding chromophores quinoline and acridine through links of variable length. The modifying activity of these 'hybrid' molecules was estimated by measuring the formation of 8-oxo-2'-deoxyguanosine (8-oxodGuo) in double-strand DNA upon exposure to [gamma]-rays in oxygen-free solution in the presence of the drugs. We show that all hybrid molecules protect the guanine moiety from oxidation more efficiently than the parent [beta]-aminothiol units. The degree of protection is the highest for the molecules in which the thiol is linked to the strong binding intercalator acridine through a long polyaminochain. (author).

  20. N10,N11-di-alkylamine indolo[3,2-b]quinolines as hemozoin inhibitors: design, synthesis and antiplasmodial activity. (United States)

    Figueiras, Marta; Coelho, Lis; Wicht, Kathryn J; Santos, Sofia A; Lavrado, João; Gut, Jiri; Rosenthal, Philip J; Nogueira, Fátima; Egan, Timothy J; Moreira, Rui; Paulo, Alexandra


    We recently reported that potent N10,O11-bis-alkylamine indolo[3,2-b]quinoline antimalarials act as hemozoin (Hz) growth inhibitors. To improve access and binding to the target we have now designed novel N10,N11-di-alkylamine bioisosteres. 3-Chloro derivatives (10a-f) showed selectivity for malaria parasite compared to human cells, high activity against Plasmodium falciparum chloroquine (CQ)-resistant strain W2 (IC50s between 20 and 158nM), good correlation with β-hematin inhibition and improved vacuolar accumulation ratios, thus suggesting inhibition of Hz growth as one possible mechanism of action for these compounds. Moreover, our studies show that Hz is a valid target for the development of new antimalarials able to overcome CQ resistance.

  1. Synthesis, crystal structure, DNA interaction and antioxidant activities of two novel water-soluble Cu2+ complexes derivated from 2-oxo-quinoline-3-carbaldehyde Schiff-bases. (United States)

    Liu, Zeng-Chen; Wang, Bao-Dui; Yang, Zheng-Yin; Li, Yong; Qin, Dong-Dong; Li, Tian-Rong


    Two novel 2-oxo-quinoline-3-carbaldehyde (4'-hydroxybenzoyl) hydrazone, thiosemicarbazone ligands and its corresponding Cu(2+) complexes were synthesized, and the two complexes' structures were determined by X-ray single crystal diffraction. The interaction of the two Cu(2+) complexes with calf thymus DNA (CT-DNA) was investigated by electronic absorption spectroscopy, fluorescence spectroscopy and viscosity measurement. The experimental evidences indicated that the two water-soluble Cu(2+) complexes could strongly bind to CT-DNA via an intercalation mechanism. The intrinsic binding constants of complexes 1 and 2 with CT-DNA were 7.31 x 10(6) and 2.33 x 10(6)M(-1), respectively. Furthermore, the antioxidant activities (hydroxyl radical and superoxide) of the two water-soluble metal complexes were determined by hydroxyl radical and superoxide scavenging method in vitro.

  2. Design of new hybrid template by linking quinoline, triazole and dihydroquinoline pharmacophoric groups: A greener approach to novel polyazaheterocycles as cytotoxic agents. (United States)

    Praveena, Koduru Sri Shanthi; Shivaji Ramarao, Edupuganti Veera Venkat; Murthy, Nandula Yadagiri Sreenivasa; Akkenapally, Surekha; Kumar, C Ganesh; Kapavarapu, Ravikumar; Pal, Sarbani


    A new hybrid template designed by linking three pharmacophoric groups, for example, quinoline, triazole and dihydroquinoline moieties have been used for the generation of a library of molecules as potential cytotoxic agents. Synthesis of these polyazaheterocycles were carried out by using a strategy that involved one-pot sequential azidation and CuAAC in water under mild conditions. A number of 1,4-disubstituted 1,2,3-triazoles possessing quinolinylmethylene at N-1 and 1,2-dihydroquinolinyl methylene at C-4 as different substituents were synthesized and evaluated for their cytotoxic effects against various cancer cells. Some of them showed encouraging activities against lung cancer cells and one of them showed inhibition of PDE4 indicating the potential medicinal value of these novel polyazaheterocycles.

  3. Synthesis, Biological Evaluation and Molecular Docking Studies of Piperidinylpiperidines and Spirochromanones Possessing Quinoline Moieties as Acetyl-CoA Carboxylase Inhibitors

    Directory of Open Access Journals (Sweden)

    Tonghui Huang


    Full Text Available Acetyl-coenzyme A carboxylases (ACCs play critical roles in the regulation of fatty acid metabolism and have been targeted for the development of drugs against obesity, diabetes and other metabolic diseases. Two series of compounds possessing quinoline moieties were designed, synthesized and evaluated for their potential to inhibit acetyl-CoA carboxylases. Most compounds showed moderate to good ACC inhibitory activities and compound 7a possessed the most potent biological activities against ACC1 and ACC2, with IC50 values of 189 nM and 172 nM, respectively, comparable to the positive control. Docking simulation was performed to position compound 7a into the active site of ACC to determine a probable binding model.

  4. Series of coordination polymers based on 4-(5-sulfo-quinolin-8-yloxy) phthalate and bipyridinyl coligands: Structure diversity and properties (United States)

    Feng, Xun; Liu, Jing; Li, Jin; Ma, Lu-Fang; Wang, Li-Ya; Ng, Seik-Weng; Qin, Guo-Zhan


    Reactions between later metal salts and conjugational N-hetrocyclic sulfonate/ carboxylic acid under the presence of bipyridyl auxiliary ligands afforded a series of manganese, nickel, zinc, silver, cadmium coordination polymers bearing with phenyl pendant arm attached to quinoline skeletons, and they have been characterized by elements analysis, thermogravimetry, infrared spectroscopy and single-crystal X-ray diffraction studying. The series of polymers show interesting structural diversity in coordination environment, dimensions and topologies. They are all built from 2-D networks constructed from metal cluster through sulfonate or carboxylate groups, as the secondary building unit (SBU). The thermalgravimetric analyses show that they display framework stabilities in solid state. Variable-temperature magnetic susceptibility studies reveal the existence of antiferromagnetic interactions between adjacent Mn (II) ions in 1, and ferromagnetic interactions between Ni(II) ions for 2, respectively. The photo-luminescence properties of 3-5 have also been investigated systemically.

  5. μ2-Iodido-bis{dimethyl[methylbis(quinolin-8-ylsilanyl-κ3N,Si,N′]platinum(IV} tetrakis(pentafluorophenylborate dichloromethane 0.66-solvate

    Directory of Open Access Journals (Sweden)

    Marcus I. Gibson


    Full Text Available The title complex, [Pt2(CH34(C19H15N2Si2I][B(C6F54]·0.66CH2Cl2, resulted from an attempt to synthesize a stable five-coordinate platinum species via ligand abstraction of a six-coordinate platinum precursor. However, dimerization occurred after ligand abstraction, thereby yielding the compound described in this study. The cation is a dinuclear PtIV organometallic complex, in which the metal centers are bridged by an I− anion. Both metal centers display a coordination geometry close to octahedral, including cis-arranged quinoline ligands connected by Si atoms, which form Pt—Si bonds, two cis-methyl groups, and the bridging I− anion. In the crystal structure, voids between cations and anions are partially filled with an average of 0.66 molecules of dichloromethane solvent.

  6. Organocatalytically Generated Donor-Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2-a]quinolines. (United States)

    Sanchez-Diez, Eduardo; Vesga, Diana L; Reyes, Efraim; Uria, Uxue; Carrillo, Luisa; Vicario, Jose L


    An easy and straightforward procedure has been developed for the synthesis of highly enantioenriched pyrrolo[1,2-a]quinolines through a one-pot process that comprises a domino cyclopropane ring opening/aza-Michael/aldol reaction followed by acid-promoted lactamization. The key feature of the synthetic approach relies on the ability of conveniently functionalized cyclopropaneacetaldehydes to undergo organocatalytic activation by a chiral secondary amine that enables the catalytic generation of a donor-acceptor cyclopropane. This intermediate has the potential to undergo a ring opening that generates an electrophilic α,β-unsaturated iminium ion that subsequently reacts through the already mentioned domino sequence and in which stereochemical information is very efficiently transferred from the amine catalyst to the final products. Moreover, one of the alkoxycarbonyl moieties can be easily removed by standard hydrolysis/decarboxylation, providing access to the target adducts as single stereoisomers.

  7. New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors. (United States)

    Luniewski, Wojciech; Wietrzyk, Joanna; Godlewska, Joanna; Switalska, Marta; Piskozub, Malgorzata; Peczynska-Czoch, Wanda; Kaczmarek, Lukasz


    Novel indolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino)ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity.

  8. Quinoline-azetidinone hybrids: Synthesis and in vitro antiproliferation activity against Hep G2 and Hep 3B human cell lines. (United States)

    Alegaon, S G; Parchure, P; Araujo, L D; Salve, P S; Alagawadi, K R; Jalalpure, S S; Kumbar, V M


    In search of new heterocyclic anticancer agents, a new quinoline-azetidinone hybrid template have been designed, synthesized and screened for their cytotoxic activity against human cancer cell lines such as Hep G2, and Hep 3B by the MTT assay and results were compared with paclitaxel, 5-fluorouracil and doxorubicin. Interestingly, some of the compounds were found significantly active against both cell lines. The compound 6f (IC50=0.04±0.01µM) exhibited potent antiproliferation activity against Hep G2 cell line, and 6j compound (IC50=0.66±0.01µM) demonstrated potent antiproliferation activity against Hep 3B cell line and provide to be more potent as cytotoxic agents than standard drugs. Morphological changes suggest the induction of apoptosis and describe the mechanism of action of these hybrid antitumor agents. Copyright © 2017 Elsevier Ltd. All rights reserved.

  9. Quinoline Phosphomolybdate Gravimetry is Better for Determination of Total Phosphorus Content in Scale Inhibitor%阻垢剂中总磷含量测定的改进

    Institute of Scientific and Technical Information of China (English)

    张振忠; 肖怡; 郭永


    This paper discusses two test methods,one is original industry standard method— spectrophotometry,another is quinoline phosphomolybdate gravimetry,for determination of total phosphorus content in scale inhibitor.Through comparing the test results obtained%对分光光度法和磷钼酸喹啉重量法测定阻垢剂中总磷含量进行了介绍。通过对2种方法测定结果进行比较,得出结论:在化肥生产企业,磷钼酸喹啉重量法比分光光度法更适合测定阻垢剂中的总磷含量。

  10. Novel series of potent, nonsteroidal, selective androgen receptor modulators based on 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. (United States)

    Higuchi, Robert I; Arienti, Kristen L; López, Francisco J; Mani, Neelakhanda S; Mais, Dale E; Caferro, Thomas R; Long, Yun Oliver; Jones, Todd K; Edwards, James P; Zhi, Lin; Schrader, William T; Negro-Vilar, Andrés; Marschke, Keith B


    Recent interest in orally available androgens has fueled the search for new androgens for use in hormone replacement therapy and as anabolic agents. In pursuit of this, we have discovered a series of novel androgen receptor modulators derived from 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. These compounds were synthesized and evaluated in competitive binding assays and an androgen receptor transcriptional activation assay. A number of compounds from the series demonstrated single-digit nanomolar agonist activity in vitro. In addition, lead compound (R)-16e was orally active in established rodent models that measure androgenic and anabolic properties of these agents. In this assay, (R)-16e demonstrated full efficacy in muscle and only partially stimulated the prostate at 100 mg/kg. These data suggest that these compounds may be utilized as selective androgen receptor modulators or SARMs. This series represents a novel class of compounds for use in androgen replacement therapy.

  11. Extremely strong temperature-dependent Davydow-splitting effects in the polarized IR spectra of the hydrogen bond: Pyrazole and quinolin-2(1H)-one crystals (United States)

    Hachuła, Barbara; Flakus, Henryk T.; Tyl, Aleksandra; Polasz, Anna


    Polarized IR spectra were recorded in the spectral range of the νN-H and νN-D proton stretching vibration bands for the isotopically neat and isotopically diluted crystals of pyrazole (Pzl) and quinolin-2(1H)-one (2HQ). The spectra measured in the temperature range of 77-293 K have shown that temperature extremely strongly influenced the magnitude of the Davydow-splitting effects in the crystalline spectra. Two different competing vibrational Davydow-coupling mechanisms involving hydrogen bonds, i.e., the ‘tail-to-head' and the ‘side-to-side', were responsible for the generation of the temperature effects in the polarized spectra.

  12. Anti-cancer agents based on N-acyl-2, 3-dihydro-1H-pyrrolo[2,3-b] quinoline derivatives and a method of making (United States)

    Gakh, Andrei; Krasavin, Mikhail; Karapetian, Ruben; Rufanov, Konstantin A; Konstantinov, Igor; Godovykh, Elena; Soldatkina, Olga; Sosnov, Andrey V


    The present disclosure relates to novel compounds that can be used as anti-cancer agents in the prostate cancer therapy. In particular, the invention relates to N-acyl derivatives of 2,3-dihydro-1H-pyrrolo[2,3-b]quinolines having the structural Formula (I), ##STR00001## stereoisomers, tautomers, racemics, prodrugs, metabolites thereof, or pharmaceutically acceptable salt and/or solvate thereof. The meaning of R1 is independently selected from H; C1-C6 Alkyl, cyclo-Alkyl or iso-Alkyl substituents; R2 is selected from C1-C6 Alkyl, cyclo-Alkyl or iso-Alkyl; substituted or non-substituted, fused or non-fused to substituted or non-substituted aromatic ring, aryl or heteroaryl groups. The invention also relates to methods for preparing said compounds, and to pharmaceutical compositions comprising said compounds.

  13. Protective effect of montelukast against quinolinic acid/malonic acid induced neurotoxicity: possible behavioral, biochemical, mitochondrial and tumor necrosis factor-α level alterations in rats. (United States)

    Kalonia, H; Kumar, P; Kumar, A; Nehru, B


    The present study has been designed to explore the protective effect of montelukast (leukotriene receptor antagonist) against intrastriatal quinolinic acid (QA; 300 nmol) and malonic acid (MA; 6 μmol) induced Huntington's like symptoms in rats. Quinolinic acid has been reported to induce excitotoxicity by stimulating the N-methyl-D-aspartate receptor, causing calcium overload which in turn leads to the neurodegeneration. On the other hand, MA, being a reversible inhibitor of mitochondrial enzyme complex-II, leads to energy crisis and free radical generation. Recent studies have reported the therapeutic potential of leukotriene receptor antagonists in different neurodegenerative disorders. However, their exact role is yet to be established. The present study accordingly, is an attempt to investigate the effect of montelukast against QA and MA induced behavioral, biochemical and molecular alterations in rat striatum. Oxidative stress, mitochondrial enzyme complex and tumor necrosis factor-alpha (TNF-α) were evaluated on day 21st and 14th post intrastriatal QA and MA treatment, respectively. Findings of the present study demonstrate significant alteration in the locomotor activity and motor coordination as well as oxidative burden (increased lipid peroxidation, nitrite concentration and decreased endogenous antioxidants), mitochondrial enzyme complex (I, II and IV) activities and TNF-α level, in both intrastriatal QA and MA treated animals. Further, montelukast (0.4, 0.8 mg/kg p.o.) treatment for 21 and 14 days respectively, attenuated the behavioral alterations, oxidative stress, mitochondrial dysfunction and TNF-α level in these models of Huntington's disease in a significant manner. In conclusion, the present study emphasizes the neuroprotective potential of montelukast in the therapeutic management of Huntington like symptoms.

  14. Structure-activity relationships of 111In- and 99mTc-labeled quinolin-4-one peptidomimetics as ligands for the vitronectin receptor: potential tumor imaging agents. (United States)

    Harris, Thomas D; Kalogeropoulos, Shirley; Nguyen, Tiffany; Dwyer, Gregory; Edwards, D Scott; Liu, Shuang; Bartis, Judit; Ellars, Charles; Onthank, Dave; Yalamanchili, Padmaja; Heminway, Stuart; Robinson, Simon; Lazewatsky, Joel; Barrett, John


    The integrin receptor alpha(v)beta(3) is overexpressed on the endothelial cells of growing tumors and on some tumor cells themselves. Radiolabeled alpha(v)beta(3) antagonists have demonstrated potential application as tumor imaging agents and as radiotherapeutic agents. This report describes the total synthesis of eight new HYNIC and DOTA conjugates of receptor alpha(v)beta(3) antagonists belonging to the quinolin-4-one class of peptidomimetics, and their radiolabeling with (99m)Tc (for HYNIC) and (111)In (for DOTA). Tethering of the radionuclide-chelator complexes was achieved at two different sites on the quinolin-4-one molecule. All such derivatives maintained high affinity for receptor alpha(v)beta(3) and high selectivity versus receptors alpha(IIb)beta(3), alpha(v)beta(5), alpha(5)beta(1). Biodistribution of the radiolabeled compounds was evaluated in the c-neu Oncomouse mammary adenocarcinoma model. DOTA conjugate (111)In-TA138 presented the best biodistribution profile. Tumor uptake at 2 h postinjection was 9.39% of injected dose/g of tissue (%ID/g). Activity levels in selected organs was as follows: blood, 0.54% ID/g; liver, 1.94% ID/g; kidney, 2.33% ID/g; lung, 2.74% ID/g; bone, 1.56% ID/g. A complete biodistribution analysis of (111)In-TA138 and the other radiolabeled compounds of this study are presented and discussed. A scintigraphic imaging study with (111)In-TA138 showed a clear delineation of the tumors and rapid clearance of activity from nontarget tissues.

  15. Cascade C═O/C═C/C-N Bond Formation: Metal-Free Reactions of 1,4-Diynes and 1-En-4-yn-3-ones with Isoquinoline and Quinoline N-Oxides. (United States)

    Zhang, Bing; Huang, Long; Yin, Shiwei; Li, Xuetong; Xu, Tao; Zhuang, Biyang; Wang, Tao; Zhang, Zunting; Hashmi, A Stephen K


    The metal-free reactions of 1,4-diynes and 1-en-4-yn-3-ones with isoquinoline and quinoline N-oxides are developed, resulting in the formation of 3,4-dihydro-2H-pyrido[2,1-a]isoquinolines and 2,3-dihydro-1H-pyrido[1,2-a]quinolines via cascade C═O/C═C/C-N bond formation. It is the first report in which in the alkyne oxidation by N-oxides both the oxygen atom of N-oxides and the nitrogen atom are involved in a second C-heteroatom bond formation. The reactions showed a broad substrate scope and functional group tolerance. Furthermore, the products were found to display green-blue fluorescence in DMSO with fluorescence quantum yields up to 0.59.

  16. Pyrolysis Mechanisms of Quinoline and Isoquinoline with Density Functional Theory%喹啉和异喹啉热解机理的密度泛函理论研究

    Institute of Scientific and Technical Information of China (English)

    凌丽霞; 章日光; 王宝俊; 谢克昌


    The pyrolysis mechanisms of quinoline and isoquinoline were investigated using the density functional theory of quantum chemistry, including eight reaction paths and a common tautomeric intermediate 1-indene imine. It is concluded that the conformational tautomerism of the intermediate decides the pyrolysis products (C_6H_6, HC(=)C-C(=)N, C_6H_5C(=)N and HC(=)CH) to be the same, and also decides the total disappearance rates of the reactants to be the same, for both original reactants quinoline and isoquinoline during the pyrolysis reaction. The results indicate that the intramolecular hydrogen migration is an important reaction step, which often appears in the paths of the pyrolysis mechanism. The activation energies of the rate determining steps are obtained. The calculated results are in good agreement with the experimental results.

  17. Mefloquine derivatives: Crystal structures and anti-tubercular activities of diphenyl[(( R*, S*)-2,8-bis(trifluoromethyl)quinolin-4-yl)-piperidin-2-yl-methanolato- O, N]boron and (±)- erythro-mefloquinium tetraphenylborate solvates (United States)

    Wardell, James L.; de Souza, Marcus V. N.; Wardell, Solange M. S. V.; Lourenço, Maria C. S.


    Thermolysis of ( R*, S*)-(2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)˜methyl}piperidin-1-ium) tetraphenylborate, (±)- erythro-mefloquinium tetraphenylborate, 3, in solution or neat, provides the oxazaborolidine derivative, diphenyl[( R*, S*)-(2,8-bis(trifluoromethyl)quinolin-4-yl)]piperidin-2-yl-methanolato- O, N]boron, 2. Crystal structures of solvates of 2 and 3 are reported. As shown by the 1H NMR spectrum, 2 undergoes a conformation equilibrium in solution. Both 2 and 3 exhibit important anti-tubercular activities as indicated by the minimum inhibitory concentrations (MIC) of 50 and 12.5 μg/ml, respectively, in in vitro assays against M. tuberculosis H37Rv ATTC 27294.

  18. Synthesis, Antibacterial and Antioxidant Evaluation of Novel 1-(5,7-Dichloro-1,3-benzoxazol-2-yl-1H-pyrazolo[3,4-b]quinoline Derivatives

    Directory of Open Access Journals (Sweden)

    N. D. Jayanna


    Full Text Available Some novel 1-(5,7-dichloro-1,3-benzoxazol-2-yl-1H-pyrazolo[3,4-b]quinoline derivatives 8(a–f were synthesized by reacting 5,7-dichloro-2-hydrazino-1,3-benzoxazole 4 and substituted-2-chloro-3-quinoline carbaldehydes using p-toluenesulfonic acid (PTSA as a catalyst for the cyclisation. The target molecules have been characterized by IR, 1H NMR, 13C NMR, and mass spectral studies. The synthesized compounds were screened for biological activities, and some of the compounds have exhibited encouraging antibacterial and antioxidant activities. The compounds 8a and 8e showed potent antibacterial activity, whereas the compounds 8e and 8f act as antioxidants.

  19. Synthesis and docking analysis of new heterocyclic system of tetrazolo[5',1':2,3][1,3,4]thiadiazepino [7,6-b]quinolines as aldose reductase inhibitors

    Directory of Open Access Journals (Sweden)

    Mohammad Saadatmandzadeh


    Conclusion: All of the best models formed strong hydrogen bonds with Trp 111 and Tyr 209 via tetrazole moiety. It was found that pi-pi interaction between Tyr 209, Trp 20 and His 110 side chain and quinolin moiety was one of the common factors in enzyme-inhibitor junction. It was found that both hydrogen bonding and hydrophobic interactions are important in the structure and function of biological molecules, especially for inhibition in a complex.

  20. Synthesis and characterization of new 3-(4,5-dihydro-5-arylisoxazol-3-yl-4-hydroxyquinolin-2(1H-ones and 3-(4-styrylisoxazolo[4,5-c]quinolin-4(5H-one derivatives

    Directory of Open Access Journals (Sweden)

    S. Sarveswari


    Full Text Available The 4-hydroxy-3-(3-arylacryloylquinolin-2(1H-ones were synthesized from 3-acetyl-4-hydroxyquinolin-2(1H-one by microwave assisted synthesis, which in turn converted into their corresponding 3-(4,5-dihydro-5-arylisoxazol-3-yl-4-hydroxyquinolin-2(1H-ones and 3-(4-styrylisoxazolo[4,5-c]quinolin-4(5H-one derivatives.

  1. Synthesis of benzo[g]indeno[2,1-b]quinoline derivatives via four-component and one-pot synthesis in presence of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate

    Institute of Scientific and Technical Information of China (English)

    Nader Ghaffari Khaligh


    A simple and facile synthesis of 12-arylbenzo[g]indeno[2,1-b]quinoline-6,11,13-trione deriv-atives was accomplished by the one-pot condensation of 2-hydroxynaphthalene-1,4-dione, aryl aldehydes, 2H-indene-1,3-dione, and ammonium acetate under solvent-free conditions in the presence of a Brönsted ionic liquid catalyst, namely 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate.

  2. ICl-mediated intramolecular twofold iodoarylation of diynes and diynyl diethers and amines: synthesis of bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety. (United States)

    Mo, Juntae; Choi, Wonseok; Min, Jiae; Kim, Cheol-Eui; Eom, Dahan; Kim, Sung Hong; Lee, Phil Ho


    Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.

  3. Synthesis of spiro[pyrazolo[3,4-] pyridine-4,3'-indoline] and spiro [benzo[ℎ]pyrazolo[3,4-]quinoline-4,3'-indoline] derivatives using wet cyanuric chloride under solvent-free conditions

    Indian Academy of Sciences (India)

    Zhikui Yin; Limin Yang; Liqiang Wu


    A simple and efficient synthesis of spiro[pyrazolo[3,4-]pyridine-4,3'-indoline] and spiro[benzo[ℎ] pyrazolo[3,4-]quinoline-4,3'-indoline] derivatives has been accomplished by the one-pot condensation of isatins, 3-methyl-1-phenyl-1-pyrazol-5- amine and Meldrum’s acid or 2-hydroxy-1,4-naphthoquinone in the presence of wet cyanuric chloride as a catalyst under solvent-free conditions.

  4. 基于2-卤甲基-3-喹啉甲酸乙酯的反应研究进展%Research progress on the reaction of ethyl 2-(halogenmethyl) quinoline-3-carboxylate

    Institute of Scientific and Technical Information of China (English)

    符鑫博; 王东方; 赵雅楠; 李阳; 高文涛


    喹啉及其衍生物是一类重要的杂环化合物,许多具有生物活性的稠杂环化合物中都含有喹啉骨架。由2-卤甲基-3-喹啉甲酸乙酯合成多环或稠杂环化合物的研究进展还未见文献报道。为更好地了解这方面的研究动态,本文综述了近几年有2-卤甲基-3-喹啉甲酸乙酯参与反应的研究进展,主要涉及了2-氯(溴)甲基-3-喹啉甲酸乙酯与酚、胺、水杨醛和芳香醛等的一系列反应。%Quinoline and its derivatives are very important heterocyclic compounds,and many quinoline-containing heterocyclic-fused compounds have been found to exhibit potent biological activities. To the best of our knowledge,there is not any review sum-marizing the literature on the use of ethyl 2-(halogenmethyl)quinoline-3-carboxylate as the building blocks for synthesis of quino-line-bearing polycyclic heterocyclic-fused systems. As such,in order to cover the recent work in this aspect,and provide useful and up-to-date data for organic chemists,the present review focuses mainly on the reaction of ethyl 2-(halogenmethyl)quinoline-3-car-boxylate with phenols,amines,salicylaldehydes,aldehydes and so on.

  5. Crystal structure of dibromido(N,N-dimethylformamide-κO{2-(1H-indol-3-yl-N-[(quinolin-2-yl-κNmethylidene]ethanamine-κN}cadmium

    Directory of Open Access Journals (Sweden)

    Md. Serajul Haque Faizi


    Full Text Available In the mononuclear title complex, [CdBr2(C20H17N3(C3H7NO], synthesized from the quinoline-derived Schiff base 2-(1H-indol-3-yl-N-(quinolin-2-ylmethyleneethanamine (IQME, the coordination geometry around the Cd2+ atom is distorted trigonal bipyramidal, the axial positions being occupied by the quinoline N atom [Cd—N = 2.401 (3 Å] and one dimethylformamide O-atom donor [Cd—O = 2.399 (2 Å]. The equatorial plane is formed by the imine N atom [Cd—N = 2.293 (3 Å] and two bromides [Cd—Br = 2.5621 (8 and 2.5676 (8 Å], with the deviation of the CdII atom from the equatorial plane being 0.046 (1 Å. An intramolecular C—H...Br interaction occurs. In the crystal, N—H...Br interactions generate [101] chains.

  6. Crystal structure of dichlorido{N1-phenyl-N4-[(quinolin-2-yl-κNmethylidene]benzene-1,4-diamine-κN4}mercury(II

    Directory of Open Access Journals (Sweden)

    Md. Serajul Haque Faizi


    Full Text Available In the mononuclear title complex, [HgCl2(C22H17N3], synthesized from the quinoline-derived Schiff base N1-phenyl-N4-[(quinolin-2-ylmethylidene]benzene-1,4-diamine (PQMBD and HgCl2, the coordination sphere around the Hg2+ atom is distorted tetrahedral, comprising two Cl atoms [Hg—Cl = 2.3487 (14 and 2.4490 (15 Å] and two N atom donors from the PQMBD ligand, viz. the quinolyl and the imine N atom [Hg—N = 2.270 (4 and 2.346 (4 Å, respectively]. The dihedral angle between the two benzene rings attached to the amino group is 43.7 (3°. In the crystal, N—H...Cl and C—H...Cl hydrogen bonds, as well as π–π stacking interactions between one phenyl ring and the pyridine ring of the quinoline moiety of an adjacent molecule [centroid-to-centroid separation = 3.617 (4 Å] are observed, resulting in a three-dimensional network.

  7. Crystal structure of bis­{μ-(E)-2-[(2-oxido­phenyl­imino)­meth­yl]quinolin-8-olato-κ4 O,N,N′,O′}bis­[di­butyl­tin(IV) (United States)

    Carlos, Camacho-Camacho; Naytzé, Ortiz-Pastrana; Ariadna, Garza-Ortiz; Irma, Rojas-Oviedo


    Condensation of 8-hy­droxy­quinoline-2-carbaldehyde with 2-amino­phenol gave the (E)-2-[(2-hy­droxy­phenyl­imino)­meth­yl]quinolin-8-ol derivative that reacted with di-n-butyl­tin oxide with release of H2O to yield the chelate title complex, [Sn2(C4H9)4(C16H10N2O2)2]. The compound crystallizes in the triclinic space group P-1, with two independent centrosymmetric dimers in the unit cell. Each features a typical pincer-type structure where the dianionic ligand is tetra­dentate, coordinating to the central tin atom through both phenolate oxygen atoms, as well as through the quinoline and imine N atoms. Each metal atom adopts a distorted penta­gonal–bipyramidal SnC2N2O3 coordination arising from the N,N′,O,O′-tetra­dentate deprotonated Schiff base, one bridging phenolate O atom of the neighbouring ligand and two butyl groups in the axial sites. PMID:28083122

  8. Synthesis and physical-chemical properties of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl-4-R-2,4-dihydro-3H-1,2,4-triazoles

    Directory of Open Access Journals (Sweden)

    T. M. Kaplaushenko


    Full Text Available The major social and economic problem of pharmaceutical industry is the search for biologically active substances, which may become the basis of new drugs, competitive with expensive imported drugs. Analysis of literature shows that in recent decades the attention is paid to researches of heterocyclic systems as potential biologically active agents of both domestic and foreign scientists. Particular interest in this regard cause 3-thio derivatives of 1,2,4-triazoles. Despite high number of publications relating to synthesis and biological properties of 1,2,4-triazole derivatives, the structure and physical-chemical properties of these compounds are studied insufficiently. In this regard, the study of synthetic, physical-chemical and biological properties of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl-4-R1-2,4-dihydro-3H-1,2,4-triazoles in our point of view is a new, theoretically and practically significant direction. Purpose - targeted synthesis of new low-toxic and highly effective compounds with potential pharmacological activity in a series of 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl-4-R-2,4-dihydro-3H-1,2,4-triazoles and the study of physical and chemical properties of the synthesized compounds. Materials and methods. As starting compounds 5-(quinoline-2-il- 2-hydroxyquinoline-4-yl-4-R1-3-thio-1,2,4-triazoles have been used. Through further cooperation with halogen alkanes (ethyl bromide, propyl bromide, amyl bromide, octyl bromide, nonyl bromide, decyl bromide, cyclohexyl chloride, benzyl chloride 3-alkylthio-5-(quinoline-2-yl, 2-hydroxyquinoline-4-yl-4-R1-2,4-dyhidro-3H-1,2,4-triazoles have been obtained. Results. 15 New compounds have been received as a result of synthetic transformations, the structure of synthesized compounds has been confirmed by modern complex of physical and chemical methods of analysis (IR-spectrophotometry, 1H NMR-spectroscopy, elemental analysis, and their individuality has been proved by

  9. Recovery and purification of quinoline base in methyl naphthalene fraction of wash oil%洗油甲基萘馏分中喹啉盐基的回收与提纯

    Institute of Scientific and Technical Information of China (English)

    赵明; 辛燕平; 李汇丰; 焦红普; 许春建


    喹啉盐基指沸点160-270℃、主要存在于洗油甲基萘馏分中的喹啉、异喹啉及其衍生物.文中建立了甲基萘馏分及喹啉盐基的气相色谱分析方法,解决了甲基萘馏分中主要组分的定性和定量分析问题.通过单级萃取实验,得到了从甲基萘馏分中萃取喹啉盐基的优化操作条件:硫酸为萃取剂,硫酸铵为稀释剂,萃取剂质量分数10%,稀释剂质量分数10%,萃取温度为室温,萃取时间15 min.为提高喹啉盐基的萃取率,采用单级萃取最佳工艺条件,对连续逆流反应萃取实验进行研究,重点考察重相进料流速对萃取率的影响.结果表明:当重相进料流速低于液泛速度时,萃取率达(质量分数)99.9%以上.通过间歇蒸馏实验,对粗喹啉盐基进行了精制,得到了纯度质量分数99%以上的精喹啉盐基产品.文中介绍的提取喹啉盐基的方法具有易实现、工序少、工艺简单和收率高的优点.%Quinoline base mainly refers to quinoline,isoquinoline and their derivatives with the boiling point of 160-270 ℃,mainly existing in the methyl naphthalene fraction of wash oil.The gas chromatography analysis method for methyl naphthalene fraction and quinoline base was established,thus solving the problem in analyzing the main components in the methyl naphthalene fraction qualitatively and quantitatively.Through the single-stage extraction experiments,the optimum extraction conditions were obtained by the selection experiments:sulfuric acid as extraction agent,ammonium sulfate as diluent,extractant mass fraction of 10%,diluent mass fraction of 10%,extraction at room temperature,extraction time of 15 min.In order to improve the extraction rate of the quinoline base,using single-stage extraction optimum conditions,the continuous countercurrent reactive extraction was investigated,focusing on the effects of the heavy-phase feed flow rate on the extraction rate.The result shows that the extraction rate

  10. 浸渍过程沥青喹啉不溶物存在状态对石墨电极生产的影响%Existence situation of quinoline insolubles in impregnating pitch and its effect on impregnation production of graphite electrode

    Institute of Scientific and Technical Information of China (English)



    在石墨电极浸渍生产过程中,浸渍沥青喹啉不溶物含量及存在状态决定和制约浸渍生产质量.本文通过对现有浸渍生产状况的分析,探讨了浸渍沥青喹啉不溶物在浸渍生产控制各环节中的存在形态及对电极浸渍生产质量的影响.%The content and existence situation of quinoline insolubles in impregnating pitch are key factors that determine the quality of impregnating pitch, which could further affect the production of the graphite electrode during impregnation process. There are some difficulties and limitations in controlling the quinoline insolubles in impregnating pitch during impregnation process because the quinoline insolubles was formed during the production of coal tar pitch. In this paper the existence situation of the quinoline insolubles during the every link of impregnation production and its effect on the impregnating quality of the electrodes were discussed on the base of analyzing the existing impregnating production. The measurements and approaches for reducing the effect of the quinoline insolubles on the quality of the electrode products were given at the present impregnation production conditions.

  11. Synthesis and biological evaluation of 4-phenoxy-6,7-disubstituted quinolines possessing semicarbazone scaffolds as selective c-Met inhibitors. (United States)

    Qi, Baohui; Tao, Haiyan; Wu, Di; Bai, Jinying; Shi, Yandan; Gong, Ping


    Novel quinoline derivatives bearing acyclic semicarbazones were prepared and their chemical structures as well as the relative stereochemistry were confirmed. All the synthesized compounds were evaluated for their c-Met kinase inhibitory activity and their cytotoxicity against the cell lines HT-29, MKN-45, and MDA-MB-231 in vitro. Several potent compounds were further evaluated against A549 cells. Most compounds displayed moderate to excellent activity, and the structure-activity relationship studies identified the most promising compound 35 as a selective c-Met kinase inhibitor (IC50  = 4.3 nM). Compound 35 showed a 3.5- and 18.8-fold increase in cytotoxicity in vitro against HT-29 and A549 cells, respectively, compared to that of foretinib. Poor off-target effects of compound 35 were further confirmed by the antiproliferative activity against the c-Met inhibition less sensitive MDA-MB-231 cell line (IC50  = 0.77 µM).

  12. A fluorescent sensor based on binaphthol-quinoline Schiff base for relay recognition of Zn²⁺ and oxalate in aqueous media

    Indian Academy of Sciences (India)



    To develop an effective fluorescent chemosensor for relay recognition of Zn²⁺ and oxalate, a new fluorescent sensor based on binaphthol quinoline Schiff base L₁ was designed and synthesized. In DMSO-H₂O (1/1, v/v, HEPES 10 mM, pH = 7.4) solution, L₁ exhibits highly selective fluorescence turn on response to Zn²⁺ over other metal ions. The Zn²⁺ recognition event is barely interfered by other coexisting metal ions except Cu²⁺, Co²⁺ and Ni²⁺. The in situ generated L₁-Zn²⁺ complex was further used as a chemosensing ensemble for oxalate detection. The complex L₁-Zn²⁺ displays high selectivity to oxalate with significant fluorescence quenching through Zn²⁺ ion displacement approach. In addition, application of L₁ for imaging of Zn²⁺ and oxalate in living HeLa cells was also examined.

  13. No effects of chlorophyllin on IQ (2-amino-3-methylimidazo[4,5-f]-quinoline)-genotoxicity and -DNA adduct formation in Drosophila. (United States)

    Negishi, Tomoe; Shinoda, Aki; Ishizaki, Nao; Hayatsu, Hikoya; Sugiyama, Chitose


    Previously we demonstrated that chlorophyllin suppressed the genotoxicities of many carcinogens. However, the genotoxicity of IQ (2-amino-3-methylimidazo[4,5-f]quinoline), a carcinogenic heterocyclic amine, was not suppressed in Drosophila. On the contrary, it has been reported that chrolophyllin suppressed the genotoxicity of IQ in rodents, rainbow trout and Salmonella. We demonstrated that the chlorophyllin-induced suppression of MeIQx (2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline)-genotoxicity was associated with a decrease in MeIQx-DNA adduct formation in Drosophila larval DNA. MeIQx represents another type of heterocyclic amine and is similar to IQ in structure. In this study we utilized (32)P-postlabeling to examine whether chlorophyllin reduced IQ-DNA adduct formation in Drosophila DNA in the same way as MeIQx. The results revealed that the formation of IQ-DNA adducts was unaffected by treatment with chlorophyllin. This was consistent with the absence of any inhibitory effect on genotoxicity as observed in the Drosophila repair test. These results suggest that IQ-behavior in Drosophila is not affected by chlorophyllin, indicating that the process of IQ-DNA adduct formation followed by expression of genotoxicity in Drosophila may be different from that in other organisms.

  14. Comparison of the antidepressive effects of trans-resveratrol and 5-methoxy-7H-dibenzo[de,h]quinolin-7-one. (United States)

    López, Miriam Cebey; Fontenla, José A; Uriarte, Eugenio; Santana, Lourdes; Sobarzo-Sánchez, Eduardo


    In this study we evaluate the in vivo antidepressant effect of a natural phenolic compound, trans-resveratrol, and a synthetic derivative from Menispermum dauricum DC (Menispermaceae) 5-methoxy-7H-dibenzo[de,h]quinolin-7- one known as 5-methoxyoxoisoaporphine (OXO 4). The antidepressant-like effect of trans-resveratrol and OXO 4 were evaluated through a Forced Swimming Test (FST), and they were compared with reference antidepressants: imipramine, desipramine, nomifensine, bupropion, nisoxetine, citalopram and moclobemide. Trans-resveratrol (10 mg/kg, intraperitoneally i.p. significantly decreased the immobility time in mouse model of despair test (69.03 ± 8.74 sec) p<0.05, as well as OXO 4 (1mg/kg, i.p. (60.92 ± 11.37 sec); p<0.05. We also evaluate the OXO 4 at 15, 30 and 45 min. affording the mayor reduction at 30 minutes after the administration. Thus, our results suggest that OXO 4 has a great antidepressant effect non-reported for this type of isoquinoline alkaloids. The pharmaceutical use of OXO 4 in the treatment of depressive disorders is a therapeutic alternative to be studied.

  15. N(1)-(quinolin-2-ylmethyl)butane-1,4-diamine, a polyamine analogue, attenuated injury in in vitro and in vivo models of cerebral ischemia. (United States)

    Cen, Juan; Liu, Lu; He, Ling; Liu, Man; Wang, Chao-Jie; Ji, Bian-Sheng


    It has been widely recognized that glutamate (Glu)-induced cytotoxicity, intracellular calcium overload and excessive free radical production are the key players in the development and progression of ischemic brain injury. Since MK-801, an antagonist of N-methyl-d-aspartate (NMDA) receptor, showed many adverse reactions that hampered its clinical applications, development of safe and effective agent for the treatment of cerebral ischemia is eagerly required. This study was to investigate the effects of N(1)-(quinolin-2-ylmethyl)butane-1,4-diamine (QMA), a polyamine analogue, on the in vitro and in vivo models of cerebral ischemic damage. The results revealed that pretreatment with QMA could attenuate Glu, putrescine (Put) and oxygen-glucose deprivation (OGD)-induced cell death, lipid peroxidation as well as the elevation of reactive oxygen species (ROS) and intracellular [Ca(2+)](i) in pheochromocytoma (PC12) cells and in rat primary cortical neurons. The results also demonstrated that QMA could inhibit NMDA-mediated intracellular [Ca(2+)](i) accumulation in rat primary cortical neurons and reduce brain infarct volume in middle cerebral artery occlusion (MCAO) rats. The present report suggested that polyamines played a crucial role in the pathological processes of cerebral ischemic damage and that QMA or other novel polyamine analogues could be promising therapeutic candidates for stroke by virtue of their anti-hypoxia and antioxidation property.

  16. Antitumor activity of amidino-substituted benzimidazole and benzimidazo[1,2-a]quinoline derivatives tested in 2D and 3D cell culture systems. (United States)

    Brajša, Karmen; Vujasinović, Ines; Jelić, Dubravko; Trzun, Marija; Zlatar, Ivo; Karminski-Zamola, Grace; Hranjec, Marijana


    Due to a poor clinical predictive power of 2D cell cultures, standard tool for in vitro assays in drug discovery process, there is increasing interest in developing 3D in vitro cell cultures, biologically relevant assay feasible for the development of robust preclinical anti-cancer drug screening platforms. Herein, we tested amidino-substituted benzimidazoles and benzimidazo[1,2-a]quinolines as a small platform for comparison of antitumor activity in 2D and 3D cell culture systems and correlation with structure-activity relationship. 3D cell culture method was applied on a human cancer breast (SK-BR-3, MDA-MB-231, T-47D) and pancreatic cancer cells (MIA PaCa-2, PANC-1). Results obtained in 2D and 3D models were highly comparable, but in some cases we have observed significant disagreement indicating that some prominent compounds can be discarded in early phase of researching because of compounds with false positive result. To confirm which of cell culture systems is more accurate, in vivo profiling is needed.

  17. Synthesis, crystal structure, biological evaluation, and molecular docking studies of quinoline-arylpiperazine derivative as potent α1A-adrenoceptor antagonist (United States)

    Xu, Wei; Jiang, Renwang; Yuan, Mu


    Arylpiperazine derivatives received special attention owing to their antagonist potency on α1-adrenoceptors (α1-ARs). In this work, quinoline-arylpiperazine derivative (1) was synthesized and its structural properties were investigated using single crystal X-ray diffraction analysis and theoretical calculations. Biological evaluation in vitro revealed that compound 1 exhibited a 3-fold higher selectivity for α1A-AR over than α1B subtype when compared to non-selective antagonist prazosin. Molecular docking studies shed light on the antagonistic activity of both 1 and prazosin on α1A and α1B-AR. The docking results suggested that residues Gln177, Phe86, Phe288, Phe308, Phe312 and Tyr316 were identified as the major sites for the two agents binding to the α1A receptor. As depicted by pharmacophoric model, 1 was deemed to be the α1A-selective antagonist on the basis of pharmacophoric features. Our present work may provide valuable information for better drug design of subtype-selective α1-AR antagonists.

  18. Quinolinic acid induced neurodegeneration in the striatum: a combined in vivo and in vitro analysis of receptor changes and microglia activation

    Energy Technology Data Exchange (ETDEWEB)

    Moresco, R.M. [San Raffaele Scientific Institute, IBFM-CNR, University of Milan Bicocca and Nuclear Medicine Department, Milano (Italy); Scientific Institute H San Raffaele, Department of Nuclear Medicine, Milano (Italy); Lavazza, T. [San Raffaele Scientific Institute, Laboratory of Neurobiology of Learning, Milano (Italy); Belloli, S.; Todde, S.; Matarrese, M.; Carpinelli, A.; Turolla, E.; Fazio, F. [San Raffaele Scientific Institute, IBFM-CNR, University of Milan Bicocca and Nuclear Medicine Department, Milano (Italy); Lecchi, M. [University of Milan Statale, San Paolo Hospital, Institute of Radiology, Milan (Italy); Pezzola, A.; Popoli, P. [Istituto Superiore di Sanita, Laboratory of Pharmacology, Rome (Italy); Zimarino, V. [San Raffaele Scientific Institute, DIBIT, Milano (Italy); Malgaroli, A. [San Raffaele Scientific Institute, Laboratory of Neurobiology of Learning, Milano (Italy); Vita-Salute San Raffaele University, Milano (Italy)


    Huntington's disease (HD) is a progressive neurodegenerative disorder, which is characterised by prominent neuronal cell loss in the basal ganglia with motor and cognitive disturbances. One of the most well-studied pharmacological models of HD is produced by local injection in the rat brain striatum of the excitotoxin quinolinic acid (QA), which produces many of the distinctive features of this human neurodegenerative disorder. Here, we report a detailed analysis, obtained both in vivo and in vitro of this pharmacological model of HD. By combining emission tomography (PET) with autoradiographic and immunocytochemical confocal laser techniques, we quantified in the QA-injected striatum the temporal behavior (from 1 to 60 days from the excitotoxic insult) of neuronal cell density and receptor availability (adenosine A{sub 2A} and dopamine D{sub 2} receptors) together with the degree of microglia activation. Both approaches showed a loss of adenosine A{sub 2A} and dopamine D{sub 2} receptors paralleled by an increase of microglial activation. This combined longitudinal analysis of the disease progression, which suggested an impairment of neurotransmission, neuronal integrity and a reversible activation of brain inflammatory processes, might represent a more quantitative approach to compare the differential effects of treatments in slowing down or reversing HD in rodent models with potential applications to human patients. (orig.)

  19. Effects of sucrose and cornstarch on 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced colon and liver carcinogenesis in F344 rats

    DEFF Research Database (Denmark)

    Lindecrona, R.H.; Dragsted, Lars Ove; Poulsen, Morten


    The purpose of the present study was to compare the effect of sucrose and cornstarch on colon and liver carcinogenesis induced by 0.02% of the food-borne carcinogen 2-amino-3-methylimidazo [4,5-f]quinoline (IQ) in the feed. Male F344 rats were allocated to four groups. Two groups were fed diets...... high in either cornstarch (68%) or sucrose (34% sucrose/34% cornstarch) and were initiated with IQ. The remaining two groups received the same two diets but did not receive any IQ. In both liver and colon, administration of IQ resulted in a higher level of DNA adducts. In animals not dosed with IQ......, sucrose increased the adduct level in both organs but to a lower level than IQ. However, simultaneous administration of IQ and sucrose did not further increase the adduct level. Both IQ and sucrose increased the expression of the DNA-repair enzyme ERCC1 in the liver. In the colon, the number of large...

  20. Detection of nanomolar concentrations of copper(II) with a Tb-quinoline-2-one probe using luminescence quenching or luminescence decay time. (United States)

    Turel, Matejka; Duerkop, Axel; Yegorova, Alla; Scripinets, Yulia; Lobnik, Aleksandra; Samec, Niko


    We present a time-resolved (gated) luminescence-based method for determination of Cu2+ ions in microtiterplate format in the nanomolar concentration range using the novel long-lived terbium-[1-methyl-4-hydroxy-3-(N-2-ethyl-5-aminothiadiazolyl-)-carbamoyl-quinoline-2-one] (TbL) complex. The probe works best in Tb:L = 1:2 stoichiometry at neutral pH. The dynamic range is from 10 to 300 nmol L(-1) of Cu2+ and the limit of detection is 4.3 nmol L(-1). This is the lowest limit of detection achieved so far for luminescent lanthanide-based probes for copper. It is shown that gating can efficiently suppress intense, short decaying background fluorescence e.g. that of Rhodamine 6G. The assay can be performed by measurement of luminescence decay time, as well. Stern-Volmer studies indicate that static quenching dominates over dynamic quenching. TbL2 was tested for the effect of some relevant interferents and the assay was applied to the determination of copper in tap water samples. The results achieved were in good agreement with those of a reference method.

  1. Rare earth complexes with a novel ligand N-(naphthalen-2-yl)- N-phenyl-2-(quinolin-8-yloxy)acetamide: Preparation and spectroscopic studies (United States)

    Wu, Wei-Na; Tang, Ning; Yan, Lan


    Six complexes of rare earth nitrates (Ln = La, Sm, Eu, Gd, Tb, Dy) with a new amide type ligand, N-(naphthalen-2-yl)- N-phenyl-2-(quinolin-8-yloxy)acetamide (L) have been prepared and characterized by elemental analysis, conductivity measurements, IR and and 1H NMR spectra. Under excitation, Eu(III) and Sm(III) complexes exhibited strong red emissions. And the luminescence intensity of Sm(III) complex is higher than that of Eu(III) complex. Thus the Eu(III) and Sm(III) complexes are the potential light conversion agent. However, the Tb(III) and Dy(III) complexes cannot exhibit characteristic emissions of terbium and dysprosium ions, respectively. The results of phosphorescence spectrum show that the triplet-state energy level of the ligand matches better to the resonance level of Eu(III) than Tb(III) ion. In addition, the luminescence of the Eu(III) complex is also relatively strong in highly diluted tetrahydrofuran solution (2 × 10 -4 mol/L) compared with the powder. This is not only due to the solvate effects but also to the changes of the structure of the Eu(III) complex after being dissolved into the solvents. Furthermore, owing to the co-luminescence effect, the proper La(III) or Gd(III) doped Eu(III) complexes show stronger luminescence than the pure Eu(III) complex.

  2. Series of coordination polymers based on 4-(5-sulfo-quinolin-8-yloxy) phthalate and bipyridinyl coligands: Structure diversity and properties

    Energy Technology Data Exchange (ETDEWEB)

    Feng, Xun [College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022 (China); Liu, Jing [College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001 (China); College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022 (China); Li, Jin; Ma, Lu-Fang [College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022 (China); Wang, Li-Ya, E-mail: [College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022 (China); College of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang 473601 (China); Ng, Seik-Weng [Department of Chemistry, University of Malaya, Kuala Lumpur 50603 (Malaysia); Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 80203 (Saudi Arabia); Qin, Guo-Zhan [College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022 (China)


    Reactions between later metal salts and conjugational N-hetrocyclic sulfonate/ carboxylic acid under the presence of bipyridyl auxiliary ligands afforded a series of manganese, nickel, zinc, silver, cadmium coordination polymers bearing with phenyl pendant arm attached to quinoline skeletons, and they have been characterized by elements analysis, thermogravimetry, infrared spectroscopy and single-crystal X-ray diffraction studying. The series of polymers show interesting structural diversity in coordination environment, dimensions and topologies. They are all built from 2-D networks constructed from metal cluster through sulfonate or carboxylate groups, as the secondary building unit (SBU). The thermalgravimetric analyses show that they display framework stabilities in solid state. Variable-temperature magnetic susceptibility studies reveal the existence of antiferromagnetic interactions between adjacent Mn (II) ions in 1, and ferromagnetic interactions between Ni(II) ions for 2, respectively. The photo-luminescence properties of 3-5 have also been investigated systemically. - Highlights: • A series of coordination polymers based on later transition metal ions have been obtained. • They contain conjugational N-hetrocyclic sulfonate-carboxylic acid and bipyridyl auxiliary ligands. • They have been characterized systemically. • They exhibit structure diversity and interesting properties.

  3. DMH1 (4-[6-(4-isopropoxyphenylpyrazolo[1,5-a]pyrimidin-3-yl]quinoline inhibits chemotherapeutic drug-induced autophagy

    Directory of Open Access Journals (Sweden)

    Yue Sheng


    Full Text Available Our previous work found that DMH1 (4-[6-(4-isopropoxyphenylpyrazolo [1,5-a]pyrimidin-3-yl]quinoline was a novel autophagy inhibitor. Here, we aimed to investigate the effects of DMH1 on chemotherapeutic drug-induced autophagy as well as the efficacy of chemotherapeutic drugs in different cancer cells. We found that DMH1 inhibited tamoxifen- and cispcis-diaminedichloroplatinum (II (CDDP-induced autophagy responses in MCF-7 and HeLa cells, and potentiated the anti-tumor activity of tamoxifen and CDDP for both cells. DMH1 inhibited 5-fluorouracil (5-FU-induced autophagy responses in MCF-7 and HeLa cells, but did not affect the anti-tumor activity of 5-FU for these two cell lines. DMH1 itself did not induce cell death in MCF-7 and HeLa cells, but inhibited the proliferation of these cells. In conclusion, DMH1 inhibits chemotherapeutic drug-induced autophagy response and the enhancement of efficacy of chemotherapeutic drugs by DMH1 is dependent on the cell sensitivity to drugs.

  4. Interaction between an 8-methoxypyrimido[4',5':4,5] thieno (2,3-)quinoline-4(3H)one antitumour drug and deoxyribonucleic acid

    Indian Academy of Sciences (India)

    M Gopal; M S Shahabuddin; Sanjeev R Inamdar


    The interaction of 8-methoxypyrimido[4',5':4,5] thieno (2,3-)quinoline-4(3H)one (MPTQ) with DNA was studied by UV-Vis and fluorescenc'e spectrophotometry as well as by hydrodynamic methods. On binding to DNA, the absorption spectrum underwent bathochromic and hypochromic shifts and the fluorescence was quenched. Binding parameters, determined from spectrophotometric measurements by Scatchard analysis, indicated a binding constant of 3.56 × 106 M-1 for calf thymus DNA at ionic strength 0.01 M. Binding to the GC-rich DNA of Micrococcus lysodeikticus was stronger than the binding to calf thymus DNA at ionic strength 0.01 M. The MPTQ increased the viscosity of sonicated rod-like DNA fragments, producing a calculated length of 2.4 Å/bound MPTQ molecule. The binding of MPTQ to DNA increased the melting temperature by about 4°C. This research offers a new intercalation functional group to DNA targetted drug design.

  5. A novel DNA intercalator, butylamino-pyrimido[4',5':4,5]selenolo(2,3-b)quinoline, induces cell cycle arrest and apoptosis in leukemic cells. (United States)

    Shahabuddin, M S; Nambiar, Mridula; Choudhary, Bibha; Advirao, Gopal M; Raghavan, Sathees C


    DNA intercalators are one of the most commonly used chemotherapeutic agents. Novel intercalating compounds of pyrimido[4',5':4,5]selenolo(2,3-b)quinoline series having a butylamino or piperazino group at fourth position (BPSQ and PPSQ, respectively) are studied. Our results showed that BPSQ induced cytotoxicity whereas PPSQ was cytostatic. The cytotoxicity induced by BPSQ was concentration- and time-dependent. Cell cycle analysis and tritiated thymidine assay revealed that BPSQ affects the cell cycle progression by arresting at S phase. The absence of p-histone H3 and reduction in the levels of PCNA in the cells treated with BPSQ further confirmed the cell cycle arrest. Further, annexin V staining, DNA fragmentation, nuclear condensation and changes in the expression levels of BCL2/BAD confirmed the activation of apoptosis. Activation of caspase 8 and lack of cleavage of caspase 9, caspase 3 and PARP suggest the possibility of BPSQ triggering extrinsic pathway for induction of apoptosis, which is discussed. Hence, we have identified a novel compound which would have clinical relevance in cancer chemotherapeutics.

  6. Studies on the potential neurotoxic and convulsant effects of increased blood levels of quinolinic acid in rats with altered blood-brain barrier permeability

    Energy Technology Data Exchange (ETDEWEB)

    Vezzani, A.; Stasi, M.A.; Wu, H.Q.; Castiglioni, M.; Weckermann, B.; Samanin, R. (Istituto di Ricerche Farmacologiche Mario Negri, Milano (Italy))


    Intravenous injection of 450 mg/kg quinolinic acid (Quin), an endogenous kynurenine metabolite with excitotoxic properties, induced only minor electroencephalographic (EEG) modifications and no neurotoxicity in rats with a mature blood-brain barrier (BBB). BBB permeability was altered in rats by focal unilateral irradiation of the cortex (7 mm in diameter and 5 mm in depth) with protons (60 Gy, 9 Gy/min). Three days after irradiation, Evans blue dye staining showed BBB breakdown in the dorsal hippocampus of the irradiated hemisphere. No neurotoxic or convulsant effects were observed as a consequence of the radiation itself. When BBB-lesioned rats were challenged with 225 mg/kg Quin iv, epileptiform activity was observed on EEG analysis. Tonic-clonic seizures were induced by 225-450 mg/kg Quin. Light microscopic analysis showed a dose-related excitotoxic type of lesion restricted to the hippocampus ipsilateral to the irradiated side. Neuro-degeneration was prevented by local injection of 120 nmol D(-)2-amino-7-phosphonoheptanoic acid, a selective N-methyl-D-aspartate receptor antagonist. No lesions or EEG or behavioral modifications occurred after 450 mg/kg nicotinic acid, an inactive analog of Quin. The potential neurotoxic and convulsant effects of increased blood levels of Quin under conditions of altered BBB permeability are discussed.

  7. Intracerebroventricular administration of inosine is anticonvulsant against quinolinic acid-induced seizures in mice: an effect independent of benzodiazepine and adenosine receptors. (United States)

    Ganzella, Marcelo; Faraco, Rafael Berger; Almeida, Roberto Farina; Fernandes, Vinícius Fornari; Souza, Diogo Onofre


    Inosine (INO) has an anticonvulsant effect against seizures induced by antagonists of GABAergic system. Quinolinic acid (QA) is an agonist NMDA receptors implicated in the neurobiology of seizures. In the present study, we investigated the anticonvulsant effect of intracerebroventricular (i.c.v.) INO administration against QA-induced seizures in adult mice. We also investigated whether the benzodiazepines (BZ) or adenosine (ADO) receptors were involved in the INO effects. Animals were pretreated with an i.c.v. injection of either vehicle or INO before an i.c.v. administration of 4 μl QA (36.8 nmol). All animals pretreated with vehicle followed by QA presented seizures. INO protected against QA-induced seizures in a time and dose dependent manner (up to 60% at 400 nmol, 5 min before QA injection). Diazepam (DZ) and ADO (i.c.v.) also exhibited anticonvulsant effect against QA induced seizures. Additionally, i.p. administration of either flumazenil, a BZ receptor antagonist, or caffeine, an ADO receptor antagonist, did not change the anticonvulsant potency of INO i.c.v. injection, but completely abolished the DZ and ADO anticonvulsant effects, respectively. In conclusion, this study demonstrated that INO exert anticonvulsant effect against hyperactivity of the glutamatergic system independently of BZ or ADO receptors activation.

  8. Trichlorido{2-dimethoxymethyl-4-methyl-6-[(quinolin-8-yliminomethyl]phenolato-κ3N,N′,O1}tin(IV

    Directory of Open Access Journals (Sweden)

    Keisuke Kawamoto


    Full Text Available In the title compound, [Sn(C20H19N2O3Cl3], the SnIV ion is surrounded by a tridentate monoanionic Schiff base and by three meridional chloride ions in a six-coordinated distorted octahedral geometry. The Sn—Cl bond [2.366 (2 Å] trans to nitrogen is shorter than the others [2.438 (2 and 2.414 (2 Å]. The N—Sn—N angle [76.19 (11°] is smaller than the O—Sn—N angle [87.89 (10°] in the Schiff base ligand. No classical intermolecular hydrogen-bonding interactions are observed. The crystal packing exhibits π–π stacking interactions, with a distance of 3.595 (2 Å between the centroids of the phenolate ring and the benzene ring of the quinoline group of inversion-related molecules.

  9. Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases. (United States)

    Liu, Zeng-Chen; Wang, Bao-Dui; Li, Bo; Wang, Qin; Yang, Zheng-Yin; Li, Tian-Rong; Li, Yong


    Three novel 2-oxo-quinoline-3-carbaldehyde Schiff-bases and their Cu(II) complexes were synthesized. The molecular structures of Cu(II) complexes were determined by X-ray crystal diffraction. The DNA-binding modes of the complexes were also investigated by UV-vis absorption spectrum, fluorescence spectrum, viscosity measurement and EB-DNA displacement experiment. The experimental evidences indicated that the ligands and Cu(II) complexes could interact with CT-DNA (calf-thymus DNA) through intercalation, respectively. Comparative cytotoxic activities of ligands and Cu(II) complexes were also determined by MTT [3-(4,5-dimethyl-2-thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide] and SRB (sulforhodamine B) methods. The results showed that the three Cu(II) complexes exhibited more effective cytotoxic activity against HL60 cells and HeLa cells than corresponding ligands. Also, CuL(3) showed higher cytotoxic activity than CuL(1) and CuL(2).

  10. Discovery of novel quinoline-based mTOR inhibitors via introducing intra-molecular hydrogen bonding scaffold (iMHBS): The design, synthesis and biological evaluation. (United States)

    Ma, Xiaodong; Lv, Xiaoqing; Qiu, Ni; Yang, Bo; He, Qiaojun; Hu, Yongzhou


    A series of quinoline derivatives featuring the novelty of introducing intra-molecular hydrogen bonding scaffold (iMHBS) were designed, synthesized and biologically evaluated for their mTOR inhibitory activity, as well as anti-proliferative efficacies against HCT-116, PC-3 and MCF-7 cell lines. As a result, six compounds exhibited significant inhibition against mTOR with IC50 values below 35nM. Compound 15a, the most potent mTOR inhibitor reported herein (IC50=14nM), also displayed the most favorable cellular activities, with the IC50 values of 0.46, 0.61 and 0.24μM against HCT-116, PC-3 and MCF-7, respectively. Besides, several compounds in this series were identified to be selective over class I PI3Ks. Further western blot analysis of 16b, a representative compound in this series, highlighted their advantage in surmounting the S6K/IRS1/PI3K negative feedback loop upon dual inhibition of mTORC1 and mTORC2. In addition to the remarkable activity, 15a demonstrated acceptable stability in simulated gastric fluid (SGF), simulated intestinal fluid (SIF) and liver microsome, thereby being valuable for extensive in vivo investigation.

  11. Synthesis, Characterization, Antimicrobial, DNA Cleavage, and Antioxidant Studies of Some Metal Complexes Derived from Schiff Base Containing Indole and Quinoline Moieties

    Directory of Open Access Journals (Sweden)

    Mahendra Raj Karekal


    Full Text Available A new Schiff base of 5-chloro-3-phenyl-1H-indole-2-carboxyhydrazide and 3-formyl-2-hydroxy-1H-quinoline (HL, and its Cu(II, Co(II, Ni(II, Zn(II, Cd(II, and Hg(II complexes have been synthesized and characterized in the light of microanalytical, IR, H1 NMR, UV-Vis, FAB-mass, ESR, XRD, and TGA spectral studies. The magnetic susceptibility measurements and low conductivity data provide evidence for monomeric and neutral nature of the complexes. On the basis of spectral studies and analytical data, it is evident that the Schiff base acts as tridentate ligand. The Cu(II, Co(II, and Ni(II complexes were octahedral, whereas Zn(II, Cd(II, and Hg(II complexes were tetrahedral in nature. The redox behavior of the Cu(II complex was investigated by electrochemical method using cyclic voltammetry. In order to evaluate the effect of metal ions upon chelation, both the ligand and its metal complexes were screened for their antibacterial and antifungal activities by minimum inhibitory concentration (MIC method. The DNA cleavage experiment performed using agarose gel electrophoresis method showed the cleavage of DNA by all the metal complexes. The free radical scavenging activity of newly synthesized compounds has been determined at a different concentration range by means of their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH.

  12. Synthesis, Structure and Quantum Chemical Study on the Organotin Complex [Di(2,4,6-trichlorobenzyl)]tin Bis(quinoline-2-formate)

    Institute of Scientific and Technical Information of China (English)


    The title compound was prepared by the reaction of di(2,4,6-trichlorobenzyl) stannic chloride with quinoline-2-formate and characterized with elemental analysis, 1H NMR, IR and X-ray diffraction methods. It crystallizes in monoclinic, space group P21/n with a = 1.3138(3), b = 1.8756(4), c = 1.4599(3) nm, β = 92.731(3)°, V = 3.5933(12) nm3, Z = 4, Dc = 1.795 g/cm3, μ(MoKα) = 1.425 mm-1, F(000) = 1920, R = 0.0778, wR = 0.2286 (for I > 2σ(I)) and R = 0.0932, wR = 0.2415 (for all data). The independent reflections were 6359, among which 5030 were observed (I > 2σ(I)) and used in the succeeding refinement. Structural analysis indicates that Sn is in a distorted octahedral coordination environment, and a three-dimensional network could be observed via intermolecular hydrogen bonds. Finally, the stability, frontier orbital composition and energy of the title compound were discussed with Lanl2dz basis set and G98W program.

  13. Biological evaluation of omega-(dialkylamino)alkyl derivatives of 6H-indolo[2,3-b]quinoline--novel cytotoxic DNA topoisomerase II inhibitors. (United States)

    Godlewska, Joanna; Luniewski, Wojciech; Zagrodzki, Bogdan; Kaczmarek, Lukasz; Bielawska-Pohl, Aleksandra; Dus, Danuta; Wietrzyk, Joanna; Opolski, Adam; Siwko, Magdalena; Jaromin, Anna; Jakubiak, Anna; Kozubek, Arkadiusz; Peczyñska-Czoch, Wanda


    A series of novel 6H-indolo[2,3-b]quinoline derivatives, substituted at C-2, C-9 or N-6 position with dialkyl(alkylamino)alkyl chains differing in the number of methylene groups, was prepared. These compounds were evaluated in vitro for their antimicrobial and cytotoxic activity against several cell lines of different origin and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. Liphophilic and calf thymus DNA-binding properties of these compounds were also investigated. All the compounds tested inhibited the growth of Gram-positive bacteria and fungi at MIC values ranging between 0.25 and 1 mM. They also showed cytotoxic activity against KB (human cervix carcinoma) cells (ID50 varied from 2.1 to 9.0 microM) and were able to overcome multidrug resistance in colorectal adenocarcinoma LoVo/DX, uterine sarcoma MES-SA/DX5 and promyelocytic leukemia HL-60/MX2 cells (the values of the resistance index RI fell between 0.54 and 2.4). The compounds induced G2M-phase cell cycle arrest in Jurkat T-cell leukemia cells, revealed DNA-binding properties and inhibited topoisomerase II activity.

  14. Synthesis and Crystal Structure of Ethyl(2-amino-4-(3-nitrophenyl)-1,4-dihydro-2H-pyrano[3,2-h]quinolin-3-)carboxylate

    Institute of Scientific and Technical Information of China (English)

    王香善; 史达清; 屠树江


    The title compound ethyl(2-amino-4-(3-nitrophenyl)-1,4-dihydro-2H-pyrano[3,2-h]quinolin-3-)carboxylate (C21H17N3O5, Mr= 391.38) was synthesized and crystallized. The crystal belongs to triclinic, space group P-1 with a = 7.886(1 ), b = 9.896(2), c = 12.575(3) A, α = 77.81 (2), β= 82.69(2), γ= 73.86(2)°, Z = 2, V= 919.0(3) A3, Dc = 1.414 g/cm3,μ(MoKα) = 0.103 mm -1, F(000)= 408, R = 0.0421 and wR = 0.0973 for 2007 observed reflections (I > 2σ(I)). X-ray analysis reveals that the C(6), C(7), C(10), C(11), C(12) and O(1) atoms form a six-membered ring which adopts a boat conformation. In the ring, the bond lengths of C(6)-C(7) and C(10)-C(11) are 1.360(2) and 1.361 (2) A, respectively, indicating they are C=C double bonds.

  15. Deficit, but Not Nondeficit, Schizophrenia Is Characterized by Mucosa-Associated Activation of the Tryptophan Catabolite (TRYCAT) Pathway with Highly Specific Increases in IgA Responses Directed to Picolinic, Xanthurenic, and Quinolinic Acid. (United States)

    Kanchanatawan, Buranee; Sirivichayakul, Sunee; Ruxrungtham, Kiat; Carvalho, André F; Geffard, Michel; Ormstad, Heidi; Anderson, George; Maes, Michael


    Evidence suggests that activation of the tryptophan catabolite (TRYCAT) pathway is involved in the pathophysiology of schizophrenia. However, no previous study examined whether TRYCAT pathway activation is associated with deficit schizophrenia. We measured IgA responses to TRYCATs, namely quinolinic acid, picolinic acid, kynurenic acid, xanthurenic acid, and anthranilic acid and 3-OH-kynurenine, in 40 healthy controls and in schizophrenic patients with (n = 40) and without (n = 40) deficit, defined according to the Schedule for the Deficit Syndrome (SDS). Primary deficit schizophrenia is accompanied by an activated TRYCAT pathway as compared to controls and nondeficit schizophrenia. Participants with deficit schizophrenia show increased IgA responses to xanthurenic acid, picolinic acid, and quinolinic acid and relatively lowered IgA responses to kynurenic and anthranilic acids, as compared to patients with nondeficit schizophrenia. Both schizophrenia subgroups show increased IgA responses to 3-OH-kynurenine as compared to controls. The IgA responses to noxious TRYCATs, namely xanthurenic acid, picolinic acid, quinolinic acid, and 3-OH-kynurenine, but not protective TRYCATS, namely anthranilic acid and kunyrenic acid, are significantly higher in deficit schizophrenia than in controls. The negative symptoms of schizophrenia are significantly and positively associated with increased IgA responses directed against picolinic acid and inversely with anthranilic acid, whereas no significant associations between positive symptoms and IgA responses to TRYCATs were found. In conclusion, primary deficit schizophrenia is characterized by TRYCAT pathway activation and differs from nondeficit schizophrenia by a highly specific TRYCAT pattern suggesting increased excitotoxicity, cytotoxicity, and neurotoxicity, as well as inflammation and oxidative stress. The specific alterations in IgA responses to TRYCATs provide further insight for the biological delineation of deficit

  16. Refined carbohydrate enhancement of aberrant crypt foci (ACF) in rat colon induced by the food-borne carcinogen 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ)

    DEFF Research Database (Denmark)

    Kristiansen, E.; Meyer, Otto A.; Thorup, I.


    ,2-dimethylhydrazine dihydrochloride (DMH) and azoxymethane (AOM), the use of a diet-related colon cancer initiator, such as the heterocyclic amine 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ) formed during meat cooking, would probably give a more relevant insight into diet-related colon carcinogenesis....... In the present study it is shown that a feeding regimen with continuous low IQ doses (0.03% in the diet) throughout a study period of 10 weeks has a significant effect on the induction of ACF in the colon of male F344 rats. In addition, the study illustrates that the incidence of the IQ-induced ACF can...

  17. Twenty six-week exposure to 2 amino-3 methylimidazo [4,5-f]quinoline (IQ) does not significantly increase the incidence of tumours in HMGCR/mts1 tg579 transgenic mice

    DEFF Research Database (Denmark)

    Mortensen, Alicja; Lukanidin, E.; Ambartsumian, N.S.


    and C57BL/6ByA (wild type) mice (15 males and 15 females of each genotype per group) received either a control diet for 53 weeks or a control diet plus 0.03% 2-amino-3 methylimidazo[4,5-f]quinoline (IQ) for 26 weeks and a control diet for the remaining 27 weeks. IQ is a food mutagen with a carcinogenic...... effect in non-human primates and rodents. IQ is a liver carcinogen and also causes lung tumours and tumours of the forestomach in mice. Body weight gain and feed intake were decreased (p...

  18. Oxidative DNA damage of mixed copper(II) complexes with sulfonamides and 1,10-phenanthroline. Crystal structure of [Cu(N-quinolin-8-yl-p-toluenesulfonamidate)2(1,10-phenanthroline)]. (United States)

    Macías, Benigno; García, Isabel; Villa, María V; Borrás, Joaquín; González-Alvarez, Marta; Castiñeiras, Alfonso


    Mixed coordination compounds of Cu(II) with sulfonamides and 1,10-phenanthroline as ligands have been prepared and characterised. Single crystal structural determination of the complex [Cu(N-quinolin-8-yl-p-toluenesulfonamidate)(2)(phen)] shows Cu(II) ions are located in a highly distorted octahedral environment, probably as a consequence of the Jahn-Teller effect. The FT-IR and electronic paramagnetic resonance (EPR) spectra are also discussed. The mixed complexes prepared undergo an extensive DNA cleavage in the presence of ascorbate and hydrogen peroxide. Two of the complexes have higher nucleolytic efficiency than the bis(o-phenanthroline)copper(II) complex.

  19. Design, Synthesis and Antifungal Activity of 6-Fiuoro-3,3a,4,5-tetrahydro-2H-pyrazolo[4,3-c]-quinoline-2-carboxamide Derivatives

    Institute of Scientific and Technical Information of China (English)

    YUAN Jing; SU Xin; ZHANG Xin; CONG Lin; GUO Chun


    A series of 6-fluoro-3,3a,4,5-tetrahydro-2H-pyrazolo[4,3-c]quinoline-2-carboxamide derivatives was designed based on the bioisosterism and combination principle in drug design.The target compounds were synthesized from substituted aniline through Michael addition,eyclization,Mannich reaction and condensation with 4-substituted semicarbazides,and the structures were confirmed by mass spectrometry(MS)and 1H NMR.The antifungal assay was carried out in vitro by two-fold dilution.The result shows that all the compounds are of antifungal activities against the tested fungi at different levels.

  20. Gold(I) complex of 1,1'-bis(diphenylphosphino) ferrocene-quinoline conjugate: a virostatic agent against HIV-1. (United States)

    Gama, Ntombenhle; Kumar, Kamlesh; Ekengard, Erik; Haukka, Matti; Darkwa, James; Nordlander, Ebbe; Meyer, Debra


    HIV infection is known for replicating in proliferating CD(+) T-cells. Treatment of these cells with cytostatic (anti-proliferation) compounds such as hydroxyurea interferes with the cells's ability support HIV replication. Combinations of such cytostatic compounds with proven anti-retroviral drugs (like ddI) are known as virostatic, and have been shown to aid in the control of the infection. The use of two different drugs in virostatic combinations however, carries the risk of adverse effects including drug-drug interactions, which could lead to augmented toxicities and reduced efficacy. Here, a novel digold(I) complex of ferrocene-quinoline (3) was investigated for cytostatic behaviour as well as anti-viral activity which if demonstrated would eliminate concerns of drug-drug interactions. The complex was synthesized and characterized by NMR, FT-IR and mass spectroscopy and the molecular structure was confirmed by X-ray crystallography. Bio-screening involved viability dyes, real time electronic sensing and whole virus assays. The complex showed significant (p = 0.0092) inhibition of virus infectivity (83 %) at 10 ug/mL. This same concentration caused cytostatic behaviour in TZM-bl cells with significant (p < 0.01) S and G2/M phase cell cycle arrest. These data supports 3 as a virostatic agent, possessing both anti-viral and cytostatic characteristics. In the absence of 3, TZM-bl cells were infected by a pseudovirus and this was demonstrated through luminescence in a luciferase assay. Pre-incubation of the virus with 3 decreased luminescence, indicating the anti-viral activity of 3. Complex 3 also showed cytostatic behavior with increased S-phase and G2/M phase cell cycle arrest.

  1. Quinine dimers are potent inhibitors of the Plasmodium falciparum chloroquine resistance transporter and are active against quinoline-resistant P. falciparum. (United States)

    Hrycyna, Christine A; Summers, Robert L; Lehane, Adele M; Pires, Marcos M; Namanja, Hilda; Bohn, Kelsey; Kuriakose, Jerrin; Ferdig, Michael; Henrich, Philipp P; Fidock, David A; Kirk, Kiaran; Chmielewski, Jean; Martin, Rowena E


    Chloroquine (CQ) resistance in the human malaria parasite Plasmodium falciparum is primarily conferred by mutations in the "chloroquine resistance transporter" (PfCRT). The resistance-conferring form of PfCRT (PfCRT(CQR)) mediates CQ resistance by effluxing the drug from the parasite's digestive vacuole, the acidic compartment in which CQ exerts its antiplasmodial effect. PfCRT(CQR) can also decrease the parasite's susceptibility to other quinoline drugs, including the current antimalarials quinine and amodiaquine. Here we describe interactions between PfCRT(CQR) and a series of dimeric quinine molecules using a Xenopus laevis oocyte system for the heterologous expression of PfCRT and using an assay that detects the drug-associated efflux of H(+) ions from the digestive vacuole in parasites that harbor different forms of PfCRT. The antiplasmodial activities of dimers 1 and 6 were also examined in vitro (against drug-sensitive and drug-resistant strains of P. falciparum) and in vivo (against drug-sensitive P. berghei). Our data reveal that the quinine dimers are the most potent inhibitors of PfCRT(CQR) reported to date. Furthermore, the lead compounds (1 and 6) were not effluxed by PfCRT(CQR) from the digestive vacuole but instead accumulated to very high levels within this organelle. Both 1 and 6 exhibited in vitro antiplasmodial activities that were inversely correlated with CQ. Moreover, the additional parasiticidal effect exerted by 1 and 6 in the drug-resistant parasites was attributable, at least in part, to their ability to inhibit PfCRT(CQR). This highlights the potential for devising new antimalarial therapies that exploit inherent weaknesses in a key resistance mechanism of P. falciparum.

  2. L-theanine prevent quinolinic acid induced motor deficit and striatal neurotoxicity: Reduction in oxido-nitrosative stress and restoration of striatal neurotransmitters level. (United States)

    Jamwal, Sumit; Singh, Shamsher; Gill, Jaskamal Singh; Kumar, Puneet


    L-theanine has been documented to possess anti-oxidant, anti-inflammatory and neuroprotective potential in various animal models of neurological disorders. The present study was anticipated to investigate the effect of L-theanine against quinolinic acid induced motor deficits, oxido-nitrosative stress, neuro-inflammation and neurotransmitters alteration in rats. Rats were stereotaxically injected QA (200nmol/2µl saline; intrastriatal); bilaterally on 0 day and L-theanine (25 & 50mg/kg; p.o.) was administered for 21 days starting from day 1 of QA injection. Either, L-NAME (10mg/kg; i.p.), a nitric oxide synthase inhibitor and L-arginine (50mg/kg; i.p.), a nitric oxide synthase precursor were administered with L-theanine in respective groups. Behavioral observations were evaluated on weekly basis using rota-rod, grip strength, narrow beam walking and open field test. QA treatment induces significant alteration in body weight, motor coordination, oxidative defense, pro-inflammatory cytokines and striatal neurotransmitters level. L-theanine treatment alone, at both the tested doses, significantly attenuated QA induced alterations. In addition, treatment of L-theanine with L-NAME significantly enhances the protective effect of L-theanine whereas treatment of L-theanine with L-arginine significantly ameliorated the protective effect of L-theanine. The protective effect of L-theanine is attributed to its anti-oxidant, anti-inflammatory and modulatory effect on nitric oxide pathway and neurotransmitters level in striatum. This suggests use of L-theanine in the clinical settings of HD. Copyright © 2017 Elsevier B.V. All rights reserved.

  3. Determination of chloridion ion in quinolinic acid by ion chromatography%离子色谱法测定喹啉酸中的氯离子

    Institute of Scientific and Technical Information of China (English)

    王敬花; 张锦梅


    本文建立了离子色谱-抑制电导法检测喹啉酸中的氯离子的方法.实验采用SH-AC-1型离子交换色谱柱,最佳色谱条件为:以1.8 mm Na2CO3和1.7 mm NaHCO3的淋洗液,柱温45℃,流速1.5 mL·min-1.在此条件下,Cl-色谱峰型对称.所测Cl-的检出限(S/N=3)分别为0.005 mg· L-1.应用本方法测定Cl-,加标回收率在96%~104%之间.本方法简单,准确,可靠,具有较好的实用性.%The determination method of chloridion ion in quinolinic acid by ion chromatography suppressed conductivity detection was established. SH-AC-1 ion exchange column was used, the selected best chromato-graphic conditions as follows: 1.8 nun sodium carbonate and 1.7 mm sodium bicarbonate mixture was as the eluent, column temperature was 45℃, the flow rate chosen was 1.5 mL·min-1. On these conditions, Cl anion was carried out with symmetric peak. The detection limit of Cl was 0.005 mg·L-1(S/N=3). The recovery to determine Cl anion was between 96%~104%. This method is simple, accurate, reliable, and better practical applicability.

  4. Severe depression is associated with increased microglial quinolinic acid in subregions of the anterior cingulate gyrus: Evidence for an immune-modulated glutamatergic neurotransmission?

    Directory of Open Access Journals (Sweden)

    Mawrin Christian


    Full Text Available Abstract Background Immune dysfunction, including monocytosis and increased blood levels of interleukin-1, interleukin-6 and tumour necrosis factor α has been observed during acute episodes of major depression. These peripheral immune processes may be accompanied by microglial activation in subregions of the anterior cingulate cortex where depression-associated alterations of glutamatergic neurotransmission have been described. Methods Microglial immunoreactivity of the N-methyl-D-aspartate (NMDA glutamate receptor agonist quinolinic acid (QUIN in the subgenual anterior cingulate cortex (sACC, anterior midcingulate cortex (aMCC and pregenual anterior cingulate cortex (pACC of 12 acutely depressed suicidal patients (major depressive disorder/MDD, n = 7; bipolar disorder/BD, n = 5 was analyzed using immunohistochemistry and compared with its expression in 10 healthy control subjects. Results Depressed patients had a significantly increased density of QUIN-positive cells in the sACC (P = 0.003 and the aMCC (P = 0.015 compared to controls. In contrast, counts of QUIN-positive cells in the pACC did not differ between the groups (P = 0.558. Post-hoc tests showed that significant findings were attributed to MDD and were absent in BD. Conclusions These results add a novel link to the immune hypothesis of depression by providing evidence for an upregulation of microglial QUIN in brain regions known to be responsive to infusion of NMDA antagonists such as ketamine. Further work in this area could lead to a greater understanding of the pathophysiology of depressive disorders and pave the way for novel NMDA receptor therapies or immune-modulating strategies.

  5. Tasquinimod (ABR-215050, a quinoline-3-carboxamide anti-angiogenic agent, modulates the expression of thrombospondin-1 in human prostate tumors

    Directory of Open Access Journals (Sweden)

    Isaacs John T


    Full Text Available Abstract Background The orally active quinoline-3-carboxamide tasquinimod [ABR-215050; CAS number 254964-60-8, which currently is in a phase II-clinical trial in patients against metastatic prostate cancer, exhibits anti-tumor activity via inhibition of tumor angiogenesis in human and rodent tumors. To further explore the mode of action of tasquinimod, in vitro and in vivo experiments with gene microarray analysis were performed using LNCaP prostate tumor cells. The array data were validated by real-time semiquantitative reversed transcriptase polymerase chain reaction (sqRT-PCR and protein expression techniques. Results One of the most significant differentially expressed genes both in vitro and in vivo after exposure to tasquinimod, was thrombospondin-1 (TSP1. The up-regulation of TSP1 mRNA in LNCaP tumor cells both in vitro and in vivo correlated with an increased expression and extra cellular secretion of TSP1 protein. When nude mice bearing CWR-22RH human prostate tumors were treated with oral tasquinimod, there was a profound growth inhibition, associated with an up-regulation of TSP1 and a down- regulation of HIF-1 alpha protein, androgen receptor protein (AR and glucose transporter-1 protein within the tumor tissue. Changes in TSP1 expression were paralleled by an anti-angiogenic response, as documented by decreased or unchanged tumor tissue levels of VEGF (a HIF-1 alpha down stream target in the tumors from tasquinimod treated mice. Conclusions We conclude that tasquinimod-induced up-regulation of TSP1 is part of a mechanism involving down-regulation of HIF1α and VEGF, which in turn leads to reduced angiogenesis via inhibition of the "angiogenic switch", that could explain tasquinimods therapeutic potential.

  6. Effect of 5-chloro-7-iodo-8-hydroxy-quinoline (clioquinol) on the uptake and distribution of nickel, zinc and mercury in mice

    Energy Technology Data Exchange (ETDEWEB)

    Tjaelve, H. (Department of Pharmacology and Toxicology, the Swedish University of Agricultural Sciences, Uppsala); Staahl, K. (Department of Toxicology, University of Uppsala, Sweden)


    5-Chloro-7-iodo-8-hydroxy-quinoline (clioquinol) was found to induce a very marked increase in the concentration of /sup 63/Ni/sup 2 +/ in various tissues of mice when given orally together with the metal, compared with oral administrations of /sup 63/Ni/sup 2 +/ only. Markedly increased tissue concentrations, although less expressed than for the /sup 63/Ni/sup 2 +/, were also observed for /sup 65/Zn/sup 2 +/. Clioquinol increased the tissue levels of /sup 203/Hg/sup 2 +/ to a lesser extent. When clioquinol was given intraperitoneally and /sup 63/Ni/sup 2 +/ was given intravenously there were also very markedly increased tissue levels of the metal, compared with intravenous injections of /sup 63/Ni/sup 2 +/ only. It was also shown that the urinary excretion of /sup 63/Ni/sup 2 +/ was greatly increased in mice given the metal orally together with clioquinol, compared with mice given the /sup 63/Ni/sup 2 +/ only. Clioquinol and other 8-hydroxyquinolines form lipophilic chelates with metallic cations and the observed effects on the tissue-disposition of the metals are probably due to a facilitated penetration through the cellular membranes. Determinations of the chloroform:water partition coefficients showed the highest lipophilicity for the nickel-clioquinol-complex followed in decreasing order by the complexes with zinc and mercury. These data suggest that the ability of the clioquinol to affect the uptake of the metals in the cells may be related to the relative lipophilicity of the metal-clioquinol-complexes.

  7. Adenosine A{sub 2A} receptor imaging with [{sup 11}C]KF18446 PET in the rat brain after quinolinic acid lesion. Comparison with the dopamine receptor imaging

    Energy Technology Data Exchange (ETDEWEB)

    Ishiwata, Kiichi; Ogi, Nobuo; Hayakawa, Nobutaka [Tokyo Metropolitan Inst. of Gerontology, Tokyo (Japan). Positron Medical Center] [and others


    We proposed [{sup 11}C]KF18446 as a selective radioligand for mapping the adenosine A{sub 2A} receptors being highly enriched in the striatum by positron emission tomography (PET). In the present study, we investigated whether [{sup 11}C]KF18446 PET can detect the change in the striatal adenosine A{sub 2A} receptors in the rat after unilateral injection of an excitotoxin quinolinic acid into the striatum, a Huntington's disease model, to demonstrate the usefulness of [{sup 11}C]KF18446. The extent of the striatal lesion was identified based on MRI, to which the PET was co-registered. The binding potential of [{sup 11}C]KF18446 significantly decreased in the quinolinic acid-lesioned striatum. The decrease was comparable to the decrease in the potential of [{sup 11}C] raclopride binding to dopamine D{sub 2} receptors in the lesioned striatum, but seemed to be larger than the decrease in the potential of [{sup 11}C]SCH23390 binding to dopamine D{sub 1} receptors. Ex vivo and in vitro autoradiography validated the PET signals. We concluded that [{sup 11}C]KF18446 PET can detect change in the adenosine A{sub 2A} receptors in the rat model, and will provide a new diagnostic tool for characterizing post-synaptic striatopallidal neurons in the stratum. (author)

  8. FT-IR, FT-Raman and NMR characterization of 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate and investigation of its reactive and optoelectronic properties by molecular dynamics simulations and DFT calculations (United States)

    Menon, Vidya V.; Fazal, Edakot; Mary, Y. Sheena; Panicker, C. Yohannan; Armaković, Stevan; Armaković, Sanja J.; Nagarajan, Subban; Van Alsenoy, C.


    The FT-IR and FT-Raman spectra of the synthesized compound, 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate is recorded and analyzed. Optimized molecular structure, wave numbers, corresponding assignments regarding 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate has become screened tentatively as well as hypothetically using Gaussian09 program package. Natural bonding orbital assessment has been completed with a reason to clarify charge transfer or conjugative interaction, the intra-molecular re-hybridization and delocalization of electron density within the molecule. The NMR spectral assessment had been made choosing structure property relationship by chemical shifts along with the magnetic shielding effects regarding the title compound. The first and second hyperpolarizabilities were calculated. The calculated first order hyperpolarizability is commensurate with the documented worth of very similar derivatives and could be an interesting object for more experiments on nonlinear optics. Local reactivity properties have been investigated using average local ionization energies and Fukui functions. Investigation of optoelectronic properties encompassed calculations of reorganization energies and hopping rates of charge carriers within the framework of Marcus semi-empiric approach. The docked ligand title compound forms a stable complex with CDK inhibitors and gives a binding affinity value of -9.7 kcal/mol and molecular docking results suggest that the compound might exhibit inhibitory activity against CDK inhibitors.

  9. Evaluation of the antipsychotic effects of 2-(dimethylamino)- and 2-(methylamino)-7H-naphtho[1,2,3-de]quinolin-7-one derivatives in experimental model of psychosis in mice. (United States)

    Moghaddam, Akbar Hajizadeh; Sobarzo-Sánchez, Eduardo; Nabavi, Seyed Fazel; Daglia, Maria; Nabavi, Seyed Mohammad


    Research into novel therapeutic strategies for schizophrenia with high efficacy and low side effects has been progressed in recent years. In the present study, anti-schizophrenia activities of 2-(dimethylamino)- and 2-(methylamino)- 7H-naphtho[1,2,3-de]quinolin-7-one derivatives (D1-D10) have been evaluated in ketamine-induced experimental schizophrenia model in mice. For this aim, experimental animals was submitted to ketamine intraperitoneal injection at 100 mg/kg/day. Then, D1-D10 were administrated intra-cerebroventricularly to mice and in next step, animals depressive-like behaviors have been examined by despair swimming test. The obtained results demonstrate that 7H-naphtho[1,2,3- de]quinolin-7-one derivatives, specifically D9, reduced depressive-like behaviors via the decrease of the immobility time and the increase of the swim and climb times. Overall, these results showed that these alkaloids have anti-schizophrenia efficacy and due to their low side effects, they can be used as a new strategy for the treatment of depressive symptoms of schizophrenia patients.

  10. 10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/-N═ Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges. (United States)

    Pozharskii, Alexander F; Ozeryanskii, Valery A; Mikshiev, Vladimir Y; Antonov, Alexander S; Chernyshev, Anatoly V; Metelitsa, Anatoly V; Borodkin, Gennady S; Fedik, Nikita S; Dyablo, Olga V


    For the first time, 10-dimethylamino derivatives of benzo[h]quinoline 6 and benzo[h]quinazoline 7a-e as mixed analogues of archetypal 1,8-bis(dimethylamino)naphthalene ("proton sponge") 1 and quino[7,8-h]quinoline 2a have been examined. Similar to 1 and 2, compounds 6 and 7 display rather high basicity, forming chelated monocations. At the same time, unexpected specifics of the protonated NMe2/-N═ systems consist of a strong shift of the NH proton to the 10-NMe2 group, contrary to the "aniline-pyridine" basicity rule. In case of 4H(+), a rapid migration (in the NMR time scale) of the NH proton between two nitrogen atoms along the N-H···N hydrogen bond was registered at room temperature and frozen below -30 °C with the proton fixed on the NMe2 group. Two different approaches for classification of strong neutral nitrogen organic bases as proton sponges (kinetically inert compounds) or pseudo-proton sponges (kinetically active) are discussed. On this basis, benzoquinoline 6 was identified as staying closer to pseudo-proton sponges while 7a-e to proton sponges due to the presence in their molecules of bulky substituents in the pyrimidine ring. Other remarkable peculiarities of 6 and 7 are their yellow color and luminescence in the visible region distinguishing them from colorless 1 and 2a.

  11. Three new Cu(Ⅱ)-Ln(Ⅲ)heterometallic coordination polymers constructed from quinolinic acid and nicotinic acid:Synthesis,structures,and magnetic properties%Three new Cu(Ⅱ)-Ln(Ⅲ)heterometallic coordination polymers constructed from quinolinic acid and nicotinic acid: Synthesis,structures,and magnetic properties

    Institute of Scientific and Technical Information of China (English)

    LIU SuiJun; SONG WeiChao; XUE Li; HAN SongDe; ZENG YongFei; WANG LiFu; BU XianHe


    Three new Cu(Ⅱ)-Ln(Ⅲ)heterometallic coordination polymers based on two N-heterocyclic carboxyllc ligands,{[LnCu(L1)2(L2)(H2O)2]· mH2O}n(Ln =La(1),Nd(2),Gd(3),m =2(for 1),1(for 2,3),H2L1 =quinolinic acid,HL2 =nicotinic acid),have been synthesized and characterized.1 has a two-dimensional(2D)layer structure with a Schl(a)fli symbol of(44.62),while complexes 2 and 3 are isostructural and have three-dimensional(3D)structures with a Schl(a)fli symbol of(3.4.5)2( 3-nodal net.Magnetic investigations suggest that antiferromagnetic coupling exists between NdⅢ and CuⅡ in 2,while weak ferromagnetic coupling between GdⅢ and CuⅡ in 3.The difference of magnetic prooerties between 2 and 3 has been discussed.

  12. Absorption Spectra of the 4f Electron Transitions of the Nd,Ho and and Er Complexes with 1—Cyclopyropyl—6—fluoro—1,4—dihydro—7—(4—ethyl—1—piperazinyl)—4—oxo—3—quinoline Carboxylic Acid

    Institute of Scientific and Technical Information of China (English)

    NaiXingWANG; XiuQinXU; 等


    The absorption spectra of the neodymium,holmium and erbium complexes with 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(4-ethyl-1-piperazimyl)-4-oxo-3-quinoline carboxylic acid hydrochloride in the presence of TX-100 have been shown. The characteristic absorption bands of the 4f electron transitions of the complexes are enhanced markedly.

  13. Absorption Spectra of the 4f Electron Transitions of the Nd, Ho and and Er Complexes with 1-Cyclopyropyl-6-fluoro-1,4-dihydro-7-(4-ethyl-1-piperazin yl)-4-oxo-3-quinoline Carboxylic Acid Hydrochloride in the Presence of TX-100

    Institute of Scientific and Technical Information of China (English)


    The absorption spectra of the neodymium, holmium and erbium complexes with l-cyclopropyl-6-fluoro-l,4-dihydro-7-(4-ethyl-l-piperazinyl)-4-oxo-3-quinoline carboxylic acid hydrochloride in the presence of TX-100 have been shown. The characteristic absorption bands of the 4f electron transitions of the complexes are enhanced markedly.

  14. EFSA CEF Panel (EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids), 2014. Scientific Opinion on Flavouring Group Evaluation 77, Revision 1 (FGE.77Rev1): Consideration of Pyridine, Pyrrole and Quinoline Derivatives evaluated by JECFA (63rd meeting)

    DEFF Research Database (Denmark)

    Beltoft, Vibe Meister; Binderup, Mona-Lise; Frandsen, Henrik Lauritz;

    evaluation is necessary, as laid down in Commission Regulation (EC) No 1565/2000. The present consideration concerns a group of 22 pyridine, pyrrole and quinoline derivatives evaluated by the JECFA (63rd meeting). The revision of this consideration is made since additional toxicity data have become available...

  15. Effect of Mentha pulegium extract and 8-hydroxy quinoline sulphate to extend the quality and vase life of rose (Rosa hybrid) cut flower. (United States)

    Hashemabadi, Davood; Torkashvand, Ali Mohammadi; Kaviani, Behzad; Bagherzadeh, Maryam; Rezaalipour, Mohaddeseh; Zarchini, Mohammad


    Rose is an ornamental plant which contains one of the world's top cut flowers. Vase life of cut rose flower is short. Extracts of Mentha pulegium and 8-hydroxy quinoline sulphate (8-HQS) were used as two preservative solutions, aiming to extend the vase life of cut rose (Rosa hybrid L.) flowers. Rose flowers were treated with a vase solution containing the extract of M. pulegium, at concentrations of 0, 10, 20 and 30%, in combination with 8-HQS at concentrations of 0, 200, 400 and 600 mg l(-1). Longevity of cut roses flowers was determined on the basis of wilting and chlorophyll retention. Cut roses flowers were kept at room temperature (20 ± 2 degrees C) under normal day light and natural ventilation. The vase life of cut flowers studied was prolonged by all 8-HQS and extract treatments. The best concentration of 8-HQS and extractwere 400 mg l(-1) and 10%, respectively. Our results indicated that the flowers treated with the extract and 8-HQS had longer vase life, higher rate of solution uptake and lower SPAD value (total chlorophyll) compared to the control. Also, cut flowers treated with the extract and 8-HQS had least bacterial colonies. The greatest longevity of vase life by 11.20 and 10.25 days was related to 400 mg I(-1) 8-HQS and 10% of extract, respectively. These treatments improved cut vase life more than the control treatment. The maximum solution uptake (1.85 ml g(-1) f.wt.) and minimum SPAD value (2.19) were calculated in 30% extract along with 200 mg l(-1) 8-HQS, and 200 mg l(-1) 8-HQS, respectively. The lowest number of bacterial colonies (55.75) was obtained in treatment of 600 mg l(-1) 8-HQS. Flower quality of specimens treated with extract and 8-HQS was better than those of the control. The experiments were repeated three times with three replicates and a completely randomized design had been used. The present study concludes that it would be possible to use preservative solutions containing extract of M. pulegium L. and 8-HQS to extend vase

  16. Geometrical and optical benchmarking of copper guanidine-quinoline complexes: insights from TD-DFT and many-body perturbation theory. (United States)

    Jesser, Anton; Rohrmüller, Martin; Schmidt, Wolf Gero; Herres-Pawlis, Sonja


    We report a comprehensive computational benchmarking of the structural and optical properties of a bis(chelate) copper(I) guanidine-quinoline complex. Using various (TD-)DFT flavors a strong influence of the basis set is found. Moreover, the amount of exact exchange shifts metal-to-ligand bands by 1 eV through the absorption spectrum. The BP86/6-311G(d) and B3LYP/def2-TZVP functional/basis set combinations were found to yield results in best agreement with the experimental data. In order to probe the general applicability of TD-DFT to excitations of copper bis(chelate) charge-transfer (CT) systems, we studied a small model system that on the one hand is accessible to methods of many-body perturbation theory (MBPT) but still contains simple guanidine and imine groups. These calculations show that large quasiparticle energies of the order of several electronvolts are largely offset by exciton binding energies for optical excitations and that TD-DFT excitation energies deviate from MBPT results by at most 0.5 eV, further corroborating the reliability of our TD-DFT results. The latter result in a multitude of MLCT bands ranging from the visible region at 3.4 eV into the UV at 5.5 eV for the bis(chelate) complex. Molecular orbital analysis provided insight into the CT within these systems but gave mixed transitions. A meaningful transition assignment is possible, however, by using natural transition orbitals. Additionally, we performed a thorough conformational analysis as the correct description of the copper coordination is crucial for the prediction of optical spectra. We found that DFT identifies the correct conformational minimum and that the MLCTs are strongly dependent on the torsion of the chelate angles at the copper center. From the results, it is concluded that extensive benchmarking allows for the quantitative analyses of the CT behavior of copper bis(chelate) complexes within TD-DFT.

  17. Discovery of a fluorinated 4-oxo-quinoline derivative as a potential positron emission tomography radiotracer for imaging cannabinoid receptor type 2. (United States)

    Slavik, Roger; Müller Herde, Adrienne; Haider, Ahmed; Krämer, Stefanie D; Weber, Markus; Schibli, Roger; Ametamey, Simon M; Mu, Linjing


    The cannabinoid receptor type 2 (CB2) is part of the endocannabinoid system and has gained growing attention in recent years because of its important role in neuroinflammatory/neurodegenerative diseases. Recently, we reported on a carbon-11 labeled 4-oxo-quinoline derivative, designated RS-016, as a promising radiotracer for imaging CB2 using PET. In this study, three novel fluorinated analogs of RS-016 were designed, synthesized, and pharmacologically evaluated. The results of our efforts led to the identification of N-(1-adamantyl)-1-(2-(2-fluoroethoxy)ethyl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide (RS-126) as the most potent candidate for evaluation as a CB2 PET ligand. [(18) F]RS-126 was obtained in ≥ 99% radiochemical purity with an average specific radioactivity of 98 GBq/μmol at the end of the radiosynthesis. [(18) F]RS-126 showed a logD7.4 value of 1.99 and is stable in vitro in rat and human plasma over 120 min, whereas 55% intact parent compound was found in vivo in rat blood plasma at 10 min post injection. In vitro autoradiographic studies with CB2-positive rat spleen tissue revealed high and blockable binding which was confirmed in in vivo displacement experiments with rats by dynamic PET imaging. Ex vivo biodistribution studies confirmed accumulation of [(18) F]RS-126 in rat spleen with a specificity of 79% under blocking conditions. The moderate elevated CB2 levels in LPS-treated mice brain did not permit the detection of CB2 by [(18) F]RS-126 using PET imaging. In summary, [(18) F]RS-126 demonstrated high specificity toward CB2 receptor in vitro and in vivo and is a promising radioligand for imaging CB2 receptor expression. Cannabinoid receptor type 2 (CB2) is an interesting target for PET imaging. Specific binding of [(18) F]RS-126 in CB2-positive spleen tissue (white arrow head) was confirmed in in vivo displacement experiments with rats. Time activity curve of [(18) F]RS-126 in the spleen after the addition of GW405833 (CB2

  18. 注水介质中喹啉缓蚀剂对管线钢的缓蚀作用研究%Research on Corrosion Inhibition Effect of Quinoline Inhibitor in Injection Water Media on Pipeline Steel

    Institute of Scientific and Technical Information of China (English)

    张颖; 董国强; 胡凌艳


    ABSTRACT:Objective To investigate the growth pattern of quinoline adsorption film on X70 steel surface in the context that the injection water with corrosion inhibitors can effectively prevent the oil devices from corrosion and the film formed on the pipeline surface can alleviate the injection water corrosion. Methods The data obtained from scratch test were calculated using high field ion conduction model by potentiostatic rapid scratch method. Results The results showed that the high field ion conduction model was only applicable for a part of adsorbing process of quinoline. The mathematic simulation by further function fitting found that the growth pattern of quinoline adsorption film on X70 steel surface in simulated media followed the equation: J(t)=C1exp(-αt)+C2 exp(-βt)+C0 . Conclusion At the concentration of 0. 3%, 0. 6% ( mass fraction) quinoline, current fluctuated obviously and the stability of the forming film was worse. There was a possibility of local corrosion in scratch area. At the concentration of 0. 9%(mass fraction) quinoline, the goodness of fit between the simulated curve and the true current decay curve reached 0. 9983, the current fluctuated slightly and the stability of inhibitor adsorption film was better. In the injection water media, the content of quin-oline was higher, the quality of the forming film was better and the difference of the current density was smaller before and after scratch. The growth state of the adsorption film on the scratch surface and no-scratch surface were in a consistent state. The quino-line adsorption film could rapidly form on the damaged steel surface at the higher concentration which had a quick and overall pro-tective effect for the sample.%目的:在注水介质中加入喹啉缓蚀剂可有效防止石油设备的腐蚀,注水管表面形成的钝化膜可减小注水介质的腐蚀,研究喹啉缓蚀剂在X70钢表面的吸附膜的生长规律。方法采用恒电位快速划伤法,利用高场

  19. 白腐真菌对低阶煤模型化合物喹啉降解机理研究1%Degradation Mechanism of Low Rank Coal Model Compound Quinoline by White-rot fungi

    Institute of Scientific and Technical Information of China (English)

    石开仪; 陶秀祥; 籍永华; 任强; 舒伟; 严毅


    白腐真菌在低阶煤炭深加工方面有很大的应用潜力。为依据低阶煤降解机理,报道以喹啉作为低阶煤含氮模型化合物,利用白腐真菌在DOX培养基中对其进行微生物降解,通过测定降解体系中木质素过氧化物酶(LiP)、锰过氧化物酶(MnP)、漆酶(Lac)和多酚氧化酶(PPO)的活性,并利用红外光谱仪、气相色谱-质谱分析仪分析了降解产物。结果发现,喹啉在Lac、LiP和PPO等共同催化下发生了羟基化、醌基化、开环、C-N断裂、氧化等作用,得到对应的8种主要降解产物,从而推测出白腐真菌对喹啉的降解历程。%White rot fungi has great potential applications in low rank coal deep processing. To study degrada-tion mechanism of low rank coal, quinoline has been used as low rank coal model compound, and degraded by white rot fungi in DOX culture. Enzymes containing lignin peroxidase (LiP), manganese peroxidase (MnP), laccase (Lac) and polyphenol oxidase (PPO) were detected in degradation systems, and degraded products were detected by FT-IR and GC-MS analyzer. Results show that Lac, LiP and PPO catalyze quino-line occur hydroxylation, quinonylation, ring opening, C-Nbreakage and oxidation reactions to receive 8 cor-responding degraded products. Thus, degradation mechanism of quinoline by white rot fungi was speculated.

  20. Preparation and characterization of ZrO2 supported Fe3O4 MNPs as an effective and reusable superparamagnetic catalyst for the riedländer synthesis of quinoline derivatives

    Directory of Open Access Journals (Sweden)

    Hejazi Seyyedeh Zoha


    Full Text Available In this study, a convenient, appropriate and eco-friendly method for the synthesis of quinoline derivatives via Friedländer reaction has been developed by using ZrO2/Fe3O4-MNPs as an effective and reusable heterogeneous catalyst. The morphology of ZrO2/Fe3O4-MNPs has been studied by XRD, FT-IR, SEM, TEM and VSM techniques. Green procedure, straight and easy work-up, high yields of the products and good reaction times are the benefits of this procedure. Further, the catalyst can be recovered by external magnetic field and reused at least for three times without a considerable decrease in its catalytic activity.

  1. Mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in colon and liver of Big Blue rats: role of DNA adducts, strand breaks, DNA repair and oxidative stress

    DEFF Research Database (Denmark)

    Moller, P.; Wallin, H.; Vogel, U.


    , indicating a higher rate of protein oxidation in the liver following IQ administration. In plasma and erythrocytes there were unaltered levels of oxidized protein, malondialdehyde, and antioxidant enzyme activities (superoxide dismutase, glutathione peroxidase, catalase, glutathione reductase) indicating....... Investigations of oxidative stress biomarkers produced inconclusive results. Oxidative DNA damage detected by the endonuclease III enzyme and 7-hydro-8-oxo-2'-deoxyguanosine in colon, liver and/or urine was unaltered by IQ. However, there was increased level of gamma-glutamyl semialdehyde in liver proteins......The contribution of oxidative stress, different types of DNA damage and expression of DNA repair enzymes in colon and liver mutagenesis induced by 2-amino-3-methylimidazo [4,5-f]quinoline (IQ) was investigated in four groups of six Big Blue rats fed diets with 0, 20, 70, and 200 mg IQ/kg for 3...

  2. mer-[Fe(pcq)(CN)3]-: a novel cyanide-containing building block and its application to assembling cyanide-bridged trinuclear FeIII2MnII complexes [pcq- = 8-(pyridine-2-carboxamido)quinoline anion]. (United States)

    Ni, Zhong-Hai; Kou, Hui-Zhong; Zhang, Li-Fang; Ni, Wei-Wei; Jiang, Yun-Bo; Cui, Ai-Li; Ribas, Joan; Sato, Osamu


    A new cyanide-containing building block K[Fe(pcq)(CN)(3)] [1; pcq(-) = 8-(pyridine-2-carboxamido)quinoline anion] containing a low-spin Fe(III) center with three cyanide groups in a meridional arrangement has been successfully designed and synthesized. Three cyanide-bridged trinuclear Fe(III)(2)Mn(II) complexes, [Fe(pcq)(CN)(3)](2)[Mn(CH(3)OH)(2)(H(2)O)(2)].2H(2)O (2), [Fe(pcq)(CN)(3)](2)[Mn(bipy)(2)].CH(3)OH.2H(2)O (3), and [Fe(pcq)(CN)(3)](2)[Mn(phen)(2)].CH(3)OH.2H(2)O (4), have been synthesized and structurally characterized. The magnetic susceptibilities of the three heterometallic complexes have been investigated.

  3. Crystal structure of hexa-aqua-nickel(II) bis-{5-bromo-7-[(2-hy-droxy-eth-yl)amino]-1-methyl-6-oxido-quinolin-1-ium-3-sulfonate} monohydrate. (United States)

    Le Thi Hong, Hai; Nguyen Thi Ngoc, Vinh; Do Thi Van, Anh; Van Meervelt, Luc


    The asymmetric unit of the title compound, [Ni(H2O)6](C12H12BrN2O5S)2·H2O, contains a half hexa-aqua-nickel(II) complex cation with the Ni(II) ion lying on an inversion center, one 5-bromo-7-[(2-hy-droxy-eth-yl)amino]-1-methyl-6-oxido-quinolin-1-ium-3-sulfonate (QAO) anion and a half lattice water mol-ecule on a twofold rotation axis. In the crystal, QAO anions are stacked in a column along the c axis by π-π stacking inter-actions [centroid-centroid distances 3.5922 (10)-3.7223 (11) Å]. The columns are inter-linked by hexa-aqua-nickel(II) cations through O-H⋯O and N-H⋯O hydrogen bonds.

  4. Synthesis of some new 2-oxo-1,4-disubstituted-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitriles and their biological evaluation as cytotoxic and antiviral agents

    Indian Academy of Sciences (India)

    Hassan M Faidallah; Khalid A Khan; Abdullah M Asiri


    A series of new 2-oxo-1,4-disubstituted-1,2,5,6-tetrahydro-benzo[h]quinoline-3-carbonitriles supported with various pharmacophoric functionalities at position-1 is described. N-formyl, N-nitroso, Narylthiocarbamoyl, N-alkyl, N-sulfonyl, and N-acetyl derivatives, 5-10 were prepared. A novel fused triazole series was also prepared. The in vitro anticancer activity of twenty synthesized compounds, 4a, 4b, 7a2, 7b2 and 8b1 showed considerable cytotoxic activity against the three tested human tumor cell lines. Compounds 7a2 and 7b2 proved to be the most active with special effect against the human colon carcinoma HT29 and human breast cancer MCF 7 cell lines. Compounds 7b2 and 7f2 also exhibited significant antivirus activity against hepatitis-C virus.

  5. Effects of dietary antioxidants and 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) on preneoplastic lesions and on oxidative damage, hormonal status, and detoxification capacity in the rat

    DEFF Research Database (Denmark)

    Breinholt, Vibeke M.; Mølck, Anne-Marie; Svendsen, Gitte Winkel


    mechanisms were assayed in blood, liver and colon and the impact of the antioxidant administrations on putative preneoplastic changes in liver and colon was assessed. The dietary carcinogen, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) (200 mg/kg diet) served as a pro-oxidant, genotoxicity and general...... toxicity control. IQ increased the levels of protein and DNA oxidation products in plasma, the area of glutathione S-transferase-placental form positive (GST-P) foci in the liver as well as the number of colonic aberrant crypt foci (ACF). All antioxidants and the antioxidant combination significantly...... increased the level of lymphocytic DNA damage, to an extent comparable with the effect induced by IQ. In contrast to the control group where no GST-P foci were detected, GST-P foci were detected in animals exposed to quercetin, lycopene and the combination of the two. However, the increase in the volume...

  6. Synthesis and positive inotropic evaluation of 1-(benzylamino)-3-(4,5-di-hydro[ 1,2,4]trizaolo[4,3-a]quinolin-7-yloxy)propan-2-ol derivatives

    Institute of Scientific and Technical Information of China (English)

    Ting Ting Li; Ling Zhang; Zhe Shan Quan; Hai Bo Zhu; Hu Ri Piao


    In an attempt to search for more potent positive inotropic agents,a series of 1-(benzylamino)-3-(4,5-dihydro[1,2,4]trizaolo[4,3-a]quinolin-7-yloxy)propan-2-ol derivatives was synthesized in four steps using 6-hydroxy-3,4-dihydro-2(1H)-quinolinone as a starting material,and their positive inotropic activities were evaluated by measuring the coronary blood flow(CBF)and the left ventricular pressure(LVP)followed by calculating the rate of pressure development(dp/dtmx values)in the preparation of rat Langendorff's heart.Three compounds(5d,5g,5j)showed favorable activities,among which 5g was shown the most potent with dp/dtmax value of 9.7% and CBF value of 17.8% at a concentration of 1×10-5 mol/L in our in vitro study.

  7. Mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in colon and liver of Big Blue rats: role of DNA adducts, strand breaks, DNA repair and oxidative stress

    DEFF Research Database (Denmark)

    Moller, P.; Wallin, H.; Vogel, U.


    The contribution of oxidative stress, different types of DNA damage and expression of DNA repair enzymes in colon and liver mutagenesis induced by 2-amino-3-methylimidazo [4,5-f]quinoline (IQ) was investigated in four groups of six Big Blue rats fed diets with 0, 20, 70, and 200 mg IQ/kg for 3...... weeks. There were dose-response relationships of DNA adducts (P-32-postlabeling) and DNA strand breaks (comet assay) in colon and liver tissues, with the highest levels of DNA adducts and strand breaks in the colon. There was dose-dependent induction of mutations in both the colon and the liver....... Investigations of oxidative stress biomarkers produced inconclusive results. Oxidative DNA damage detected by the endonuclease III enzyme and 7-hydro-8-oxo-2'-deoxyguanosine in colon, liver and/or urine was unaltered by IQ. However, there was increased level of gamma-glutamyl semialdehyde in liver proteins...

  8. Synthesis, characterization, antimicrobial, DNA-cleavage and antioxidant activities of 3-((5-chloro-2-phenyl-1H-indol-3-ylimino)methyl)quinoline-2(1H)-thione and its metal complexes (United States)

    Vivekanand, B.; Mahendra Raj, K.; Mruthyunjayaswamy, B. H. M.


    Schiff base 3-((5-chloro-2-phenyl-1H-indol-3-ylimino)methyl)quinoline-2(1H)-thione and its Cu(II), Co(II), Ni(II), Zn(II) and Fe(III), complexes have been synthesized and characterized by elemental analysis, UV-Visible, IR, 1H NMR, 13C NMR and mass spectra, molar conductance, magnetic susceptibility, ESR and TGA data. The ligand and its metal complexes have been screened for their antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa, antifungal activity against Aspergillus niger and Aspergillus flavus in minimum inhibition concentration (MIC) by cup plate method respectively, antioxidant activity using 1,1-diphenyl-2-picryl hydrazyl (DPPH), which was compared with that of standard drugs vitamin-C and vitamin-E and DNA cleavage activity using calf-thymus DNA.

  9. Synthesis and preliminary mechanistic evaluation of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid amides with potent antiproliferative activity on human cancer cell lines. (United States)

    Cankara Pirol, Şeyma; Çalışkan, Burcu; Durmaz, Irem; Atalay, Rengül; Banoglu, Erden


    We synthesized a series of novel amide derivatives of 5-(p-tolyl)-1-(quinolin-2-yl)pyrazole-3-carboxylic acid and assessed their antiproliferative activities against three human cancer cell lines (Huh7, human liver; MCF7, breast and HCT116, colon carcinoma cell lines) with the sulforhodamine B assay. Compound 4j with 2-chloro-4-pyridinyl group in the amide part exhibited promising cytotoxic activity against all cell lines with IC50 values of 1.6 μM, 3.3 μM and 1.1 μM for Huh7, MCF7 and HCT116 cells, respectively, and produced dramatic cell cycle arrest at SubG1/G1 phase as an indicator of apoptotic cell death induction. On the basis of their high potency in cellular environment, these straightforward pyrazole-3-carboxamide derivatives may possess potential in the design of more potent compounds for intervention with cancer cell proliferation.

  10. Crystal structure of (3S*,4R*)-4-fluoro-3-(4-meth-oxy-phen-yl)-1-oxo-2-phenyl-1,2,3,4-tetra-hydro-iso-quinoline-4-carb-oxy-lic acid. (United States)

    Lehmann, Anna; Lechner, Lisa; Radacki, Krzysztof; Braunschweig, Holger; Holzgrabe, Ulrike


    The title compound, C23H18FNO4, crystallized as a racemate. It exhibits a cis conformation with respect to the F atom and the methine H atom. The piperidine ring has a screw-boat conformation. The meth-oxy-phenyl ring and the phenyl ring are inclined to the mean plane of the iso-quinoline ring system by 89.85 (4) and 46.62 (5)°, respectively, and by 78.15 (5)° to one another. In the crystal, mol-ecules are linked by an O-H⋯O hydrogen bond forming chains propagating along the a-axis direction. The chains are linked by C-H⋯F hydrogen bonds, forming layers lying parallel to the ab plane.

  11. Synthesis of new cis-fused tetrahydrochromeno[4,3-b]quinolines and their antiproliferative activity studies against MDA-MB-231 and MCF-7 breast cancer cell lines. (United States)

    Nagaiah, K; Venkatesham, A; Srinivasa Rao, R; Saddanapu, V; Yadav, J S; Basha, S J; Sarma, A V S; Sridhar, B; Addlagatta, A


    New cis-fused tetrahydrochromeno[4,3-b]quinolines have been synthesized by intramolecular [4+2] imino-Diels-Alder reactions of 2-azadienes derived in situ from aromatic amines and 7-O-prenyl derivatives of 8-formyl-2,3-disubstituted chromenones in the presence of 20mol% Yb(OTf)(3) in acetonitrile under reflux conditions in good to excellent yields. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis. These compounds were evaluated for their antiproliferative activity against MDA-MB-231 and MCF-7 breast cancer cells. The results showed that compounds 3e, 3f, and 3k exhibit significant antiproliferative activity against MCF-7 breast cancer cells and low inhibitory activity against MDA-MB-231 breast cancer cell lines. Compound 3h displayed activity as comparable to tamoxifen on both the cell lines.

  12. Synthesis and evaluation of radioiodinated 1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}piperidin-4-amine derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging. (United States)

    Effendi, Nurmaya; Ogawa, Kazuma; Mishiro, Kenji; Takarada, Takeshi; Yamada, Daisuke; Kitamura, Yoji; Shiba, Kazuhiro; Maeda, Takehiko; Odani, Akira


    Platelet-derived growth factor receptor β (PDGFRβ) is a transmembrane tyrosine kinase receptor and it is upregulated in various malignant tumors. Radiolabeled PDGFRβ inhibitors can be a convenient tool for the imaging of tumors overexpressing PDGFRβ. In this study, [(125)I]-1-{5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinoline-8-yl}piperidin-4-amine ([(125)I]IIQP) and [(125)I]-N-3-iodobenzoyl-1-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}-piperidin-4-amine ([(125)I]IB-IQP) were designed and synthesized, and their potential as PDGFRβ imaging agents was evaluated. In cellular uptake experiments, [(125)I]IIQP and [(125)I]IB-IQP showed higher uptake by PDGFRβ-positive cells than by PDGFRβ-negative cells, and the uptake in PDGFRβ-positive cells was inhibited by co-culture with PDGFRβ ligands. The biodistribution of both radiotracers in normal mice exhibited hepatobiliary excretion as the main route. In mice inoculated with BxPC3-luc (PDGFRβ-positive), the tumor uptake of radioactivity at 1h after the injection of [(125)I]IIQP was significantly higher than that after the injection of [(125)I]IB-IQP. These results indicated that [(125)I]IIQP can be a suitable PDGFRβ imaging agent. However, further modification of its structure will be required to obtain a more appropriate PDGFRβ-targeted imaging agent with a higher signal/noise ratio. Copyright © 2017. Published by Elsevier Ltd.

  13. Effects of Structure and Environment on the Spectroscopic Properties of (3-Amino-Substituted-Thieno[2,3-b] Pyridine-2-yl)Pyridine/Quinolin-2-yl)(Phenyl)Methanones: Experimental and Theoretical Study. (United States)

    Al-Ansari, Ibrahim Ahmed Z


    The electronic absorption, excitation and fluorescence properties of two 3-amino-substituted-thieno[2,3-b]pyridine/quinolin-2-yl)(phenyl)methanones; (referred to as compounds 1-2: where 3-amino-4,5,6-trimethyl-thieno[2,3-b]pyridin-2-yl)(phenyl)methanone (1); and 3-amino-5,6,7,8-tetrahydro-thieno[2,3-b]quinolin-2-yl)(phenyl)methanone (2)) have been investigated in solvents of various polarity and hydrogen-bonding abilities. Results based on the electronic absorption, excitation and emission study of these compounds; indicated that singlets (S1 and S2) excited-states are populated in non-polar and polar protic/aprotic solvents giving dual fluorescence with weak charge transfer separation. The experimental results were interpreted with the aid of quantum chemistry calculations carried out with the DFT and TD-DFT/B3lyp/6-31 + G(d,p) methods. Based on these calculations, compounds 1-2 exist in two rotamers: anti and syn, separated by ca. 5-6 kcal mol(-1) energy barriers in favor of the anti-conformer. The anti-structure, was shown to be stabilized through existence of intramolecular NH…O hydrogen bond (H-b), which plays a dominant role in affecting the energy of the HOMO-1 molecular orbital. Further, methyl/alkyl substitution in the pyridyl-thiophene ring was shown to involve in σ-π hyper-conjugation and destabilization of the HOMO-1 MO's.

  14. Prebiotics and age, but not probiotics affect the transformation of 2-amino-3-methyl-3H-imidazo[4,5-f]quinoline (IQ) by fecal microbiota - An in vitro study. (United States)

    Nowak, Adriana; Czyżowska, Agata; Huben, Krzysztof; Sójka, Michał; Kuberski, Sławomir; Otlewska, Anna; Śliżewska, Katarzyna


    Heterocyclic aromatic amines (HAAs) are carcinogens which are formed in meat cooked using high-temperature methods. The human gastrointestinal (GI) microbiota plays a crucial role in maintaining health in humans of different ages, and especially in the elderly. However, the GI microbiota, whose metabolism and composition changes with age, may also be responsible for the activation of mutagenic substances reaching the colon with diet. Probiotics and prebiotics are promising in terms of reducing the destructive effects of HAAs. The aim of the study was to determine if fecal microbiota derived from the feces of 27 volunteers: infants (up to 18 months), adults (aged 23-39 years), the sub-elderly (aged 64-65 years), and the elderly (aged 76-87 years), and the presence of probiotics or prebiotics, affected the transformation of IQ (2-amino-3-methylimidazo[4,5-f]quinoline) to 7-OH-IQ (2-amino-3,6-dihydro-3-methyl-7H-imidazo[4,5-f]quinoline-7-one). The compounds were identified using LC-MS(n), NMR, and FTIR. Their genotoxicity was compared in the comet assay. Individual strains capable of IQ transformation were also identified. 7-OH-IQ was detected in six persons (two children and four elderly individuals). The degree of IQ conversion ranged from 26% (4-month-old girl) to 94% (81-year-old woman) of the initial quantity. Four Enterococcus isolates: two Enterococcus faecium and two Enterococcus faecalis strains, as well as one Clostridium difficile strain (LOCK 1030, from the culture collection) converted IQ to 7-OH-IQ. The genotoxicity of samples containing 7-OH-IQ was even three times higher (P < 0.05) than those with IQ and was correlated with the degree of IQ conversion and 7-OH-IQ concentration.

  15. Study on the reaction of ethyl 6-chloro-2-(chloromethyl) quinoline-3-carboxylate with amines%6-氯-2-氯甲基-3-喹啉甲酸乙酯与胺的反应研究

    Institute of Scientific and Technical Information of China (English)

    高文涛; 符鑫博; 李凯; 王东方; 赵雅楠; 李阳


    In the present investigation,ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate(1)as starting compound was subjec-ted to the reaction with different amines such as aromatic amines(2a-i),aliphatic amine(2j-m),and diamines(2n-p)to give the corresponding N-aryl-substituted(3a-i),N-alkyl-substituted(3j-m),and symmetrical N,N′-alkyl-bridged(3n-p)7-chloropyrrolo [3,4-b]quinolin-1-one derivatives,respectively,with good yields ranging 64. 8-77. 7%. The procedure had the advantages of simple operation,mild reaction. All of compounds were new and their structures were determined by IR,1 H NMR,13 C NMR, MS and HRMS.%以6-氯-2-氯甲基-3-喹啉甲酸乙酯(1)为底物,在溶剂无水乙醇中与胺及胺的衍生物2a-p反应,以较好的收率(64.8-77.7%)得到7-氯-2,3-二氢-1H-吡咯并[3,4-b]喹啉-1-酮衍生物,其中与芳胺反应生成N-芳基取代的化合物3a-i,与氨水、甲胺、乙胺和苄胺反应生成N-烷基取代的化合物3j-m,与乙二胺、丙二胺及丁二胺反应生成具有对称结构的化合物3 n-p.该反应具有操作简便、条件温和等特点.所有化合物均为新化合物,其结构经IR、1 H NMR、13 C NMR、MS和HRMS得以证实.

  16. Dual roles of extracellular signal-regulated kinase (ERK) in quinoline compound BPIQ-induced apoptosis and anti-migration of human non-small cell lung cancer cells. (United States)

    Fong, Yao; Wu, Chang-Yi; Chang, Kuo-Feng; Chen, Bing-Hung; Chou, Wan-Ju; Tseng, Chih-Hua; Chen, Yen-Chun; Wang, Hui-Min David; Chen, Yeh-Long; Chiu, Chien-Chih


    2,9-Bis[2-(pyrrolidin-1-yl)ethoxy]-6-{4-[2-(pyrrolidin-1-yl)ethoxy] phenyl}-11H-indeno[1,2-c]quinoline-11-one (BPIQ), is a synthetic quinoline analog. A previous study showed the anti-cancer potential of BPIQ through modulating mitochondrial-mediated apoptosis. However, the effect of BPIQ on cell migration, an index of cancer metastasis, has not yet been examined. Furthermore, among signal pathways involved in stresses, the members of the mitogen-activated protein kinase (MAPK) family are crucial for regulating the survival and migration of cells. In this study, the aim was to explore further the role of MAPK members, including JNK, p38 and extracellular signal-regulated kinase (ERK) in BPIQ-induced apoptosis and anti-migration of human non-small cell lung cancer (NSCLC) cells. Western Blot assay was performed for detecting the activation of MAPK members in NSCLC H1299 cells following BPIQ administration. Cellular proliferation was determined using a trypan blue exclusion assay. Cellular apoptosis was detected using flow cytometer-based Annexin V/propidium iodide dual staining. Cellular migration was determined using wound-healing assay and Boyden's chamber assay. Zymography assay was performed for examining MMP-2 and -9 activities. The assessment of MAPK inhibition was performed for further validating the role of JNK, p38, and ERK in BPIQ-induced growth inhibition, apoptosis, and migration of NSCLC cells. Western Blot assay showed that BPIQ treatment upregulates the phosphorylated levels of both MAPK proteins JNK and ERK. However, only ERK inhibitor rescues BPIQ-induced growth inhibition of NSCLC H1299 cells. The results of Annexin V assay further confirmed the pro-apoptotic role of ERK in BPIQ-induced cell death of H1299 cells. The results of wound healing and Boyden chamber assays showed that sub-IC50 (sub-lethal) concentrations of BPIQ cause a significant inhibition of migration in H1299 cells accompanied with downregulating the activity of MMP-2 and -9, the

  17. Comparative study of radiolabelling quinolines by {sup 99m}Tc and {sup 111}In; Etude comparative du radiomarquage de quinolones par le {sup 99m}Tc et l`{sup 111}In

    Energy Technology Data Exchange (ETDEWEB)

    Celerier, C.; Robert, N. [Service de Medecine Nucleaire CHU du Haut Leveque, Bordeaux 33076 (France); Bertrand-Barat, J. [Service de Medecine Nucleaire CHU de Pellegrin, Bordeaux 33076 (France); Ducassou, D. [Service de Medecine Nucleaire CHU du Haut Leveque, Bordeaux 33076 (France)


    Quinolines, chemical compounds interacting directly with bacteria, are highly specific potential labellers for infections. The goal of this study was to compare the labelling of 4-fluoro-quinolines by {sup 99m}Tc and {sup 111}In, respectively. The labelling of Ciprofloxacin (C), Pefloxacin (P), Enoxacin (E) and Sparfloxacin (S) by {sup 99m}Tc were achieved in a reducing medium (Sn{sup 2+} 50 {mu}M or 10 mg/mL of acid sulfonic formamidine (ASF)), with a pH 6 and 11, during 30 min. at 100 deg. C. The labelling yield is determined by ITCL-SG in NaCl (0.9%) and paper chromatography in an Acetonitrile/Water medium (50/50). The labelling by {sup 111}In is achieved in acetate buffer 0.3 M (pH 5.5), at 25 deg.C. The radiochemical purity is determined by ITLC-ESG, as citrate of 0.1 N (pH 5). At pH 6, in an Sn{sup 2+} medium, the labelling of these molecules is hindered by the overwhelming formation of reduced Tc. After filtration on 0.22 {mu}, the average yields are 33.6 {+-} 6.3% (n=2), 47.8% (n=1), 23.2 {+-} 5.8% (n=3), 20.6 {+-} 2.6% (n=2) for C, E, P and S, respectively. Preliminary attempts seem to show that in a de-protonating medium the labelling yields are superior for S [61.0 {+-} 4.3% (n=2)] and P [54.3% (n=1)]; inversely, they are inferior for E [33.7% (n=1)] and C [25.3% (n=1)], without formation of precipitate. The yields obtained by ASF are inferior to those obtained by tin for C [18.2 {+-} 3.5% (n=3)], E [46.4 {+-} 8.2% (n=3)]. On the other side, the labelling yields of these molecules by {sup 111}In are 92.0 {+-} 6.4% (n=4), 92.5 {+-} 4.1% (n=4), 92.8 {+-} 3.0% (n=14), 84.1 {+-} 9.6% (n=4) for C, E, P and S, respectively. The first studies of stability realised on In-labelled Pefloxacin allowed estimating the value of complexation constant K{sub c} as 8.5. In conclusion, this delicate labelling may lead, after optimization, to acceptable yields. Current studies of stability and structural chemistry will allow to determine the exact nature of these complexes

  18. Comparative effects in rats of intact wheat bran and two wheat bran fractions on the disposition of the mutagen 2-amino-3-methylimidazo[4,5-f]quinoline

    Energy Technology Data Exchange (ETDEWEB)

    Ferguson, Lynnette R., E-mail: [Discipline of Nutrition, Faculty of Medicine and Health Sciences, University of Auckland, Auckland (New Zealand); Auckland Cancer Society Research Centre, Faculty of Medicine and Health Sciences, University of Auckland, Auckland (New Zealand); Harris, Philip J. [School of Biological Sciences, University of Auckland, Auckland (New Zealand); Kestell, Philip [Auckland Cancer Society Research Centre, Faculty of Medicine and Health Sciences, University of Auckland, Auckland (New Zealand); Zhu, Shuotun [Discipline of Nutrition, Faculty of Medicine and Health Sciences, University of Auckland, Auckland (New Zealand); Auckland Cancer Society Research Centre, Faculty of Medicine and Health Sciences, University of Auckland, Auckland (New Zealand); Munday, Rex; Munday, Christine M. [Agresearch, Ruakura Agricultural Research Centre, Hamilton (New Zealand)


    Wheat bran protects against mutations and cancer, but contains different plant cell types that are likely to have different protective effects. We previously described the production and chemical characterisation of an aleurone-rich fraction (ARF) and a pericarp-rich fraction (PRF) from wheat grain. We compared these with whole bran (WB), fed to rats as 10% of a high fat AIN-76 diet. All bran-supplemented diets increased faecal bulk, in the order PRF > WB > ARF. PRF increased the activity of NAD(P)H:quinone acceptor oxidoreductase only in the forestomach, whereas ARF and WB enhanced levels of glutathione S-transferase in the duodenum. ARF but not PRF was digested and fermented, and also encouraged bacterial growth. Rats were gavaged with the radioactive mutagen {sup 14}C-labelled IQ (2-amino-3-methylimidazo[4,5-f]quinoline), and effects of the brans on plasma radioactivity measured. Compared with the control diet, all bran-supplemented diets reduced the concentration of radioactivity in plasma, in the order ARF > PRF > WB. All brans increased faecal elimination of radioactivity, but only ARF and PRF enhanced urinary radioactivity. These data suggest that wheat bran may reduce mutation and cancers through direct adsorption and enhanced elimination of a dietary mutagen and/or its metabolites, and that wheat bran enriched in pericarp or aleurone cell walls may exert protective effects through different mechanisms.

  19. Short-term carcinogenicity testing of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and 2-amino-3-methylimidazo[4,5-f] quinoline (IQ) in E mu-pim-1 transgenic mice

    DEFF Research Database (Denmark)

    Sørensen, Ilona Kryspin; Mortensen, Alicja; Kristiansen, E.


    ]pyridine (PhIP) for 7 months or with 0.03% 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) for 6 months, PhIP and IQ are heterocyclic amines formed during cooking of meat and fish and are mutagenic to bacteria and cultured mammalian cells, PhIP is a potent mouse lymphomagen, while IQ is a liver carcinogen...... and also causes lung tumors and tumors of the forestomach in mice. We found that transgenic E mu-pim-1 mice are highly susceptible to PhIP induced lymphomagenesis but do not respond to the IQ treatment, PhIP feeding of E mu-pim-1 mice not only increased the total number of T-cell lymphomas but also...... to non-transgenic mice. Our results suggest that the transgenic E mu-pim-1 mouse may be a useful model for short-term carcinogenicity screening of potential genotoxic carcinogens having the lymphoid system as target tissue, The carcinogen IQ which does not have the lymphoid system as a target...

  20. Estimation of protein concentration at high sensitivity using SDS-capillary gel electrophoresis-laser induced fluorescence detection with 3-(2-furoyl)quinoline-2-carboxaldehyde protein labeling. (United States)

    Arrell, Miriam S; Kálmán, Franka


    3-(2-furoyl)quinoline-2-carboxaldehyde (FQ) is a sensitive fluorogenic dye, used for derivatization of proteins for SDS-CGE with LIF detection (SDS-CGE-LIF) at silver staining sensitivity (ng/mL). FQ labels proteins at primary amines, found at lysines and N-termini, which vary in number and accessibility for different proteins. This work investigates the accuracy of estimation of protein concentration with SDS-CGE-LIF in real biological samples, where a different protein must be used as a standard. Sixteen purified proteins varying in molecular weight, structure, and sequence were labeled with FQ at constant mass concentration applying a commonly used procedure for SDS-CGE-LIF. The fluorescence of these proteins was measured using a spectrofluorometer and found to vary with a RSD of 36%. This compares favorably with other less sensitive methods for estimation of protein concentration such as SDS-CGE-UV and SDS-PAGE-Coomassie and is vastly superior to the equivalently sensitive silver stain. Investigation into the number of labels bound with UHPLC-ESI-QTOF-MS revealed large variations in the labeling efficiency (percentage of labels to the number of labeling sites given by the sequence) for different proteins (from 3 to 30%). This explains the observation that fluorescence per mole of protein was not proportional to the number of lysines in the sequence. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. QSAR analysis of a series of 2-aryl(heteroaryl)-2,5-dihydropyrazolo[4,3-c]quinolin-3-(3H)-ones using piecewise hyper-sphere modeling by particle swarm optimization

    Energy Technology Data Exchange (ETDEWEB)

    Lin Li [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China); Lin Weiqi [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China); Jiang Jianhui [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China); Zhou Yanping [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China); Shen Guoli [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China); Yu Ruqin [State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China)]. E-mail:


    In the present work, we employed piecewise hyper-sphere modeling by particle swarm optimization (PHMPSO) which splits the dataset into subsets with desired linearity in each model for QSAR studies of a series of 2-aryl(heteroaryl)-2,5-dihydropyrazolo[4,3-c]quinolin-3-(3H)-ones (PQs) for their affinity to benzodiazepine receptor (BzR). The results were compared to those obtained by MLR modeling in a single model with the whole data set as well as in submodels based on K-means clustering analysis. It has been clearly shown that electronic descriptors and spatial descriptors play the important roles in the compounds' affinity to BzR. In addition, the molecular density, the Y component of the principal moment of inertia, the magnitude and the Y component of the dipole moment of the molecules can detrimentally affect PQ analogue BzR affinity, while the X component of the dipole moment of the molecules can favorably affect compounds' affinity.


    Institute of Scientific and Technical Information of China (English)

    沈梅红; 马骋; 李忠仁


    Objective To probe into the protective mechanism of electro-acupuncture (EA) on anti-oxygen stress in dementia-model rats. Methods A total of 30 male SD rats of cleaning grade were randomized into three groups, named sham-operation (n=10), model (n=10), model+EA (n=10). The dementia-model rat was made with hippocampal CA1 lesions by quinolinic acid (QA). On the second day of modeling, in model+EA group, EA (3 Hz, 2-4 mA, continuous waves) was applied to "Dàzhuī" (大椎GV 14) and "Shènshū" (肾俞BL 23) for 10 min. The capability of learning and memory was evaluated by step-down test to observe the changes of nitric oxide (NO), nitric oxide synthase (NOS) activity, superoxide dismutase (SOD) activity and malondialdehyde (MDA) of the hippocampal tissues in rats separately by biochemical methods. Results EA improved learning and memory of dementia rats with hippocampal CA1 lesions induced by QA at different degrees. It significantly increased SOD activity, reduced MDA content and improved NO level and NOS activity. Conclusion EA improves significantly the learning and memory of the dementia rats due to hippocampal CA1 lesions induced by QA, which is probably relevant with the anti-oxygen stress of EA.

  3. Thermodynamic study of complex formation between 3,5-di iodo-hydroxy quinoline and Zn2+, Ni2+ and Co2+ cations in some binary solvents using a conductometric method

    Directory of Open Access Journals (Sweden)

    A. Nezhadali


    Full Text Available The complexation reactions between 3,5-di iodo-8-hydroxy quinoline (IQN and Zn2+, Ni2+ and Co2+ were studied in dimethylformamide (DMF-ethanol (EtOH binary solvent systems at different temperatures using a conductometric method. The stoichiometry of complexes was established 1:1. It was found that the stability of complexes formed between cations and this ligand increases with increases temperature. The standard enthalpies and standard entropies of complexes were obtained from the temperature dependence of stability constants. The results obtained by conductometric technique show that there is an inverse relationship between the formation constants of complexes and donor number of solvents. In all cases, the formation constants increased with increasing amounts of EtOH versus DMF in these binary systems. The standard enthalpy and standard entropies of complexes were obtained from the temperature dependence of stability constant. In all cases, ΔH° was positive and ΔS° was negative. The selectivity order for IQN complexes among various neat studied solvents varies in the order: Zn–IQN2+› Ni–IQN2+›Co–IQN2+.

  4. Structural, Optical, Electrical and Photoelectrical Properties of 2-Amino-4-(5-bromothiophen-2-yl)-5,6-dihydro-6-methyl-5-oxo-4H-pyrano[3,2-c] quinoline-3-carbonitrile Films (United States)

    Mansour, A. M.; El-Taweel, F. M. A.; Abu El-Enein, R. A. N.; El-Menyawy, E. M.


    2-Amino-4-(5-bromothiophen-2-yl)-5,6-dihydro-6-methyl-5-oxo-4H-pyrano[3,2-c] quinoline-3-carbonitrile (ABDQC) powder was synthesized and showed thermal stability up to 535 K. ABDQC films were successfully prepared using thermal evaporation. X-ray diffraction showed that the prepared ABDQC powder had a polycrystalline structure, whereas the deposited film had an amorphous structure. The surface morphology of the films was characterized by using a transmission electron microscope. Optical absorption properties of ABDQC films were investigated by spectrophotometric measurements of the transmittance and reflectance in the wavelength range 200-2500 nm. The films were found to have indirect allowed optical band gap of 2.5 eV. Current-voltage characteristics of Au/ABDQC/p-Si/Al were measured at different temperatures (300-420 K) in which the temperature dependence of the diode parameters has been discussed. Under illumination, the device showed open-circuit voltage and short-circuit current of 0.09 V and 3.26 × 10-4 A, respectively.

  5. Synthesis, physicochemical and antimicrobial studies of first row transition metal complexes with quinoline derivatives nitroquinolino (3,2-b(1,5benzodixazepine and nitroquinolino(3,2-b(1,5benzoxazepine

    Directory of Open Access Journals (Sweden)

    Neeraj Sharma


    Full Text Available div align="justify">Metal complexes of Mn (II, Cu (II, Ni (II & Co (II with quinoline derivatives have been synthesized and characterized by elemental analysis, molar conductance, magnetic movement, electronic spectra, thermal analysis and IR spectral data. The molecular formula of complexes corresponds to [ML(NO32] where M = Mn ,Cu , Ni , Co , Zn , Fe, and Cr. The physicochemical and IR spectral data shows that the ligand coordinates to the metal ion in bidentate fashion (through the C=N and N-H groups. The antimicrobial studies of ligand and its metal, metal complexes have been screened for selected bacteria (E. Coli , S. typhi , B. subtilis and S. aureus and fungi (A. flavous, A. niger, P. triticena and F. species. Antimicrobial studies shows that the Mn (II complexes are more toxic than other metal complexes. Magnetic susceptibility measurements reveal octahedral geometry around the metal ion. The complexes were found to be non electrolyte in nature on the basis of low value of molar conductance.

  6. A novel aromatic mutagen, 5-amino-6-hydroxy-8H-benzo[6,7]azepino[5,4,3-de]quinolin-7-one (ABAQ, induces colonic preneoplastic lesions in mice

    Directory of Open Access Journals (Sweden)

    Takahiro Kochi


    Full Text Available The benzoazepinoqunolinone derivative, 5-amino-6-hydroxy-8H-benzo[6,7]azepino[5,4,3-de]quinolin-7-one (ABAQ, which is produced in a mixture of glucose and tryptophan incubated at 37 °C under physiological conditions in the presence or absence of hydroxyl radicals caused by the Fenton reaction, is a novel aromatic mutagen. In the current study, we determined the tumor-initiating potency of ABAQ using an inflammation-relate, two-stage mouse colon carcinogenesis model. Male Crj: CD-1 (ICR mice were treated with the single intragastric administration (100 or 200 mg/kg body weight of ABAQ followed by subsequent 1-week oral exposure to 2% dextran sodium sulfate (DSS in drinking water. The ABAQ treatment alone resulted in high-grade dysplasia, which is a precursor to colorectal cancer, in the colon. Following the administration of DSS after ABAQ treatment, the incidence and frequency of high-grade dysplastic lesions increased; the values were highest in the mice treated with 200 mg/kg body weight of ABAQ followed by DSS. The lesions expressing β-catenin in their nuclei and cytoplasm exhibited high proliferation activity without the expression of programmed cell death 4. These findings indicate that ABAQ has a tumor-initiating activity in the mouse colon, with or without inflammation, although the potential pro-inflammatory effect of high doses of ABAC should be investigated.

  7. Influence of pH, buffers and role of quinolinic acid, a novel iron chelating agent, in the determination of hydroxyl radical scavenging activity of plant extracts by Electron Paramagnetic Resonance (EPR). (United States)

    Fadda, Angela; Barberis, Antonio; Sanna, Daniele


    The Fenton reaction is used to produce hydroxyl radicals for the evaluation of the antioxidant activity of plant extracts. In this paper the parameters affecting the production of hydroxyl radicals and their spin trapping with DMPO were studied. The use of quinolinic acid (Quin) as an Fe(II) ligand was proposed for antioxidant activity determination of Green tea, orange juice and asparagus extracts. Quin, buffers and pH affect the DMPO-OH signal intensity of the EPR spectra. Quin/Fe(II) and low pH enhance the OH generation. Phosphate and Tris-HCl buffers decrease the signal intensity measured in Fe(II)-sulfate and Fe(II)-Quin systems. The extracts were analyzed with Fenton systems containing Fe(II)-sulfate and Fe(II)-Quin with and without buffer. The highest activity was shown with Fe(II)-Quin without buffer, this system being less influenced by pH and chelating agents present in the extracts. This paper will help researchers to better design spin trapping experiments for food matrices. Copyright © 2017 Elsevier Ltd. All rights reserved.

  8. Simultaneous preconcentration of vanadium(V/IV) species with palmitoyl quinolin-8-ol bonded to amberlite XAD 2 and their separate spectrophotometric determination with 4-(2-pyridylazo)-resorcinol using CDTA as masking agent

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    Filik, Hayati; Berker, Kadriye Isil; Balkis, Nuray; Apak, Resat


    This paper reports the simultaneous preconcentration and separation of trace amounts of V species in synthetic solutions and seawater with palmitoyl quinolin-8-ol bonded amberlite XAD 2 copolymer resin column prior to simultaneous speciation analysis. Both V(IV) and V(V) species could be sorbed and preconcentrated by the resin. Both vanadium species were quantitatively eluted together from the resin column using HCl as stripping agent and used for speciation studies. For the speciation analysis of eluted V species, the selected route involved spectrophotometric determination of total vanadium with 4-(2-pyridylazo)-resorcinol (PAR) and vanadate estimation by masking vanadyl with 1,2 cyclohexanediaminetetraacetic acid (CDTA). The preconcentrated V species were assayed spectrophotometrically with PAR at 542 nm, and the results were compared with those of FAAS. The detection limits of V(V) with spectrophotometry and FAAS were 1.6 and 0.9 {mu}g l{sup -1}, respectively. The optimal experimental parameters such as pH, sample flow rate, desorption flow rate, redox behaviour of V(IV) and V(V) in resin and volume of eluent and sample were investigated. The values obtained for the preconcentration factor by the two methods were nearly consistent, and were in the range 150-fold. Analysis of certified reference material (IAEA-405) by the proposed method showed good agreement with the certified value. The established procedure was employed for preconcentrating the vanadium species from artificial and real seawater.

  9. Dammar resin, a non-mutagen, induces [corrected] oxidative stress and metabolic enzymes in the liver of gpt delta transgenic mouse which is different from a mutagen, 2-amino-3-methylimidazo[4,5-f]quinoline. (United States)

    Xie, Xiao-Li; Wei, Min; Kakehashi, Anna; Yamano, Shotaro; Okabe, Kyoko; Tajiri, Masaki; Wanibuchi, Hideki


    Dammar resin has long been used in foods as either a clouding or a glazing agent. In a recent study, 2% Dammar resin showed significant hepatocarcinogenicity in a rat 2-year bioassay. Therefore, for an accurate estimate of human risk, it is necessary to understand whether Dammar resin induces liver genotoxicity and the underlying mechanisms of its hepatocarcinogenicity. Modifying effects of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), a typical genotoxic carcinogen produced during cooking of protein-rich foods, was also studied in the present study. Exposure of gpt delta mice to Dammar resin at a dose of 2% for 12 weeks did not induce any obvious mutagenicity in the liver. However, the index of cell proliferation, the level of 8-OHdG, and bax, bcl-2, p53, cyp1a2, cyp2e1, gpx1 and gstm2 gene expression were all significantly increased when compared with the control group. In the IQ treatment group, at a dose of 300ppm, mutagenicity was readily detected, the index of cell proliferation increased, and p53, cyp2e1 and gpx1 gene expression was down-regulated in the liver. Down-regulation of p53, P450s, and gpx1 in the livers of IQ treated mice are consistent with its genotoxic mechanism of carcinogenicity observed in a 675-day study. In contrast, our results using gpt delta mice suggest that Dammar resin is not genotoxic. Instead, the Dammar resin-induced hepatocarcinogenicity seen in our previous 2-year study with rats may have been mediated by non-genotoxic mechanisms, including increased P450 enzyme activity, increased oxidative stress, altered gene expression, and promotion of cell proliferation.

  10. Synthesis, characterization and biological activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) complexes with a new Schiff Base hydrazone: O-hydroxyacetophenone-7-chloro-4-quinoline hydrazone. (United States)

    Al-Shaalan, Nora H


    The Schiff base hydrazone ligand HL was prepared by the condensation reaction of 7-chloro-4-quinoline with o-hydroxyacetophenone. The ligand behaves either as monobasic bidentate or dibasic tridentate and contain ONN coordination sites. This was accounted for be the presence in the ligand of a phenolic azomethine and imine groups. It reacts with Cu(II), Ni(II), Co(II), Mn(II), UO(2) (VI) and Fe(II) to form either mono- or binuclear complexes. The ligand and its metal complexes were characterized by elemental analyses, IR, NMR, Mass, and UV-Visible spectra. The magnetic moments and electrical conductance of the complexes were also determined. The Co(II), Ni(II) and UO(2) (VI) complexes are mononuclear and coordinated to NO sites of two ligand molecules. The Cu(II) complex has a square-planar geometry distorted towards tetrahedral, the Ni(II) complex is octahedral while the UO(2) (VI) complex has its favoured heptacoordination. The Co(II), Mn(II) complexes and also other Ni(II) and Fe(III) complexes, which were obtained in the presence of Li(OH) as deprotonating agent, are binuclear and coordinated via the NNNO sites of two ligand molecules. All the binuclear complexes have octahedral geometries and their magnetic moments are quite low compared to the calculated value for two metal ions complexes and thus antiferromagnetic interactions between the two adjacent metal ions. The ligand HL and metal complexes were tested against a strain of Gram +ve bacteria (Staphylococcus aureus), Gram -ve bacteria (Escherichia coli), and fungi (Candida albicans). The tested compounds exhibited high antibacterial activities.

  11. Synthesis, Characterization and Biological Activities of Cu(II, Co(II, Mn(II, Fe(II, and UO2(VI Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone

    Directory of Open Access Journals (Sweden)

    Nora H. Al-Shaalan


    Full Text Available The Schiff base hydrazone ligand HL was prepared by the condensation reaction of 7-chloro-4-quinoline with o-hydroxyacetophenone. The ligand behaves either as monobasic bidentate or dibasic tridentate and contain ONN coordination sites. This was accounted for be the presence in the ligand of a phenolic azomethine and imine groups. It reacts with Cu(II, Ni(II, Co(II, Mn(II, UO2 (VI and Fe(II to form either mono- or binuclear complexes. The ligand and its metal complexes were characterized by elemental analyses, IR, NMR, Mass, and UV-Visible spectra. The magnetic moments and electrical conductance of the complexes were also determined. The Co(II, Ni(II and UO2 (VI complexes are mononuclear and coordinated to NO sites of two ligand molecules. The Cu(II complex has a square-planar geometry distorted towards tetrahedral, the Ni(II complex is octahedral while the UO2 (VI complex has its favoured heptacoordination. The Co(II, Mn(II complexes and also other Ni(II and Fe(III complexes, which were obtained in the presence of Li(OH as deprotonating agent, are binuclear and coordinated via the NNNO sites of two ligand molecules. All the binuclear complexes have octahedral geometries and their magnetic moments are quite low compared to the calculated value for two metal ions complexes and thus antiferromagnetic interactions between the two adjacent metal ions. The ligand HL and metal complexes were tested against a strain of Gram +ve bacteria (Staphylococcus aureus, Gram −ve bacteria (Escherichia coli, and fungi (Candida albicans. The tested compounds exhibited high antibacterial activities.

  12. Spin crossover iron(II) coordination polymer chains: syntheses, structures, and magnetic characterizations of [Fe(aqin)2(μ2-M(CN)4)] (M = Ni(II), Pt(II), aqin = quinolin-8-amine). (United States)

    Setifi, Fatima; Milin, Eric; Charles, Catherine; Thétiot, Franck; Triki, Smail; Gómez-García, Carlos J


    New Fe(II) coordination polymeric neutral chains of formula [Fe(aqin)2(μ2-M(CN)4)] (M = Ni(II) (1) and Pt(II) (2)) (aqin = Quinolin-8-amine) have been synthesized and characterized by infrared spectroscopy, X-ray diffraction, and magnetic measurements. The crystal structure determinations of 1-2 reveal in both cases a one-dimensional structure in which the planar [M(CN)4](2-) (M = Ni(II) (1) and Pt(II) (2)) anion acts as a μ2-bridging ligand, and the two aqin molecules as chelating coligands. Examination of the intermolecular contacts in the two compounds reveals that the main contacts are ascribed to hydrogen bonding interactions involving the amine groups of the aqin chelating ligands and the nitrogen atoms of the two non bridging CN groups of the [M(CN)4](2-) (M = Ni(II) (1) and Pt(II) (2)) anion. The average values of the six Fe-N distances observed respectively at room temperature (293 K) and low temperature (120 K), that is, 2.142(3) and 2.035(2) Å for 1, and 2.178(3) and 1.990(2) Å for 2, and the thermal variation of the cell parameters (performed on 2) are indicative of the presence of an abrupt HS-LS spin crossover (SCO) transition in both compounds. The thermal dependence of the product of the molar magnetic susceptibility times the temperature (χmT), in cooling and warming modes, confirms the SCO behavior at about 145 and 133 K in 1 and 2, respectively, and reveals the presence of a small thermal hysteresis of about 2 K for each compound.

  13. Xanthohumol, a prenylated flavonoid contained in beer, prevents the induction of preneoplastic lesions and DNA damage in liver and colon induced by the heterocyclic aromatic amine amino-3-methyl-imidazo[4,5-f]quinoline (IQ)

    Energy Technology Data Exchange (ETDEWEB)

    Ferk, Franziska; Huber, Wolfgang W. [Institute of Cancer Research, Department of Medicine I, Medical University of Vienna, Borschkegasse 8a, A-1090 Vienna (Austria); Filipic, Metka [National Institute of Biology, Department of Genetic Toxicology and Cancer Biology, University of Ljubljana, 1000 Ljubljana (Slovenia); Bichler, Julia; Haslinger, Elisabeth; Misik, Miroslav; Nersesyan, Armen; Grasl-Kraupp, Bettina [Institute of Cancer Research, Department of Medicine I, Medical University of Vienna, Borschkegasse 8a, A-1090 Vienna (Austria); Zegura, Bojana [National Institute of Biology, Department of Genetic Toxicology and Cancer Biology, University of Ljubljana, 1000 Ljubljana (Slovenia); Knasmueller, Siegfried, E-mail: [Institute of Cancer Research, Department of Medicine I, Medical University of Vienna, Borschkegasse 8a, A-1090 Vienna (Austria)


    Xanthohumol (XN) is a hop derived prenylated flavonoid contained in beer. Earlier findings indicated that it has promising chemopreventive properties and protects cells against DNA damage by carcinogens via inhibition of their activation. Furthermore, it was found that XN inhibits DNA synthesis and proliferation of cancer cells in vitro, inactivates oxygen radicals and induces apoptosis. Since evidence for its chemoprotective properties is restricted to results from in vitro experiments, we monitored the impact of XN on the formation of amino-3-methyl-imidazo[4,5-f]quinoline (IQ)-induced preneoplastic foci in livers and colons of rats (9/group). Additionally, we studied its effects on IQ-induced DNA damage in colonocytes and hepatocytes in single cell gel electrophoresis assays and on the activities of a panel of drug metabolising enzymes. Consumption of the drinking water supplemented with XN (71 {mu}g/kg b.w.) before and during carcinogen treatment led to a significant reduction of the number of GST-p{sup +} foci in the liver by 50% and also to a decrease of the foci area by 44%. DNA migration was decreased significantly in both, colon mucosa and liver cells, but no alterations of the activities of different phases I and II enzymes were found in hepatic tissue. Our findings indicate that XN protects against DNA damage and cancer induced by the cooked food mutagen. Since the effects were observed with low doses of XN which are reached after consumption of brews with high XN levels, our findings may be relevant for humans.

  14. Facile synthesis of bistridentate Ru(II) complexes based on 2,6-di(quinolin-8-yl)pyridyl ligands: sensitizers with microsecond 3MLCT excited state lifetimes. (United States)

    Jäger, Michael; Kumar, Rohan J; Görls, Helmar; Bergquist, Jonas; Johansson, Olof


    Synthetic routes to meridional bistridentate ruthenium(II) complexes based on 2,6-di(quinolin-8-yl)pyridyl (dqp) ligands have been investigated. Microwave-assisted synthesis at 200 degrees C allowed the high yield (49-87%) preparation of homoleptic meridional [Ru(dqp)(2)](2+)-based complexes containing inert functional groups. Applying this protocol for the synthesis of mer-[Ru(dqp)(2)](2+) (mer-1) but lowering the temperature to 180 degrees C and shorter reaction times revealed the formation of the facial isomers cis,fac-1 and trans,fac-1 (56% and 12% yields, respectively). The facial isomers were characterized by NMR spectroscopy and X-ray diffraction analysis. In a stepwise protocol, the reaction of Ru(dqp)Cl(3) or Ru(dqp)(L)Cl(2) (L = MeCN or DMSO) and a second equivalent dqp gave mer-1 in 12-26% yields and N(5)Cl-coordinated [Ru(dqp)(2)Cl](+) (28-46%). [Ru(dqp(2))Cl](+) was photochemically, or thermally in the presence of Ag(I), converted to mer-1. By using mer-[Ru(dqp)(MeCN)(3)] (2+), which was crystallographically characterized, a wide range of homo- and heteroleptic meridional [Ru(dqp)(2)](2+)-based complexes was synthesized in up to 77% yield. The synthetic utility of meridional [Ru(dqp)(2)](2+)-based complexes as building blocks was demonstrated by palladium-catalyzed homocoupling of mer-[Ru(dqp)(dqpPhBr)](2+) to form a dinuclear complex. The redox and photophysical properties of the meridional complexes are discussed.

  15. 水杨醛缩乙醇胺及8-羟基喹啉氧钒三元配合物的合成、晶体结构及热分解研究%Synthesis,Crystal Structure and Thermal Decomposition of Oxovanadium(V) Ternary Complex with N-salicylidene-N'-aminoethanol and 8-hydroxy Quinoline

    Institute of Scientific and Technical Information of China (English)

    李连之; 许涛; 陶绪泉; 杜茂喜; 刘颖; 杜凌云


    A new oxovanadium(V) ternary complex, VO (L) (hq) [H2L: N-salicylidene-N'-aminoethanol;hq:8-hydroxy quinoline],was synthesized by the reaction of salicyaldehyde, aminoethanol and 8-hydroxy quinoline with vanadyl sulfate.It was characterized by elemental analysis,IR and X-ray diffraction analysis.The crystal of the title complex (C18H15N2O4V,Mr=374.26) belongs to monoclinic,space group P21/n with the following crystallographic parameters:a=1.543 5(5) nm,b=0.6620(2)nm,c=1.648 9(6) nm,β=105.043(7)°,V=1.627 3(10) nm3,Z=4,,μ(MoKa)=0.636 mm-1,F(000)=768,and final R1=0.056 8,wR2=0.106 7 for observed reflections 957(I>2σ(I)).The complex is six-coordinate in distorted octahedral geometry.The thermal decomposition for the complex was studied by TG-DTG curves and the apparent activation energy was obtained by the Kissinger formula.CCDC:218497.

  16. The Effect of Dexmedetomidine on Impairment of Spatial Memory of Adult Rats Induced by Quinolinic Acid%右美托咪定对喹啉酸引发的成年大鼠空间记忆损害的影响作用

    Institute of Scientific and Technical Information of China (English)

    耿霞; 于剑锋; 王钢


    Objective To evaluate the effect of dexmedetomidine on impairment of spatial memory of adult rats induced by quin -olinic acid and its possible mechanism .Methods Thirty healthy adult male Wistar rats were randomly divided into 3 groups:normal saline (NS group),quinoline acid group(QA group) and dexmedetomidine plus quinoline acid group (D+Q group).Eight-arm radial maze task and open-field test was detected to evaluate the spatial memory and exploratory behavior .Once the test were finished ,rats were killed to meas-ure the expression of ChAT of hippocampus by Western Blotting methods .Results Compared with NS group ,spatial memory and spontaneous activity in QA group and D +Q group was declined significantly,the expression of ChAT decreased (P0.05).The ex-pression of ChAT increased significantly (P0.05),ChAT表达有所增加(P<0.05). 结论 QA所致空间记忆障碍可能与海马内ChAT表达下调有关系,右美托咪定可部分逆转ChAT表达下调.

  17. Structure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9 H -pyrimido[4,5- b ]indol-7-yl)-3,5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor

    Energy Technology Data Exchange (ETDEWEB)

    Zhao, Yujun; Bai, Longchuan; Liu, Liu; McEachern, Donna; Stuckey, Jeanne A.; Meagher, Jennifer L.; Yang, Chao-Yie; Ran, Xu; Zhou, Bing; Hu, Yang; Li, Xiaoqin; Wen, Bo; Zhao, Ting; Li, Siwei; Sun, Duxin; Wang, Shaomeng (Michigan)


    We have designed and synthesized 9H-pyrimido[4,5-b]indole-containing compounds to obtain potent and orally bioavailable BET inhibitors. By incorporation of an indole or a quinoline moiety to the 9H-pyrimido[4,5-b]indole core, we identified a series of small molecules showing high binding affinities to BET proteins and low nanomolar potencies in inhibition of cell growth in acute leukemia cell lines. One such compound, 4-(6-methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (31) has excellent microsomal stability and good oral pharmacokinetics in rats and mice. Orally administered, 31 achieves significant antitumor activity in the MV4;11 leukemia and MDA-MB-231 triple-negative breast cancer xenograft models in mice. Determination of the cocrystal structure of 31 with BRD4 BD2 provides a structural basis for its high binding affinity to BET proteins. Testing its binding affinities against other bromodomain-containing proteins shows that 31 is a highly selective inhibitor of BET proteins. Our data show that 31 is a potent, selective, and orally active BET inhibitor.

  18. Type 1 cannabinoid receptor mapping with [{sup 18}F]MK-9470 PET in the rat brain after quinolinic acid lesion: a comparison to dopamine receptors and glucose metabolism

    Energy Technology Data Exchange (ETDEWEB)

    Casteels, Cindy [KU Leuven and University Hospital Leuven, Division of Nuclear Medicine, Leuven (Belgium); KU Leuven, MoSAIC, Molecular Small Animal Imaging Center, Leuven (Belgium); University Hospital Gasthuisberg, Division of Nuclear Medicine, Leuven (Belgium); Martinez, Emili; Camon, Lluisa; Vera, Nuria de; Planas, Anna M. [IDIBAPS, Institute for Biomedical Research (IIBB-CSIC), Barcelona (Spain); Bormans, Guy [KU Leuven, MoSAIC, Molecular Small Animal Imaging Center, Leuven (Belgium); KU Leuven, Laboratory for Radiopharmacy, Leuven (Belgium); Baekelandt, Veerle [KU Leuven, Laboratory for Neurobiology and Gene Therapy, Leuven (Belgium); Laere, Koen van [KU Leuven and University Hospital Leuven, Division of Nuclear Medicine, Leuven (Belgium); KU Leuven, MoSAIC, Molecular Small Animal Imaging Center, Leuven (Belgium)


    Several lines of evidence imply early alterations in metabolic, dopaminergic and endocannabinoid neurotransmission in Huntington's disease (HD). Using [{sup 18}F]MK-9470 and small animal PET, we investigated cerebral changes in type 1 cannabinoid (CB{sub 1}) receptor binding in the quinolinic acid (QA) rat model of HD in relation to glucose metabolism, dopamine D{sub 2} receptor availability and amphetamine-induced turning behaviour. Twenty-one Wistar rats (11 QA and 10 shams) were investigated. Small animal PET acquisitions were conducted on a Focus 220 with approximately 18 MBq of [{sup 18}F]MK-9470, [{sup 18}F]FDG and [{sup 11}C]raclopride. Relative glucose metabolism and parametric CB{sub 1} receptor and D{sub 2} binding images were anatomically standardized to Paxinos space and analysed voxel-wise using Statistical Parametric Mapping (SPM2). In the QA model, [{sup 18}F]MK-9470 uptake, glucose metabolism and D{sub 2} receptor binding were reduced in the ipsilateral caudate-putamen by 7, 35 and 77%, respectively (all p < 2.10{sup -5}), while an increase for these markers was observed on the contralateral side (>5%, all p < 7.10{sup -4}). [{sup 18}F]MK-9470 binding was also increased in the cerebellum (p = 2.10{sup -5}), where it was inversely correlated to the number of ipsiversive turnings (p = 7.10{sup -6}), suggesting that CB{sub 1} receptor upregulation in the cerebellum is related to a better functional outcome. Additionally, glucose metabolism was relatively increased in the contralateral hippocampus, thalamus and sensorimotor cortex (p = 1.10{sup -6}). These data point to in vivo changes in endocannabinoid transmission, specifically for CB{sub 1} receptors in the QA model, with involvement of the caudate-putamen, but also distant regions of the motor circuitry, including the cerebellum. These data also indicate the occurrence of functional plasticity on metabolism, D{sub 2} and CB{sub 1} neurotransmission in the contralateral hemisphere. (orig.)

  19. Base-Displaced Intercalated Conformation of the 2-Amino-3-methylimidazo[4,5-f]quinoline N(2)-dG DNA Adduct Positioned at the Nonreiterated G(1) in the NarI Restriction Site. (United States)

    Stavros, Kallie M; Hawkins, Edward K; Rizzo, Carmelo J; Stone, Michael P


    The conformation of an N(2)-dG adduct arising from the heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), a potent food mutagen, was determined in 5'-d(C(1)T(2)C(3)X(4)G(5)C(6)G(7)C(8)C(9)A(10)T(11)C(12))-3':5'-d(G(13)A(14)T(15)G(16)G(17)C(18)G(19)C(20)C(21)G(22)A(23)G(24))-3'; X = N(2)-dG-IQ, in which the modified nucleotide X(4) corresponds to G(1) in the 5'-d(G(1)G(2)CG(3)CC)-3' NarI restriction endonuclease site. Circular dichroism (CD) revealed blue shifts relative to the unmodified duplex, consistent with adduct-induced twisting, and a hypochromic effect for the IQ absorbance in the near UV region. NMR revealed that the N(2)-dG-IQ adduct adopted a base-displaced intercalated conformation in which the modified guanine remained in the anti conformation about the glycosidic bond, the IQ moiety intercalated into the duplex, and the complementary base C(21) was displaced into the major groove. The processing of the N(2)-dG-IQ lesion by hpol η is sequence-dependent; when placed at the reiterated G(3) position, but not at the G(1) position, this lesion exhibits a propensity for frameshift replication [Choi, J. Y., et al. (2006) J. Biol. Chem., 281, 25297-25306]. The structure of the N(2)-dG-IQ adduct at the nonreiterated G(1) position was compared to that of the same adduct placed at the G(3) position [Stavros, K. M., et al. (2014) Nucleic Acids Res., 42, 3450-3463]. CD indicted minimal spectral differences between the G(1) vs G(3) N(2)-dG-IQ adducts. NMR indicated that the N(2)-dG-IQ adduct exhibited similar base-displaced intercalated conformations at both the G(1) and G(3) positions. This result differed as compared to the corresponding C8-dG-IQ adducts placed at the same positions. The C8-dG-IQ adduct adopted a minor groove conformation when placed at position G(1) but a base-displaced intercalated conformation when placed at position G(3) in the NarI sequence. The present studies suggest that differences in lesion bypass by hpol η may be

  20. Preconcentrative separation of palladium(II) using palladium(II) ion-imprinted polymer particles formed with different quinoline derivatives and evaluation of binding parameters based on adsorption isotherm models. (United States)

    Daniel, Sobhi; Babu, Prem E J; Rao, T Prasada


    Palladium(II) ion-imprinted polymer (IIP) materials were synthesized by thermally polymerizing the ternary complexes of palladium(II) with amino (AQ) or hydroxy (HQ) or mercapto (MQ) derivatives of quinoline and 4-vinyl-pyridine. The functional and crosslinking monomers used during polymerization were 2-hydroxyethyl methacrylate (HEMA) and ethylene glycol dimethacrylate (EGDMA). 2,2'-Azobisisobutyronitrile (AIBN) and 2-methoxy ethanol were used as the initiator and porogen, respectively. The resulting polymer materials were dried in an oven at 80 degrees C, ground and sieved to obtain IIP particles which were then subjected to leaching with 50% (v/v) HCl to obtain the leached palladium(II) IIP particles. Control polymer (CP) particles were also prepared by following the above procedure described for IIP particles. The CP particles, unleached and leached AQ-based IIP particles were then characterized by IR, XRD and microanalysis studies. Analytical studies such as preconcentration of palladium(II) from dilute aqueous solutions and separation studies in the presence of selected noble and base metals which co-exist with palladium(II) in its ore or mineral deposits were systematically studied using CP and IIP particles and are compared. AQ-based IIP particles gave higher percent extraction and selectivity coefficients compared to HQ- or MQ-based IIP particles. Five replicate determinations of 25mug of palladium(II) present in 500ml of aqueous solution, when subjected to preconcentration and determination by iodide-Rhodamine 6G procedure gave a mean absorbance of 0.104 with a relative standard deviation of 2.25%. The detection limit corresponding to three times the standard deviation of the blank was found to be 5.0mug of palladium(II) per litre. The rebinding studies using AQ-, HQ- and MQ-based IIPs were carried out and were fitted to the different adsorption isotherm models, viz. Langmuir (L), Freundlich (F) and Langmuir-Freundlich (LF). These adsorption models were

  1. 喹啉缓蚀剂对N80石油管道钢小孔腐蚀的影响%Influence of Quinoline Corrosion Inhibitor on Micropore Corrosion of N80 Petroleum Pipeline Steel

    Institute of Scientific and Technical Information of China (English)

    陈蕊; 李善建; 冯拉俊; 李向红


    模拟石油开采环境中石油管道的小孔腐蚀,通过对闭塞区内、外溶液进行腐蚀介质浓度分析、电化学分析以及对闭塞区内金属表面腐蚀形貌进行观察,研究了喹啉缓蚀剂(QA)对N80石油管道钢在0.5%CH3COOH+5%NaCl的饱和H2S溶液体系中小孔腐蚀的缓蚀性。结果表明:55℃时随着本体溶液中QA缓蚀剂浓度的增加,闭塞区Cl-和S2-浓度逐渐降低,抑制闭塞区溶液的pH值下降,对闭塞区的缓蚀效率逐渐增加。在本体溶液中添加0.6%~0.8%的QA缓蚀剂时,对小孔内材料的缓蚀率可达96.58%以上。%Simulating micropore corrosion of pipeline in petroleum exploitation environment, it studied the influence of quinoline corrosion inhibitor on micropore corrosion of N80 pipeline steel in 0.5%CH3COOH+ 5%NaCl saturated H2S solution system, through analysis on corrosion medium concentration of occlusion area inside and outside solution ,electrochemical analysis and corrosion morphology observation of metal surface. The result indicated that at 55℃with concentration of QA corrosion inhibitor increasing in solution, the concentration of Cl-and S2-gradually decrease in occlusion area, and control pH value in occlusion area solution decreasing can increase corrosion inhibition efficiency gradually. When adding 0.6%~0.8%QA corrosion inhibitor, the inhibition rate of micropore can reach more than 96.58%.

  2. Synthesis in aqueous medium and organic praseodymium complexes with ligands derived from Schiff base quinolinic. Characterization and physicochemical study; Sintesis en medio acuoso y organico de complejos de praseodimio con ligantes derivados de base de Schiff quinolicos. Caracterizacion y estudio fisicoquimico

    Energy Technology Data Exchange (ETDEWEB)

    Garcia G, A.


    It was investigated the coordination ability of the quinolinic Schiff base organic tetradentate quinolinic ligand (Q Schiff-(OH){sub 2}) towards the trivalent praseodymium by UV/Vis spectrophotometric titration (St). By St, was studied the formed species between the Q Schiff-(OH){sub 2} ligand and the praseodymium nitrate salt in equimolar concentrations (5.86 x 10{sup -4} M: 5.22 x 10{sup -4} M) in methanol. The statistical analysis of the experimental results suggested three complexed species with 1Pr:3L, 1Pr:2L y 1Pr:1L stoichiometries. The predominant stoichiometries were the second and the latter. Based on these results and data from the scientific literature, the methodology for the syntheses of the complexes Q Schiff-(OH){sub 2}-Pr in aqueous-organic and organic media was established and a molar ratio M:L= 1:2 of praseodymium nitrate and the ligand was used. The new complexes were characterized by UV/Vis, Infrared, X-ray Photoelectron Spectroscopy (XP S), Diffuse Reflectance (Dr) and Thermogravimetric Analysis/Differential Scanning Calorimetry (TGA/DSC). Elemental analysis of C, N, O and Pr by XP S suggested 1Pr:2L:1Na (PrC{sub 32}H{sub 20}N{sub 4}O{sub 4}Na) stoichiometry of the complex synthesized by the aqueous-organic medium while for the complex synthesized by the organic medium it was 1Pr:3L (PrC{sub 48}H{sub 33}N{sub 6}O{sub 6}). In the first case, the praseodymium ion charge was neutralized by the anionic ligands whose remaining charge was compensated by the sodium ion. In the second case, the ion charge was neutralized by the ligands. The minimum formula was Pr(Q Schiff){sub 2}Na for the pure coordination compound from the aqueous-organic medium and the minimum formula Pr(Q Schiff){sub 3} for that from the organic medium. XP S also indicated that the oxidation state of praseodymium ion was maintained. Both complexes were stable in methanol, ethanol and acetonitrile at least for 5 days. The photophysical properties of the studied complexes were

  3. 2-(取代哌嗪-1-甲基)-3-喹啉甲酸乙酯及其衍生物的合成、表征及晶体结构%Synthesis, Characterization and Single Crystal Structure of Ethyl 2-(Substituted-piperazin-1-ylmethyl)-quinoline-3-carboxylate Derivatives

    Institute of Scientific and Technical Information of China (English)

    吴利欢; 杨定乔


    以邻硝基苯甲醛为起始原料,经还原、Friedlander缩合反应合成2-甲基-3-喹啉甲酸乙酯(2),2经N-溴代丁二酰亚胺(NBS)溴代得到化合物3,3再与N-取代哌嗪5a~5p发生SN2亲核取代反应,合成一系列2-(取代哌嗪-1-甲基)-3-喹啉甲酸乙酯及其衍生物6a~6p.它们的结构通过元素分析,IR,1H NMR,13C NMR和MS进行了鉴定和表征,并用X射线衍射法测定了化合物6n的晶体结构.%2-Methyl-quinoline-3-carboxylic acid ethyl ester (2) was prepared by reduction of o-nitrobenzaldehydebe and Friedlander condensation with o-aminobenzaldehyde, followed by bromination with N-bromosuccinimide (NBS) to give compound 3. The SN2 reaction of compound 3 with N-substitutedpiperazine 5a~5p yielded a series of ethyl 2-(substituted-piperazin-1-ylmethyl)-quinoline-3-carboxylate derivatives 6a~6p. The structures of the title compounds 6a~6p were characterized by elemental analysis, IR,1H NMR, 13C NMR and MS techniques. The compound 6n was confirmed by X-ray single crystal diffraction analysis.

  4. Removing of quinoline insoluble in modified coal tar pitch by single solvent-extraction hot filtration%单溶剂萃取热过滤法脱除改质煤沥青的喹啉不溶物

    Institute of Scientific and Technical Information of China (English)

    徐妍; 高丽娟; 吴红运; 赵雪飞


    以鞍钢改质沥青为原料,采用单溶剂萃取法过滤脱除原料沥青中的喹啉不溶物(QI),再用常压蒸馏去除溶剂,得到QI含量小于0.1%的净化沥青。考察了料液比、恒温时间和恒温温度对改质煤沥青QI净化效果的影响。结果表明,净化最佳工艺参数为料液比1∶1.5~1∶3,恒温时间1 h,恒温温度140℃。在最佳工艺条件下得到的净化沥青软化点为62℃,QI含量为0,TI含量为19.1%,结焦值为47.77%。采用红外光谱对净化沥青进行表征,结果表明,原料沥青经过萃取过滤后芳香烃类结构减少,脂肪烃类结构增加。该净化沥青QI较低,结焦残炭率较高,可作为制备浸渍剂沥青、煤基炭纤维等炭素材料的优质原料。%Quinoline insolubles (QI) in raw coal pitch was filtrated and removed by using the single solvent-extraction method in this paper, and then the solvent was removed by atmospheric distillation to obtain refined coal pitch with low QI content (<0.1%). The effects of the ratio of pitch to solvent, thermostatic time and thermostatic temperature on the removal rate of QI in refined coal pitch were investigated. The results showed that the optimum purification process parameters were: the range of solid and solvent of 1∶1.5~1∶3, the constant temperature time of 1 h, and the thermostatic temperature of 140℃. The softening point, QI content, TI con-tent and coking value of refined asphalt under the condition of optimum process were 62℃, 0, 19.1%and 47.77%, respectively. The purification asphalt was characterized by infrared spectrum, which showed that the content of aromatic hydrocarbons decreased and that of fat hydrocarbons increased after extraction filter. This purified tar exhibits low QI and high coking value, which could be used as the quality raw materials for the impregnant pitch and coal based carbon fibers.

  5. synthesis and characterisation of quinoline functionalised ...

    African Journals Online (AJOL)


    particularly important in catalysis. The weak hemilabile ... vacant coordinating sites during catalytic cycles and stabilising the metal ... diethyl ether (Et2O), and hexane were dried and ... methanol (MeOH) and acetonitrile (MeCN) were dried.

  6. A Novel Anticancer Agent, 8-Methoxypyrimido[4',5':4,5]thieno(2,3-b Quinoline-4(3H-One Induces Neuro 2a Neuroblastoma Cell Death through p53-Dependent, Caspase-Dependent and -Independent Apoptotic Pathways.

    Directory of Open Access Journals (Sweden)

    Upasana Sahu

    Full Text Available Neuroblastoma is the most common cancer in infants and fourth most common cancer in children. Despite recent advances in cancer treatments, the prognosis of stage-IV neuroblastoma patients continues to be dismal which warrant new pharmacotherapy. A novel tetracyclic condensed quinoline compound, 8-methoxypyrimido [4',5':4,5]thieno(2,3-b quinoline-4(3H-one (MPTQ is a structural analogue of an anticancer drug ellipticine and has been reported to posses anticancer property. Study on MPTQ on neuroblastoma cells is very limited and mechanisms related to its cytotoxicity on neuroblastoma cells are completely unknown. Here, we evaluated the anticancer property of MPTQ on mouse neuro 2a and human SH-SY5Y neuroblastoma cells and investigated the mechanisms underlying MPTQ-mediated neuro 2a cell death. MPTQ-mediated neuro 2a and SH-SY5Y cell deaths were found to be dose and time dependent. Moreover, MPTQ induced cell death reached approximately 99.8% and 90% in neuro 2a and SH-SY5Y cells respectively. Nuclear oligonucleosomal DNA fragmentation and Terminal dUTP Nick End Labelling assays indicated MPTQ-mediated neuro 2a cell death involved apoptosis. MPTQ-mediated apoptosis is associated with increased phosphorylation of p53 at Ser15 and Ser20 which correlates with the hyperphosphorylation of Ataxia-Telangiectasia mutated protein (ATM. Immunocytochemical analysis demonstrated the increased level of Bax protein in MPTQ treated neuro 2a cells. MPTQ-mediated apoptosis is also associated with increased activation of caspase-9, -3 and -7 but not caspase-2 and -8. Furthermore, increased level of caspase-3 and cleaved Poly (ADP Ribose polymerase were observed in the nucleus of MPTQ treated neuro 2a cells, suggesting the involvement of caspase-dependent intrinsic but not extrinsic apoptotic pathway. Increased nuclear translocation of apoptosis inducing factor suggests additional involvement of caspase-independent apoptosis pathway in MPTQ treated neuro 2a cells

  7. The C8-2'-deoxyguanosine adduct of 2-amino-3-methylimidazo[1,2-d]naphthalene, a carbocyclic analogue of the potent mutagen 2-amino-3-methylimidazo[4,5-f]quinoline, is a block to replication in vitro. (United States)

    Christov, Plamen P; Chowdhury, Goutam; Garmendia, Craig A; Wang, Feng; Stover, James S; Elmquist, C Eric; Kozekova, Albena; Angel, Karen C; Turesky, Robert J; Stone, Michael P; Guengerich, F Peter; Rizzo, Carmelo J


    2-Amino-3-methylimidazo[1,2-d]naphthalene (cIQ) is a carbocyclic analogue of the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in which a naphthalene ring system replaces the quinoline unit of IQ. The activity of cIQ in Ames Salmonella typhimurium tester strain TA98 is known to be 4-5 orders of magnitude lower than IQ. cIQ undergoes efficient bioactivation with rat liver microsomes. The C8-dGuo adduct was formed when calf thymus DNA was treated with the N-hydroxy-cIQ metabolite and either acetic anhydride or extracts from cells that overexpress N-acetyl transferase (NAT). These studies indicate that bioactivation, the stability of the N-hydroxylamine ester, and the reactivity of the nitrenium ion with DNA of cIQ are similar to IQ and that none of these factors account for the differences in mutagenic potency of these analogues in Ames assays. Oligonucleotides were synthesized that contain the C8-dGuo adduct of cIQ in the frameshift-prone CG-dinucleotide repeat unit of the NarI recognition sequence. We have examined the in vitro translesion synthesis of this adduct and have found it to be a strong replication block to Escherichia coli DNA polymerase I, Klenow fragment exo(-) (Kf(-)), E. coli DNA polymerase II exo(-) (pol II(-)), and Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4). Previous studies by Fuchs and co-workers identified E. coli pol II as the polymerase responsible for two-base deletions of the C8-dGuo adduct of N-acetyl-2-aminofluorene in the NarI sequence. Our observation that pol II is strongly inhibited by the C8-dGuo adduct of cIQ suggests that one of the other SOS inducible polymerases (E. coli pol IV or pol V) is required for its bypass, and this accounts for the greatly attenuated mutagenicity in the Ames assays as compared with IQ.

  8. Fast Determination of Acrylonitrile, Crotonaldehyde, Pyridine and Quinoline in Environmental Tobacco Smoke with APCI-MS/MS%APCI-MS/MS法快速测定环境烟气中的丙烯腈、巴豆醛、吡啶和喹啉

    Institute of Scientific and Technical Information of China (English)

    蒋成勇; 王慧; 孙世豪; 宗永立; 王宏伟; 张建勋; 李炎强


    In order to determine the chemical pollutants in environmental tobacco smoke (ETS) which might possess potential risks to human health and environment, an atmospheric pressure chemical ionization (APCI)-tandem mass spectrometry (MS/MS) method was established to fast analyze four volatile and semi-volatile organic compounds (acrylonitrile, crotonaldehyde, pyridine and quinoline) in ETS. The ETS samples without any pretreatment was directed into a modified APCI ion source via inlet end of mass spectrometer and analyzed under multi-reaction monitoring (MRM) mode. The results showed that the calibration curves of the four compounds exhibited good linear relations (R2>0.999) with the limits of detection from 0.39 to 0.70 ng/L and the relative standard deviations (RSDs) from 5.14% to 9.42%. This method is simple in operation and features higher sensitivity, it is suitable for the fast analysis of acrylonitrile, crotonaldehyde, pyridine, and quinoline in ETS.%为了测定环境烟气(ETS)中对人体和环境有潜在危害的化学污染物,建立了一种快速分析丙烯腈、巴豆醛、吡啶和喹啉4种挥发性、半挥发性有机化合物的大气压化学电离(APCI)-串联质谱(MS/MS)方法.采集的ETS样品不经任何前处理,由质谱进样端直接引入到改造后的APCI离子源内,采用多反应监测模式(MRM)对其进行快速定量分析.结果表明:4种有机化合物的定量分析标准工作曲线线性关系较好(R2>0.999),检测限和相对标准偏差分别为0.39 ~ 0.70 ng/L和5.14% ~ 9.42%.该方法操作简单、灵敏度高,适合于快速检测ETS中的丙烯腈、巴豆醛、吡啶和喹啉.

  9. 15-(4-Chlorophenyl-6b-hydroxy-17-methyl-6b,7,16,17-tetrahydro-7,14a-methanonaphtho[1′,8′:1,2,3]pyrrolo[3′,2′:8,8a]azuleno[5,6-b]quinolin-14(15H-one methanol hemisolvate

    Directory of Open Access Journals (Sweden)

    J. M. Joseph


    Full Text Available In the title solvate, C35H25ClN2O3·0.5CH3OH, the conformation of the central 1-methylpyrrolidine ring is best described as an envelope with the N atom as the flap. The cyclopentane ring adopts a twist conformation on the CH—CH2 bond and the cyclohexane ring has an envelope conformation with the CH2 atom as the flap. The pyrrolidine ring makes dihedral angles of 40.87 (12, 67.89 (11, 81.86 (9 and 70.86 (12° with the mean planes of the cyclopentane, cyclohexane, acenaphthylene and chlorobenzene rings, respectively. The quinoline ring system is inclined to the naphthalene ring system by 54.14 (6°. There is a short O—H...N contact in the molecule making an S(5 ring motif. In the crystal, there is a disordered and partially occupied ethan-1,2-diol solvent molecule present, located about an inversion centre, which links the title molecules via O—H...O and C—H...O hydrogen bonds, forming chains propagating along the a-axis direction.

  10. Synthesis and structural investigation of some pyrimido[5,4-c]quinolin-4(3H)-one derivatives with a long-chain arylpiperazine moiety as potent 5-HT(1A/2A) and 5-HT(7) receptor ligands. (United States)

    Lewgowd, Wieslawa; Bojarski, Andrzej J; Szczesio, Malgorzata; Olczak, Andrzej; Glowka, Marek L; Mordalski, Stefan; Stanczak, Andrzej


    A series of new pyrimido[5,4-c]quinolin-4(3H)-ones with variable length of the spacer between amide and 4-arylpiperazine moiety were prepared to further explore the role of a terminal portion in the serotonergic activity. The majority of compounds demonstrated high in vitro affinity for 5-HT(1A) receptor, and moderate-to-low affinity for 5-HT(2A) and 5-HT(7) receptors. X-ray analysis, two-dimensional NMR, conformational studies and docking into the 5-HT(1A) receptor model were conducted to investigate conformational preferences of selected 5-HT(1A) receptor ligands in different environments. The extended conformation of tetramethylene derivatives was found in a solid state, in DMSO (for a protonated form) and as a global energy minimum during conformational analysis in simulated water environment. Ligand geometry in top-scored complexes, obtained by docking to a set of 100 receptor models, were either fully extended or with central spacer torsion in synclinal conformation.

  11. Synthesis and anticonsulvant activity of 1,2,4-triazolo[4,3-a] quinolines%1,2,4-三唑并[4,3-a]喹啉衍生物的合成及其抗惊厥活性

    Institute of Scientific and Technical Information of China (English)

    李元春; 邓先清; 全哲山


    In our previous work, 5-hexyloxy- [ 1,2,4 ] triazolo [ 4,3-a ] quinoline ( compound Ⅰ ) showed potent anticonvulsant activity ,with ED50 value of 19.0 mg·kg- 1 and protective index( PI = TD50/ED50 ) values of 5.8 in the MES test. As part of our continuous effort to find better anticonvulsant candidate in this area,twelve derivatives of leading compound Ⅰ were synthesized by the modification of 1,2, and 5 positions of it. In addition, their anticonvulsant activity and neurotoxicity were evaluated using the MES test and the rotarod test in mice ,respectively. In the same condition, the 50% toxic dose( TD50 ) and 50% effective dose (ED50) of the reference drugs carbamazepine and the leading compound Ⅰ were evaluated in MES test and the rotarod test in our laboratory. The results of pharmacological tests demonstrated that some target compounds ( 6a, 10a, 10b) displayed anticonvulsant activities in different doses, and 5-hexyloxy-1 -methyl- [ 1,2,4] triazolo[4,3-a] quinoline(10b) showed good activity with an ED50 value of 18.0 mg·kg -1 and protective index ( PI = TD50/ED50 ) value of 7.9. The anticonvulsant activity ( ED50 and PI) of 10b is better than that of the leading compound Ⅰ. Compared to the reference drugs, compound 10b exhibited the weaker activity ,while it possessed the higher PI value ,which mean that compound 10b is safer than marketed drug carbamazepine.%目的 设计合成一系列1,2,4-三唑并[4,3-a]喹啉衍生物,并评价其抗惊厥活性和神经毒性.方法 以4-羟基喹啉-2(1H)酮为起始原料,经烷基化、氯代、肼代、环合等反应合成1,2,4-三唑并[4,3-a]喹啉衍生物.通过最大电惊厥实验(MES)和旋转棒法(Rotarod),分别测定目标化合物的抗惊厥活性和神经毒性.结果 合成了12个新化合物,其结构经1H-NMR、EI-MS和IR谱确证.结论 药理学实验结果表明,部分化合物在不同剂量下显示出抗惊厥活性,其中,5-苄氧基-1-甲基-[1,2,4]三唑并[4,3-a]喹啉(10b

  12. Protective effects of xanthohumol against the genotoxicity of benzo(a)pyrene (BaP), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and tert-butyl hydroperoxide (t-BOOH) in HepG2 human hepatoma cells. (United States)

    Plazar, Janja; Zegura, Bojana; Lah, Tamara T; Filipic, Metka


    Xanthohumol is the major prenylated flavonoid present in the hop plant Humulus lupulus L. (Cannabinaceae) and a common ingredient of beer. Recently, xanthohumol has gained considerable interest due to its potential cancer chemo-preventive effect. The aim of this study was to reveal the possible anti-genotoxic activity of xanthohumol in metabolically competent human hepatoma HepG2 cells, by use of the comet assay. Xanthohumol by itself was neither cytotoxic nor genotoxic to the cells at concentrations below 10microM. However, a significant protective effect against the pro-carcinogens benzo(a)pyrene (BaP) and 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) was observed at concentrations as low as 0.01microM. In cells treated with xanthohumol in combination with tert-butyl hydroperoxide (t-BOOH) - an inducer of reactive oxygen species (ROS) - no protective effect was observed and xanthohumol also showed no significant scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. On the other hand, HepG2 cells pre-treated with xanthohumol showed significantly reduced levels of t-BOOH-induced DNA strand breaks, indicating that its protective effect is mediated by induction of cellular defence mechanisms against oxidative stress. As xanthohumol is known to be an effective inhibitor of cytochrome P450 enzymes and an inducer of NAD(P)H: quinone reductase (QR), our findings can be explained by an inhibition of metabolic activation of pro-carcinogens and/or by induction of carcinogen-detoxifying and anti-oxidative enzymes by xanthohumol. These results provide evidence that xanthohumol displays anti-genotoxic activity in metabolically competent human cells.

  13. Synthesis and in vivo evaluation of the putative breast cancer resistance protein inhibitor [{sup 11}C]methyl 4-((4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl) amino-carbonyl)-2-(quinoline-2-carbonylamino)benzoate

    Energy Technology Data Exchange (ETDEWEB)

    Mairinger, Severin [Department of Medicinal Chemistry, University of Vienna, 1090 Vienna (Austria); Molecular Medicine, AIT Austrian Institute of Technology GmbH, 2444 Seibersdorf (Austria); Department of Clinical Pharmacology, Medical University of Vienna, Vienna (Austria); Langer, Oliver, E-mail: [Molecular Medicine, AIT Austrian Institute of Technology GmbH, 2444 Seibersdorf (Austria); Department of Clinical Pharmacology, Medical University of Vienna, Vienna (Austria); Kuntner, Claudia; Wanek, Thomas [Molecular Medicine, AIT Austrian Institute of Technology GmbH, 2444 Seibersdorf (Austria); Bankstahl, Jens P.; Bankstahl, Marion [Department of Pharmacology, Toxicology and Pharmacy, University of Veterinary Medicine Hanover (Germany); Stanek, Johann [Department of Clinical Pharmacology, Medical University of Vienna, Vienna (Austria); Doerner, Bernd [Department of Medicinal Chemistry, University of Vienna, 1090 Vienna (Austria); Bauer, Florian [Department of Medicinal Chemistry, University of Vienna, 1090 Vienna (Austria); Department of Clinical Pharmacology, Medical University of Vienna, Vienna (Austria); Baumgartner, Christoph [2nd Neurological Department, General Hospital Hietzing with Neurological Center Rosenhuegel, Vienna (Austria); Loescher, Wolfgang [Department of Pharmacology, Toxicology and Pharmacy, University of Veterinary Medicine Hanover (Germany); Erker, Thomas, E-mail: [Department of Medicinal Chemistry, University of Vienna, 1090 Vienna (Austria); Mueller, Markus [Department of Clinical Pharmacology, Medical University of Vienna, Vienna (Austria)


    Introduction: The multidrug efflux transporter breast cancer resistance protein (BCRP) is highly expressed in the blood-brain barrier (BBB), where it limits brain entry of a broad range of endogenous and exogenous substrates. Methyl 4-((4-(2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl)phenyl) amino-carbonyl)-2-(quinoline-2-carbonylamino)benzoate (1) is a recently discovered BCRP-selective inhibitor, which is structurally derived from the potent P-glycoprotein (P-gp) inhibitor tariquidar. The aim of this study was to develop a new PET tracer based on 1 to map BCRP expression levels in vivo. Methods: Compound 1 was labelled with {sup 11}C in its methyl ester function by reaction of the corresponding carboxylic acid 2 with [{sup 11}C]methyl triflate. Positron emission tomography (PET) imaging of [{sup 11}C]-1 was performed in wild-type, Mdr1a/b{sup (-/-)}, Bcrp1{sup (-/-)} and Mdr1a/b{sup (-/-)}Bcrp1{sup (-/-)} mice (n=3 per mouse type) and radiotracer metabolism was assessed in plasma and brain. Results: Brain-to-plasma ratios of unchanged [{sup 11}C]-1 were 4.8- and 10.3-fold higher in Mdr1a/b{sup (-/-)} and in Mdr1a/b{sup (-/-)}Bcrp1{sup (-/-)} mice, respectively, as compared to wild-type animals, but only modestly increased in Bcrp1{sup (-/-)} mice. [{sup 11}C]-1 was rapidly metabolized in vivo giving rise to a polar radiometabolite which was taken up into brain tissue. Conclusion: Our data suggest that [{sup 11}C]-1 preferably interacts with P-gp rather than BCRP at the murine BBB which questions its reported in vitro BCRP selectivity. Consequently, [{sup 11}C]-1 appears to be unsuitable as a PET tracer to map cerebral BCRP expression.

  14. L-NAME (N omega-nitro-L-arginine methyl ester), a nitric-oxide synthase inhibitor, and WIN 55212-2 [4,5-dihydro-2-methyl-4(4-morpholinylmethyl)-1-(1-naphthalenyl-carbonyl)-6H-pyrrolo[3,2,1ij]quinolin-6-one], a cannabinoid agonist, interact to evoke synergistic hypothermia. (United States)

    Rawls, S M; Tallarida, R J; Gray, A M; Geller, Ellen B; Adler, Martin W


    Cannabinoids evoke profound hypothermia in rats by activating central CB(1) receptors. Nitric oxide (NO), a prominent second messenger in central and peripheral neurons, also plays a crucial role in thermoregulation, with previous studies suggesting pyretic and antipyretic functions. Dense nitric-oxide synthase (NOS) staining and CB(1) receptor immunoreactivity have been detected in regions of the hypothalamus that regulate body temperature, suggesting that intimate NO-cannabinoid associations may exist in the central nervous system. The present study investigated the effect of N(omega)-nitro-L-arginine methyl ester (L-NAME), a NO synthase inhibitor, on the hypothermic response to WIN 55212-2 [4,5-dihydro-2-methyl-4(4-morpholinylmethyl)-1-(1-naphthalenylcarbonyl)-6H-pyrrolo[3,2,1ij]quinolin-6-one], a selective cannabinoid agonist, in rats. WIN 55212-2 (1-5 mg/kg, i.m.) produced dose-dependent hypothermia that peaked 45 to 90 min post-injection. L-NAME (10-100 mg/kg, i.m.) by itself did not significantly alter body temperature. However, a nonhypothermic dose of L-NAME (50 mg/kg) potentiated the hypothermia caused by WIN 55212-2 (0.5-5 mg/kg). The augmentation was strongly synergistic, indicated by a 2.5-fold increase in the relative potency of WIN 55212-2. The inactive enantiomer of WIN 55212-2, WIN 55212-3 [S-(-)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo[1,2,3-de]-1,4-benzoxazinyl]-(1-napthanlenyl) methanone mesylate] (5 mg/kg, i.m.), did not produce hypothermia in the absence or presence of L-NAME (50 mg/kg), confirming that cannabinoid receptors mediated the synergy. The present data are the first evidence that drug combinations of NOS blockers and cannabinoid agonists produce synergistic hypothermia. Thus, NO and cannabinoid systems may interact to induce superadditive hypothermia.

  15. Synthetic and Analytical Application of 5-(4-Sodium Sulphonate Phenylazo)-8-(p-Toluenesulphonamido) Quinoline%5-(4-磺酸钠苯基偶氮)-8-(对-甲苯磺酰氨基)喹啉的合成及其分析应用

    Institute of Scientific and Technical Information of China (English)

    李晓阳; 赵建为; 周康; 王英; 刘述忠; 郭玉忠


    A new spectrofluorimetric reagent, 5-(4-sodium sulphonatephenoylazo)-8-(p-toluenesulphonamido) quinoline (SPTSQ) has been synthesized, and its identity has been confirmed by infrared spectrometry, thermogravimetry and elemental analysis. Its chromogenic and fluorimetric properties and reactivities with metal ions have been investigated. A simple, rapid ,selective and sensitive new spectrophotometric method for determination of copper is developed. In the presence of cetyltrimethy1 ammonium bromide cationic surfactant (CTMAB), SPTSQ reacts with copper to form a violet-red 1:2 (metal:ligand) complex with an absorption maximum at 585 nm. Beer's law is obeyed over the concentration range 0~0.8 μg/mL copper. The molar absorptivity and sandell's sentitivity of the method are 8.5×104L·mol-1·cm-1 and 0.000 75μg·cm-2, respectively. The interference of various ions has been studied and the method has been used for the determination of microamount of copper in crude lead and alloys.%合成了一种光度荧光新试剂,5-(4-磺酸钠苯基偶氮)-8-(对-甲苯磺酰氨基)喹啉(SPTSQ),其结构经红外光谱、热重分析和元素分析确证.研究了试剂及其与金属离子的显色反应和荧光反应特性.建立了一种简单、灵敏、快速、选择性的光度测定铜的新方法.在阳离子表面活性剂溴化十六烷基三甲铵存在下,SPTSQ与Cu(Ⅱ) 形成2∶1的紫红色络合物,其最大吸收峰位于585 nm,铜在0~0.8 μg·mL-1浓度范围内符合比尔定律.摩尔吸光系数和桑德尔灵敏度分别为8.5×104 L·mol-1·cm-1和0.000 75μg·cm-2.研究了不同离子的干扰,该法已用于粗铅和合金样品中微量铜的测定.

  16. Crystal structure of N-(quinolin-6-ylhydroxylamine

    Directory of Open Access Journals (Sweden)

    Anuruddha Rajapakse


    Full Text Available The title compound, C9H8N2O, crystallized with four independent molecules in the asymmetric unit. The four molecules are linked via one O—H...N and two N—H...N hydrogen bonds, forming a tetramer-like unit. In the crystal, molecules are further linked by O—H...N and N—H...O hydrogen bonds forming layers parallel to (001. These layers are linked via C—H...O hydrogen bonds and a number of weak C—H...π interactions, forming a three-dimensional structure. The crystal was refined as a non-merohedral twin with a minor twin component of 0.319.

  17. 2-((Pyren-1-ylmethylamino)methyl)quinolin-8-ol


    Carlos Lodeiro; Javier Fernández-Lodeiro; Cristina Nuñez; José Luis Capelo


    A new fluorescent compound L1 derived from 1-pyrenemethylamine hydrochloride (A) has been synthesized by classical Schiff-base reaction between (A) and 8-hydroxyquinoline-2-carbaldehyde (B) followed by a chemical reduction with NaBH4. The chemical structure was confirmed by elemental analysis, FAB-MS spectrometry and by IR, UV-vis and 1H-NMR spectroscopy. The photophysical characterization was achieved by UV-vis and emission spectroscopy and lifetime measurements. Compound L1 was explored as ...

  18. Synthesis of quinoline based heterocyclic compounds for blue lighting application (United States)

    Kumar, Vinod; Gohain, Mukut; Van Tonder, Johannes H.; Ponra, S.; Bezuindenhoudt, B. C. B.; Ntwaeaborwa, O. M.; Swart, H. C.


    2,4-Diphenylquinoline (DPQ), derivatives 6-chloro-2,4-diphenylquinoline (DPQ-Cl) and 4‧,6-dichloro-2,4-diphenylquinoline (DPQ-Cl2) were synthesized using a three-component domino reaction. The DPQ, DPQ-Cl and DPQ-Cl2 were characterized by nuclear magnetic resonance spectroscopy, scanning electron microscopy, thermogravimetric analysis (TGA). Fourier transformed infra-red spectroscopy, X-ray photoelectron spectroscopy (XPS), Ultraviolet-visible (UV-vis) spectroscopy and photoluminescence spectroscopy. The TGA results showed that the DPQ was more thermally stable with respect to the DPQ-Cl and DPQ-Cl2. The synthesized organic phosphors showed bright emission in the blue region under an UV excitation wavelength of 325 nm with the power of 18 mW. These organic phosphors were found to be efficient candidate and may be used in organic blue light emitting devices.

  19. Synthesis and Antiproliferative Activity of Some Quinoline and Oxadiazole Derivatives

    Directory of Open Access Journals (Sweden)

    Mohamed Jawed Ahsan


    Full Text Available In continuance of our search for newer antiproliferative agents we report herein the synthesis and antiproliferative studies of two series (5a–j and 10a–c of heterocyclic compounds. All the new compounds were characterized by IR, NMR, and mass spectral data. The antiproliferative activity of 10 compounds (5a–j was carried out on HeLa (cervix cancer cell line and MDA-MB-435 (melanoma and LC50, TGI, and GI50 were calculated, while the antiproliferative activity of 3 compounds (10a–c was carried out against nine different panels of nearly 60 cell lines (NCI-60 according to the National Cancer Institute (NCI US Protocol at 10 μM. 1-(7-Hydroxy-4-methyl-2-oxoquinolin-1(2H-yl-3-(4-methoxylphenylurea (5j was found to have antiproliferative activity with GI50 of 35.1 μM against HeLa (cervix cancer cell line and 60.4 μM against MDA-MB-435 (melanoma, respectively. The compounds 10a, 10b, and 10c showed antiproliferative activity with comparatively higher selectivity towards HOP-92 (Non-Small Cell Lung Cancer with percent growth inhibitions (GIs of 34.14, 35.29, and 31.59, respectively.

  20. 1,2,3,4-四氢化-1-羟基-3-对甲基苯基苯并[f ]喹啉-1,2-二羧酸二甲酯的合成和晶体结构%Synthesis and crystal structure of dimethyl 1,2,3,4-tetrahydro-1-hydroxy-3-p-tolylbenzo[f ]quinoline-1,2-dicarboxylate

    Institute of Scientific and Technical Information of China (English)

    陈隆重; 王香善; 张梅梅


    The title compound of 1,2,3,4-tetrahydro-1-hydroxy-3-p-tolylbenzo[f]quinoline-1,2-dicarboxylate is syn-thesized by a three-component reaction of 4-methylbenzaldehyde,naphthalene-2-amine,and dimethyl but-2-ynedio-ate catalyzed by iodine.The structure was determined by single crystal X-ray diffraction which is triclinic system, space group P-1,a=0.893 67(2)nm,b=1.042 18(3)nm,c =1.181 06(3)nm,α=106.783(2)°,β=96.067(2)°,γ=96.640(2 )°,Mr =405.43,V = 1.034 83 (5 )nm3 ,D c = 1.301 Mg/m3 ,Z = 2,μ(Mo Kα)= 0.091 mm-1 , F(000)=428.The crystal structure of title compound is solved by direct method,and refined by full-matrix least squares method to give final R 1 =0.041 8,R 2 =0.114 9.%标题化合物1,2,3,4-四氢化-1-羟基-3-对甲基苯基苯并[f ]喹啉-1,2-二羧酸二甲酯通过单质碘催化对甲基苯甲醛、2-萘胺和丁炔二酸二甲酯三组分反应制备.通过单晶 X 射线衍射分析确定其结构为三斜晶系,空间群 P-1, a=0.89367(2)nm,b=1.04218(3)nm,c =1.18106(3)nm,α=106.783(2)°,β=96.067(2)°,γ=96.640(2)°,Mr=405.43,V =1.03483(5)nm3,D c =1.301 Mg/m3,Z =2,μ(Mo Kα)=0.091 mm-1,F (000)=428.晶体结构使用直接法解出,并通过全矩阵最小二乘法对原子参数进行修正,获得偏离因子 R 1=0.0418,R 2=0.1149.

  1. Quinoline Group Modified Carbon Nanotubes for the Detection of Zinc Ions

    Directory of Open Access Journals (Sweden)

    Dong Zhengping


    Full Text Available Abstract Carbon nanotubes (CNTs were covalently modified by fluorescence ligand (glycine-N-8-quinolylamide and formed a hybrid material which could be used as a selective probe for metal ions detection. The anchoring to the surface of the CNTs was carried out by the reaction between the precursor and the carboxyl groups available on the surface of the support. Fourier transform infrared spectroscopy (FTIR and Thermogravimetric analysis (TGA unambiguously proved the existence of covalent bonds between CNTs and functional ligands. Fluorescence characterization shows that the obtained organic–inorganic hybrid composite is highly selective and sensitive (0.2 μM to Zn(II detection.

  2. Photo-physics study of an hydroxy-quinoline derivative as inhibitor of Pim-1 kinase

    DEFF Research Database (Denmark)

    Lamhasni, T.; Aitlyazidi, S.; Hnach, M.


    The photophysical properties of the antiviral 7-nicotinoyl-styrylquinoline (MB96) were investigated by means of UV-Vis linear dichroism (LD) spectroscopy on molecular samples aligned in stretched polyvinylalcohol (PVA), supported by Time Dependent Density Functional Theory (TD-DFT) calculations...

  3. Synthesis, characterization and antimicrobial screening of hybrid molecules containing quinoline, pyrimidine and morpholine analogues

    Indian Academy of Sciences (India)

    N C Desai; K M Rajpara; V V Joshi; H V Vaghani; H M Satodiya


    In an attempt to find new bio-active molecules, a series of compounds -(4-(2-chloroquinolin-3-yl)-6-(aryl)pyrimidin-2-yl)-2-morpholinoacetamides (5a-l) were synthesized by multistep reactions. Compounds were characterized by IR, NMR and mass spectra. Antimicrobial screening of title compounds (5a-l) was carried out against Gram-positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), Gramnegative bacteria (Escherichia coli, Pseudomonas aeruginosa) and fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus) using serial broth dilution method. On the basis of statistical analysis, it is observed that these compounds gave significant co-relation. Newly synthesized compounds 5e, 5f, 5g, 5i and 5l showed significant potency against different microbial strains.

  4. Anti-malarial activity of a non-piperidine library of next-generation quinoline methanols

    Directory of Open Access Journals (Sweden)

    Melendez Victor


    Full Text Available Abstract Background The clinical utility for mefloquine has been eroded due to its association with adverse neurological effects. Better-tolerated alternatives are required. The objective of the present study was the identification of lead compounds that are as effective as mefloquine, but exhibit physiochemical properties likely to render them less susceptible to passage across the blood-brain barrier. Methods A library of drug-like non-piperidine analogs of mefloquine was synthesized. These compounds are diverse in structure and physiochemical properties. They were screened in appropriate in vitro assays and evaluated in terms of their potential as lead compounds. The correlation of specific structural attributes and physiochemical properties with activity was assessed. Results The most potent analogs were low molecular weight unconjugated secondary amines with no heteroatoms in their side-chains. However, these compounds were more metabolically labile and permeable than mefloquine. In terms of physiochemical properties, lower polar surface area, lower molecular weight, more freely rotatable bonds and fewer H-bond acceptors were associated with greater potency. There was no such relationship between activity and LogP, LogD or the number of hydrogen bond donors (HBDs. The addition of an H-bond donor to the side-chain yielded a series of active diamines, which were as metabolically stable as mefloquine but showed reduced permeability. Conclusions A drug-like library of non-piperidine analogs of mefloquine was synthesized. From amongst this library an active lead series of less permeable, but metabolically stable, diamines was identified.

  5. Simplified Reversed Chloroquines To Overcome Malaria Resistance to Quinoline-Based Drugs. (United States)

    Gunsaru, Bornface; Burgess, Steven J; Morrill, Westin; Kelly, Jane X; Shomloo, Shawheen; Smilkstein, Martin J; Liebman, Katherine; Peyton, David H


    Building on our earlier work of attaching a chemosensitizer (reversal agent) to a known drug pharmacophore, we have now expanded the structure-activity relationship study to include simplified versions of the chemosensitizer. The change from two aromatic rings in this head group to a single ring does not appear to detrimentally affect the antimalarial activity of the compounds. Data from in vitro heme binding and β-hematin inhibition assays suggest that the single aromatic RCQ compounds retain activities against Plasmodium falciparum similar to those of CQ, although other mechanisms of action may be relevant to their activities. Copyright © 2017 Gunsaru et al.

  6. 2-(Methoxycarbonylquinolinium tetrachlorido(quinoline-2-carboxylato-κ2N,Ostannate(IV methanol solvate

    Directory of Open Access Journals (Sweden)

    Marzieh Vafaee


    Full Text Available In the title salt, (C11H10NO2[SnCl4(C10H6NO2]·CH3OH, the Sn atom is chelated by the quinolincarboxylate unit and it exists in a distorted octahedral coordination geometry. The cation is linked to the solvent molecule by an N—H...O hydrogen bond; the solvent molecule is linked to the anion by an O—H...O hydrogen bond.

  7. Facile Synthesis of 5, 6, 7, 8-Tetrahydropyrimido [4, 5-b]-quinoline Derivatives

    Directory of Open Access Journals (Sweden)

    Mohamed Abdelhamed Morsy


    Full Text Available 2–Amino–4-phenyl–5,6,7,8–tetrahydroquinoline–3–carbonitrile (3 was synthesized by treating cyclohexanone (1 with 2–benzylidenemalononitrile (2 in the presence of ammonium acetate. The reactivity of compound 3 towards dimethylformamide dimethyl acetal (DMF-DMA, carbon disulfide, urea, thiourea, formamide, formic acid, acetyl chloride and isothiocyanate were studied. In addition, the antimicrobial activity of some selected derivatives is reported.

  8. Regioselective acceptorless dehydrogenative coupling of N-heterocycles toward functionalized quinolines, phenanthrolines, and indoles. (United States)

    Talwar, Dinesh; Gonzalez-de-Castro, Angela; Li, Ho Yin; Xiao, Jianliang


    A new strategy has been developed for the oxidant- and base-free dehydrogenative coupling of N-heterocycles at mild conditions. Under the action of an iridium catalyst, N-heterocycles undergo multiple sp(3) CH activation steps, generating a nucleophilic enamine that reacts in situ with various electrophiles to give highly functionalized products. The dehydrogenative coupling can be cascaded with Friedel-Crafts addition, resulting in a double functionalization of the N-heterocycles.

  9. New cross-linking quinoline- and quinolone-based luminescent lanthanide probes for sensitive labeling (United States)

    Pillai, Shyamala; Wirpsza, Laura; Kozlov, Maxim; Marras, Salvatore A. E.; Krasnoperov, Lev N.; Mustaev, Arkady


    New luminescent lanthanide chelates containing thiol-, amine-, and click-reactive groups in antenna-fluorophore moieties were synthesized. The chelates include diethylenetriaminepentaacetic acid (DTPA) coupled to two types of chromophores: 7-amino-4-trifluoromethyl-2(1H) quinolinone, and 7-amino-4-trifluoromethyl-2-alkoxyquinoline. The synthesized compounds were characterized using NMR, light absorption, steady-state and time-resolved fluorescent spectroscopy. Some of the compounds displayed high brightness with Tb3+, Eu3+, and Dy3+. Obtained reactive lanthanide chelates can be easily attached to biological molecules. The probes demonstrated high performance in molecular beaconbased DNA hybridization assays (sub-pico molar detection limit), in bacterial proteome labeling, and in live cell imaging.

  10. Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands. (United States)

    Zajdel, Paweł; Marciniec, Krzysztof; Maślankiewicz, Andrzej; Paluchowska, Maria H; Satała, Grzegorz; Partyka, Anna; Jastrzębska-Więsek, Magdalena; Wróbel, Dagmara; Wesołowska, Anna; Duszyńska, Beata; Bojarski, Andrzej J; Pawłowski, Maciej


    Novel arene- and quinolinesulfonamides were synthesized using different solutions and a solid-support methodology, and were evaluated for their affinity for 5-HT(1A), 5-HT(2A), 5-HT(6), and 5-HT(7) receptors. Compound 54 (N-Ethyl-N-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-yl)butyl]-8-quinolinesulfonamide) was identified as potent 5-HT(7) antagonist (K(i)=13 nM, K(B)=140 nM) with good selectivity over 5-HT(1A), 5-HT(2A), 5-HT(6) receptors. In the FST in mice, it reduced immobility in a manner similar to the selective 5-HT(7) antagonist SB-269970.

  11. Luminescent Enhancement of Heterostructure Organic Light-Emitting Devices Based on Aluminum Quinolines

    Institute of Scientific and Technical Information of China (English)

    Jun-Sheng Yu; Lu Li; Ya-Dong Jiang; Xing-Qiao Ji; Tao Wang


    High performance organic light-emitting devices (OLEDs) have been investigated by using fluorescent bis (2-methyl-8-quinolinolato)(para-phenyl-phenolato)aluminum(BAlq) as an emissive layer on the performance of multicolor devices consisting of N, N'-bis-(1-naphthyl)-N,N'diphenyI-l,l'-biphenyI-4,4'-diamine (NPB) as hole transport layer. The results show that the performance of heterostructure blue light-emitting device composed of 8-hydroxyquinoline aluminum (Alq3) as an electron transport layer has been dramatically enhanced. In the case of high performance heterostructure devices, the electroluminescent spectra has been perceived to vary strongly with the thickness of the organic layers due to the different recombination region, which indicates that various color devices composed of identical components could be implemented by changing the film thickness of different functional layers.

  12. Synthesis of novel quinolines using TsOH/ionic liquid under microwave

    Energy Technology Data Exchange (ETDEWEB)

    Prola, Lizie D.T.; Buriol, Lilian; Frizzo, Clarissa P.; Caleffi, Guilherme S.; Marzari, Mara R.B.; Moreira, Dayse N.; Bonacorso, Helio G.; Zanatta, Nilo; Martins, Marcos A.P., E-mail: [Nucleo de Quimica de Heterociclos (NUQUIMHE), Departamento de Quimica, Universidade Federal de Santa Maria (UFSM), Santa Maria, RS (Brazil)


    In this work, 3-haloacetyl-4-methylquinolines were synthesized from the reaction of 4-alkoxy-3-alkene-2-ones [R{sup 1}C(O)CH=C(R{sup 2})OCH{sub 3}, where R{sup 1} = CF{sub 3}, CCl{sub 3}, CHCl{sub 2}, CF{sub 2}Cl, CF{sub 2}CF{sub 3}and R{sub 2}= Me, Et, Pr, Bu, i-Bu and i-Pe] and 2-aminoacetophenone. The reaction was performed in ionic liquid and 4-toluene sulfonic acid under microwave irradiation. Results showed that the catalytic method was effective. Products were formed in a short time (10-20 min) and presented good yields (70-91%). (author)

  13. New insights on the mechanism of quinoline-based DNA Methyltransferase inhibitors. (United States)

    Gros, Christina; Fleury, Laurence; Nahoum, Virginie; Faux, Céline; Valente, Sergio; Labella, Donatella; Cantagrel, Frédéric; Rilova, Elodie; Bouhlel, Mohamed Amine; David-Cordonnier, Marie-Hélène; Dufau, Isabelle; Ausseil, Frédéric; Mai, Antonello; Mourey, Lionel; Lacroix, Laurent; Arimondo, Paola B


    Among the epigenetic marks, DNA methylation is one of the most studied. It is highly deregulated in numerous diseases, including cancer. Indeed, it has been shown that hypermethylation of tumor suppressor genes promoters is a common feature of cancer cells. Because DNA methylation is reversible, the DNA methyltransferases (DNMTs), responsible for this epigenetic mark, are considered promising therapeutic targets. Several molecules have been identified as DNMT inhibitors and, among the non-nucleoside inhibitors, 4-aminoquinoline-based inhibitors, such as SGI-1027 and its analogs, showed potent inhibitory activity. Here we characterized the in vitro mechanism of action of SGI-1027 and two analogs. Enzymatic competition studies with the DNA substrate and the methyl donor cofactor, S-adenosyl-l-methionine (AdoMet), displayed AdoMet non-competitive and DNA competitive behavior. In addition, deviations from the Michaelis-Menten model in DNA competition experiments suggested an interaction with DNA. Thus their ability to interact with DNA was established; although SGI-1027 was a weak DNA ligand, analog 5, the most potent inhibitor, strongly interacted with DNA. Finally, as 5 interacted with DNMT only when the DNA duplex was present, we hypothesize that this class of chemical compounds inhibit DNMTs by interacting with the DNA substrate.

  14. Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

    KAUST Repository

    Xu, Jun


    Achieving site selectivity in carbon-hydrogen (C-H) functionalization reactions is a formidable challenge in organic chemistry. Herein, we report a novel approach to activating remote C-H bonds at the C5 position of 8-aminoquinoline through copper-catalyzed sulfonylation under mild conditions. Our strategy shows high conversion efficiency, a broad substrate scope, and good toleration with different functional groups. Furthermore, our mechanistic investigations suggest that a single-electron-transfer process plays a vital role in generating sulfonyl radicals and subsequently initiating C-S cross-coupling. Importantly, our copper-catalyzed remote functionalization protocol can be expanded for the construction of a variety of chemical bonds, including C-O, C-Br, C-N, C-C, and C-I. These findings provide a fundamental insight into the activation of remote C-H bonds, while offering new possibilities for rational design of drug molecules and optoelectronic materials requiring specific modification of functional groups. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  15. Nanoparticulate Radiolabelled Quinolines Detect Amyloid Plaques in Mouse Models of Alzheimer's Disease

    Directory of Open Access Journals (Sweden)

    Celeste A. Roney


    Full Text Available Detecting aggregated amyloid peptides (Aβ plaques presents targets for developing biomarkers of Alzheimer's disease (AD. Polymeric n-butyl-2-cyanoacrylate (PBCA nanoparticles (NPs were encapsulated with radiolabelled amyloid affinity I125-clioquinol (CQ, 5-chloro-7-iodo-8-hydroxyquinoline as in vivo probes. I125-CQ-PBCA NPs crossed the BBB (2.3±0.9 ID/g (P<.05 in the WT mouse (N = 210, compared to I125-CQ (1.0±0.4 ID/g. I125-CQ-PBCA NP brain uptake increased in AD transgenic mice (APP/PS1 versus WT (N = 38; 2.54×105±5.31×104 DLU/mm2; versus 1.98×105±2.22×104 DLU/mm2 and in APP/PS1/Tau. Brain increases were in mice intracranially injected with aggregated Aβ42 peptide (N = 17; 7.19×105±1.25×105 DLU/mm2, versus WT (6.07×105±7.47×104 DLU/mm2. Storage phosphor imaging and histopathological staining of the plaques, Fe2+ and Cu2+, validated results. I125-CQ-PBCA NPs have specificity for Aβ in vitro and in vivo and are promising as in vivo SPECT (I123, or PET (I124 amyloid imaging agents.

  16. Energetics, electronic structures and geometries of naphthalene, quinoline and isoquinoline analogues of 1,2-didehydrobenzene (United States)

    Cioslowski, Jerzy; Szarecka, Agnieszka; Moncrieff, David


    B3LYP/cc-pVTZ electronic structure calculations employed in conjunction with additive corrections derived from experimental data for 1,2-didehydrobenzene predict the standard enthalpies of formation of 1,2- and 2,3-didehydronaphthalenes to be equal to 121.0 and 123.7 kcal mol -1 , respectively. The corresponding singlet-triplet splittings amount to 40.1 and 35.4 kcal mol -1 . The positional dependence of both of these quantities is preserved in those didehydroquinolines and didehydroisoquinolines in which the didehydrogenation sites are separated by at least one carbon from the heteroatoms. The effect of the adjacent heteroatoms on the singlet-triplet splittings is significantly more pronounced than that on the standard enthalpies of formation. Test G3 calculations on 2,3-didehydronaphthalene confirm the reliability of the additive correction scheme in the prediction of properties of annelated analogues of 1,2-didehydrobenzene. Such a scheme opens an avenue to facile electronic structure calculations on didehydrogenation reactions of polycondensed heterocyclic compounds with six-membered rings.

  17. Research progress in biodegradation of Quinoline and treatment methods for wastewater containing Quinoline%含喹啉废水的处理和生物降解研究进展

    Institute of Scientific and Technical Information of China (English)

    张翠萍; 刘益平; 朱丽红



  18. Bis(μ-2-methyl-quinolin-1-ium-8-olato-κO:O')bis-[(2-methyl-quinolin-1-ium-8-olato-κO)tris-(nitrato-κO,O')lanthanum(III)]. (United States)

    Fazaeli, Yousef; Najafi, Ezzatollah; Amini, Mostafa M; Ng, Seik Weng


    The two independent N-heterocycles in the centrosymmetric title compound, [La(2)(C(10)H(9)NO)(4)(NO(3))(6)], exist in the zwitterionic form. One of these binds to one metal center, whereas the other bridges two metal centers. The La atom is chelated by three nitrate groups and is surrounded by nine O atoms in a coordination environment based on a distorted monocapped square-anti-prism. The dinuclear structure is further stabilized by intra-molecular N-H⋯O(nitrate) hydrogen bonds.

  19. Modular Copper-Catalyzed Synthesis of Chromeno[4,3-b]quinolines with the Utilization of Diaryliodonium Salts. (United States)

    Aradi, Klára; Bombicz, Petra; Novák, Zoltán


    A novel, highly modular synthetic method with high functional group tolerance was developed for the construction of chromenoquinoline derivatives from arylpropynyloxy-benzonitriles and diaryliodonium triflates via an oxidative arylation-cyclization path. The copper(I) chloride catalyzed reaction is presumed to involve the formation of highly active arylcopper(III) species.

  20. (4R)-4-(Biphenyl-4-yl)-7-chloro-1,2,3,4-tetra­hydro­quinoline (United States)

    Theissmann, Thomas; Bolte, Michael


    The title compound, C21H18ClN, was synthesized by an enanti­oselective Brønsted acid-catalysed transfer hydrogenation reaction. The six-membered heterocycle adopts a half-chair conformation. It has the biphenyl residue in an axial position. The two rings of the biphenyl residue are almost coplanar [dihedral angle = 2.65 (9)°]. The crystal packing is stabilized by N—H⋯Cl hydrogen bonds, which connect the mol­ecules into chains running along the a axis. PMID:22064825

  1. (4R)-4-(Biphenyl-4-yl)-7-chloro-1,2,3,4-tetra-hydro-quinoline. (United States)

    Theissmann, Thomas; Bolte, Michael


    The title compound, C(21)H(18)ClN, was synthesized by an enanti-oselective Brønsted acid-catalysed transfer hydrogenation reaction. The six-membered heterocycle adopts a half-chair conformation. It has the biphenyl residue in an axial position. The two rings of the biphenyl residue are almost coplanar [dihedral angle = 2.65 (9)°]. The crystal packing is stabilized by N-H⋯Cl hydrogen bonds, which connect the mol-ecules into chains running along the a axis.

  2. Production of 9-thioxo-2,3,4,9-tetrahydro-pyrrolo[3,4-b]quinolin-1 ...

    African Journals Online (AJOL)

    b Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, P.O. .... S. Afr. J. Chem., 2003, 56, 30–33,. . ..... 3 Diagrams in Scheme 1 correspond merely to their nomenclature in.

  3. Chemistry, photophysics, and ultrafast kinetics of two structurally related Schiff bases containing the naphthalene or quinoline ring (United States)

    Fita, P.; Luzina, E.; Dziembowska, T.; Radzewicz, Cz.; Grabowska, A.


    The two structurally related Schiff bases, 2-hydroxynaphthylidene-(8-aminoquinoline) (HNAQ) and 2-hydroxynaphthylidene-1'-naphthylamine (HNAN), were studied by means of steady-state and time resolved optical spectroscopies as well as time-dependent density functional theory (TDDFT) calculations. The first one, HNAQ, is stable as a keto tautomer in the ground state and in the excited state in solutions, therefore it was used as a model of a keto tautomer of HNAN which exists mainly in its enol form in the ground state at room temperature. Excited state intramolecular proton transfer in the HNAN molecule leads to a very weak (quantum yield of the order of 10-4) strongly Stokes-shifted fluorescence. The characteristic time of the proton transfer (about 30fs) was estimated from femtosecond transient absorption data supported by global analysis and deconvolution techniques. Approximately 35% of excited molecules create a photochromic form whose lifetime was beyond the time window of the experiment (2ns). The remaining ones reach the relaxed S1 state (of a lifetime of approximately 4ps), whose emission is present in the decay associated difference spectra. Some evidence for the back proton transfer from the ground state of the keto form with the characteristic time of approximately 13ps was also found. The energies and orbital characteristics of main electronic transitions in both molecules calculated by TDDFT method are also discussed.

  4. Crystal structure of poly[μ-acetato-bis[μ-2-oxo-2-(quinolin-8-ylethanoato]trisodium

    Directory of Open Access Journals (Sweden)

    Rachel L. Nicholls


    Full Text Available The title compound [Na3(C11H6NO32(C2H3O2]n, crystallized through diffusion of diethyl ether into methanol as needles. There are three crystallographically independent Na+ cations present, each exhibiting a distorted octahedral coordination geometry, two through coordination by five O atoms and one N atom, and one through coordination by six O atoms. A series of intermolecular O...Na and N...Na contacts leads to the formation of chains along the a-axis direction.


    Energy Technology Data Exchange (ETDEWEB)

    Parker, Dorian S. N.; Yang, Tao; Dangi, Beni B.; Kaiser, Ralf I. [Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822 (United States); Bera, Partha P.; Lee, Timothy J., E-mail:, E-mail: [Space Science and Astrobiology Division, NASA Ames Research Center, Moffett Field, Mountain View, CA 94035 (United States)


    Meteorites contain bio-relevant molecules such as vitamins and nucleobases, which consist of aromatic structures with embedded nitrogen atoms. Questions remain over the chemical mechanisms responsible for the formation of nitrogen-substituted polycyclic aromatic hydrocarbons (PANHs) in extraterrestrial environments. By exploiting single collision conditions, we show that a radical mediated bimolecular collision between pyridyl radicals and 1,3-butadiene in the gas phase forms nitrogen-substituted polycyclic aromatic hydrocarbons (PANHs) 1,4-dihydroquinoline and to a minor amount 1,4-dihydroisoquinoline. The reaction proceeds through the formation of a van der Waals complex, which circumnavigates the entrance barrier implying it can operate at very low kinetic energy and therefore at low temperatures of 10 K as present in cold molecular clouds such as TMC-1. The discovery of facile de facto barrierless exoergic reaction mechanisms leading to PANH formation could play an important role in providing a population of aromatic structures upon which further photo-processing of ice condensates could occur to form nucleobases.

  6. Protein (Cyanobacteria): 423043 [PGDBj - Ortholog DB

    Lifescience Database Archive (English)


  7. Crystal Structure and Mechanism of Tryptophan 2,3-Dioxygenase, a Heme Enzyme Involved in Tryptophan Catabolism and in Quinolinate Biosynthesis

    Energy Technology Data Exchange (ETDEWEB)

    Zhang,Y.; Kang, S.; Mukherjee, T.; Bale, S.; Crane, B.; Begley, T.; Ealick, S.


    The structure of tryptophan 2,3-dioxygenase (TDO) from Ralstonia metallidurans was determined at 2.4 {angstrom}. TDO catalyzes the irreversible oxidation of L-tryptophan to N-formyl kynurenine, which is the initial step in tryptophan catabolism. TDO is a heme-containing enzyme and is highly specific for its substrate L-tryptophan. The structure is a tetramer with a heme cofactor bound at each active site. The monomeric fold, as well as the heme binding site, is similar to that of the large domain of indoleamine 2,3-dioxygenase, an enzyme that catalyzes the same reaction except with a broader substrate tolerance. Modeling of the putative (S)-tryptophan hydroperoxide intermediate into the active site, as well as substrate analogue and mutagenesis studies, are consistent with a Criegee mechanism for the reaction.

  8. Synthesis, Characterization and Antimicrobial Activity of Metal Chelates of 5-[4-Chloro phenyl(1, 3, 4thiadiazol-2-ylamino methylene]-8-hydroxy quinoline

    Directory of Open Access Journals (Sweden)

    Divyesh K. Patel


    Full Text Available 5-Chloromethyl-8-quinolinol was condensed stoichiometrically with 5-(4-chlorophenyl-(1,3,4 thiadiazol-2-ylamine in the presence of sodium bicarbonate. The resulting 5-[4-chlorophenyl-(1,3,4thiadiazol-2-ylamino methylene]-8-quinolinol (CTAQ was characterized by elemental analysis and spectral studies. The transition metal chelates viz. Cu2+, Ni2+, Co2+, Mn2+ and Zn2+ of CTAQ were prepared and characterized by metal-ligand (M:L ratio, IR and reflectance spectroscopies and magnetic properties. The antifungal activity of CTAQ and its metal chelates was screened against various fungi. The results show that all these samples are good antifungal agents.

  9. A 2-(2'-hydroxyphenyl)benzothiazole (HBT)-quinoline conjugate: a highly specific fluorescent probe for Hg(2+) based on ESIPT and its application in bioimaging. (United States)

    Sahana, Sunanda; Mishra, Gargi; Sivakumar, Sri; Bharadwaj, Parimal K


    A benzothiazole derived chemosensor L has been designed based on the excited-state intramolecular proton transfer (ESIPT) mechanism to afford a fluorescence turn-on response specifically in the presence of Hg(2+) ions over a host of biologically relevant metal ions as well as toxic heavy metal ions. The chemosensor exhibits high sensitivity with the detection limit down to 0.11 μM. The metal binding is supported by (1)H NMR titrations, ESI-MS spectral analysis and substantiated by theoretical calculations using the density functional theory. The probe shows cell membrane permeability and efficiency for the detection of Hg(2+) in HeLa cells.

  10. 8,8-Dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione

    Directory of Open Access Journals (Sweden)

    Thothadri Srinivasan


    Full Text Available In the title compound, C18H15NO3, the fused benzopyran and pyridine rings are essentially coplanar [r.m.s. deviation = 0.0533 Å with a maximum deviation of 0.080 (1 Å for a benzene C atom]. The cyclohexanone ring adopts an envelope conformation with the dimethyl-substituted C atom 0.660 (2 Å out of the plane formed by the remaining ring atoms (r.m.s. deviation = 0.0305 Å. The dihedral angle between the mean planes of the pyran and cyclohexanone rings is 12.95 (6°. In the crystal, molecules are linked via C—H...O hydrogen bonds, leading to chains running along [011].

  11. 2-Chloro-8,8-dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione

    Directory of Open Access Journals (Sweden)

    Thothadri Srinivasan


    Full Text Available The asymmetric unit of the title compound, C18H14ClNO3, contains two independent molecules (A and B. In both molecules, the cyclohexanone ring has a chair conformation. The dihedral angles between the pyran ring and the pyridine and chlorophenyl rings are 2.13 (9 and 2.19 (9°, respectively, in A, and 0.82 (9 and 1.93 (9°, respectively, in B. The carbonyl O atoms deviate from the pyran and benzene rings to which they are attached by −0.092 (2 and 0.064 (2 Å, respectively, in A, and by −0.080 (2 and −0.063 (2 Å, respectively, in B. In the crystal, the A molecules are linked via C—H...O hydrogen bonds, forming double-stranded chains along [100]. They lie parallel to the double-stranded chains formed by the B molecules, which are also linked via C—H...O hydrogen bonds. The chains stack up the c axis in an –A–A–B–B–A–A– manner, with a number of π–π interactions involving A and B molecules; the centroid–centroid distances vary from 3.4862 (11 to 3.6848 (11 Å


    Institute of Scientific and Technical Information of China (English)


    报道了8种新的苯并[h]喹啉的13C NMR谱.应用13C NMR等谱确定了这8种新化合物的分子结构,并对全部谱峰进行了归属,初步探讨了分子结构对13C NMR化学位移的影响.

  13. Tandem Reduction/Cyclization of O-Nitrophenyl Propargyl Alcohols-A Novel Synthesis of 2- & 2,4-Disubstituted Quinolines and Application to the Synthesis of Streptonigrin (United States)


    pathways: (1) cyclization by a distinctly different mechanism, propagated by the electonic nature of the pyridyl substituent, or (2) reductive...X-ray lab book No. 1575 Crystal ID DeShong/Sandelier MJS-I-85Y Empirical formula C7H6N2O6 Formula weight 214.14 Temperature...Soc. 2001, 123, 3239-3242. (22) Thayer, A. M. Chemical & Engineering News 2005, 83, 69-82. (23) Madrid, P. B.; Sherrill, J.; Liou, A

  14. Methyl 4-methyl-2-oxo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxylate

    Directory of Open Access Journals (Sweden)

    Yulia A. Zhuravleva


    Full Text Available In the title molecule, C14H15NO3, the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C—H...π interactions link the molecules into centrosymmetric dimers, and weak intermolecular C—H...O hydrogen bonds link these dimers into columns propagated along [100].

  15. Photo-physics study of an hydroxy-quinoline derivative as inhibitor of Pim-1 kinase: ultraviolet-visible linear dichroism spectroscopy and quantum chemical calculations. (United States)

    Lamhasni, T; Ait Lyazidi, S; Hnach, M; Haddad, M; Desmaële, D; Spanget-Larsen, J; Nguyen, D D; Ducasse, L


    The photophysical properties of the antiviral 7-nicotinoyl-styrylquinoline (MB96) were investigated by means of UV-Vis linear dichroism (LD) spectroscopy on molecular samples aligned in stretched polyvinylalcohol (PVA), supported by time dependent density functional theory (TD-DFT) calculations. Experimentally, the directions of the transitions moments with respect to the long axis of the molecule were deduced from the orientation K factors, determined by means of "trial-and-error" procedure. The absorption spectrum presents two parts. The main transition in the lowest energy part, observed around 365 nm and showing the highest K value 0.8, is longitudinally in-plane polarized. The highest energy part which is extended between 230 and 320 nm, large, diffuse, and of weak intensity, shows estimated K values between 0.2 and 0.5. This complex structure is transversally polarized with some contamination by the longitudinal character of the first strong band. The TD-DFT results agree fairly well with the LD measurements.

  16. Synthesis of quinoline attached-furan-2(3H-ones having anti-inflammatory and antibacterial properties with reduced gastro-intestinal toxicity and lipid peroxidation

    Directory of Open Access Journals (Sweden)

    Akhter Mymoona


    Full Text Available A series of 3-[2-chloroquinolin-3-ylmethylene]-5-aryl-furan-2(3H-ones {3(a-p} were synthesized. The required 3-(substitutedbenzoyl propionic acids {2(a-d} were prepared under Friedal Craft acylation reaction conditions. The substituted 2-chloroquinoline-3-carbaldehydes {1(a-d} were synthesized by reaction of substitutedphenylethanone-oxime with phosphorus oxychloride in presence of dimethyl formamide using the Vilsmeir Haack reaction method. These compounds were screened for their anti-inflammatory and antibacterial activities along with their ulcerogenic and lipid peroxidation potentials. The compounds that showed significant anti-inflammatory activity were further screened for their analgesic activity. The compounds were less toxic in terms of ulcerogenicity as compared to a standard, which was also supported by lipid peroxidation studies. The antibacterial activities were performed against Staphylococcus aureus and Escherichia coli. Compounds 3f, 3n and 3o showed significant activity against both S. aureus and E. coli having an MIC value of 6.25μg mL-1.

  17. Co-localization of brain-derived neurotrophic factor (BDNF) and wild-type huntingtin in normal and quinolinic acid-lesioned rat brain. (United States)

    Fusco, Francesca R; Zuccato, Chiara; Tartari, Marzia; Martorana, Alessandro; De March, Zena; Giampà, Carmela; Cattaneo, Elena; Bernardi, Giorgio


    Loss of huntingtin-mediated brain-derived neurotrophic factor (BDNF) gene transcription has been described in Huntington's disease (HD) [Zuccato et al. (2001) Science, 293, 493-498]. It has been shown that BDNF is synthesized in the pyramidal layer of cerebral cortex and released in the striatum [Altar et al. (1997) Nature, 389, 856-860; Conner et al. (1997) J. Neurosci., 17, 2295-2313]. Here we show the cellular localization of BDNF in huntingtin-containing neurons in normal rat brain; our double-label immunofluorescence study shows that huntingtin and BDNF are co-contained in approximately 99% of pyramidal neurons of motor cortex. In the striatum, huntingtin is expressed in 75% of neurons containing BDNF. In normal striatum we also show that BDNF is contained in cholinergic and in NOS-containing interneurons, which are relatively resistant to HD degeneration. Furthermore, we show a reduction in huntingtin and in BDNF immunoreactivity in cortical neurons after striatal excitotoxic lesion. Our data are confirmed by an ELISA study of BDNF and by a Western blot analysis of huntingtin in cortex of quinolic acid (QUIN)-lesioned hemispheres. In the lesioned striatum we describe that the striatal subpopulation of cholinergic neurons, surviving degeneration, contain BDNF. The finding that BDNF is contained in nearly all neurons that contain huntingtin in the normal cortex, along with the reduced expression of BDNF after QUIN injection of the striatum, shows that huntingtin may be required for BDNF production in cortex.

  18. Synthesis, Characterization, Antimicrobial, DNA Cleavage, and In Vitro Cytotoxic Studies of Some Metal Complexes of Schiff Base Ligand Derived from Thiazole and Quinoline Moiety

    Directory of Open Access Journals (Sweden)

    Nagesh Gunvanthrao Yernale


    Full Text Available A novel Schiff base ligand N-(4-phenylthiazol-2yl-2-((2-thiaxo-1,2-dihydroquinolin-3-ylmethylenehydrazinecarboxamide (L obtained by the condensation of N-(4-phenylthiazol-2-ylhydrazinecarboxamide with 2-thioxo-1,2-dihydroquinoline-3-carbaldehyde and its newly synthesized Cu(II, Co(II, Ni(II, and Zn(II complexes have been characterized by elemental analysis and various spectral studies like FT-IR, 1H NMR, ESI mass, UV-Visible, ESR, TGA/DTA, and powder X-ray diffraction studies. The Schiff base ligand (L behaves as tridentate ONS donor and forms the complexes of type [ML(Cl2] with square pyramidal geometry. The Schiff base ligand (L and its metal complexes have been screened in vitro for their antibacterial and antifungal activities by minimum inhibitory concentration (MIC method. The DNA cleavage activity of ligand and its metal complexes were studied using plasmid DNA pBR322 as a target molecule by gel electrophoresis method. The brine shrimp bioassay was also carried out to study the in vitro cytotoxicity properties for the ligand and its metal complexes against Artemia salina. The results showed that the biological activities of the ligand were found to be increased on complexation.

  19. 2-Ethyl-6-(2-pyridyl-5,6,6a,11b-tetrahydro-7H-indeno[2,1-c]quinoline

    Directory of Open Access Journals (Sweden)

    Alexander Briceño


    Full Text Available The title compound, C23H22N2, was obtained using the three-component imino Diels–Alder reaction via a one-pot condensation between anilines, α-pyridinecarboxyaldehyde and indene using BF3·OEt2 as the catalyst. The molecular structure reveals the cis-form as the unique diastereoisomer. The crystal structure comprises one-dimensional zigzag ribbons connected via N—H...N hydrogen bonds. C—H...π interactions also occur.

  20. 提高沥青中喹啉不溶物含量的研究%Research on increasing quinoline insolubles content in pitch

    Institute of Scientific and Technical Information of China (English)

    章真杰; 李峻海; 杜亚平; 刘建中


    As the QI content in coal tar and pitch of Meishan branch appears lower than normal,this paper introduced a solution that a blended oil and/ or the coal tar with high QI content bought from outside the company are used to increase the QI content in the pitch. This blended oil can be used to produce medium-temperature pitch and modified pitch so that the ratio of first - grade products can be increased due to the improved QI content.%针对煤焦油和沥青中 QI 含量较低的情况,将来自针状焦项目的 QI 残渣与原料焦油按一定比例混合,配制成调制油,采用这种调制油生产中温沥青和改质沥青,提高了产品的 QI,显著提高了产品的一级品率。

  1. 3-Ethyl-3-hy-droxy-8-meth-oxy-quinoline-2,4(1H,3H)-dione monohydrate. (United States)

    Kafka, Stanislav; Pevec, Andrej; Proisl, Karel; Kimmel, Roman; Košmrlj, Janez


    In the title hydrate, C(12)H(13)NO(4)·H(2)O, the piperidine ring that is fused to the benzene ring is in a sofa conformation with the chiral C atom lying 0.4084 (18) Å out of the plane of the nine fused-ring atoms. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the organic mol-ecules and water mol-ecules into chains running along the b-axis direction. The chains are further connected into layers parallel to the bc plane by π-π inter-actions between inversion-related benzene rings [centroid-centroid distance = 3.8846 (9) Å].

  2. Geometrical and optical benchmarking of copper(II) guanidine-quinoline complexes: insights from TD-DFT and many-body perturbation theory (part II). (United States)

    Hoffmann, Alexander; Rohrmüller, Martin; Jesser, Anton; dos Santos Vieira, Ines; Schmidt, Wolf Gero; Herres-Pawlis, Sonja


    Ground- and excited-state properties of copper(II) charge-transfer systems have been investigated starting from density-functional calculations with particular emphasis on the role of (i) the exchange and correlation functional, (ii) the basis set, (iii) solvent effects, and (iv) the treatment of dispersive interactions. Furthermore (v), the applicability of TD-DFT to excitations of copper(II) bis(chelate) charge-transfer systems is explored by performing many-body perturbation theory (GW + BSE), independent-particle approximation and ΔSCF calculations for a small model system that contains simple guanidine and imine groups. These results show that DFT and TD-DFT in particular in combination with hybrid functionals are well suited for the description of the structural and optical properties, respectively, of copper(II) bis(chelate) complexes. Furthermore, it is found an accurate theoretical geometrical description requires the use of dispersion correction with Becke-Johnson damping and triple-zeta basis sets while solvent effects are small. The hybrid functionals B3LYP and TPSSh yielded best performance. The optical description is best with B3LYP, whereby heavily mixed molecular transitions of MLCT and LLCT character are obtained which can be more easily understood using natural transition orbitals. An natural bond orbital analysis sheds light on the donor properties of the different donor functions and the intraguanidine stabilization during coordination to copper(I) and (II).

  3. Antimicrobial Activity and Spectral, Magnetic and Thermal Studies of Some Transition Metal Complexes of a Schiff Base Hydrazone Containing a Quinoline Moiety

    Directory of Open Access Journals (Sweden)

    Nora H Al-Sha’alan


    Full Text Available A series of new copper(II, cobalt(II, nickel(II, manganese(II, iron(III, and uranyl(VI complexes of the Schiff base hydrazone 7-chloro-4-(benzylidene-hydrazoquinoline (HL were prepared and characterized. The Schiff base behaves as a monobasic bidentate ligand. Mononuclear complexes with the general composition [ML2(Clm(H2O2(OEtn]·xEtOH (M = Cu(II, Co(II, Ni(II, Mn(II, Fe(III or UO2(VI; m and n = 0-1; x = 1-3 were obtained in the presence of Li(OH as a deprotonating agent. The nature of bonding and the stereochemistry of the complexes have been deduced from elemental analyses, infrared, electronic spectra, magnetic susceptibility and conductivity measurements. An octahedral geometry was suggested for all the complexes except the Cu(II and UO2(VI ones. The Cu(II complex has a square-planar geometry distorted towards tetrahedral, while the UO2(VI complex displays its favored heptacoordination. The Schiff base ligand, HL, and its complexes were tested against one strain Gram +ve bacteria (Staphylococcus aureus, Gram -ve bacteria (Escherichia coli, and Fungi (Candida albicans. The prepared metal complexes exhibited higher antibacterial activities than the parent ligand and their biopotency is discussed.

  4. 1 H-pyrazolo[3,4- b]quinoline and 1 H-pyrazolo[3,4- b]quinoxaline derivatives as promising materials for optoelectronic applications (United States)

    Danel, Andrzej; Gondek, Ewa; Kityk, Iwan


    A review of recent studies of pyrazoloquinoline and quinoxaline derivative chromophore used as organic light emitting diodes and photovoltaic elements is done. We present both the principal ways of modifications of these materials as well as a possible chemical modifications to achieve more suitable technological parameters.

  5. Tetra­kis(5,7-dimethyl­quinolin-8-olato-κ2 N,O)zirconium(IV) dimethyl­form­amide disolvate


    Steyn, Maryke; Visser, Hendrik G.; Roodt, Andreas


    In the title compound, [Zr(C11H10NO)4]·2C3H7NO, the ZrIV ion is coordinated by four bidentate 5,7-dimethylquinolin-8-olate ligands in a slightly distorted square-anti­prismatic coordination environment. The asymmetric unit also contains two N,N′-dimethyl­formamide (DMF) solvent mol­ecules. In the crystal, a weak C—H⋯O hydrogen bond links the complex mol­ecule to a solvent mol­ecule and weak π–π stacking inter­actions [centroid–centroid distance = 3.671 (3) Å] also occur. One of the DMF solven...

  6. Tetra-kis(5,7-dimethyl-quinolin-8-olato-κ(2)N,O)zirconium(IV) dimethyl-form-amide disolvate. (United States)

    Steyn, Maryke; Visser, Hendrik G; Roodt, Andreas


    In the title compound, [Zr(C(11)H(10)NO)(4)]·2C(3)H(7)NO, the Zr(IV) ion is coordinated by four bidentate 5,7-dimethylquinolin-8-olate ligands in a slightly distorted square-anti-prismatic coordination environment. The asymmetric unit also contains two N,N'-dimethyl-formamide (DMF) solvent mol-ecules. In the crystal, a weak C-H⋯O hydrogen bond links the complex mol-ecule to a solvent mol-ecule and weak π-π stacking inter-actions [centroid-centroid distance = 3.671 (3) Å] also occur. One of the DMF solvent mol-ecules was refined as disordered over three sets of sites, with refined occupancies in the ratio of 0.391 (9):0.342 (10):0.267 (7).

  7. 一株喹啉降解菌的分离与鉴定%Isolation and Identification of a Strain for Quinoline Degradation

    Institute of Scientific and Technical Information of China (English)

    张秀霞; 王基成; 吴伟林; 房苗苗; 鲁军


    为了研究石油污染土壤中含氮杂环化合物的降解情况,本文采用选择性富集培养的方法.以喹啉作为目标污染物,从45份石油污染土壤样品中,分离得到155株降解喹啉污染物的高效降解菌株,其中降解效率最高的-株喹啉降解菌命名为Q5,在72h内对于浓度为500 mg·L-1喹啉的降解率达到72.6%.并通过形态学、生理生化试验和16S rDNA序列比对分析对Q5进行了鉴定.结果表明,株菌Q5为革兰氏阳性菌,在LB平板上菌落呈圆形,边缘整齐,乳白色,表面光滑,有黏稠感,是发酵乳酸杆菌(Lactobacillus),属酵母菌,与Lactobacillus fermentam同源性最高,为99.6%.

  8. Chloro({2-[mesityl(quinolin-8-yl-κNboryl]-3,5-dimethyl-phenyl}methyl-κCpalladium(II as a Catalyst for Heck Reactions

    Directory of Open Access Journals (Sweden)

    Sem Raj Tamang


    Full Text Available We recently reported an air and moisture stable 16-electron borapalladacycle formed upon combination of 8-quinolyldimesitylborane with bis(benzonitriledichloropalladium(II. The complex features a tucked mesityl group formed upon metalation of an ortho-methyl group on a mesityl; however it is unusually stable due to contribution of the boron pz orbital in delocalizing the carbanion that gives rise to an η4-boratabutadiene fragment coordinated to Pd(II, as evidenced from crystallographic data. This complex was observed to be a highly active catalyst for the Heck reaction. Data of the catalyst activity are presented alongside data found in the literature, and initial comparison reveals that the borapalladacycle is quite active. The observed catalysis suggests the borapalladacycle readily undergoes reductive elimination; however the Pd(0 complex has not yet been isolated. Nevertheless, the ambiphilic ligand 8-quinolyldimesitylborane may be able to support palladium in different redox states.

  9. CCDC 1419409: Experimental Crystal Structure Determination : (benzo[h]quinolin-10-ylmethylene)-dichloro-(1,3-bis(2-methylphenyl)imidazolidin-2-ylidene)-ruthenium

    KAUST Repository

    Pump, Eva


    An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

  10. Catalytic behaviors of molybdenum carbide catalyst for quinoline hydrodenitrogenation(HDN)%碳化钼催化剂的喹啉加氢脱氮反应性能

    Institute of Scientific and Technical Information of China (English)

    罗运强; 靳广洲


    用程序升温还原法在CH4/H2气氛中将MoO3碳化制备了Mo2C催化剂, 并对Mo2C催化剂进行了XRD和BET表征.以喹啉/环己烷溶液为模型化合物, 通过高压微反评价实验考察了Mo2C催化剂的喹啉加氢脱氮活性.结果表明, MoO3在CH4/H2气氛中程序升温至终点温度675 ℃,并在此终点温度下还原碳化150 min,可制得高纯度的β-Mo2C.当还原碳化温度高于675 ℃,随着还原碳化温度的升高,Mo2C催化剂的比表面积降低, 表面积炭增多, 导致喹啉加氢脱氮活性下降.而当还原碳化时间少于150 min时,MoO3未能充分转化为Mo2C,导致喹啉加氢脱氮活性较低.因此,较适宜的Mo2C催化剂的合成条件为:还原碳化温度675 ℃,还原碳化时间150 min.在反应压力3.0 MPa、空速8 h-1、H2与原料液体积比500∶ 1以及氮含量为1 000 ng·μL-1的喹啉/环己烷溶液中, Mo2C催化剂的喹啉加氢脱氮活性明显高于MoS2和MoO3催化剂.Mo2C催化剂在反应温度360 ℃的喹啉加氢脱氮转化率达到58.69%,表现出较高的喹啉加氢脱氮活性.

  11. Multicomponent Self-assembly:Spontaneous Formation of a Metallomacrocycle from Two Quinoline Based Linear Ligands and Four Silver(Ⅰ) Nitrates

    Institute of Scientific and Technical Information of China (English)


    @@ Using metal ions to control the self-assembly of metallosupramolecules of varying architecture is one of the fascinating developments in supramolecular chemistry[1,2],particularly those concerned with the deliberate construction of molecular aggregates,like helices,rotaxanes,catenanes,knots,cages[3~6] and the crystal engineering of two or three dimensional networks with varied topology and interpenetration[7~10].Coordination bonds have proved themselves to be one of the most useful connectors in supramolecular self-assembly due to their versatile geometrical modes(e.g.linear,trigonal,square plane,tetrahedral,octahedral) in bond formations.By careful design of tailored ligands,various novel supramolecular architectures have been constructed.Recently,angular bi- or tridentate and other polydentate ligands have aroused a special interest,and a variety of molecular squares,boxes and cages[1~14] with internal cavity or void have been reported,in which many nanoscale structures are formed[6,15,16].We have been interested in the construction of metal based supramolecular structures with polydentate ligands[17~20] and herein report a new metallomacrocyclic complex assembled from two linear polydentate ligands and silver(Ⅰ) nitrate.

  12. Anti-HIV cytotoxicity enzyme inhibition and molecular docking studies of quinoline based chalcones as potential non-nucleoside reverse transcriptase inhibitors (NNRT). (United States)

    Hameed, Asima; Abdullah, Muhammad Imran; Ahmed, Ejaz; Sharif, Ahsan; Irfan, Ahmad; Masood, Sara


    A series of fourteen (A1 - A14) qunioline based chalcones were screened for reverse transcriptase inhibitors (RT) and found potentially active against RT. Bioassay, theoretical and dockings studies with RT (the enzyme required for reverse transcription of viral RNA) results showed that the type and positions of the substituents seemed to be critical for their inhibition against RT. The bromo and chloro substituted chalcone displayed high degree of inhibition against RT. The A4 andA6 showed high interaction with RT, contributing high free binding energy (ΔG -9.30 and -9.13kcal) and RT inhibition value (IC50 0.10μg/ml and 0.11μg/ml).

  13. 喹啉类杂环化合物的设计与合成研究%Design and synthesis of quinoline heterocyclic compounds

    Institute of Scientific and Technical Information of China (English)



    Vilsmeier’s intermediate were introduced to the 2-chloro-3-formylquinoline and synthesize with aromatic amines. Some new compounds have synthesized and fully characterized by1HNMR and IR spectral data.%通过Vilsmeier反应合成了2-氯-3-甲酰基喹啉中间体,利用该化合物设计合成了一系列新的多杂原子稠环化合物,并通过核磁氢谱、红外光谱、元素分析对它们进行了结构表征。

  14. An expeditious I sub(2)-catalyzed entry into 6H-indolo[2,3-b]quinoline system of cryptotackieine

    Digital Repository Service at National Institute of Oceanography (India)

    Parvatkar, P.T.; Parameswaran, P.S.; Tilve, S.G.

    .; Haemers, A.; Dommisse, R. A. Synlett 2003, 615-618. (14) Shi, C.; Zhang, Q.; Wang, K. K. J. Org. Chem.. 1999, 64, 925-932. (15) Molina, P.; Fresneda, P. M.; Delgado, S. Synthesis 1999, 326-329. (16) Alajarin, M.; Molina, P.; Vidal, A. J...

  15. 4,4'-喹啉酸锌(Ⅱ)配位聚合物%Zinc(Ⅱ) Coordination Polymer with 4,4'-quinoline Ligand

    Institute of Scientific and Technical Information of China (English)



    Hydrothermal treatment of racemic atropisomeric ligand diethyl (R,S)-7,7'-dimethyl-4,4'-biquinoline-3,3'-dicarboxylate (DDBD) in the presence of pyridine over 4 days at 140 ℃ with Zn(OAc)2 offers zinc coordination polymer [{Zn(DBD)(pyridine)2(H2O)}n{Zn(DBD)(H2O)1/2}]n (1), which shows weak fluorescence at about 490 nm at solid state at room temperature. CCDC: 631007.

  16. Studies on the de novo biosynthesis of NAD in Escherichia coli. The separation of the nadB gene product from the nadA gene product and its purification. (United States)

    Griffith, G R; Chandler, J L; Gholson, R K


    Quinolinic acid (pyridine 2,3-dicarboxylic acid) which is an immediate precursor of the pyridine nucleotides, is synthesised from L-asparate and dihydroxyacetone phosphate in Escherichia coli. Extracts from certain nadB mutants complement the extracts prepared from all nadA mutants for the enzymic synthesis of quinolinate. Using the complementation assay, the quinolinate synthetase B protein has been purified more than 300-fold. The quinolinate synthetase B protein exists in all nadA and nadC mutants examined. The quinolinate synthetase A protein was present in all nadC mutants and most (but not all) nadB mutants. The facile separation of the wild-type quinolinate synthetase A and B proteins out of a nadC mutant suggests that quinolinate synthetase does not exists as a tightly bound complex. The partially purified quinolinate synthetase is inhibited by physiological concetrations of NAD and NADH but not by NADP or NADPH.

  17. Drug: D00471 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available UCTS, INSECTICIDES AND REPELLENTS P02 ANTHELMINTICS P02B ANTITREMATODALS P02BA Quinoline derivatives and related substances...nfectives [BR:br08307] Antiparasitics Antitrematodal agents Quinoline derivatives and related substances Pra

  18. Bis(μ-2-methyl­quinolin-1-ium-8-olato-κ2 O:O′)bis­[(2-methyl­quinolin-1-ium-8-olato-κO)tris­(nitrato-κ2 O,O′)lanthanum(III)


    Fazaeli, Yousef; Najafi, Ezzatollah; Mostafa M. Amini; Ng, Seik Weng


    The two independent N-heterocycles in the centrosymmetric title compound, [La2(C10H9NO)4(NO3)6], exist in the zwitterionic form. One of these binds to one metal center, whereas the other bridges two metal centers. The La atom is chelated by three nitrate groups and is surrounded by nine O atoms in a coordination environment based on a distorted monocapped square-anti­prism. The dinuclear structure is further stabilized by intra­molecular N—H⋯O(nitrate) hydrogen bonds.

  19. Synthesis and Crystal Structure of 3,7,7-Trimethyl-1-phenyl-4-(3-nitrophenyl)-4,5,6,7,8,9-hexahydro-1H-pyrazolo[3,4-b]quinoline-5(6H)-one

    Institute of Scientific and Technical Information of China (English)

    徐佳宁; 屠树江; 蒋虹; 张金鹏; 朱晓彤; 王倩


    The title compound (C25H24N4O3) has been prepared by the cyclocondensation of 5-amino-3-methyl-1-phenypyrazol, m-nitrobenaldehyde and dimedone in glycol under microwave irradiation without catalyst. The crystal structure was determined by single-crystal X-ray diffraction to be orthorhombic, space group Pbca with a = 16.3331(10), b = 13.8329(9), c = 19.4163(12) (A), V= 4386.8(5) (A)3, Z = 8, Dc = 1.298 g/cm3,μ = 0.087 mm-1, F(000) = 1808, Mr = 428.48, the final R =0.0519 and wR = 0.1019. X-ray analysis revealed that the pyridine ring is of boat conformation and the six-membered ring fused with it adopts twist boat conformation.

  20. (9E)-9-benzylidene-2-methylsulfanyl-5-phenyl-6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-4(3H)-one: a hydrogen-bonded R2(2)(8) dimer. (United States)

    Becerra, Diana; Insuasty, Braulio; Cobo, Justo; Glidewell, Christopher


    In the molecule of the title compound, C25H21N3OS, which was prepared by mild oxidation of the corresponding 5,6,7,8,9,10-hexahydro analogue, the fused carbocyclic ring adopts an envelope conformation. Pairs of molecules are linked into cyclic centrosymmetric dimers by pairs of inversion-related N-H···O hydrogen bonds.

  1. 含氟喹啉酰胺类化合物的合成及杀菌活性%Synthesis and Fungicidal Activity of a Series of Fluorinated Quinoline Amide Compounds

    Institute of Scientific and Technical Information of China (English)

    倪芸; 许天明; 钟良坤; 孔晓燕; 史建俊; 刘幸海; 孔小林; 姬文娟; 谭成侠


    为寻求具有较高生物活性的农药先导化合物,笔者采用活性亚结构拼接方法设计合成一类含氟喹啉酰胺类化合物.以5-氯靛红与2,6-二氟苯乙酮为起始原料,经过环合、酰化等多步反应,得到13个未见文献报道的含氟喹啉酰胺类化合物.其结构均经1H NMR和HRMS确证.初步生物活性测定结果表明,在50 mg/L质量浓度下,目标化合物对小麦全蚀病(Gaeumannomyces graminis)、小麦赤霉病(Fusahum graminearum sehw)、小麦纹枯病(Rhizoctonia cerealis)、水稻稻瘟病(Pyricularia grisea)均具有杀菌活性.而部分化合物对小麦全蚀病(Gaeumannomyces graminis)的杀菌活性达到90%以上.

  2. An interplay between infrared multiphoton dissociation Fourier-transform ion cyclotron resonance mass spectrometry and density functional theory computations in the characterization of a tripodal quinolin-8-olate Gd(III) complex. (United States)

    De Bonis, Margherita; Bianco, Giuliana; Amati, Mario; Belviso, Sandra; Cataldi, Tommaso R I; Lelj, Francesco


    A new hexadentate, tripodal 8-hydroxyquinoline based ligand (QH3) and its gadolinium(III) tris-chelated (GdQ) complex with hemicage structure was investigated by using high resolution Fourier-transform ion cyclotron resonance mass spectrometry (FTICRMS). The protonated adduct of the free ligand and its hemicage tripodal Gd(III) complex, [GdQ + H](+), were first observed in experiments of electrospray ionization (ESI) with a linear ion trap (LTQ) mass spectrometer and further investigated by using high resolution FTICRMS. Gas-phase dissociation of the protonated Gd(III) complex, by infrared multiphoton dissociation (IRMPD) FTICR MS, demonstrated a fragmentation pattern with six main product cluster ions labeled as [Fn](+) (n = 1 up to 6). These product ions suggest the elimination of 7-amino-alkyl or 7-alkyl chains of the hemicage moiety. High resolution MS conditions allowed the elucidation of the fragmentation pattern and product ion structures along with the determination, among the isotopic pattern of Gd, of the chemical compositions of closely related species, which differ in terms of hydrogen content. Among the Gd six naturally stable isotopes, (158)Gd is the most abundant, and its peak within each cluster was used as a reference for distinguishing each product ions. Computational DFT investigations were applied to give support to some hypothesis of fragmentation pathways, which could not have been easily justified on the basis of the experimental work. Furthermore, computational studies suggested the coordination geometry of the protonated parent complex and the five- and four-coordinated complexes, which derive from its fragmentation. Furthermore, experimental and computational evidences were collected about the octet spin state of the parent compound.

  3. catena-Poly[[lead(II-bis(μ2-quinolin-8-olato-κ3N,O:O;κ3O:N,O] N,N-dimethylformamide hemisolvate

    Directory of Open Access Journals (Sweden)

    Akbar Ghaemi


    Full Text Available The asymmetric unit of the title compound, {[Pb(C9H6NO2]·0.5C3H7NO}n, comprises Pb(quinolate2 and half a dimethylformamide molecule (which is disordered about a centre of inversion. The quinolate ligands N,O-chelate to a PbII ion and simultaneously bridge a neighbouring PbII ion to form a polymeric chain along [100] comprising Pb-linked Pb2O2 distorted rhombi. These chains pack to form a square grid, with the channels thus defined occupied by the disordered solvent molecules.

  4. Combining structure-based pharmacophore modeling, virtual screening, and in silico ADMET analysis to discover novel tetrahydro-quinoline based pyruvate kinase isozyme M2 activators with antitumor activity

    Directory of Open Access Journals (Sweden)

    Chen C


    Full Text Available Can Chen,1,2,* Ting Wang,1,3,* Fengbo Wu,1,* Wei Huang,4 Gu He,1 Liang Ouyang,1 Mingli Xiang,1 Cheng Peng,4 Qinglin Jiang1,2 1State Key Laboratory of Biotherapy and Department of Pharmacy, West China Hospital, Sichuan University, Chengdu, 2College of Pharmacy and the First Affiliated Hospital, Chengdu Medical College, Chengdu, 3Department of Cardiology, Genenal Hospital of Chengdu Military Command, Chengdu, 4State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine, Chengdu University of Traditional Chinese Medicine, Chengdu, People’s Republic of China*These authors contributed equally to this workAbstract: Compared with normal differentiated cells, cancer cells upregulate the expression of pyruvate kinase isozyme M2 (PKM2 to support glycolytic intermediates for anabolic processes, including the synthesis of nucleic acids, amino acids, and lipids. In this study, a combination of the structure-based pharmacophore modeling and a hybrid protocol of virtual screening methods comprised of pharmacophore model-based virtual screening, docking-based virtual screening, and in silico ADMET (absorption, distribution, metabolism, excretion and toxicity analysis were used to retrieve novel PKM2 activators from commercially available chemical databases. Tetrahydroquinoline derivatives were identified as potential scaffolds of PKM2 activators. Thus, the hybrid virtual screening approach was applied to screen the focused tetrahydroquinoline derivatives embedded in the ZINC database. Six hit compounds were selected from the final hits and experimental studies were then performed. Compound 8 displayed a potent inhibitory effect on human lung cancer cells. Following treatment with Compound 8, cell viability, apoptosis, and reactive oxygen species (ROS production were examined in A549 cells. Finally, we evaluated the effects of Compound 8 on mice xenograft tumor models in vivo. These results may provide important information for further research on novel PKM2 activators as antitumor agents.Keywords: pharmacophore, molecular docking, pyruvate kinase, virtual screening

  5. 3-Benzyl-7-bromo-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo[3,4-b]quinoline

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun


    Full Text Available In the title compound, C31H29BrN2O2S, the pyrrolidine ring is in a twist conformation and the tetrahydropyridine ring adopts an envelope conformation with the methine C atom adjacent to the NH group as the flap atom; the two rings are trans-fused. The bromobenzene ring and the nearest phenyl ring form a dihedral angle of 82.72 (10°. The benzyl phenyl and the tosyl phenyl rings are oriented at a dihedral angle of 75.57 (11°. An intramolecular N—H...π interaction is observed. In the crystal, molecules are linked into chains running along [101] by C—H...O hydrogen bonds and the chains are cross-linked via weak C—H...π interactions.

  6. 9-(1H-Benzo[d]imidazol-2-yl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline

    Directory of Open Access Journals (Sweden)

    Gerardo García González


    Full Text Available The title compound, C19H19N3, is a 2-heteroaryl benzimidazole derivative obtained through a straightforward and efficient protocol starting from julolidine-9-carbaldehyde and 1,2-phenylendiamine. The mean planes of the heterocyclic moieties in the molecule, benzimidazole and julolidine, form a dihedral angle of 40.9 (1°. In the crystal, N—H...N hydrogen bonds link the imidazole rings, forming chains along the c-axis direction.

  7. A kryptoracemic salt: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium (+)-3,3,3-tri-fluoro-2-meth-oxy-2-phenyl-propanoate. (United States)

    Wardell, James L; Wardell, Solange M S V; Tiekink, Edward R T


    The asymmetric unit of the title salt, C17H17F6N2O(+)·C10H8F3O3 (-), comprises two piperidin-1-ium cations and two carboxyl-ate anions. The cations, each having an l-shaped conformation owing to the near orthogonal relationship between the quinolinyl and piperidin-1-ium residues, are pseudo-enanti-omeric. The anions have the same absolute configuration but differ in the relative orientations of the carboxyl-ate, meth-oxy and benzene groups. Arguably, the most prominent difference between the anions occurs about the Cq-Om bond as seen in the Cc-Cq-Om-Cm torsion angles of -176.1 (3) and -67.1 (4)°, respectively (q = quaternary, m = meth-oxy and c = carboxyl-ate). The presence of Oh-H⋯Oc and Np-H⋯Oc hydrogen bonds leads to the formation of a supra-molecular chain along the a axis (h = hy-droxy and p = piperidin-1-ium); weak intra-molecular Np-H⋯Oh hydrogen bonds are also noted. Chains are connected into a three-dimensional architecture by C-H⋯F inter-actions. Based on a literature survey, related mol-ecules/cations adopt a uniform conformation in the solid state based on the letter L.

  8. Theory study on biradical systems with quinoline as coupling unit%以喹啉为耦合单元双自由基体系的理论研究

    Institute of Scientific and Technical Information of China (English)

    王立敏; 储德清; 张景萍; 王荣顺



  9. 3-Benzyl-7-chloro-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo[3,4-b]quinoline

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun


    Full Text Available In the title compound, C31H29ClN2O2S, the pyrrolidine ring adopts an envelope conformation with the methine C atom adjacent to the NH group as the flap atom. The tetrahydropyridine ring has a half-chair conformation. The two rings are trans-fused. The chlorobenzene ring and the adjacent phenyl ring form a dihedral angle of 77.9 (1°. The benzyl phenyl and the tosyl phenyl rings are oriented at a dihedral angle of 88.0 (1°. In the crystal, molecules are linked into chains along the a axis by N—H...Cl and C—H...Cl hydrogen bonds and the adjacent chains are cross-linked via C—H...π interactions.

  10. Photovoltaic effect in single layer 1H-pyrazolo[3,4-b]quinoline and 1H-pyrazolo[3,4-b]quioxaline/poly(3-decylthiophene) polymer cells

    Energy Technology Data Exchange (ETDEWEB)

    Gondek, Ewa [Inst. of Physics, Technical Univ. of Cracow (Poland); Kityk, Ivan V. [Electrical Engineering Dept., Technological Univ. of Czestochowa (Poland); Danel, Andrzej [Dept. of Chemistry, Agricultural Univ. of Krakow (Poland)


    We have explored photovoltaic (PV) reponse for the pyrazoloquinoline and pyrazoloquinoxaline dyes incorporated into the poly(3-decylthiophene) (PDT) polymer matrices. The photovoltaic response correlates generally with the enhancement of the state dipole moments. Generally we have shown that enhanced state dipole moments lead to an increase of the open circuit voltage. The surrounded polymer matrix of the polythiophene enhances the ground state dipole moments and its relative changes are decreased with the increase of the particular state dipole moments. An appearance of the three-phenyl backside groups substantially diminishes the effect. (orig.)

  11. 8,8-Dimethyl-5-(4-methylphenyl-8,9-dihydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H-trione N,N-dimethylformamide solvate

    Directory of Open Access Journals (Sweden)

    Daqing Shi


    Full Text Available The title compound, C20H19N3O3·C3H7NO, was synthesized by the reaction of 6-aminopyrimidine-2,4(1H,3H-dione and 4-methylbenzaldehyde with 5,5-dimethyl-1,3-cyclohexanedione in 1-butyl-3-methylimidazolium bromide at 363 K. The pyrimidine ring adopts a half-chair conformation while the six-membered ring fused to the pyridine ring adopts a skew-boat conformation. The dihedral angle between the pyridine ring and the attached benzene ring is 2.38(8°

  12. The Identification and Pharmacological Characterization of 6-(tert-Butylsulfonyl)-N-(5-fluoro-1H-indazol-3-yl)quinolin-4-amine (GSK583), a Highly Potent and Selective Inhibitor of RIP2 Kinase. (United States)

    Haile, Pamela A; Votta, Bartholomew J; Marquis, Robert W; Bury, Michael J; Mehlmann, John F; Singhaus, Robert; Charnley, Adam K; Lakdawala, Ami S; Convery, Máire A; Lipshutz, David B; Desai, Biva M; Swift, Barbara; Capriotti, Carol A; Berger, Scott B; Mahajan, Mukesh K; Reilly, Michael A; Rivera, Elizabeth J; Sun, Helen H; Nagilla, Rakesh; Beal, Allison M; Finger, Joshua N; Cook, Michael N; King, Bryan W; Ouellette, Michael T; Totoritis, Rachel D; Pierdomenico, Maria; Negroni, Anna; Stronati, Laura; Cucchiara, Salvatore; Ziółkowski, Bartłomiej; Vossenkämper, Anna; MacDonald, Thomas T; Gough, Peter J; Bertin, John; Casillas, Linda N


    RIP2 kinase is a central component of the innate immune system and enables downstream signaling following activation of the pattern recognition receptors NOD1 and NOD2, leading to the production of inflammatory cytokines. Recently, several inhibitors of RIP2 kinase have been disclosed that have contributed to the fundamental understanding of the role of RIP2 in this pathway. However, because they lack either broad kinase selectivity or strong affinity for RIP2, these tools have only limited utility to assess the role of RIP2 in complex environments. We present, herein, the discovery and pharmacological characterization of GSK583, a next-generation RIP2 inhibitor possessing exquisite selectivity and potency. Having demonstrated the pharmacological precision of this tool compound, we report its use in elucidating the role of RIP2 kinase in a variety of in vitro, in vivo, and ex vivo experiments, further clarifying our understanding of the role of RIP2 in NOD1 and NOD2 mediated disease pathogenesis.

  13. Methyl 7,8-diacetoxy-11-oxo-5-(2-oxopyrrolidin-1-yl-7,9-epoxycyclopenta[4,5]pyrido[1,2-a]quinoline-10-carboxylate sesquihydrate

    Directory of Open Access Journals (Sweden)

    Atash V. Gurbanov


    Full Text Available The title compound, C26H28N2O9·1.5H2O, the product of an acid-catalysed Wagner–Meerwein skeletal rearrangement, crystallizes as a sesquihydrate with the O atom of one of the two independent water molecules occupying a special position on a twofold axis. The organic molecule comprises a fused pentacyclic system containing two five-membered rings (cyclopentane and tetrahydrofuran and three six-membered rings (piperidinone, tetrahydropyridine and benzene. The five-membered rings have the usual envelope conformations, and the central six-membered piperidinone and tetrahydropyridine rings adopt boat and sofa conformations, respectively. In the crystal, there are three independent O—H...O hydrogen bonds, which link the organic molecules and water molecules into complex two-tier layers parallel to (001. The layers are further linked into a three-dimensional framework by attractive intermolecular carbonyl–carbonyl interactions.

  14. A novel four-component route to synthesis 11-amino-12-(4-aryl-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ol derivatives

    Directory of Open Access Journals (Sweden)

    Saman Damavandi


    Full Text Available A series of chromeno[2,3-b]quinolinol derivatives were synthesized through one-pot four-component reaction of resorcinol, malononitrile, aromatic aldehydes and cyclohexanone using iron(III triflate Fe(OTf3, under solvent-free and ultrasonic irradiation conditions. The products were afforded in good to excellent yields. The advantages of this method are the use of an inexpensive and readily available catalyst, short reaction time, easy workup and improved yields.

  15. Spectroscopic and structural studies of quinoline derivatives—II. Forrier transform i.r. spectroscopy. 1. Rotational isomerism in 3-ethoxycarbonyl-4(1H)-quinolone and some of its substituted derivatives, (United States)

    Mirek, Julian; Urbanek, Zbigniew H.

    Rotational isomerism associated with internal rotation about the ring carbon(3)-ester carbonyl carbon single bond in a series of 3-ethoxycarbonyl-4(1H)-quinolones have been investigated spectroscopically in the solid state using Fourier transform i.r. and laser Raman spectroscopy. Particular attention is given to the 1700, 1300 and 1100 cm -1 spectral regions related primarily to the vibrations of the CO 2C 2H 5 group. Within these regions rotational isomerism appeared in the compounds examined. The conformational changes are discussed and evidence is reported for occurrence of the unsubstituted compound 1 itself in the solid state at ambient temperature as an equilibrium mixture of both the s-trans ( 1a) and s-cis ( 1b) rotamers (this is in contrast to previous findings), and of its Bz-substituted derivatives.

  16. 吲哚并[3,2-c]喹啉衍生物的微波辅助合成%Microwave irradiation assisted synthesis of indolo [3,2-c] quinoline derivatives

    Institute of Scientific and Technical Information of China (English)

    张稳稳; 周忠华; 曾红; 何菱


    目的 合成吲哚并[3,2-c]喹啉衍生物并优化其工艺.方法 微波辅助Michael加成、环合、Fischer吲哚合成.结果 合成了6个吲哚并[3,2-c]喹啉衍生物.结论 微波能缩短反应时间,提高Michael加成和Fischer吲哚合成反应的收率.

  17. 化妆品中喹诺酮类和异喹啉类抗生素的高效液相色谱测定法%Determination of Ouinolones and ISO Quinolines of Antibiotics in Cosmetics by HPLC

    Institute of Scientific and Technical Information of China (English)

    杨艳伟; 朱会卷; 朱英; 张卫强


    Objective To establish a method for simultaneous determination of 10 kinds of antibiotics in cosmetic by high performance liquid chromatography. Methods Ten kinds of antibiotics were separated on a CB column using acetonitrile-0.05 mol/L ammonium dihydrogen phosphate solution as mobile phase at a flow rate of 1.2 ml/min,with the column temperature 25℃ and detection wave 280 nm. Results There was a good linear relationships between the concentration of antibiotics and peak area in the rang of 2-100 mg/L. The limits of detection were 0.05-0.1 mg/L. The RSDs were less than 3.80% and the rates of recovery were 90.5%-104.8%. Conclusion This method is simple,fast ccurate and is applicable to simultaneous determination of 10 kinds of antibiotics in cosmetics.%目的 建立同时测定化妆品中10种抗生素的高效液相色谱(HPLC)法.方法 在C18(4.6 mm×250mm,5 μm)色谱柱上,以乙腈-0.05 mol/L磷酸二氢铵溶液为流动相进行梯度洗脱,流量为1.2 ml/min,检测波长为280 nm,柱温为25℃下进行HPLC检验.结果 在2~100 mg/L的线性范围内,所得10种抗生素的回归方程均呈较好的线性关系,r≥0.999 5.该方法的检出限为0.05~0.1 mg/L,RSD<3.80%,平均回收率为90.5%~104.8%.结论 该方法操作简便快速,灵敏度高,适用于化妆品中10种抗生素的同时测定.

  18. 使用喹诺酮类抗生素人畜的排泄物对环境的污染%Environmental Pollution by Quinolines Antibiotics from Human and Animal Excreta

    Institute of Scientific and Technical Information of China (English)




  19. Synthesis and studies of novel 2-(4-cyano-3-trifluoromethylphenyl amino)-4-(quinoline-4-yloxy)-6-(piperazinyl/piperidinyl)-s-triazines as potential antimicrobial, antimycobacterial and anticancer agents. (United States)

    Patel, Rahul V; Kumari, Premlata; Rajani, Dhanji P; Chikhalia, Kishor H


    A series of novel s-triazine analogs were synthesized and characterized by IR, (1)H NMR, (13)C NMR, (19)F NMR spectroscopy and elemental analysis. Preliminary screening of target compounds against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneria), four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus clavatus, Candida albicans) and Mycobacterium tuberculosis H37Rv indicated that 5d, 5h, 5n, 5p, 5q, 5r, 5s, 5t and 5u were the most active compounds among twenty one studied. Thus, they were further subjected to in vitro biological evaluation against human prostate cancer cell line (DU-145) and the results indicate that two compounds 5n and 5s were markedly active.

  20. Microwave assisted synthesis of 2-(2-(tetrazolo[1,5-a]quinolin-4-yl-2,3-dihydro-1h-benzo[b][1,4]diazepin-4-yl substituted phenols and evaluation of their antimicrobial activity

    Directory of Open Access Journals (Sweden)

    Ashok Dongamanti


    Full Text Available A series of new benzodiazepines 4a-h have been synthesized by Michael addition of chalcones 3a-h with o-phenylenediamine (OPDA in presence of sodium acetate under conventional heating and microwave irradiation. Structures of the newly synthesized benzodiazepines 4a-h have been established on the basis of IR, 1H & 13C NMR and mass spectral data and tested for antimicrobial activity.