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Sample records for quinolines

  1. Wet oxidation of quinoline

    DEFF Research Database (Denmark)

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

    1998-01-01

    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 reactio...

  2. Quinoline-2-sulfonamide

    Directory of Open Access Journals (Sweden)

    Joachim Kusz

    2013-08-01

    Full Text Available In the title compound, C9H8N2O2S, the sulfamoyl –NH2 group is involved in intermolecular hydrogen bonding with the sulfonamide O and quinoline N atoms. In the crystal, molecules are linked into dimers via pairs of N—H...N hydrogen bonds, forming an R22(10 motif. The dimers are further assembled into chains parallel to the b axis through N—H...O hydrogen bonds, generating a C(4 motif. The crystal packing is additionally stabilized by intermolecular C—H...O interactions. The crystal studied was a non-merohedral twin with a domain ratio of 0.938 (2:0.062 (2. Density functional theory (DFT calculations, at the B3LYP/6–31 G(d,p level of theory, were used to optimize the molecular structure and to determine interaction energies for the title compound. The resulting interaction energy is ∼4.4 kcal mol−1 per bridge for the C(4 chain and ∼5.9 kcal mol−1 per bridge for the R22(10 motif.

  3. Glycoconjugates of Quinolines: Application in Medicinal Chemistry.

    Science.gov (United States)

    Oliveri, Valentina; Vecchio, Graziella

    2016-09-02

    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. Methyl 3-(Quinolin-2-ylindolizine-1-carboxylate

    Directory of Open Access Journals (Sweden)

    Roumaissa Belguedj

    2015-12-01

    Full Text Available A novel compound, methyl 3-(quinolin-2-ylindolizine-1-carboxylate (2 has been synthesized by cycloaddition reaction of 1-(quinolin-2-ylmethylpyridinium ylide (1 with methyl propiolate in presence of sodium hydride in THF. The structure of this compound was established by IR, 1H-NMR, 13C-NMR and MS data

  5. Dissociative photoionization of quinoline and isoquinoline

    NARCIS (Netherlands)

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

    2015-01-01

    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

  6. 2-Isopropyl-5-methylcyclohexyl quinoline-2-carboxylate

    Directory of Open Access Journals (Sweden)

    E. Fazal

    2014-01-01

    Full Text Available In the title compound, C20H25NO2, the cyclohexyl ring adopts a slightly disordered chair conformation. The dihedral angle between the mean planes of the quinoline ring and the carboxylate group is 22.2 (6°. In the crystal, weak C—H...N interactions make chains along [010].

  7. Zeolites Promoting Quinoline Synthesis via Friedlander Reaction

    Czech Academy of Sciences Publication Activity Database

    López-Sanz, J.; Pérez-Mayoral, E.; Vitvarová, Dana; Martín-Aranda, R. M.; López-Peinado, A. J.

    2010-01-01

    Roč. 53, 19-20 (2010), s. 1430-1437 ISSN 1022-5528 R&D Projects: GA ČR GD203/08/H032 Institutional research plan: CEZ:AV0Z40400503 Keywords : heterogeneous catalysis * zeolites * quinolines Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 2.359, year: 2010

  8. Quinoline-Based Hybrid Compounds with Antimalarial Activity

    Directory of Open Access Journals (Sweden)

    Xhamla Nqoro

    2017-12-01

    Full Text Available The application of quinoline-based compounds for the treatment of malaria infections is hampered by drug resistance. Drug resistance has led to the combination of quinolines with other classes of antimalarials resulting in enhanced therapeutic outcomes. However, the combination of antimalarials is limited by drug-drug interactions. In order to overcome the aforementioned factors, several researchers have reported hybrid compounds prepared by reacting quinoline-based compounds with other compounds via selected functionalities. This review will focus on the currently reported quinoline-based hybrid compounds and their preclinical studies.

  9. γ-radiolysis of the quinoline

    International Nuclear Information System (INIS)

    Vieira, E.M.

    1989-06-01

    The chemical and radiolytic stability of products by radiation from quinoline in isopropanol solution was studied. Doses were from 2 x 10 4 to 3 x 10 5 Gy and concentration in the samples was L:L by volume. It has observed significant effects for high radiation doses. Lower doses affected the solvent with the production of long polymeric hydrocarbons. Products formed were characterized by capillary gas chromatography coupled to mass spectrometry (CG/MS). (author)

  10. Synthesis of 2-azetidinones substituted quinoline derivative

    Directory of Open Access Journals (Sweden)

    Mashelkar Uday C.

    2013-01-01

    Full Text Available Acetanilide is converted into 2-chloro-3-formyl quinoline by reacting with DMF-POCl3 at 80-90ºC and then condensed with aromatic primary amines to give Schiff bases (3a-3c. These Schiff bases are then reacted with acid chlorides in the presence of base in toluene to give 1, 3, 4-substituted 2-azetidinones.

  11. Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

    NARCIS (Netherlands)

    Vandekerckhove, S.; Mueller, C.; Vogt, D.; Lategan, C.; Smith, P.J.; Chibale, K.; Kimpe, de N.; D'hooghe, M.W.A.

    2013-01-01

    A variety of 5-, 6- and 8-(4-aminobutyloxy)quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of

  12. Kinetic investigations of quinoline oxidation by ferrate(VI).

    Science.gov (United States)

    Luo, Zhiyong; Li, Xueming; Zhai, Jun

    2016-01-01

    Quinoline is considered as one of the most toxic and carcinogenic compounds and is commonly found in industrial wastewaters, which require treatment before being discharged. Removal of quinoline by the use of an environmentally friendly oxidant, potassium ferrate(VI) (K2FeO4), was assessed by studying the kinetics of the oxidation of quinoline by ferrate(VI) (Fe(VI)) as a function of pH (8.53-10.53) and temperature (21-36°C) in this work. The reaction of quinoline with Fe(VI) was found to be first order in Fe(VI), half order in quinoline, and 1.5 order overall. The observed rate constant at 28°C decreased non-linearly from 0.5334 to 0.2365 M(-0.5) min(-1) with an increase in pH from 8.53 to 10.03. Considering the equilibria of Fe(VI) and quinoline, the reaction between quinoline and Fe(VI) contained two parallel reactions under the given pH conditions. The individual rate constants of these two reactions were determined. The results indicate that the protonated species of Fe(VI) reacts more quickly with quinoline than the deprotonated form of Fe(VI). The reaction activation energy Ea was obtained to be 51.44 kJ·mol(-1), and it was slightly lower than that of conventional chemical reaction. It reveals that the oxidation of quinoline by Fe(VI) is feasible in the routine water treatment.

  13. Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines.

    Science.gov (United States)

    Vandekerckhove, Stéphanie; Müller, Christian; Vogt, Dieter; Lategan, Carmen; Smith, Peter J; Chibale, Kelly; De Kimpe, Norbert; D'hooghe, Matthias

    2013-01-01

    A variety of 5-, 6- and 8-(4-aminobutyloxy)quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC(50)-values ranging between 150 and 680 nM. Copyright © 2012 Elsevier Ltd. All rights reserved.

  14. 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: jagl@termo.uva.es; Domanska, Urszula; Zawadzki, Maciej [Physical Chemistry Division, Faculty of Chemistry, Warsaw University of Technology, 00-664 Warsaw (Poland)

    2008-08-15

    (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.

  15. SYNTHESIS AND IN-VITRO STUDIES OF SOME NEW QUINOLINE ...

    African Journals Online (AJOL)

    KEY WORDS: Synthesis, Quinoline, 1,3,4-thiadiazolo pyrimidin, Spectral data, ... aqueous sodium hydroxide (1.0 mL) solution in drop wise. ... small amount of anhydrous potassium carbonate and suitable aryl isothiocyantes in DMF (15.

  16. Recent Advances in Metal-Free Quinoline Synthesis

    Directory of Open Access Journals (Sweden)

    Ginelle A. Ramann

    2016-07-01

    Full Text Available The quinoline ring system is one of the most ubiquitous heterocycles in the fields of medicinal and industrial chemistry, forming the scaffold for compounds of great significance. These include anti-inflammatory and antitumor agents, the antimalarial drugs quinine and chloroquine, and organic light-emitting diodes. Quinolines were first synthesized in 1879, and since then a multitude of synthetic routes have been developed. Many of these methods, such as the Skraup, Doebner–Von Miller, and Friedlander quinoline syntheses, are well-known but suffer from inefficiency, harsh reaction conditions, and toxic reagents. This review focuses on recent transition metal-free processes toward these important heterocycles, including both novel routes and modifications to established methods. For example, variations on the Skraup method include microwave irradiation, ionic liquid media, and novel annulation partners, all of which have shown increased reaction efficiency and improved yield of the heteroring-unsubstituted quinoline products. Similarly, modifications to other synthetic routes have been implemented, with the quinoline products displaying a wide variety of substitution patterns.

  17. Structure of Quinolinate Synthase from Pyrococcus horikoshii in the Presence of Its Product, Quinolinic Acid.

    Science.gov (United States)

    Esakova, Olga A; Silakov, Alexey; Grove, Tyler L; Saunders, Allison H; McLaughlin, Martin I; Yennawar, Neela H; Booker, Squire J

    2016-06-15

    Quinolinic acid (QA) is a common intermediate in the biosynthesis of nicotinamide adenine dinucleotide (NAD(+)) and its derivatives in all organisms that synthesize the molecule de novo. In most prokaryotes, it is formed from the condensation of dihydroxyacetone phosphate (DHAP) and aspartate-enamine by the action of quinolinate synthase (NadA). NadA contains a [4Fe-4S] cluster cofactor with a unique, non-cysteinyl-ligated, iron ion (Fea), which is proposed to bind the hydroxyl group of a postulated intermediate in the last step of the reaction to facilitate a dehydration. However, direct evidence for this role in catalysis has yet to be provided. Herein, we present the structure of NadA in the presence of the product of its reaction, QA. We find that N1 and the C7 carboxylate group of QA ligate to Fea in a bidentate fashion, which is confirmed by Hyperfine Sublevel Correlation (HYSCORE) spectroscopy. This binding mode would place the C5 hydroxyl group of the postulated final intermediate distal to Fea and virtually incapable of coordinating to it. The structure shows that three strictly conserved amino acids, Glu198, Tyr109, and Tyr23, are in close proximity to the bound product. Substitution of these amino acids with Gln, Phe, and Phe, respectively, leads to complete loss of activity.

  18. Dynamics of Excited State Proton Transfer in Nitro Substituted 10-Hydroxybenzo[h]quinolines

    DEFF Research Database (Denmark)

    Marciak, H; Hristova, S.; Deneva, V

    2017-01-01

    The ground state tautomerism and excited state intramolecular proton transfer (ESIPT) of 10-hydroxybenzo[h]quinoline (HBQ) and its nitro derivatives, 7-nitrobenzo[h]quinolin-10-ol (2) and 7,9-dinitrobenzo[h]quinolin-10-ol (3), have been studied in acetonitrile using steady state as well as time d...

  19. Kinetic interaction in hydrogenitrogenation of quinoline and acridine

    International Nuclear Information System (INIS)

    El-Bishtawi, R.F.; Seapan, M.

    1988-01-01

    Liquid fossil fuels contain numerous nitrogen compounds. During hydrodenitrogenation processes, these compounds for the active catalytic sites, with each compound affecting the kinetics of the other compounds. An understanding of the kinetic interaction is essential in using the results of model compound kinetics to predict the behavior of complex mixtures. In this work, the authors study the hydrodenitrogenation of quinoline and acridine in n-hexadecane over a commercial nickel-molybdenum catalyst in a batch autoclave reactor at 8.3 MPa (1200 psig) and 357-390 0 C. The reaction networks and kinetics of individual compounds were developed. These results confirm the existing knowledge of reaction networks for quinoline and acridine. Furthermore, their experiments show that formation for o-ethylaniline, o-toluidine and aniline are also important steps in quinoline denitrogenation. For total nitrogen removal, a dual site Langmuir-Hinshelwood type model considering separate sites for adsorption of hydrogen and nitrogen compounds give the best fit

  20. Biological Activity Predictions and Hydrogen Bonding Analysis in Quinolines

    Science.gov (United States)

    Gupta, Palvi; Kamni

    The paper has been designed to make a comprehensive review of a particular series of organic molecular assembly in the form of compendium. An overview of general description of fifteen quinoline derivatives has been given. The biological activity spectra of quinoline derivatives have been correlated on structure activity relationships base which provides the different Pa (possibility of activity) and Pi (possibility of inactivity) values. Expositions of the role of intermolecular interactions in the identified derivatives have been discussed with the standard distance and angle cut-off criteria criteria as proposed by Desiraju and Steiner (1999) in an International monogram on crystallography. Distance-angle scatter plots for intermolecular interactions are presented for a better understanding of the packing interactions which exist in quinoline derivatives.

  1. Raman Spectra and Intermolecular Hydrogen Bonds of Quinoline in Solutions

    International Nuclear Information System (INIS)

    Tukhvatullin, F.H.; Jumabayev, A.; Hushvaktov, H.; Absanov, A.; Hudoyberdiev, B.

    2012-01-01

    The half-widths of the 1014- and 1033-cm -1 bands of the Raman spectrum of quinoline at its dilution in neutral solvents (benzene, CCl 4 ) are narrowed by 1.3-1.5 times at high dilutions. This effect is associated with the increased time of the vibrational relaxation. For the 520-cm -1 band in pure liquid quinoline, the parallel polarized component at 20 o C is asymmetric in the high-frequency region. The shape of the perpendicular polarized component is complicated. A non-coincidence of the peak frequencies of the parallel and perpendicular polarized components is observed (∼ 2 cm -1 ). Quantum-chemical calculations showed that, in the region of 520 cm -1 for a monomer molecule, we should really have two near located lines with the wavenumbers 530 and 527 cm -1 (scaling factor 0.97), and with the depolarization ratios 0.61 and 0.26. In the solutions with propan-2-ol, the 1033.8-cm -1 band becomes of a doublet character. The resolution of the doublet becomes better by the dilution of a binary quinoline-alcohol solution with a large amount of a neutral solvent (benzene). The wavenumbers of bands in the triple mixture are 1033 cm -1 and 1039 cm -1 . The doublet nature of the band in the binary and triple mixtures is associated with the presence of monomer molecules and quinoline-propan-2-ol aggregates (the high-frequency line) in the liquid mixture. Quantum-chemical calculations showed that the hydrogen bonds with a length of 1.958 A and an energy gain of 22.0 kJ/mole can be formed between molecules of quinoline and alcohol. The formation of aggregates can be also detected in the 820-cm -1 band of propan-2-ol. A similar picture is observed for the 667-cm -1 band of chloroform in its solution with quinoline.

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

    DEFF Research Database (Denmark)

    Thomsen, A.B.

    1998-01-01

    The high temperature, high pressure wet oxidation reaction of quinoline has been studied as a function of initial concentration, pH and temperature. At neutral to acidic pH, it is effective in the oxidation of quinoline at 240 degrees C and above, whereas under alkaline conditions the reaction...... is markedly slowed down. The results indicate that the reaction is an auto-catalysed, free radical chain reaction transforming 99% of quinoline to other substances. Of the quinoline. 30-50% was oxidised to CO2 and H2O depending on the initial concentration. Wet oxidation of deuterium-labelled quinoline...

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

    Indian Academy of Sciences (India)

    Unknown

    An efficient synthesis of quinolines under solvent-free conditions. 201 was then irradiated with microwaves in a microwave oven (Samsung model# CE118KF) at 1050W (70% of total power) for 5 minutes (3 + 2 with an inter- mission of 5 minutes). The reaction mixture was cooled at room temperature and rendered basic (pH.

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

    DEFF Research Database (Denmark)

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

    1996-01-01

    kinetics. The kinetic parameters for indole were an apparent maximum specific transformation rate (V-Amax) of 263 mu mol mg total protein(-1) day(-1) and an apparent half-saturation constant (K-Am) of 139 mu M. The V-Amax for quinoline was 170 mu mol mg total protein(-1) day(-1) and K-Am was 92 mu M...

  5. Synthesis, characterization and emission properties of quinolin-8 ...

    Indian Academy of Sciences (India)

    Unknown

    chelated ruthenium organometallics. BIKASH KUMAR PANDA. Department of Inorganic ... Ruthenium organometallics; quinolin-8-olato chelation; emission properties; trivalent ruthenium. 1. Introduction. There is continuing ... chem.istry of orthometallated ruthenium compounds is of current interest in the context of synthesis ...

  6. Quinoline hybrids and their antiplasmodial and antimalarial activities.

    Science.gov (United States)

    Hu, Yuan-Qiang; Gao, Chuan; Zhang, Shu; Xu, Lei; Xu, Zhi; Feng, Lian-Shun; Wu, Xiang; Zhao, Feng

    2017-10-20

    Malaria, in particular infection with P. falciparum (the most lethal of the human malaria parasite species, responsible for nearly one million deaths every year), is one of the most devastating and common infectious disease throughout the world. Beginning with quinine, quinoline containing compounds have long been used in clinical treatment of malaria and remained the mainstays of chemotherapy against malaria. The emergence of P. falciparum strains resistant to almost all antimalarials prompted medicinal chemists and biologists to study their effective replacement with an alternative mechanism of action and new molecules. Combination with variety of quinolines and other active moieties may increase the antiplasmodial and antimalarial activities and reduce the side effects. Thus, hybridization is a very attractive strategy to develop novel antimalarials. This review aims to summarize the recent advances towards the discovery of antiplasmodial and antimalarial hybrids including quinoline skeleton to provide an insight for rational designs of more active and less toxic quinoline hybrids antimalarials. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  7. 2-Carboxy-6-(quinolin-1-ium-8-yloxybenzoate

    Directory of Open Access Journals (Sweden)

    Jin Xie

    2012-05-01

    Full Text Available In the zwitterionic title compound, C17H11NO5, the dihedral angle between the two aromatic rings is 76.90 (7°. The dihedral angles between the carboxyl groups and the benzene ring are 64.02 (9 and 21.67 (9°, the larger angle being associated with an intramolecular N—H...Ocarboxyl hydrogen bond, resulting from proton transfer from the carboxylic acid group to the quinoline N atom and giving an S(9 ring motif. In the crystal, molecules are connected by O—H...O hydrogen bonds into chains extending along the b-axis direction. An overall two-dimensional network structure is formed through π–π interactions between the quinoline rings [minimum ring-centroid separation = 3.6068 (6 Å].

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

    Directory of Open Access Journals (Sweden)

    Naphtali A. O’Connor

    2014-06-01

    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.

  9. Degradation of pyridine and quinoline in aqueous solution by gamma radiation

    Science.gov (United States)

    Chu, Libing; Yu, Shaoqing; Wang, Jianlong

    2018-03-01

    In present work, the degradation of two N-heteroaromatic pollutants, i.e., pyridine and quinoline was investigated by gamma irradiation in the presence of TiO2 nanoparticle. The experimental results showed that quinoline has a higher degradation rate than pyridine. The removal efficiency of the pollutants, TOC and TN reached 93.0%, 11.9% and 12.0% for quinoline, 71.0%, 10.6% and 4.4% for pyridine, respectively at 7.0 kGy and initial concentration of 50 mg/L. Ammonium was detected for both pyridine and quinoline within the absorbed doses, suggesting that the organic nitrogen was transformed into ammonium. The degradation rate constant of pyridine and quinoline was increased by 1.1-1.5 times with addition of TiO2. TiO2 nanoparticles were especially effective to enhance the mineralization. The removal efficiency of TOC and TN was increased by 15-12% for pyridine and 23-25% for quinoline, respectively in the presence of 2.0 g/L TiO2. Following gamma irradiation, 2-hydroxypyridine, 3-hydroxypyridine, oxalic acid and formic acid were identified for pyridine and the hydroxyl quinoline and formic acid were detected for quinoline. Accordingly, the degradation mechanism of pyridine and quinoline by gamma irradiation was tentatively proposed.

  10. Structural Analysis of Quinoline 2-Oxidoreductase from Pseudomonas putida 86

    OpenAIRE

    Bonin, Irena

    2007-01-01

    The crystal structure of the Quinoline 2-Oxidoreductase (Qor), a member of the molybdenum hydroxylase family, was solved at 1.8 Å resolution. Still controversial for molybdenum hydroxylases is the nature of the molybdenum apical ligand. In Qor the sulfido-ligand was found in the equatorial position while the oxo-ligand occupied the apical position. In addition, structural studies were carried out on two Nus family proteins. These resulted in the crystal structures of the transcription factors...

  11. Microwave-Assisted Synthesis of Phenothiazine and Quinoline Derivatives

    Science.gov (United States)

    Găină, Luiza; Cristea, Castelia; Moldovan, Claudia; Porumb, Dan; Surducan, Emanoil; Deleanu, Călin; Mahamoud, Abdalah; Barbe, Jacques; Silberg, Ioan A.

    2007-01-01

    Application of a dynamic microwave power system in the chemical synthesis of some phenothiazine and quinoline derivatives is described. Heterocyclic ring formation, aromatic nucleophilic substitution and heterocyclic aldehydes/ketones condensation reactions were performed on solid support, or under solvent free reaction conditions. The microwave-assisted Duff formylation of phenothiazine was achieved. Comparison of microwave-assisted synthesis with the conventional synthetic methods demonstrates advantages related to shorter reaction times and in some cases better reaction yields.

  12. Enhanced solid state emission of quinoline derivatives for fluorescent sensors

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Hyong-Jun, E-mail: hkim@kongju.ac.kr

    2016-08-15

    Excited-state intramolecular proton transfer (ESIPT) molecules are of utmost interest in the fields of organic light emitting diode, photo-patterning, chemosensor, proton transfer laser, and photostabilizer. Fine control of the functional substituents as well as the molecular structure of core ESIPT unit is primarily demanded for specific applications. Here, the photophysics of quinoline derivatives of 2-quinolin-2-yl-phenol and 2-(8-chloroquinolin-2-yl)phenol is explored. Straightening the twist between the hydroxyphenyl and the quinoline moieties with the aid of the hydrogen bonding promoted the excited energy to flow through a radiative decay pathway via proton transfer to the nitrogen. Furthermore, close molecular packing of J-aggregates and thus resulted vibration restriction in a dense matter opens an ESIPT corridor and is characterized to show enhanced emission. The mechanism is applied to the selective Cu{sup 2+} or Fe{sup 2+} cation detection and further immunofluorescence labeling using avidin–biotin protein specific binding is demonstrated with the aid of nano self-assembly technique. - Highlights: • New orange fluorescent hydroxyphenylquinoline derivative was synthesized. • Molecular structure planarization induced enhanced fluorescence with large Stokes' shift. • Selective solution phase cation detection and solid state bio-sensing were demonstrated successfully.

  13. Application of Heteropoly Acids as Heterogeneous and Recyclable Catalysts for Friedländer Synthesis of Quinolines

    Directory of Open Access Journals (Sweden)

    Majid M. Heravi

    2010-01-01

    Full Text Available New convenient conditions for the Friedländer synthesis of quinolines are described. Quinolines were readily prepared in the presence of heteropolyacids as heterogeneous and recyclable catalysts in good yields.

  14. Electrochemical sensor for hazardous food colourant quinoline yellow based on carbon nanotube-modified electrode.

    Science.gov (United States)

    Zhao, Jun; Zhang, Yu; Wu, Kangbing; Chen, Jianwei; Zhou, Yikai

    2011-09-15

    A novel electrochemical method using multi-wall carbon nanotube (MWNT) film-modified electrode was developed for the detection of quinoline yellow. In pH 8 phosphate buffer, an irreversible oxidation peak at 0.71V was observed for quinoline yellow. Compared with the unmodified electrode, the MWNT film-modified electrode greatly increases the oxidation peak current of quinoline yellow, showing notable enhancement effect. The effects of pH value, amount of MWNT, accumulation potential and time were studied on the oxidation peak current of quinoline yellow. The linear range is from 0.75 to 20mgL(-1), and the limit of detection is 0.5mgL(-1). It was applied to the detection of quinoline yellow in commercial soft drinks, and the results consisted with the value that obtained by high-performance liquid chromatography. Copyright © 2011 Elsevier Ltd. All rights reserved.

  15. Degradation of quinoline and isoquinoline by vacuum ultraviolet light and mechanism thereof

    International Nuclear Information System (INIS)

    Zhu Dazhang; Ni Yaming; Sun Dongmei; Wang Shilong; Sun Xiaoyu; Yao Side

    2010-01-01

    Since the wavelength is shorter than 190 nm, vacuum ultraviolet light has high energy enough to break the H-O bonds of water to produce HO·, as well as the protection is very easy, degradation of organic contaminants in water by vacuum ultraviolet light has obviously excellent feature of no reagent adding to the wastewater among advanced oxidation technologies. In this paper, it was reported that quinoline and isoquinoline were degraded in water by the irradiation of low-pressure quartz mercury light with the electric power of 200 W which mainly emitted the light of 185 nm and 254 nm. The change regulation of the concentration of substrates, chemical oxygen demand (COD) and total organic carbon (TOC) were investigated as well as the degradation processes of quinoline and isoquinoline were compared. It showed that both quinoline and isoquinoline could be degraded very fast under the given conditions. The concentration of the substrates decreased to nearly 0 in 10 minutes while the apparent first reaction rate constants were 0.41 ± 0.02 min -1 and 0.19 ± 0.01 min -1 , respectively. Meanwhile, the COD and TOC decreased to nearly 0 in 30 minutes. Quinoline has the faster degradation rate. In order to investigate mechanism thereof, pulse radiolysis and laser flash photolysis of quinoline and isoquinoline aqueous solution were performed, respectively. Pulse radiolysis indicated that the reaction rate constant of quinoline and HO· was faster than that of isoquinoline. In the meanwhile, laser flash photolysis indicated that both quinoline and isoquinoline could be ionized by the UV-C light while the photo-ionization efficiency of quinoline was higher than that of quinoline. These two reasons caused the faster degradation rate of quinoline. (authors)

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

    DEFF Research Database (Denmark)

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

    2011-01-01

    using the electrostatic storage ring ELISA, an electrospray ion source and 3 ns UV laser pulses. Results. It is shown that the absorption profile is both redshifted and broadened when moving the methyl group from the heterocycle containing nitrogen to the homoatomic ring. The absorption profiles......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 range...

  17. Genotoxicity risk assessment of diversely substituted quinolines using the SOS chromotest.

    Science.gov (United States)

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

    2015-03-01

    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. © 2013 Wiley Periodicals, Inc.

  18. Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates.

    Science.gov (United States)

    Zhao, Hongyang; Xing, Yanpeng; Lu, Ping; Wang, Yanguang

    2016-10-10

    Cyclopenta[b]quinolines and cyclohexa[b]quinolines were prepared via the reactions of α-diazo ketones with N-(2-cyclopropylidenemethylphenyl)phosphanimines and N-(2-cyclobutylidenemethylphenyl) phosphanimine, respectively. The reaction proceeds in a cascade involving ketenimine formation, 6 π-electron ring closure, and 1,3-alkyl shift. A similar approach was developed for the synthesis of dihydropyrrolo-[2,3-b]quinolines from N-(2-cyclopropylidenemethylphenyl)phosphanimines and isocyanates. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Carbon and hydrogen isotope fractionation during aerobic biodegradation of quinoline and 3-methylquinoline.

    Science.gov (United States)

    Cui, Mingchao; Zhang, Wenbing; Fang, Jun; Liang, Qianqiong; Liu, Dongxuan

    2017-08-01

    Compound-specific isotope analysis has been used extensively to investigate the biodegradation of various organic pollutants. To date, little isotope fractionation information is available for the biodegradation of quinolinic compounds. In this study, we report on the carbon and hydrogen isotope fractionation during quinoline and 3-methylquinoline aerobic microbial degradation by a Comamonas sp. strain Q10. Degradation of quinoline and 3-methylquinoline was accompanied by isotope fractionation. Large hydrogen and small carbon isotope fractionation was observed for quinoline while minor carbon and hydrogen isotope fractionation effects occurred for 3-methylquinoline. Bulk carbon and hydrogen enrichment factors (ε bulk ) for quinoline biodegradation were -1.2 ± 0.1 and -38 ± 1‰, respectively, while -0.7 ± 0.1 and -5 ± 1‰ for 3-methylquinoline, respectively. This reveals a potential advantage for employing quinoline as the model compound and hydrogen isotope analysis for assessing aerobic biodegradation of quinolinic compounds. The apparent kinetic isotope effects (AKIE C ) values of carbon were 1.008 ± 0.0005 for quinoline and 1.0048 ± 0.0005 for 3-methylquinoline while AKIE H values of hydrogen of 1.264 ± 0.011 for quinoline and 1.0356 ± 0.0103 for 3-methylquinoline were obtained. The combined evaluation of carbon and hydrogen isotope fractionation yields Λ values (Λ = Δδ 2 H/Δδ 13 C ≈ εH bulk /εC bulk ) of 29 ± 2 for quinoline and 8 ± 2 for 3-methylquinoline. The results indicate that the substrate specificity may have a significant influence on the isotope fractionation for the biodegradation of quinolinic compounds. The substrate-specific isotope enrichment factors would be important for assessing the behavior and fate of quinolinic compounds in the environment.

  20. Synthesis of pyrrolo(2,3-b)quinolines by palladium-catalyzed heteroannulation

    International Nuclear Information System (INIS)

    Gee, Moon Bae; Lee, Won Jung; Yum, Eul Kgun

    2003-01-01

    Palladium-catalyzed heteroannulation of 2-amino-3-iodoquinoline derivatives and 1-trimethylsilyl internal alkynes provided highly regioselective pyrrolo(2,3-b)quinolines with trimethylsilyl group next to the nitrogen atom in the pyrrole ring

  1. Chlorine- and Sulphur-substituted Pyrrolo[3,4-b]quinolines and ...

    African Journals Online (AJOL)

    Chlorine- and Sulphur-substituted Pyrrolo[3,4-b]quinolines and Related Derivatives .... J. Chem., 2003, 56, 40–46,. . .... It is evident from the above that by judicious selection and application of reagents ...

  2. Quinolinic Acid: An Endogenous Neurotoxin with Multiple Targets

    Directory of Open Access Journals (Sweden)

    Rafael Lugo-Huitrón

    2013-01-01

    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.

  3. The ytterbium nitrate-quinoline (piperidine) nitrate-water system

    International Nuclear Information System (INIS)

    Khisaeva, D.A.; Boeva, M.K.; Zhuravlev, E.F.

    1985-01-01

    Using the method of cross sections the solubility of solid phases in the ytterbium nitrate-quinoline nitrate - water (1) and ytterbium nitrate-piperidine nitrate-water (2) systems is studied at 25 and 50 deg C. It is established, that in system 1 congruently melting compound of the composition Yb(NO 3 ) 3 x2C 9 H 7 NxHNO 3 x3H 2 O is formed. The new solid phase has been isolated as a preparation and subjected to chemical X-ray diffraction, differential thermal and IR spectroscopic analyses. Isotherms of system 2 in the studied range of concentrations and temperatures consist of two branches, corresponding to crystallization of tetruaqueous ytterbi um nitrate and nitric acid piperidine

  4. 2,3,8-Trisubstituted Quinolines with Antimalarial Activity.

    Science.gov (United States)

    Martinez, Pablo D G; Krake, Susann H; Poggi, Maitia L; Campbell, Simon F; Willis, Paul A; Dias, Luiz C

    2018-01-01

    Combination therapy drugs are considered a fundamental way to control malaria as it mimimizes the risk of emergence of resistance to the individual partner drugs. Consequently, this type of therapy constitutes a driving force for the discovery of new drugs with different modes of action, since this will provide options for combining different drugs to achieve the optimum antimalarial treatment. In this context, a 2,3,8-trisubstitued quinoline compound was found in a high throughput screen (HTS) to show an excellent inhibition of P. falciparum NF54 (IC50 = 22 nM) and low cytotoxicity. We performed a detailed evaluation of the substituents to improve the metabolic stability and solubility liabilities of the original hit and identified derivatives with enhanced physicochemical and/or PK properties and that maintained biological activity. However the high potency was not retained on testing against drug resistant plasmodium strains.

  5. 2,3,8-Trisubstituted Quinolines with Antimalarial Activity

    Directory of Open Access Journals (Sweden)

    PABLO D.G. MARTINEZ

    2018-05-01

    Full Text Available ABSTRACT Combination therapy drugs are considered a fundamental way to control malaria as it mimimizes the risk of emergence of resistance to the individual partner drugs. Consequently, this type of therapy constitutes a driving force for the discovery of new drugs with different modes of action, since this will provide options for combining different drugs to achieve the optimum antimalarial treatment. In this context, a 2,3,8-trisubstitued quinoline compound was found in a high throughput screen (HTS to show an excellent inhibition of P. falciparum NF54 (IC50 = 22 nM and low cytotoxicity. We performed a detailed evaluation of the substituents to improve the metabolic stability and solubility liabilities of the original hit and identified derivatives with enhanced physicochemical and/or PK properties and that maintained biological activity. However the high potency was not retained on testing against drug resistant plasmodium strains.

  6. Giant negative magnetoresistance in Ni(quinoline-8-selenoate)2.

    Science.gov (United States)

    Black, Nicholas; Daiki, Tonouchi; Matsushita, Michio M; Woollins, J Derek; Awaga, Kunio; Robertson, Neil

    2017-12-20

    The magnetic, structural, conductivity and magnetoresistance properties of [Ni(quinoline-8-selenoate) 2 ] ([Ni(qs) 2 ]) have been studied. Despite the insolubility of the material necessitating its study as a powdered sample, a remarkably high conductivity has been measured. The conductivity is an order of magnitude greater than the thin-film processable thiol analogue previously reported and has been interpreted through the same space-charge limited conduction mechanism with charges injected from the electrodes. The introduction of selenium, results in a material with conductivity approaching metallic due to the enhanced interaction between adjacent molecules. Additionally, under an applied magnetic field, the material displays a negative magnetoresistance effect above 35% at 2 K. The effect can still be observed at 200 K and is interpreted in terms of a double-exchange mechanism.

  7. Quinolines in clothing textiles--a source of human exposure and wastewater pollution?

    Science.gov (United States)

    Luongo, Giovanna; Thorsén, Gunnar; Ostman, Conny

    2014-05-01

    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.

  8. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives

    International Nuclear Information System (INIS)

    Elhadi, S. A.

    2004-09-01

    Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, 1 H-and 13 C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl -6-sulphanilamide-quinolin-4-carboxylic acid showed the highest activity against the four standard tested organisms.(Author)

  9. Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Elhadi, S A [Department of Chemistry, Faculty of Education, University of Khartoum, Khartoum (Sudan)

    2004-09-01

    Quinolin derivatives are a group of compounds known to possess a wide range of biological activities. The chemistry of quinolines together with their corresponding aldehydes were dealt with in chapter one of this study. Special emphasis was given to the chemistry of benzaldehyde. Twenty five 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives together with their corresponding intermediates were prepared in this work. Basically, the synthetic design of these compounds arise from the appropriate disconnections of the target 2-phenyl and 2,3-diphenyl-quinolin-4-carboxylic acids. The retro synthesis analysis of these compounds reveals pyruvic acid, aromatic amine and benzaldehyde or phenyl pyruvic acid, aromatic amine and benzaldehyde as possible logical precursors for 2-phenyl-and 2,3-diphenyl- quinoline-4-carboxylic acids respectively. The purity and identities of the synthesized compounds were elucidated through chromatographic and spectroscopic techniques. The compounds were heavily subjected to spectroscopic analysis (UV, IR, GC/MS, {sup 1}H-and {sup 13}C- NMR). The appropriate disconnections and the mechanisms of the corresponding reactions were given and discussed in chapter three. The spectral data were interpreted and correlated with the target structures. The prepared 2-phenyl- and 2,3-diphenyl-quinoline-4-carboxylic acid derivatives were screened for their antibacterial activity. The compounds were tested against the standard bacterial organisms B. subtilis, S. aureus, E. coli and P. vulgaris. Some of these compounds were devoid of antibacterial activity against S. aureus and P. vulgaris, while others showed moderate activity. All of the tested compounds showed an activity against B. subtilis and E. coli. 2,3-diphenyl -6-sulphanilamide-quinolin-4-carboxylic acid showed the highest activity against the four standard tested organisms.(Author)

  10. Novel Basic Mesoporous Catalysts for Friedländer Reaction from 2-Aminoaryl Ketones: Quinolin-2(1H)-ones vs. Quinolines

    Czech Academy of Sciences Publication Activity Database

    Domínguez-Fernández, F.; López-Sanz, J.; Pérez-Mayoral, E.; Bek, David; Martín-Aranda, R. M.; López-Peinado, A. J.; Čejka, Jiří

    2009-01-01

    Roč. 1, č. 2 (2009), s. 241-243 ISSN 1867-3880 R&D Projects: GA AV ČR KAN100400701 Institutional research plan: CEZ:AV0Z40400503 Keywords : quinolines * heterogeneous catalysis * basicity Subject RIV: CF - Physical ; Theoretical Chemistry

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

    DEFF Research Database (Denmark)

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

    2012-01-01

    . Characterised products include the previously published 1 : 1 salt, C9H8N+center dot C4H3O4-, and a new 2 : 1 quinoline/fumaric acid co-crystal, (C9H7N)(2)center dot C4H4O4. Attempts to influence the crystallisation outcome by addition of 6-methylquinoline yielded a second co-crystal, also with an inherent 2......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...... : 1 quinoline/fumaric acid ratio, as a solid solution containing ca. 75% 6-methylquinoline and 25% quinoline. The corresponding co-crystal with pure 6-methylquinoline, (C10H9N)(2)center dot C4H4O4, was prepared, but the analogous structure with pure quinoline could not be obtained. Energy minimisation...

  12. Uptake and fate of phenol, aniline and quinoline in terrestrial plants

    International Nuclear Information System (INIS)

    Cataldo, D.A.; Bean, R.M.; Fellows, R.J.

    1987-06-01

    The bioavailability and chemical fate of xenobiotics in terrestrial plants can influence the impact of fossil fuel development on the human food chain. To determine the relative behavior of organic residues representing a range of chemical classes, we compared the rates of root absorption, tissue distribution and chemical fate of phenol, aniline and quinoline in soybean plants. Root absorption rates for these compounds were 180, 13 and 30 μg/g (fresh weight) root/day, respectively. Following uptake, aniline was concentrated in the root, while phenol and quinoline were evenly distributed in roots and leaves. After accumulation, phenol was readily decomposed, and its carbon was respired. While aniline was susceptible to oxidative decomposition, it persisted in leaves and roots; 25% of the soluble activity represented aniline, and a significant fraction was bound or conjugated to cell constitutents. Quinoline persisted both in the parent form and as metabolic products. However, in leaves, additional compounds were found that were chemically similar to quinoline; these were not found in unexposed plants. A substantial fraction of the quinoline accumulated by leaves was emitted to the atmosphere by volatilization. 12 refs., 5 tabs., 2 figs

  13. An Efficient Synthesis of Substituted Quinolines via Indium(III) Chloride Catalyzed Reaction of Imines with Alkynes

    International Nuclear Information System (INIS)

    Zhu, Mei; Fu, Weijun; Xun, Chen; Zou, Guanglong

    2012-01-01

    An efficient synthetic method for the preparation of quinolines through indium(III) chloride-catalyzed tandem addition-cyclization-oxidation reactions of imines with alkynes was developed. The processes can provide a diverse range of quinoline derivatives in good yields from simple imines and alkynes

  14. Synthesis of 2-Alkenylquinoline by Reductive Olefination of Quinoline N-Oxide under Metal-Free Conditions.

    Science.gov (United States)

    Xia, Hong; Liu, Yuanhong; Zhao, Peng; Gou, Shaohua; Wang, Jun

    2016-04-15

    Synthesis of 2-alkenylquinoline by reductive olefination of quinoline N-oxide under metal-free conditions is disclosed. Practically, the reaction could be performed with quinoline as starting material via a one-pot, two-step process. A possible mechanism is proposed that involves a sequential 1,3-dipolar cycloaddition and acid-assisted ring opening followed by a dehydration process.

  15. Crystallization and preliminary X-ray crystallographic analysis of human quinolinate phosphoribosyltransferase

    International Nuclear Information System (INIS)

    Kang, Gil Bu; Kim, Mun-Kyoung; Youn, Hyung-Seop; An, Jun Yop; Lee, Jung-Gyu; Park, Kyoung Ryoung; Lee, Sung Hang; Kim, Yongseong; Fukuoka, Shin-Ichi; Eom, Soo Hyun

    2010-01-01

    H. sapiens quinolinate phosphoribosyltransferase has been expressed, purified and crystallized. A diffraction data set has been collected and processed at 2.8 Å resolution. Quinolinate phosphoribosyltransferase (QPRTase) is a key NAD-biosynthetic enzyme which catalyzes the transfer of quinolinic acid to 5-phosphoribosyl-1-pyrophosphate, yielding nicotinic acid mononucleotide. Homo sapiens QPRTase (Hs-QPRTase) appeared as a hexamer during purification and the protein was crystallized. Diffraction data were collected and processed at 2.8 Å resolution. Native Hs-QPRTase crystals belonged to space group P2 1 , with unit-cell parameters a = 76.2, b = 137.1, c = 92.7 Å, β = 103.8°. Assuming the presence of six molecules in the asymmetric unit, the calculated Matthews coefficient is 2.46 Å 3 Da −1 , which corresponds to a solvent content of 49.9%

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

    Science.gov (United States)

    Swathy, S S; Indira, M

    2010-01-01

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

    Directory of Open Access Journals (Sweden)

    Ghorab Mostafa M.

    2016-06-01

    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.

  18. SYNTHESIS OF NOVEL INDOLO[3,2-c]QUINOLINES; ETHYL 3-CHLORO-9,11-DIMETHOXY INDOLO[3,2-c]QUINOLINE-6-CARBOXYLATE

    Directory of Open Access Journals (Sweden)

    Tutik Dwi Wahyuningsih

    2010-06-01

    Full Text Available -Carboline and its derivatives are significant due to their pharmacological importance. The synthesis of indolo[3,2-c]quinolines as a benzo analog of -carboline has been carried out via an oxime ether intermediate. Reaction of 2'-glyoxylic ester with hydroxylamine hydrochloride in the presence of sodium acetate afforded the oxime acetate in 82%. It was then treated with natrium and fluoro-2,4-dinitrobenzene in ethanol to give an orange solid of oxime ether acetate which is in subsequent treatment with a base yielded a pale yellow solid of indolo[3,2-c]carboline in 43%. Keywords: -carboline, oxime, indolo[3,2-c]quinoline.

  19. Synthesis of Quinolines through Three-Component Cascade Annulation of Aryl Diazonium Salts, Nitriles, and Alkynes.

    Science.gov (United States)

    Wang, Hao; Xu, Qian; Shen, Sheng; Yu, Shouyun

    2017-01-06

    An efficient and rapid synthesis of multiply substituted quinolines is described. This method is enabled by a three-component cascade annulation of readily available aryl diazonium salts, nitriles, and alkynes. This reaction is catalyst- and additive-free. Various aryl diazonium salts, nitriles, and alkynes can participate in this transformation, and the yields are up to 83%.

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

    Science.gov (United States)

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

    2015-03-21

    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.

  1. Electrochemical mineralization pathway of quinoline by boron-doped diamond anodes.

    Science.gov (United States)

    Wang, Chunrong; Ma, Keke; Wu, Tingting; Ye, Min; Tan, Peng; Yan, Kecheng

    2016-04-01

    Boron-doped diamond anodes were selected for quinoline mineralization, and the resulting intermediates, phenylpropyl aldehyde, phenylpropionic acid, and nonanal were identified and followed during quinoline oxidation by gas chromatography-mass spectrometry and high-performance liquid chromatography. The evolutions of formic acid, acetic acid, oxalic acid, NO2(-), NO3(-), and NH4(+) were quantified. A new reaction pathway for quinoline mineralization by boron-doped diamond anodes has been proposed, where the pyridine ring in quinoline is cleaved by a hydroxyl radical giving phenylpropyl aldehyde and NH4(+). Phenylpropyl aldehyde is quickly oxidized into phenylpropionic acid, and the benzene ring is cleaved giving nonanal. This is further oxidized to formic acid, acetic acid, and oxalic acid. Finally, these organic intermediates are mineralized to CO2 and H2O. NH4(+) is also oxidized to NO2(-) and on to NO3(-). The results will help to gain basic reference for clearing intermediates and their toxicity. Copyright © 2016 Elsevier Ltd. All rights reserved.

  2. Quinoline Fluorescent Probes for Zinc - from Diagnostic to Therapeutic Molecules in Treating Neurodegenerative Diseases.

    Science.gov (United States)

    Czaplinska, Barbara; Spaczynska, Ewelina; Musiol, Robert

    2018-01-01

    Fluorescent compounds had gained strong attention due to their wide and appealing applications. Microscopic techniques and visualization are good examples among others. Introduction of fluorescent dyes into microbiology opens the possibility to observe tissues, organisms or organelle with exceptional sensitivity and resolution. Probes for detection of biologically relevant metals as zinc, iron or copper seems to be particularly important for drug design and pharmaceutical sciences. Quinoline derivatives are well known for their good metal affinity and wide spectrum of biological activity. In this regard, molecular sensors built on this scaffold may be useful not only as analytical but also as therapeutic agents. In the present review, application of quinoline moiety in designing of novel fluorescent probes for zinc is presented and discussed. Zinc cations are relevant for vast majority of processes and recently attract a great deal of attention for their role in neurodegenerative diseases. Compounds interacting with Zn2+ may be used for early diagnosis of such disorders, for example the Alzheimer disease. Quinoline-based zinc probes may exert some beneficial role in organism acting as theranostic agents. First preliminary drugs for Alzheimer therapy that are based on quinoline moiety are good example of this trend. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  3. 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

  4. 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.

    2013-01-01

    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 to be nega...

  5. 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)

    2002-07-01

    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.

  6. 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.

    2015-09-01

    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: http://dx.doi.org/10.17807/orbital.v7i3.692 

  7. 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

    2016-12-01

    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.

  8. Removal of pyridine and quinoline by bio-zeolite composed of mixed degrading bacteria and modified zeolite

    International Nuclear Information System (INIS)

    Bai Yaohui; Sun Qinghua; Xing Rui; Wen Donghui; Tang Xiaoyan

    2010-01-01

    In the process of the biodegradation of pyridine and quinoline, ammonium is often generated because of the transformation of N from pyridine and quinoline. Zeolite has been proven to be an effective sorbent for the removal of the ammonium. The natural zeolite can be modified to be the macroporous carrier in the biological wastewater treatment process. In this study, a specific bio-zeolite composed of mixed bacteria (a pyridine-degrading bacterium and a quinoline-degrading bacterium) and modified zeolite was used for biodegradation and adsorption in two types of wastewater: sterile synthetic and coking wastewater. The experimental results indicated that pyridine and quinoline could be degraded simultaneously by the mixed bacteria. Furthermore, NH 4 + -N transformed from pyridine and quinoline could be removed by the modified zeolite. In addition, the bacterial community structures of the coking wastewater and the bio-zeolite were monitored by the amplicon length heterogeneity polymerase-chain reaction (LH-PCR) technique. Both LH-PCR results and scanning electron microscope (SEM) observations indicated that the microorganisms, including BW001 and BW003, could be easily attached on the surface of the modified zeolite and that the bio-zeolite could be used in the treatment of wastewater containing pyridine and/or quinoline.

  9. The systems cerium(3) (samarium) nitrate-quinoline nitrate-water

    International Nuclear Information System (INIS)

    Khisaeva, D.A.; Zhuravlev, E.F.; Semenova, Eh.B.

    1982-01-01

    Using the method of cross sections at 25 and 50 deg C the solubility in the systems cerium (3) nitrate-quinoline nitrate-water and samarium nitrate-quinoline nitrate-water has been studied. It is established that in the systems during chemical interaction of components congruently melting compounds of the composition: Ce(NO 3 ) 2 x2[C 9 H 7 NxHNO 3 ]x6H 2 O and Sm(NO 3 ) 3 x2[C 9 H 7 NxHNO 3 ]x2H 2 O are formed. New solid phases are separated preparatively and are subjected to chemical, differential thermal and IR spectroscopic analyses. The investigation results are compared with similar ones for nitrates of other representatives of lanthanide group

  10. Microstructural characteristics of toluene and quinoline-insolubles from coal-tar pitch and their cokes

    Energy Technology Data Exchange (ETDEWEB)

    Panaitescu, C. [University POLITEHNICA Bucharest, Faculty of Industrial Chemistry, Fuel Laboratory, Polizu St. 1, Sector 1, 011061, Bucharest (Romania); Predeanu, G. [Metallurgical Research Institute, Department of Raw Materials, Mehadia St. 39, Sector 6, 060543 Bucharest (Romania)

    2007-08-01

    The structural composition of coal-tar pitch used in the preparation of the special binder-pitch, was determined with special emphasis on the optical properties of the {beta}-resins, as typical components necessary to obtain electrodes of best quality through the pyrogenetic processes of baking and graphitization. In addition to raw toluene- and quinoline-insolubles (TI, QI), the corresponding cokes were analysed to evaluate, by structural composition and microtexture, the behaviour of pitch fractions during carbonization. The results suggest the dependence of the texture development on the type of toluene- and quinoline-insolubles and {beta}-resins during processing conditions, which influence the mesophase formation. An original and important result of the carbopetrographical study is represented by the identification and evaluation of {beta}-resins in the coke texture. (author)

  11. Antiviral Activity of Novel Quinoline Derivatives against Dengue Virus Serotype 2

    Directory of Open Access Journals (Sweden)

    Carolina de la Guardia

    2018-03-01

    Full Text Available Dengue virus causes dengue fever, a debilitating disease with an increasing incidence in many tropical and subtropical territories. So far, there are no effective antivirals licensed to treat this virus. Here we describe the synthesis and antiviral activity evaluation of two compounds based on the quinoline scaffold, which has shown potential for the development of molecules with various biological activities. Two of the tested compounds showed dose-dependent inhibition of dengue virus serotype 2 in the low and sub micromolar range. The compounds 1 and 2 were also able to impair the accumulation of the viral envelope glycoprotein in infected cells, while showing no sign of direct virucidal activity and acting possibly through a mechanism involving the early stages of the infection. The results are congruent with previously reported data showing the potential of quinoline derivatives as a promising scaffold for the development of new antivirals against this important virus.

  12. Synthesis of Naphthyl-, Quinolin- and Anthracenyl Analogues of Clofibric Acid as PPARα Agonists.

    Science.gov (United States)

    Giampietro, Letizia; Ammazzalorso, Alessandra; Bruno, Isabella; Carradori, Simone; De Filippis, Barbara; Fantacuzzi, Marialuigia; Giancristofaro, Antonella; Maccallini, Cristina; Amoroso, Rosa

    2016-03-01

    PPARα is a ligand activated transcription factor belonging to the nuclear receptor subfamily, involved in fatty acid metabolism in tissues with high oxidative rates such as muscle, heart and liver. PPARα activation is important in steatosis, inflammation and fibrosis in preclinical models of non-alcoholic fatty liver disease identifying a new potential therapeutic area. In this work, three series of clofibric acid analogues conjugated with naphthyl, quinolin, chloroquinolin and anthracenyl scaffolds were synthesized. In an effort to obtain new compounds active as PPARα agonists, these molecules were evaluated for PPARα transactivation activity. Naphthyl and quinolin derivatives showed a good activation of PPARα; noteworthy, optically active naphthyl derivatives activated PPARα better than corresponding parent compound. © 2015 John Wiley & Sons A/S.

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

    Directory of Open Access Journals (Sweden)

    Shikha S. Dave

    2016-09-01

    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.

  14. Rapid establishment of phenol- and quinoline-degrading consortia driven by the scoured cake layer in an anaerobic baffled ceramic membrane bioreactor.

    Science.gov (United States)

    Wang, Wei; Wang, Shun; Ren, Xuesong; Hu, Zhenhu; Yuan, Shoujun

    2017-11-01

    Although toxic and refractory organics, such as phenol and quinoline, are decomposed by anaerobic bacteria, the establishment of specific degrading consortia is a relatively slow process. An anaerobic membrane bioreactor allows for complete biomass retention that can aid the establishment of phenol- and quinoline-degrading consortia. In this study, the anaerobic digestion of phenol (500 mg L -1 ) and quinoline (50 mg L -1 ) was investigated using an anaerobic baffled ceramic membrane bioreactor (ABCMBR). The results showed that, within 30 days, 99% of phenol, 98% of quinoline and 88% of chemical oxygen demand (COD) were removed. The substrate utilisation rates of the cake layer for phenol and quinoline, and specific methanogenic activity of the cake layer, were 7.58 mg phenol g -1  mixed liquor volatile suspended solids (MLVSS) day -1 , 8.23 mg quinoline g -1  MLVSS day -1 and 0.55 g COD CH4  g -1  MLVSS day -1 , respectively. The contribution of the cake layer to the removals of phenol and quinoline was extremely underestimated because the uncounted scoured cake layer was disregarded. Syntrophus was the key population for phenol and quinoline degradation, and it was more abundant in the cake layer than in the bulk sludge. The highly active scattered cake layer sped up the establishment of phenol- and quinoline-degrading consortia in the ABCMBR.

  15. Tandem Reduction/Cyclization of O-Nitrophenyl Propargyl Alcohols-A Novel Synthesis of 2- & 2,4-Disubstituted Quinolines and Application to the Synthesis of Streptonigrin

    National Research Council Canada - National Science Library

    Sandelier, Matthew J

    2008-01-01

    The quinoline ring system is a common structural component of a wide variety of natural products with highly desirable biological activity, including antimalarial agents such as quinine, chloroquine...

  16. Quinoline-3-carboxamide Derivatives as Potential Cholesteryl Ester Transfer Protein Inhibitors

    Directory of Open Access Journals (Sweden)

    Jing-Kang Shen

    2012-05-01

    Full Text Available A series of novel quinoline-3-carboxamide derivatives 1017 and 2327 were designed and synthesized as cholesteryl ester transfer protein (CETP inhibitors. All of them exhibited activity against CETP. Particularly, compounds 24 and 26 displayed the best activity against CETP with the same inhibitory rate of 80.1%.

  17. 8-[(3-Phenyl-1,2,4-oxadiazol-5-ylmethoxy]quinoline monohydrate

    Directory of Open Access Journals (Sweden)

    Shu-Yuan Bai

    2013-07-01

    Full Text Available In the title compound, C18H13N3O2·H2O, the oxadiazole ring forms dihedral angles 7.21 (10 and 21.25 (11° with the quinoline and benzene rings, respectively. The crystal structure features O—H...N hydrogen bonds and is further consolidated by C—H...O hydrogen-bonding interactions involving the water molecule of hydration.

  18. 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: dipanalka@yahoo.com [Department of Chemistry, Sardar Patel University Gujarat (India)

    2012-10-15

    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)

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

    Directory of Open Access Journals (Sweden)

    Yu-Hong Wang

    2012-08-01

    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.

  20. Synthesis and Antimicrobial Activity of Novel Substituted Ethyl 2-(Quinolin-4-yl-propanoates

    Directory of Open Access Journals (Sweden)

    Yong Zhou

    2013-03-01

    Full Text Available Substituted 4-hydroxyquinolines were synthesized from anilines and diethyl 2-(ethoxymethylenemalonate by the Gould-Jacobs reaction via cyclization of the intermediate anilinomethylenemalonate followed by hydrolysis and decarboxylation. The 4-hydroxyquinolines reacted with phosphorous oxychloride to form 4-chloroquinolines, which reacted on heating with diethyl sodiomethylmalonate in DMF to yield moderate yields of substituted ethyl 2-(quinolin-4-ylpropanoates, many of which showed potent antimicrobial activity against Helicobacter pylori.

  1. In vivo photoacoustic tumor tomography using a quinoline-annulated porphyrin as NIR molecular contrast agent.

    Science.gov (United States)

    Luciano, Michael; Erfanzadeh, Mohsen; Zhou, Feifei; Zhu, Hua; Bornhütter, Tobias; Röder, Beate; Zhu, Quing; Brückner, Christian

    2017-01-25

    The synthesis and photophysical properties of a tetra-PEG-modified and freely water-soluble quinoline-annulated porphyrin are described. We previously demonstrated the ability of quinoline-annulated porphyrins to act as an in vitro NIR photoacoustic imaging (PAI) contrast agent. The solubility of the quinoline-annulated porphyrin derivative in serum now allowed the assessment of the efficacy of the PEGylated derivative as an in vivo NIR contrast agent for the PAI of an implanted tumor in a mouse model. A multi-fold contrast enhancement when compared to the benchmark dye ICG could be shown, a finding that could be traced to its photophysical properties (short triplet lifetimes, low fluorescence and singlet oxygen sensitization quantum yields). A NIR excitation wavelength of 790 nm could be used, fully taking advantage of the optical window of tissue. Rapid renal clearance of the dye was observed. Its straight-forward synthesis, optical properties with the possibility for further optical fine-tuning, nontoxicity, favorable elimination rates, and contrast enhancement make this a promising PAI contrast agent. The ability to conjugate the PAI chromophore with a fluorescent tag using a facile and general conjugation strategy was also demonstrated.

  2. 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: n.sekar@ictmumbai.edu.in

    2014-11-15

    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.

  3. Ultrasound mediated catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones leading to novel quinoline derivatives: their evaluation as potential anti-cancer agents.

    Science.gov (United States)

    Mulakayala, Naveen; Rambabu, D; Raja, Mohan Rao; M, Chaitanya; Kumar, Chitta Suresh; Kalle, Arunasree M; Rama Krishna, G; Malla Reddy, C; Basaveswara Rao, M V; Pal, Manojit

    2012-01-15

    A facile and catalyst free synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-ones has been accomplished via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with various aromatic amines in the presence of ultrasound. Some of these compounds were converted to the corresponding 2-(3-(hydroxymethyl)quinolin-2-yl)phenols and further structure elaboration of a representative quinoline derivative is presented. Molecular structure of two representative compounds was confirmed by single crystal X-ray diffraction study. Many of these compounds were evaluated for their anti-proliferative properties in vitro against four cancer cell lines and several compounds were found to be active. Further in vitro studies indicated that inhibition of sirtuins could be the possible mechanism of action of these molecules. Copyright © 2011 Elsevier Ltd. All rights reserved.

  4. 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.

    A synthesis of a series of novel 6H-indolo[2,3-b]- quinolines with different substituents on the quinoline ring is described. The method involves reaction of indole-3-carboxyaldehyde with aryl amines in the presence of a catalytic amount of iodine...

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

    International Nuclear Information System (INIS)

    Cuca-Suarez, Luis Enrique; Barrera, Ericsson David Coy; Alvarez Caballero, Juan Manuel

    2011-01-01

    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 ( 1 H, 13 C, 1 D, 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)

  6. 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

    2011-07-01

    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)

  7. 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

    2011-05-15

    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.)

  8. Crystallization and preliminary X-ray crystallographic analysis of quinolinate phosphoribosyltransferase from porcine kidney in complex with nicotinate mononucleotide

    International Nuclear Information System (INIS)

    Youn, Hyung-Seop; Kim, Mun-Kyoung; Kang, Gil Bu; Kim, Tae Gyun; An, Jun Yop; Lee, Jung-Gyu; Park, Kyoung Ryoung; Lee, Youngjin; Fukuoka, Shin-Ichi; Eom, Soo Hyun

    2012-01-01

    Crystals of S. scrofa quinolinate phosphoribosyltransferase purified from porcine kidney in complex with nicotinate mononucleotidewere obtained and diffraction data were collected and processed to 2.1 Å resolution. Quinolinate phosphoribosyltransferase (QAPRTase) is a key enzyme in NAD biosynthesis; it catalyzes the formation of nicotinate mononucleotide (NAMN) from quinolinate and 5-phosphoribosyl-1-pyrophosphate. In order to elucidate the mechanism of NAMN biosynthesis, crystals of Sus scrofa QAPRTase (Ss-QAPRTase) purified from porcine kidney in complex with NAMN were obtained and diffraction data were collected and processed to 2.1 Å resolution. The Ss-QAPRTase–NAMN cocrystals belonged to space group P321, with unit-cell parameters a = 119.1, b = 119.1, c = 93.7 Å, γ = 120.0°. The Matthews coefficient and the solvent content were estimated as 3.10 Å 3 Da –1 and 60.3%, respectively, assuming the presence of two molecules in the asymmetric unit

  9. Crystal structure of bis(azido-κNbis(quinolin-8-amine-κ2N,N′iron(II

    Directory of Open Access Journals (Sweden)

    Fatima Setifi

    2016-10-01

    Full Text Available The search for new molecular materials with interesting magnetic properties using the pseudohalide azide ion and quinolin-8-amine (aqin, C9H8N2 as a chelating ligand, led to the synthesis and structure determination of the title complex, [Fe(N32(C9H8N22]. The complex shows an octahedral geometry, with the FeII atom surrounded by six N atoms; the two N3− anions coordinate in a cis configuration, while the remaining N atoms originate from the two quinolin-8-amine ligands with the quinoline N atoms lying on opposite sides of the Fe atom. The crystal packing is dominated by layers of hydrophilic and aromatic regions parallel to the ac plane, stabilized by a two-dimensional hydrogen-bonded network and π–π stacking.

  10. GAS PHASE SYNTHESIS OF (ISO)QUINOLINE AND ITS ROLE IN THE FORMATION OF NUCLEOBASES IN THE INTERSTELLAR MEDIUM

    International Nuclear Information System (INIS)

    Parker, Dorian S. N.; Kaiser, Ralf I.; Kostko, Oleg; Troy, Tyler P.; Ahmed, Musahid; Mebel, Alexander M.; Tielens, Alexander G. G. M.

    2015-01-01

    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

  11. Grafting polyethylenimine with quinoline derivatives for targeted imaging of intracellular Zn2+ and logic gate operations

    International Nuclear Information System (INIS)

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

    2016-01-01

    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 38.1 nM, 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. - Graphical abstract: The fluorescent Zn 2+ probe, PEIQ, is facilely synthesized by grafting PEI with 8-CAAQ, and demonstrated for the pratical applications in Zn 2+ imaging and implementation of molecular logic operations within biological cells. - Highlights: • PEIQ, fluorescent Zn 2+ probe, is synthesized by grafting PEI with quinoline derivatives. • PEIQ exhibits high sensitivity and selectivity in absolute aqueous solution. • PEIQ is biocompatible, water soluble, and cell-membrane permeable. • Elementary logic operations have been demonstrated for PEIQ/Zn 2+ /EDTA system. • The practical application of PEIQ in living cell imaging is demonstrated.

  12. Visible-light-promoted and one-pot synthesis of phenanthridines and quinolines from aldehydes and O-acyl hydroxylamine.

    Science.gov (United States)

    An, Xiao-De; Yu, Shouyun

    2015-06-05

    A one-pot synthesis of phenanthridines and quinolines from commercially available or easily prepared aldehydes has been reported. O-(4-Cyanobenzoyl)hydroxylamine was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes catalyzed by Brønsted acid. O-Acyl oximes were then subjected to visible light photoredox catalyzed cyclization via iminyl radicals to furnish aza-arenes. A variety of phenanthridines and quinolines have been prepared assisted by Brønsted acid and photocatalyst under visible light at room temperature with satisfactory yields.

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

    Science.gov (United States)

    Jaglarz, Janusz; Kępińska, Mirosława; Sanetra, Jerzy

    2014-06-01

    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].

  14. Synthesis of Novel Benzimidazolyl-substituted Acrylonitriles and Amidino-substituted Benzimidazo[1,2-a]Quinolines

    Directory of Open Access Journals (Sweden)

    Grace Karminski-Zamola

    2006-08-01

    Full Text Available A series of novel benzimidazole derivatives 3-10 were synthesized. Benzimidazolyl-substituted acrylonitriles 3 and 4 underwent a photochemical dehydrocyclization reaction to give the corresponding mono- and dicyano-substituted benzimidazo[1,2-a] quinolines 5 and 6. Pinner reaction of these compounds did not give the expected mono- and diamidines, but rather only compounds 7-10, with amido groups at 6-position were isolated. A mechanism for the reaction is proposed. Acyclic compounds 3 and 4, as well as cyclic benzimidazo[1,2-a]quinolines 5-8, exhibit interesting spectroscopic properties and are potential biologically active compounds.

  15. Crystal structure of bis(3-bromomesityl(quinolin-1-ium-8-ylboron(III tribromide

    Directory of Open Access Journals (Sweden)

    Jungho Son

    2015-09-01

    Full Text Available The title compound, C27H26.82BBr2.18N+·Br3−, is a cationic triarylborane isolated as its tribromide salt. The aryl substituents include a protonated 8-quinolyl group and two 3-bromomesityl groups. The molecule was prepared on combination of 3:1 Br2 and dimesityl(quinolin-8-ylborane in hexanes. The refinement of the structure indicated a degree of `over-bromination' (beyond two bromine atoms for the cation. There are two tribromide ions in the asymmetric unit, both completed by crystallographic inversion symmetry.

  16. Effect of quinolinic acid in the nucleus basalis magnocellularis on cortical high-affinity choline uptake

    Energy Technology Data Exchange (ETDEWEB)

    Metcalf, R.H.; Boegman, R.J.; Quirion, R.; Riopelle, R.J.; Ludwin, S.K.

    1987-08-01

    A transient 45% increase in cortical high-affinity choline uptake (HACU) was observed after an injection of quinolinic acid (QUIN) into the nucleus basalis magnocellularis (nbM) of the rat. This was followed by a steady decline in choline uptake, which resulted in a 46% decrease by day 7. Specific (/sup 3/H)hemicholinium-3 binding to coronal brain sections showed a similar pattern following injections of QUIN into the nbM. The increase in cortical HACU elicited by QUIN appeared to be dose dependent.

  17. Ternary systems, consist of erbium nitrates, water and nitrates of pyridines, quinolines

    International Nuclear Information System (INIS)

    Starikova, L.I.; Zhuravlev, E.F.; Khalfina, L.R.

    1979-01-01

    At 25 and 50 deg C investigated is solubility of solid phases in ternary water salt systems: erbium nitrate-pyridine nitrate-water; erbium nitrate-quinoline nitrate-water. Formation of congruently soluble compounds of the Er(NO 3 ) 3 x2C 5 H 5 NxHNO 3 , Er(NO 3 ) 3 x2C 9 H 7 NxHNO 3 x4H 2 O composition is established. X-ray phase and thermogravimetric analyses have been carried out

  18. Electronic structure and magnetism in transition metals doped 8-hydroxy-quinoline aluminum.

    Science.gov (United States)

    Baik, Jeong Min; Shon, Yoon; Lee, Seung Joo; Jeong, Yoon Hee; Kang, Tae Won; Lee, Jong-Lam

    2008-10-15

    We report the room-temperature ferromagnetism in transition metals (Co, Ni)-doped 8-hydroxy-quinoline aluminum (Alq3) by thermal coevaporation of high purity metal and Alq3 powders. For 5% Co-doped Alq3, a maximum magnetization of approximately 0.33 microB/Co at 10 K was obtained and ferromagnetic behavior was observed up to 300 K. The Co atoms interact chemically with O atoms and provide electrons to Alq3, forming new states acting as electron trap sites. From this, it is suggested that ferromagnetism may be associated with the strong chemical interaction of Co atoms and Alq3 molecules.

  19. 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.

    1997-01-01

    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....

  20. Ring-substituted 4-Hydroxy-1H-quinolin-2-ones: Preparation and Biological Activity

    Directory of Open Access Journals (Sweden)

    Jiri Dohnal

    2009-03-01

    Full Text Available In the study, a series of twelve ring-substituted 4-hydroxy-1H-quinolin-2-one derivatives were prepared. The procedures for synthesis of the compounds are presented. The compounds were analyzed using RP-HPLC to determine lipophilicity and tested for their photosynthesis-inhibiting activity using spinach (Spinacia oleracea L. chloroplasts. All the synthesized compounds were also evaluated for antifungal activity using in vitro screening with eight fungal strains. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds are discussed, as well as their structure-activity relationships (SAR.

  1. T3P- A Novel Catalyst for Aza-Diels-Alder Reaction: One-Pot Synthesis of Pyrano[3,2-c]quinolines and furano[3,2-c]quinolines

    Directory of Open Access Journals (Sweden)

    T. S. R. Prasanna

    2011-01-01

    Full Text Available T3P was found to be an efficient catalyst for the Aza-Diels–Alder reactions of aldimines with dihydropyran or dihydrofuran to afford the corresponding pyrano-and furo [3,2-c]quinolines in high yields with high diastereoselectivity in a short period of time.

  2. Spectroscopic determination of ionization constants of quinoline and 3-aminoquinoline at different temperature

    International Nuclear Information System (INIS)

    Indhar, H.A.B.

    2000-01-01

    Quinoline and its derivative are chemically and biologically important heterocylic compounds. Its ionization constant (pK/sub a/ values have been previously determined only at 18 or 20 deg. C. We have enhanced this work at different temperatures from 20-50 deg. C at the interval of 5 deg. C. The dissociation constants (pk/sub a/s), and Gibb's free energies of quinoline and 3-aminoquinoline have been determined by UV-Spectrophotometer (lambda 2) equipped with a temperature control of - + 0.1 deg. C at temperatures ranging from 20-50 deg. C in water. The experimental data have been used for the determination of thermodynamic ionization constants (pk /sub a //sup t/) sub t/, concentration ionization constants (pK/sub a//sup M/) and Gibbs's free energy values of pK/sub a/sup M/. The ionization constant values decrease with increase of temperature. The significance of relative magnitudes of the values is discussed and some useful generalization are obtained. The curves are parabolic. A computer program in GW-BASIC calculates the values of dissociation constants. From the pK/sub a/ values, Gibb's free energies are compared and discussed. (author)

  3. Experimental and theoretical studies on IR, Raman, and UV-Vis spectra of quinoline-7-carboxaldehyde.

    Science.gov (United States)

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

    2015-01-05

    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. Copyright © 2014 Elsevier B.V. All rights reserved.

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

    Energy Technology Data Exchange (ETDEWEB)

    Nuri Kursunlu, Ahmed, E-mail: ankursunlu@gmail.com; Guler, Ersin

    2014-01-15

    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.

  5. Surface protection of mild steel in acidic chloride solution by 5-Nitro-8-Hydroxy Quinoline

    Directory of Open Access Journals (Sweden)

    R. Ganapathi Sundaram

    2018-03-01

    Full Text Available The effect of commercially available quinoline nucleus based pharmaceutically active compound 5-Nitro-8-Hydroxy Quinoline (NHQ against the corrosion of mild steel (MS in 1 M acidic chloride (HCl solution was investigated by chemical (weight loss – WL and electrochemical (Tafel polarization, Linear polarization and Electrochemical impedance spectroscopy techniques. From all the four methods, it is inferred that the percentage of inhibition efficiency increases with increasing the inhibitor concentration from 50 to 300 ppm. The adsorption behavior of inhibitor obeyed through Langmuir isotherm model. Thermodynamic parameters were also calculated and predict that the process of inhibition is a spontaneous reaction. EIS technique exhibits one capacitive loop indicating that, the corrosion reaction is controlled by charge transfer process. Tafel polarization studies revealed that the investigated inhibitor is mixed type and the mode of adsorption is physical in nature. The surface morphologies were examined by FT-IR, SEM and EDX techniques. Theoretical quantum chemical calculations were performed to confirm the ability of NHQ to adsorb onto mild steel surface. Keywords: Acidic chloride solution, MS, NHQ, WL, SEM, FT-IR

  6. Essential role of Bordetella NadC in a quinolinate salvage pathway for NAD biosynthesis.

    Science.gov (United States)

    Brickman, Timothy J; Suhadolc, Ryan J; McKelvey, Pamela J; Armstrong, Sandra K

    2017-02-01

    Nicotinamide adenine dinucleotide (NAD) is produced via de novo biosynthesis pathways and by salvage or recycling routes. The classical Bordetella bacterial species are known to be auxotrophic for nicotinamide or nicotinic acid. This study confirmed that Bordetella bronchiseptica, Bordetella pertussis and Bordetella parapertussis have the recycling/salvage pathway genes pncA and pncB, for use of nicotinamide or nicotinic acid, respectively, for NAD synthesis. Although these Bordetellae lack the nadA and nadB genes needed for de novo NAD biosynthesis, remarkably, they have one de novo pathway gene, nadC, encoding quinolinate phosphoribosyltransferase. Genomic analyses of taxonomically related Bordetella and Achromobacter species also indicated the presence of an 'orphan' nadC and the absence of nadA and nadB. When supplied as the sole NAD precursor, quinolinate promoted B. bronchiseptica growth, and the ability to use it required nadC. Co-expression of Bordetella nadC with the nadB and nadA genes of Paraburkholderia phytofirmans allowed B. bronchiseptica to grow in the absence of supplied pyridines, indicative of de novo NAD synthesis and functional confirmation of Bordetella NadC activity. Expression of nadC in B. bronchiseptica was influenced by nicotinic acid and by a NadQ family transcriptional repressor, indicating that these organisms prioritize their use of pyridines for NAD biosynthesis. © 2016 John Wiley & Sons Ltd.

  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

    2011-01-01

    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...

  8. New inorganic-organic hybrid materials based on SBA-15 molecular sieves involved in the quinolines synthesis

    Czech Academy of Sciences Publication Activity Database

    López-Sanz, J.; Pérez-Mayoral, E.; Soriano, E.; Sturm, M.; Martín-Aranda, R. M.; López-Peinado, A. J.; Čejka, Jiří

    2012-01-01

    Roč. 187, č. 1 (2012), s. 97-103 ISSN 0920-5861 R&D Projects: GA AV ČR KAN100400701 Institutional support: RVO:61388955 Keywords : mesoporous molecular sieves * heterogeneous catalysis * quinolines Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 2.980, year: 2012

  9. Approaches for introducing high molecular diversity in scaffolds: fast parallel synthesis of highly substituted 1H-quinolin-4-one libraries.

    Science.gov (United States)

    Kuznetsov, Vladimir; Gorohovsky, Sofia; Levy, Amalia; Meir, Simcha; Shkoulev, Vladimir; Menashe, Naim; Greenwald, Moshe; Aizikovich, Alexander; Ofer, Dror; Byk, Gerardo; Gellerman, Garry

    2004-01-01

    We have developed a two steps strategy for the parallel synthesis of highly diversified quinolin-ones. In the first step we have combined and improved different synthetic methods for generating quinolin-4-ones bearing four different substitutions at specific positions using round bottomed flasks. The synthesis was assessed for a large number of substituted quinolin-4-ones. In the second step, the improved method was adapted to a parallel array synthesis using a 12 positions carrousel as demonstrated for the synthesis of 42-variable quinolin-4-ones. The first combinatorial library set 14(a-x) was obtained with a chemical purity of more than 95% without purification, the second library set 15(a-r), which included two synthetic steps, needed combinatorial purification using an innovative parallel purifier. The proposed approach contributes to a more extensive diversification of molecular scaffolds in general and provides access to highly substituted quinolinones in particular.

  10. HIV, prospective memory, and cerebrospinal fluid concentrations of quinolinic acid and phosphorylated Tau.

    Science.gov (United States)

    Anderson, Albert M; Croteau, David; Ellis, Ronald J; Rosario, Debra; Potter, Michael; Guillemin, Gilles J; Brew, Bruce J; Woods, Steven Paul; Letendre, Scott L

    2018-06-15

    There is mounting evidence that prospective memory (PM) is impaired during HIV infection despite treatment. In this prospective study, 66 adults (43 HIV+ and 23 HIV negative) underwent PM assessment and cerebrospinal fluid (CSF) examination. HIV+ participants had significantly lower PM but significantly higher CSF concentrations of CXCL10 and quinolinic acid (QUIN). Higher CSF phosphorylated Tau (pTau) was associated with worse PM. In a secondary analysis excluding outliers, higher QUIN correlated with higher pTau. CSF QUIN is thus elevated during HIV infection despite antiretroviral therapy and could indirectly contribute to impaired PM by influencing the formation of pTau. Copyright © 2018 Elsevier B.V. All rights reserved.

  11. 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: i.kityk@wsp.czest.pl; 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)

    2004-11-15

    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.

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

    Science.gov (United States)

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

    2004-11-01

    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.

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

    International Nuclear Information System (INIS)

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

    2004-01-01

    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

  14. Hydrogen-Bonding Interactions in Luminescent Quinoline-Triazoles with Dominant 1D Crystals

    Directory of Open Access Journals (Sweden)

    Shi-Qiang Bai

    2017-09-01

    Full Text Available Quinoline-triazoles 2-((4-(diethoxymethyl-1H-1,2,3-triazol-1-ylmethylquinoline (1, 2-((4-(m-tolyl-1H-1,2,3-triazol-1-ylmethylquinoline (2 and 2-((4-(p-tolyl-1H-1,2,3-triazol-1-ylmethylquinoline (3 have been prepared with CuAAC click reactions and used as a model series to probe the relationship between lattice H-bonding interaction and crystal direction of growth. Crystals of 1–3 are 1D tape and prism shapes that correlate with their intermolecular and solvent 1D lattice H-bonding interactions. All compounds were thermally stable up to about 200 C and blue-green emissive in solution.

  15. Quinoline-substituted Zinc(II) phthalocyanine for the dual detection of ferric and zinc ions

    Energy Technology Data Exchange (ETDEWEB)

    Gupta, Ankush [Lyallpur Khalsa College of Engineering, Jalandhar (India); Kim, A Rong [Dong-A University, Busan (Korea, Republic of); Kim, Kyung Sub; Na, Kun [The Catholic University, Seoul (Korea, Republic of); Choi, Myung Seok [Konkuk University, Seoul (Korea, Republic of); Park, Jong S. [Pusan National University, Busan (Korea, Republic of)

    2015-09-15

    Here we present the synthesis and properties of quinoline-substituted zinc(II) phthalocyanine, Zn[Pc(O-QN){sub 4} ]. Zn[Pc(O-QN){sub 4} ] can function as a highly selective chemosensor against Fe{sup 3+} and Zn{sup 2+} ions, exhibiting efficient fluorescence quenching and enhancement, respectively. Various characterization techniques were employed to investigate the intermolecular interactions of Zn[Pc(O-QN){sub 4} ] with metal ions. A double-electron exchange and a forbidden photoinduced electron transfer behavior in Zn[Pc(O-QN){sub 4} ] were attributed to such opposite responses. Furthermore, by taking advantage of selectivity, we successfully employed Zn[Pc(O-QN)-4 ] to stain and record confocal fluorescence microscopy images of Chang liver cells in the presence of metal ions.

  16. Quinolinium 8-hy-droxy-7-iodo-quinoline-5-sulfonate 0.8-hydrate.

    Science.gov (United States)

    Smith, Graham

    2012-12-01

    In the crystal structure of the title hydrated quinolinium salt of ferron (8-hy-droxy-7-iodo-quinoline-5-sulfonic acid), C9H7N(+)·C9H5INO4S(-)·0.8H2O, the quinolinium cation is fully disordered over two sites (occupancy factors fixed at 0.63 and 0.37) lying essentially within a common plane and with the ferron anions forming π-π-associated stacks down the b axis [minimum ring centroid separation = 3.462 (6) Å]. The cations and anions are linked into chains extending along c through hy-droxy O-H⋯O and quinolinium N-H⋯O hydrogen bonds to sulfonate O-atom acceptors which are also involved in water O-H⋯O hydrogen-bonding inter-actions along b, giving a two-dimensional network.

  17. Uridine monophosphate synthetase enables eukaryotic de novo NAD+ biosynthesis from quinolinic acid.

    Science.gov (United States)

    McReynolds, Melanie R; Wang, Wenqing; Holleran, Lauren M; Hanna-Rose, Wendy

    2017-07-07

    NAD + biosynthesis is an attractive and promising therapeutic target for influencing health span and obesity-related phenotypes as well as tumor growth. Full and effective use of this target for therapeutic benefit requires a complete understanding of NAD + biosynthetic pathways. Here, we report a previously unrecognized role for a conserved phosphoribosyltransferase in NAD + biosynthesis. Because a required quinolinic acid phosphoribosyltransferase (QPRTase) is not encoded in its genome, Caenorhabditis elegans are reported to lack a de novo NAD + biosynthetic pathway. However, all the genes of the kynurenine pathway required for quinolinic acid (QA) production from tryptophan are present. Thus, we investigated the presence of de novo NAD + biosynthesis in this organism. By combining isotope-tracing and genetic experiments, we have demonstrated the presence of an intact de novo biosynthesis pathway for NAD + from tryptophan via QA, highlighting the functional conservation of this important biosynthetic activity. Supplementation with kynurenine pathway intermediates also boosted NAD + levels and partially reversed NAD + -dependent phenotypes caused by mutation of pnc-1 , which encodes a nicotinamidase required for NAD + salvage biosynthesis, demonstrating contribution of de novo synthesis to NAD + homeostasis. By investigating candidate phosphoribosyltransferase genes in the genome, we determined that the conserved uridine monophosphate phosphoribosyltransferase (UMPS), which acts in pyrimidine biosynthesis, is required for NAD + biosynthesis in place of the missing QPRTase. We suggest that similar underground metabolic activity of UMPS may function in other organisms. This mechanism for NAD + biosynthesis creates novel possibilities for manipulating NAD + biosynthetic pathways, which is key for the future of therapeutics. © 2017 by The American Society for Biochemistry and Molecular Biology, Inc.

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

    Directory of Open Access Journals (Sweden)

    Daghastanli N.A.

    2004-01-01

    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.

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

    Science.gov (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

    2012-05-15

    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.

  20. Iodine-Mediated Intramolecular Dehydrogenative Coupling: Synthesis of N-Alkylindolo[3,2-c]- and -[2,3-c]quinoline Iodides.

    Science.gov (United States)

    Volvoikar, Prajesh S; Tilve, Santosh G

    2016-03-04

    An I2/TBHP-mediated intramolecular dehydrogenative coupling reaction is developed for the synthesis of a library of medicinally important 5,11-dialkylindolo[3,2-c]quinoline salts and 5,7-dimethylindolo[2,3-c]quinoline salts. The annulation reaction is followed by aromatization to yield tetracycles in good yield. This protocol is also demonstrated for the synthesis of the naturally occurring isocryptolepine in salt form.

  1. Synthesis and antibacterial activity of novel Pyrazolo [3, 4-B] quinoline based heterocyclic azo compounds and their dyeing performance

    International Nuclear Information System (INIS)

    Thaokar, Sanjay F.; Patel, Dinesh M.; Patel, Manish P.; Patel, Ranjan G.

    2007-01-01

    3-Amino-6-methyl-1H- pyrazolo [3, 4-B] quinoline was synthesized in good yield. Monoazo compounds were prepared using this intermediate as diazo component with various heterocyclic coupling components. All the azo compounds were characterized by their percentage yield, melting point, elemental analysis, UV-visible spectra, IR-spectra and dyeing performance on nylon and polyester fibres and by their antibacterial activity against gram positive and gram negative bacteria. (author)

  2. Detection of Quinoline in G. boninense-Infected Plants Using Functionalized Multi-Walled Carbon Nanotubes: A Field Study.

    Science.gov (United States)

    Akanbi, Fowotade Sulayman; Yusof, Nor Azah; Abdullah, Jaafar; Sulaiman, Yusran; Hushiarian, Roozbeh

    2017-07-01

    Carbon nanotubes (CNTs) reinforced with gold nanoparticles (AuNPs) and chitosan nanoparticles (CTSNPs) were anchored on a screen-printed electrode to fabricate a multi-walled structure for the detection of quinoline. The surface morphology of the nanocomposites and the modified electrode was examined by an ultra-high resolution field emission scanning electron microscope (FESEM), and Fourier-transform infrared (FT-IR) spectroscopy was used to confirm the presence of specific functional groups on the multi-walled carbon nanotubes MWCNTs. Cyclic voltammetry (CV) and linear sweep voltammetry (LSV) were used to monitor the layer-by-layer assembly of ultra-thin films of nanocomposites on the surface of the electrode and other electrochemical characterizations. Under optimized conditions, the novel sensor displayed outstanding electrochemical reactivity towards the electro-oxidation of quinoline. The linear range was fixed between 0.0004 and 1.0 μM, with a limit of detection (LOD) of 3.75 nM. The fabricated electrode exhibited high stability with excellent sensitivity and selectivity, specifically attributable to the salient characteristics of AuNPs, CTSNPs, and MWCNTs and the synergistic inter-relationship between them. The newly developed electrode was tested in the field. The Ipa increased with an increase in the amount of quinoline solution added, and the peak potential deviated minimally, depicting the real capability of the newly fabricated electrode.

  3. Detection of Quinoline in G. boninense-Infected Plants Using Functionalized Multi-Walled Carbon Nanotubes: A Field Study

    Directory of Open Access Journals (Sweden)

    Fowotade Sulayman Akanbi

    2017-07-01

    Full Text Available Carbon nanotubes (CNTs reinforced with gold nanoparticles (AuNPs and chitosan nanoparticles (CTSNPs were anchored on a screen-printed electrode to fabricate a multi-walled structure for the detection of quinoline. The surface morphology of the nanocomposites and the modified electrode was examined by an ultra-high resolution field emission scanning electron microscope (FESEM, and Fourier-transform infrared (FT-IR spectroscopy was used to confirm the presence of specific functional groups on the multi-walled carbon nanotubes MWCNTs. Cyclic voltammetry (CV and linear sweep voltammetry (LSV were used to monitor the layer-by-layer assembly of ultra-thin films of nanocomposites on the surface of the electrode and other electrochemical characterizations. Under optimized conditions, the novel sensor displayed outstanding electrochemical reactivity towards the electro-oxidation of quinoline. The linear range was fixed between 0.0004 and 1.0 μM, with a limit of detection (LOD of 3.75 nM. The fabricated electrode exhibited high stability with excellent sensitivity and selectivity, specifically attributable to the salient characteristics of AuNPs, CTSNPs, and MWCNTs and the synergistic inter-relationship between them. The newly developed electrode was tested in the field. The Ipa increased with an increase in the amount of quinoline solution added, and the peak potential deviated minimally, depicting the real capability of the newly fabricated electrode.

  4. Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn(II complexes

    Directory of Open Access Journals (Sweden)

    Mustapha C. Mandewale

    2018-02-01

    Full Text Available The quinoline hydrazone ligands were synthesized through multi-step reactions. The 2-hydroxy-3-formylquinoline derivatives (1a–1c were prepared from acetanilide derivatives as starting materials using Vilsmeier–Haack reaction. Then the condensation of 2-hydroxy-3-formylquinoline derivatives with hydrazide derivatives (2a–2c yielded quinoline hydrazone ligands (3a–3i. The synthesis of a new series of Zn(II complexes carried out by refluxing with these quinoline hydrazone ligands (3a–3i is reported. The molecular structures of the ligands (3a–3i and the Zn complexes were characterized by elemental analysis and spectral studies like FT-IR, 1H and 13C NMR, MS, UV–Visible and fluorescence. The preliminary results of antituberculosis study showed that most of the Zn(II complexes 4a–4i demonstrated very good antituberculosis activity while the ligands 3a–3i showed moderate activity. Among the tested compounds 4e and 4g were found to be most active with minimum inhibitory concentration (MIC of 8.00μM and 7.42 μM respectively against Mycobacterium tuberculosis (H37 RV strain ATCC No-27294 which is comparable to “first and second line” drugs used to treat tuberculosis.

  5. The purification of coal tar by the addition of quinoline and Zn(oh)/sub 2/

    International Nuclear Information System (INIS)

    Zhou, P.; Chen, Q.L.; Ao, X.Q.; Kang, C

    2017-01-01

    The coal tar was purified by the addition of quinoline and Zn(OH)2, in order to decrease the content of carbon and inorganic oxide particles. The effect on the viscosity and ash content of the coal tar were investigated by altering temperature, time, and the amount of quinolone and Zn(OH)2 . When the volume ratio between quinolone and coal tar was 20:1 and the static time was 24 h. The viscosity of three layers decreased with rising temperature. When the static temperature and time was 45 °C and 24 h, respectively. The viscosity of three layers decreased with the arising amount of quinoline. And when the volume ratio between quinolone and coal tar was 20:1 and the temperature was 45 °C. The viscosity of three layers decreased first and then increased with the prolonging of static time. And when the static time of coal tar was 24 h, the viscosity of coal tar is the lowest. Because of the lower viscosity of coal tar, decreasing the content of carbon and ash particles in upper and middle layer, the ash content decreased from 0.168% to 0.092%. The addition of Zn(OH)2 can lead ash content in middle layer decrease to 0.058%. Zn2SiO4 and ZnAl2O4 may be produced due to the reaction between Zn (OH) 2 and SiO2 or Al2O3, which can settle down easily. The results show that the content of carbon and inorganic oxide particles in upper-middle-class (the middle 4/5 of the whole volume) decreased with the addition of quinolone and Zn(OH)2 . When the volume ratio between quinolone and coal tar was 50:2, quality ratio between coal tar and Zn(OH)2 was 20000:1, the mixture were heated up to 45 °C at atmospheric pressure and keeping this constant temperature for 24 h, the ash content in upper-middle-class can decreased to 0.058%. (author)

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

    International Nuclear Information System (INIS)

    Pierozan, Paula; Ferreira, Fernanda; Ortiz de Lima, Bárbara; Gonçalves Fernandes, Carolina; Totarelli Monteforte, Priscila; Castro Medaglia, Natalia de; Bincoletto, Claudia; Soubhi Smaili, Soraya; Pessoa-Pureur, Regina

    2014-01-01

    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 32 P-orthophosphate and/or protein kinase A (PKA), protein kinase dependent of Ca 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 2+ quelators (1 mM EGTA; 10 µM BAPTA-AM, respectively) prevented QUIN-mediated effect, while Ca 2+ influx through voltage-dependent Ca 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 disorders. - Highlights:

  7. 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: rpureur@ufrgs.br [Departamento de Bioquímica, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS 90035-003 (Brazil)

    2014-04-01

    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

  8. Kinetics on the reaction of substituted quinolines and p-substituted benzoylchlorides under various pressures

    International Nuclear Information System (INIS)

    Kim, Young Cheul; Lim, Jong Wan; Choi, Sung Yong; Kim, Se Kyong

    1999-01-01

    The reaction rates of substituted quinolines(6-CH 3 C 9 H 7 N, C 9 H 7 N) with p-substituted benzoylchlorides(p-CH 3 , p-H, p-NO 2 ) have been measured by conductometry in acetonitrile, and the rate constants are determined at various temperatures (10,15, 20, 25 .deg. C) and pressures(1, 200, 500, 1000bar). From the values of rate constants, the activation parameters(Ea, ΔV ≠ , ΔS ≠ , and ΔG ≠ ) and the pressure dependence of Hammett ρ values were determined. The rate constants increase as a function of temperatures and pressures, and are further increase by introduction the electron donor substituents in nucleophile(p-CH 3 ) or electron acceptor(p-NO 2 ) substituents in substrate. The activation volume, and the activation entropy are all negative. Hammett ρ values are also negative for nucleophile (ρ X ) and positive for the substrate (ρ Y ) over the pressure range studied. The results of kinetic studies for pressure and substituent show that these reactions proceed in typical S N 2 reaction mechanism and 'associative S N 2' in which bond formation favored with increasing pressures

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

    Directory of Open Access Journals (Sweden)

    Ales Imramovsky

    2012-01-01

    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.

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

    Directory of Open Access Journals (Sweden)

    N.C. Desai

    2014-12-01

    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.

  11. N-Mesityl-C-acylketenimines: 1,5-Sigmatropic Shifts and Electrocyclization to Quinolines.

    Science.gov (United States)

    Rao, V. V. Ramana; Fulloon, Belinda E.; Bernhardt, Paul V.; Koch, Rainer; Wentrup, Curt

    1998-08-21

    Flash vacuum thermolysis (FVT) of triazoles 6a-c generates alpha-oxoketenimines 10, the ester 10a being isolable. FVT of pyrroledione 8 generates the isomeric imidoylketene 9a. Ketenes 9 and ketenimines 10 undergo thermal interconversion by 1,3-shifts of methoxy and dimethylamino groups under mild FVT conditions (ca. 350-400 degrees C). Both 9 and 10 are directly observable by IR spectroscopy at either 77 K or on Ar matrix isolation at 12 K. On FVT at temperatures above ca. 400 degrees C, the ketenimines 10 undergo a 1,5-H shift to o-quinoid imines 12/13, followed by electrocyclization to dihydroquinolines 14 (unobserved) and 15 (observed by NMR). The latter are easily oxidized to alkylquinoline-3-carboxylates or quinoline-3-carboxamides 16 by atmospheric oxygen. Ab initio calculations on model compounds 18-23 predict an energy barrier of ca. 38 kcal mol(-)(1) (161 kJ mol(-)(1)) for the 1,5-H shift in N-(o-methylphenyl)ketenimines via the transition state TS19 followed by an electrocyclization barrier to dihydroquinoline 23a via TS22a of ca. 16 kcal mol(-)(1).

  12. 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)

    2014-04-15

    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)

  13. Crystal structure of Sus scrofa quinolinate phosphoribosyltransferase in complex with nicotinate mononucleotide.

    Directory of Open Access Journals (Sweden)

    Hyung-Seop Youn

    Full Text Available We have determined the crystal structure of porcine quinolinate phosphoribosyltransferase (QAPRTase in complex with nicotinate mononucleotide (NAMN, which is the first crystal structure of a mammalian QAPRTase with its reaction product. The structure was determined from protein obtained from the porcine kidney. Because the full protein sequence of porcine QAPRTase was not available in either protein or nucleotide databases, cDNA was synthesized using reverse transcriptase-polymerase chain reaction to determine the porcine QAPRTase amino acid sequence. The crystal structure revealed that porcine QAPRTases have a hexameric structure that is similar to other eukaryotic QAPRTases, such as the human and yeast enzymes. However, the interaction between NAMN and porcine QAPRTase was different from the interaction found in prokaryotic enzymes, such as those of Helicobacter pylori and Mycobacterium tuberculosis. The crystal structure of porcine QAPRTase in complex with NAMN provides a structural framework for understanding the unique properties of the mammalian QAPRTase active site and designing new antibiotics that are selective for the QAPRTases of pathogenic bacteria, such as H. pylori and M. tuberculosis.

  14. Quinoline Alkaloids in Suspension Cultures of Cinchona ledgeriana Treated with Various Substances

    Directory of Open Access Journals (Sweden)

    DIAH RATNADEWI

    2010-12-01

    Full Text Available Cinchona alkaloids are in extensive uses, not only for drugs but also for soft drink industries. They are harvested from the bark of trees Cinchona spp. after certain ages and therefore are available over a limited time. Cell culture is an alternative way to continuously produce such secondary metabolites in a much shorter time. Various substances were added in the normal growth media to promote quinoline alkaloids production by cell cultures of Cinchona ledgeriana. At the sixth week of culture, quinine and cinchonine contents were suppressed by paclobutrazol (PBZ, abscisic acid (ABA, or even by precursor tryptophan, while cinchonidine content was enhanced by 0.2 mg/l tryptophan to 43 fold of that produced by untreated cells (2.8% dry weight. At the seventh week of culture, the production of quinine and quinidine started to grow whereas the production of cinchonine and cinchonidine tended to decrease. An addition of 5 mg/l PBZ to culture media yielded the highest level of total quinine/quinidine after seven weeks, e.g. quinine 11 times more abundant and quinidine 23 fold higher compared to the untreated cells. Particularly the level of quinine which is the most demanded for medical and industrial purposes still need to be improved to approach to or even higher than that of extracted from the conventional source.

  15. OF MICE, RATS AND MEN: REVISITING THE QUINOLINIC ACID HYPOTHESIS OF HUNTINGTON’S DISEASE

    Science.gov (United States)

    Schwarcz, R.; Guidetti, P.; Sathyasaikumar, K. V.; Muchowski, P. J.

    2009-01-01

    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 the early stages of the disease. PMID:19394403

  16. Synthesis and study of the α-amylase inhibitory potential of thiadiazole quinoline derivatives.

    Science.gov (United States)

    Taha, Muhammad; Tariq Javid, Muhammad; Imran, Syahrul; Selvaraj, Manikandan; Chigurupati, Sridevi; Ullah, Hayat; Rahim, Fazal; Khan, Fahad; Islam Mohammad, Jahidul; Mohammed Khan, Khalid

    2017-10-01

    α-Amylase is a target for type-2 diabetes mellitus treatment. However, small molecule inhibitors of α-amylase are currently scarce. In the course of developing small molecule α-amylase inhibitors, we designed and synthesized thiadiazole quinoline analogs (1-30), characterized by different spectroscopic techniques such as 1 HNMR and EI-MS and screened for α-amylase inhibitory potential. Thirteen analogs 1, 2, 3, 4, 5, 6, 22, 23, 25, 26, 27, 28 and 30 showed outstanding α-amylase inhibitory potential with IC 50 values ranges between 0.002±0.60 and 42.31±0.17μM which is many folds better than standard acarbose having IC 50 value 53.02±0.12μM. Eleven analogs 7, 9, 10, 11, 12, 14, 15, 17, 18, 19 and 24 showed good to moderate inhibitory potential while seven analogs 8, 13, 16, 20, 21 and 29 were found inactive. Our study identifies novel series of potent α-amylase inhibitors for further investigation. Structure activity relationship has been established. Copyright © 2017 Elsevier Inc. All rights reserved.

  17. Quinolinic Acid, an Endogenous Molecule Combining Excitotoxicity, Oxidative Stress and Other Toxic Mechanisms

    Directory of Open Access Journals (Sweden)

    Verónica Pérez-De La Cruz

    2012-01-01

    Full Text Available Quinolinic acid (QUIN, an endogenous metabolite of the kynurenine pathway, is involved in several neurological disorders, including Huntington's disease, Alzheimer's disease, schizophrenia, HIV associated dementia (HAD etc. QUIN toxicity involves several mechanisms which trigger various metabolic pathways and transcription factors. The primary mechanism exerted by this excitotoxin in the central nervous system (CNS has been largely related with the overactivation of N-methyl-D-aspartate receptors and increased cytosolic Ca 2+ concentrations, followed by mitochondrial dysfunction, cytochrome c release, ATP exhaustion, free radical formation and oxidative damage. As a result, this toxic pattern is responsible for selective loss of middle size striatal spiny GABAergic neurons and motor alterations in lesioned animals. This toxin has recently gained attention in biomedical research as, in addition to its proven excitotoxic profile, a considerable amount of evidence suggests that oxidative stress and energetic disturbances are major constituents of its toxic pattern in the CNS. Hence, this profile has changed our perception of how QUIN-related disorders combine different toxic mechanisms resulting in brain damage. This review will focus on the description and integration of recent evidence supporting old and suggesting new mechanisms to explain QUIN toxicity.

  18. 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)

    2016-06-15

    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.

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

    International Nuclear Information System (INIS)

    Park, Hee Jung; Yang, Ok-Kyung; Park, Young Chul; Yum, Eul Kgun

    2016-01-01

    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

  20. Structure of pyridine and quinoline vinyl ethers according to data from 1H and 13C NMR spectra and quantum-chemical calculations

    International Nuclear Information System (INIS)

    Afonin, A.V.; Voronov, V.K.; Andriankov, M.A.; Danovich, D.K.

    1987-01-01

    A systematic investigation of the structure of the vinyl ethers of heterocyclic compounds has not been undertaken. The present work was devoted to investigation of the stereochemical and electronic structure of the vinyl ethers of pyridine and quinoline. The PMR spectra of the samples were recorded for 5% solutions in deuterochloroform on a Tesla BS-497 spectrometer at 100 MHz. The 13 C NMR spectra were recorded on a Tesla BS-567A spectrometer at 25.1 MHz in deuterochloroform with the samples at concentrations of 30%. The internal standard was HMDS. The vinyl ethers of pyridine and quinoline exist preferentially in the nonplanar S-trans conformation. In the vinyl esters of pyridine and quinoline the p-π conjugation is concurrent in nature and depends on the position of the vinyloxy group in the heterocycle

  1. Grafting polyethylenimine with quinoline derivatives for targeted imaging of intracellular Zn{sup 2+} and logic gate operations

    Energy Technology Data Exchange (ETDEWEB)

    Pan, Yi; Shi, Yupeng; Chen, Junying; Wong, Chap-Mo; Zhang, Heng [Key Laboratory of Sensing Technology and Biomedical Instruments (Guangdong Province), School of Engineering, Sun Yat-Sen University, Guangzhou (China); Li, Mei-Jin [Key Laboratory of Analysis and Detection Technology for Food Safety, Ministry of Education and Fujian Province, Department of Chemistry, Fuzhou University, Fuzhou (China); Li, Cheuk-Wing [Institute of Chinese Medical Sciences, University of Macau (China); Yi, Changqing, E-mail: yichq@mail.sysu.edu.cn [Key Laboratory of Sensing Technology and Biomedical Instruments (Guangdong Province), School of Engineering, Sun Yat-Sen University, Guangzhou (China); Research Institute of Sun Yat-Sen University in Shenzhen, Shenzhen (China)

    2016-12-01

    In this study, a highly sensitive and selective fluorescent Zn{sup 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{sup 2+} and reduce the potential cytotoxicity of PEI. Basing on fluorescence off-on mechanism, PEIQ demonstrated excellent sensing capability towards Zn{sup 2+} in absolute aqueous solution, where a high sensitivity with a detection limit as low as 38.1 nM, 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{sup 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. - Graphical abstract: The fluorescent Zn{sup 2+} probe, PEIQ, is facilely synthesized by grafting PEI with 8-CAAQ, and demonstrated for the pratical applications in Zn{sup 2+} imaging and implementation of molecular logic operations within biological cells. - Highlights: • PEIQ, fluorescent Zn{sup 2+} probe, is synthesized by grafting PEI with quinoline derivatives. • PEIQ exhibits high sensitivity and selectivity in absolute aqueous solution. • PEIQ is biocompatible, water soluble, and cell-membrane permeable. • Elementary logic operations have been demonstrated for PEIQ/Zn{sup 2+}/EDTA system. • The practical application of PEIQ in living cell imaging is demonstrated.

  2. Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activities of β-Carboline and Quinoline Alkaloids Derivatives from the Plants of Genus Peganum

    Directory of Open Access Journals (Sweden)

    Ting Zhao

    2013-01-01

    Full Text Available It was reported that the main chemical constituents in plants of genus Peganum were a serial of β-carboline and quinoline alkaloids. These alkaloids were quantitatively assessed for selective inhibitory activities on acetylcholinesterase (AChE and butyrylcholinesterase (BChE by in vitro Ellman method. The results indicated that harmane was the most potent selective AChE inhibitor with an IC50 of 7.11 ± 2.00 μM and AChE selectivity index (SI, IC50 of BChE/IC50 of AChE of 10.82. Vasicine was the most potent BChE inhibitor with feature of dual AChE/BChE inhibitory activity, with an IC50 versus AChE/BChE of 13.68 ± 1.25/2.60 ± 1.47 μM and AChE SI of 0.19. By analyzing and comparing the IC50 and SI of those chemicals, it was indicated that the β-carboline alkaloids displayed more potent AChE inhibition but less BChE inhibition than quinoline alkaloids. The substituent at the C7 position of the β-carboline alkaloids and C3 and C9 positions of quinoline alkaloids played a critical role in AChE or BChE inhibition. The potent inhibition suggested that those alkaloids may be used as candidates for treatment of Alzheimer’s disease. The analysis of the quantitative structure-activity relationship of those compounds investigated might provide guidance for the design and synthesis of AChE and BChE inhibitors.

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

    Directory of Open Access Journals (Sweden)

    Mullié Catherine

    2012-03-01

    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.

  4. Investigation of prototypal MOFs consisting of polyhedral cages with accessible Lewis-acid sites for quinoline synthesis.

    Science.gov (United States)

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

    2015-03-21

    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.

  5. Antiperoxidative and antiinflammatory effect of Sida cordifolia Linn. on quinolinic acid induced neurotoxicity.

    Science.gov (United States)

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

    2010-09-01

    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.

    Science.gov (United States)

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

    2015-02-01

    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. © 2014 Wiley Periodicals, Inc.

  7. Kynurenic Acid Prevents Cytoskeletal Disorganization Induced by Quinolinic Acid in Mixed Cultures of Rat Striatum.

    Science.gov (United States)

    Pierozan, Paula; Biasibetti-Brendler, Helena; Schmitz, Felipe; Ferreira, Fernanda; Pessoa-Pureur, Regina; Wyse, Angela T S

    2018-06-01

    Kynurenic acid (KYNA) is a neuroactive metabolite of tryptophan known to modulate a number of mechanisms involved in neural dysfunction. Although its activity in the brain has been widely studied, the effect of KYNA counteracting the actions of quinolinic acid (QUIN) remains unknown. The present study aims at describing the ability of 100 μM KYNA preventing cytoskeletal disruption provoked by QUIN in astrocyte/neuron/microglia mixed culture. KYNA totally preserved cytoskeletal organization, cell morphology, and redox imbalance in mixed cultures exposed to QUIN. However, KYNA partially prevented morphological alteration in isolated primary astrocytes and failed to protect the morphological alterations of neurons caused by QUIN exposure. Moreover, KYNA prevented QUIN-induced microglial activation and upregulation of ionized calcium-binding adapter molecule 1 (Iba-1) and partially preserved tumor necrosis factor-α (TNF-α) level in mixed cultures. TNF-α level was also partially preserved in astrocytes. In addition to the mechanisms dependent on redox imbalance and microglial activation, KYNA prevented downregulation of connexin-43 and the loss of functionality of gap junctions (GJs), preserving cell-cell contact, cytoskeletal organization, and cell morphology in QUIN-treated cells. Furthermore, the toxicity of QUIN targeting the cytoskeleton of mixed cultures was not prevented by the N-methyl-D-aspartate (NMDA) antagonist MK-801. We suggest that KYNA protects the integrity of the cytoskeleton of mixed cultures by complex mechanisms including modulating microglial activation preventing oxidative imbalance and misregulated GJs leading to disrupted cytoskeleton in QUIN-treated cells. This study contributed to elucidate the molecular basis of KYNA protection against QUIN toxicity.

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

    Directory of Open Access Journals (Sweden)

    Sukhbir Lal Khokra

    2016-11-01

    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.

  9. 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.

  10. Neuroprotective Activity of Curcumin in Combination with Piperine against Quinolinic Acid Induced Neurodegeneration in Rats.

    Science.gov (United States)

    Singh, Shamsher; Kumar, Puneet

    2016-01-01

    Quinolinic acid (QA) is an excitotoxin that induces Huntington's-like symptoms in animals and humans. Curcumin (CMN) is a well-known antioxidant but the major problem is its bioavailability. Therefore, the present study was designed to investigate the effect of CMN in the presence of piperine against QA-induced excitotoxic cell death in rats. QA was administered intrastriatally at a dose of 200 nmol/2 µl saline, bilaterally. CMN (25 and 50 mg/kg/day, p.o.) and combination of CMN (25 mg/kg/day, p.o.) and with piperine (2.5 mg/kg/day, p.o.) was administered daily for the next 21 days. Body weight and behavioral parameters were observed on 1st, 7th, 14th and 21st day. On the 22nd day, animals were sacrificed and striatum was isolated for biochemical (LPO, nitrite and GSH), neuroinflammatory (interleukin (IL)-1β, IL-6 and TNF-α) and neurochemical (dopamine, norepinephrine, GABA, glutamate, 5-HT, 3,4-dihydroxyphenylacetic acid and homovanillic acid) estimation. CMN treatment showed beneficial effect against QA-induced motor deficit, biochemical and neurochemical abnormalities in rats. Combination of piperine (2.5 mg/kg/day, p.o.) with CMN (25 mg/kg/day, p.o.) significantly enhanced its protective effect as compared to treatment with CMN alone. This study has revealed that the combination of CMN and piperine showed strong antioxidant and protective effect against QA-induced behavioral and neurological alteration in rats. © 2016 S. Karger AG, Basel.

  11. Interference with hemozoin formation represents an important mechanism of schistosomicidal action of antimalarial quinoline methanols.

    Directory of Open Access Journals (Sweden)

    Juliana B R Corrêa Soares

    Full Text Available BACKGROUND: The parasitic trematode Schistosoma mansoni is one of the major causative agents of human schistosomiasis, which afflicts 200 million people worldwide. Praziquantel remains the main drug used for schistosomiasis treatment, and reliance on the single therapy has been prompting the search for new therapeutic compounds against this disease. Our group has demonstrated that heme crystallization into hemozoin (Hz within the S. mansoni gut is a major heme detoxification route with lipid droplets involved in this process and acting as a potential chemotherapeutical target. In the present work, we investigated the effects of three antimalarial compounds, quinine (QN, quinidine (QND and quinacrine (QCR in a murine schistosomiasis model by using a combination of biochemical, cell biology and molecular biology approaches. METHODOLOGY/PRINCIPAL FINDINGS: Treatment of S. mansoni-infected female Swiss mice with daily intraperitoneal injections of QN, and QND (75 mg/kg/day from the 11(th to 17(th day after infection caused significant decreases in worm burden (39%-61% and egg production (42%-98%. Hz formation was significantly inhibited (40%-65% in female worms recovered from QN- and QND-treated mice and correlated with reduction in the female worm burden. We also observed that QN treatment promoted remarkable ultrastructural changes in male and female worms, particularly in the gut epithelium and reduced the granulomatous reaction to parasite eggs trapped in the liver. Microarray gene expression analysis indicated that QN treatment increased the expression of transcripts related to musculature, protein synthesis and repair mechanisms. CONCLUSIONS: The overall significant reduction in several disease burden parameters by the antimalarial quinoline methanols indicates that interference with Hz formation in S. mansoni represents an important mechanism of schistosomicidal action of these compounds and points out the heme crystallization process as a

  12. Synthesis of samarium complexes with the derivative binder of Schiff Quinolinic base. Characterization and photophysical study

    International Nuclear Information System (INIS)

    Lucas H, J.

    2016-01-01

    In this work we determined the metal: binder stoichiometry of the species formed during the UV/Vis spectrophotometric titration of the derivative binder of Schiff quinolinic base, L1 with the samarium nitrate pentahydrate in methanol. Statistical analysis of the data allowed proposing the metal: binder stoichiometry for the synthesis of the complexes which was one mole of samarium salt by 2.5 moles of binder and thus favor the formation of complexes with 1M: 1L and 1M: 2L stoichiometries. They were synthesized in aqueous-organic medium (water-ethanol), isolated and purified two complexes with stoichiometry 1 Sm: 1 L1, complex 1 and 1 Sm: 2 L1, complex 2. The overall yield of the reaction was 76%. The characterization of the formed complexes was performed by visible ultraviolet spectrometry (UV/Vis), nuclear magnetic resonance, X-ray photoelectron spectroscopy (XP S), thermal gravimetric analysis with differential scanning calorimetry (TGA/DSC), and radial distribution function. These complexes were studied by fluorescence and emission phosphorescence at variable temperature. Spectroscopic techniques used in both solution and solid demonstrated the formation and stability of these complexes. In addition XP S indicated that in both complexes the samarium retains its oxidation state 3+. Luminescence studies indicated that there is intra-binding charge transfer which decreases the transfer of light energy from the binder to the samarium. Based on the experimental results, L1 binder molecules and complexes 1 and 2 were modeled that demonstrated the proposed Nc for each complex, as well as allowed to visualize the structural arrangement of the molecules, complexes and binder. (Author)

  13. Molecular reorganization of selected quinoline derivatives in the ground and excited states—Investigations via static DFT

    Science.gov (United States)

    Błaziak, Kacper; Panek, Jarosław J.; Jezierska, Aneta

    2015-07-01

    Quinoline derivatives are interesting objects to study internal reorganizations due to the observed excited-state-induced intramolecular proton transfer (ESIPT). Here, we report on computations for selected 12 quinoline derivatives possessing three kinds of intramolecular hydrogen bonds. Density functional theory was employed for the current investigations. The metric and electronic structure simulations were performed for the ground state and first excited singlet and triplet states. The computed potential energy profiles do not show a spontaneous proton transfer in the ground state, whereas excited states exhibit this phenomenon. Atoms in Molecules (AIM) theory was applied to study the nature of hydrogen bonding, whereas Harmonic Oscillator Model of aromaticity index (HOMA) provided data of aromaticity evolution as a derivative of the bridge proton position. The AIM-based topological analysis confirmed the presence of the intramolecular hydrogen bonding. In addition, using the theory, we were able to provide a quantitative illustration of bonding transformation: from covalent to the hydrogen. On the basis of HOMA analysis, we showed that the aromaticity of both rings is dependent on the location of the bridge proton. Further, the computed results were compared with experimental data available. Finally, ESIPT occurrence was compared for the three investigated kinds of hydrogen bridges, and competition between two bridges in one molecule was studied.

  14. Molecular reorganization of selected quinoline derivatives in the ground and excited states—Investigations via static DFT

    International Nuclear Information System (INIS)

    Błaziak, Kacper; Panek, Jarosław J.; Jezierska, Aneta

    2015-01-01

    Quinoline derivatives are interesting objects to study internal reorganizations due to the observed excited-state-induced intramolecular proton transfer (ESIPT). Here, we report on computations for selected 12 quinoline derivatives possessing three kinds of intramolecular hydrogen bonds. Density functional theory was employed for the current investigations. The metric and electronic structure simulations were performed for the ground state and first excited singlet and triplet states. The computed potential energy profiles do not show a spontaneous proton transfer in the ground state, whereas excited states exhibit this phenomenon. Atoms in Molecules (AIM) theory was applied to study the nature of hydrogen bonding, whereas Harmonic Oscillator Model of aromaticity index (HOMA) provided data of aromaticity evolution as a derivative of the bridge proton position. The AIM-based topological analysis confirmed the presence of the intramolecular hydrogen bonding. In addition, using the theory, we were able to provide a quantitative illustration of bonding transformation: from covalent to the hydrogen. On the basis of HOMA analysis, we showed that the aromaticity of both rings is dependent on the location of the bridge proton. Further, the computed results were compared with experimental data available. Finally, ESIPT occurrence was compared for the three investigated kinds of hydrogen bridges, and competition between two bridges in one molecule was studied

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

    International Nuclear Information System (INIS)

    Pirali, O.; Gruet, S.; Kisiel, Z.; Goubet, M.; Martin-Drumel, M. A.; Cuisset, A.; Hindle, F.; Mouret, G.

    2015-01-01

    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 9 H 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 45 and ν 44 vibrational modes (located at about 168 cm −1 and 178 cm −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

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

    Science.gov (United States)

    Pirali, O.; Kisiel, Z.; Goubet, M.; Gruet, S.; Martin-Drumel, M. A.; Cuisset, A.; Hindle, F.; Mouret, G.

    2015-03-01

    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 C9H7N, an N-bearing naphthalene derivative. While the pure rotational ground state spectrum of quinoline is unperturbed, severe complications appear in the spectra of the ν45 and ν44 vibrational modes (located at about 168 cm-1 and 178 cm-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.

  17. Laboratory Infrared Spectra of Polycyclic Aromatic Nitrogen Heterocycles: Quinoline, and Phenanthridine in Solid Argon and H2O

    Science.gov (United States)

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

    2004-01-01

    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.

  18. Quinoline group based fluorescent sensor for detecting zinc ions in aqueous media and its logic gate behaviour

    International Nuclear Information System (INIS)

    Dong, Zhengping; Guo, Yueping; Tian, Xin; Ma, Jiantai

    2013-01-01

    A highly sensitive method for quantitative determination of Zn 2+ in water has been developed by using a novel fluorescent sensor NQA: (N-Quinolin-8-yl-2-[(quinolin-8-ylcarbamoylmethyl)-amino]-acetamide). The sensor displays great selectivity for Zn 2+ in the presence of other metal ions in aqueous solution and possesses an excellent sensitivity of about 2×10 −8 M for Zn 2+ . The binding stoichiometry, binding affinity, and pH sensitivity of the sensor have also been studied. Furthermore, the fluorescent changes of NQA upon the addition of cations (Cu 2+ and Zn 2+ ) are utilized to construct an INHIBIT logic gate at the molecular level, using Cu 2+ and Zn 2+ as chemical inputs and the fluorescence intensity as output. NQA has ideal chemical and spectroscopic properties that satisfy the criteria for further biological and environmental applications. - Highlights: ► A novel fluorescent sensor for Zn 2+ in water has been synthesized. ► The sensor displays high selectivity for Zn 2+ in the presence of other ions. ► The sensor exhibits excellent sensing ability under the physiological pH window. ► The sensor can be utilized as an INHIBIT logic gate at the molecular level.

  19. TDDFT study on excited state intramolecular proton transfer mechanism in 2-amino-3-(2‧-benzazolyl)-quinolines

    Science.gov (United States)

    Jia, Xueli; Li, Chaozheng; Li, Donglin; Liu, Yufang

    2018-03-01

    The intramolecular proton transfer reaction of the 2-amino-3-(2‧-benzoxazolyl)-quinoline (ABO) and 2-amino-3-(2‧-benzothiazolyl)-quinoline (ABT) molecules in both S0 and S1 states at B3LYP/6-311 ++G(d,p) level in ethanol solvent have been studied to reveal the deactivation mechanism of the tautomers of the two molecules from the S1 state to the S0 state. The results show that the tautomers of ABO and ABT molecules may return to the S0 state by emitting fluorescence. In addition, the bond lengths, angles and infrared spectra are analyzed to confirm the hydrogen bonds strengthened upon photoexcitation, which can facilitate the proton transfer process. The frontier molecular orbitals (MOs) and natural bond orbital (NBO) are also calculated to indicate the intramolecular charge transfer which can be used to explore the tendency of ESIPT reaction. The potential energy surfaces of the ABO and ABT molecules in the S0 and S1 states have been constructed. According to the energy potential barrier of 9.12 kcal/mol for ABO molecule and 5.96 kcal/mol for ABT molecule, it can be indicated that the proton transfer may occur in the S1 state.

  20. Deconstructing Quinoline-Class Antimalarials to Identify Fundamental Physicochemical Properties of Beta-Hematin Crystal Growth Inhibitors.

    Science.gov (United States)

    Olafson, Katy N; Nguyen, Tam Q; Vekilov, Peter G; Rimer, Jeffrey D

    2017-10-04

    A versatile approach to control crystallization involves the use of modifiers, which are additives that interact with crystal surfaces and alter their growth rates. Elucidating a modifier's binding specificity to anisotropic crystal surfaces is a ubiquitous challenge that is critical to their design. In this study, we select hematin, a byproduct of malaria parasites, as a model system to examine the complementarity of modifiers (i.e., antimalarial drugs) to β-hematin crystal surfaces. We divide two antimalarials, chloroquine and amodiaquine, into segments consisting of a quinoline base, common to both drugs, and side chains that differentiate their modes of action. Using a combination of scanning probe microscopy, bulk crystallization, and analytical techniques, we show that the base and side chain work synergistically to reduce the rate of hematin crystallization. In contrast to general observations that modifiers retain their function upon segmentation, we show that the constituents do not act as modifiers. A systematic study of quinoline isomers and analogues shows how subtle rearrangement and removal of functional moieties can create effective constituents from previously ineffective modifiers, along with tuning their inhibitory modes of action. These findings highlight the importance of specific functional moieties in drug compounds, leading to an improved understanding of modifier-crystal interactions that could prove to be applicable to the design of new antimalarials. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  1. Effects of Tranilast on the Urinary Excretion of Kynurenic and Quinolinic Acid under Conditions of L Tryptophan Loading

    Directory of Open Access Journals (Sweden)

    Rowland R. Noakes

    2013-01-01

    Full Text Available The pathogenesis of morphea and other cutaneous sclerosing disorders remain poorly understood. Although they are considered to be autoimmune disorders, abnormal tryptophan metabolism may be involved. Current therapy is directed to supressing the autoimmune response. Demonstration of a therapeutic response to manipulation of the kynurenine pathway would both support a role for abnormal tryptophan metabolism and offer additional targets for therapy. Tranilast is a 3-hydroxyanthranilic acid derivative known to target the kynurenine pathway. The aim of this study was to see if tranilast lowered the urinary excretion of the kynurenine metabolites kynurenic and quinolinic acid under condition of L tryptophan loading in a volunteer. Mean baseline value for kynurenic acid and quinolinic acid were 1.1 and 2.1 mmol/mol creatinine, respectively. This rose to 5.6 and 3.8 mmol/mol creatinine respectively under conditions of L tryptophan loading 2 grams daily. Adding 1 g of tranilast daily lowered the values to 2.0 and 2.9 mmol/mol creatinine, respectively. These data suggest that tranilast acts as a competitive inhibitor of either indoleamine 2, 3-dioxygenase (IDO, tryptophan 2, 3 di-oxygenase (TDO or both. As it involved only 1 subject, the results may not be representative of the larger population and must be considered preliminary.

  2. Silica sulfuric acid and as an efficient catalyst for the Friedlander quinoline synthesis from simple ketones and ortho - amino aryl ketones under microwave irradiation

    International Nuclear Information System (INIS)

    Zolfigol, M. A.; Salehi, P.; Shiri, M.; Faal Rastegar, T.; Ghaderi, A.

    2008-01-01

    The synthesis of quinoline derivatives via Friedlander method from ortho-amino aryl ketones in the presence of a catalytic amount of silica sulfuric acid under solvent-free condition and microwave irradiation was described. A good range of simple ketones such as cyclohexanone and deoxybenzoin were used

  3. 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.P.; 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...

  4. Discovery of Quinoline-Derived Trifluoromethyl Alcohols, Determination of Their in vivo Toxicity and Anticancer Activity in a Zebrafish Embryo Model.

    Science.gov (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

    2015-11-01

    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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. Computer prediction of biological activity of 2-methyl(phenyl-6,9-epoksybenzo[g]quinoline-4,5,10-Trion and 5-methyl-(1,2,4-triazolo[4,3-a] quinoline

    Directory of Open Access Journals (Sweden)

    Yu. V. Karpenko

    2015-04-01

    Full Text Available , One of the priority measures, which are evaluated in the creation of new effective medicines, is their high selective effect and lack of side effects. A considerable interest is the possibility of combining several structures of heterocycles in one molecule, such as quinoline and furan, which may cause an increase in biological activity of these combined compounds or an emergence of new properties. It is known that derivatives of 1,2,4-triazolo[4,3-a]quinoline have anticonvulsant effect and treat the syndrome of disorders with the nervous system. The aim of research. The main purpose of this work was an establishment of combinatorial library of bioregulators, which combines structures 5,8-dioksoquinoline and furan (1-8, quinoline and triazole (9-12, using computer program PASS (Prediction Activitity Spectra for Substances. Virtual screening of heterocycles derivatives was conducted to determine the direction of their bioactivity researches. Materials and methods. The virtual screening of compounds was performed by using the computer program PASS (Prediction Activity Spectra for Substances. For the specific activity the increase of Pa quantity and the decrease of the Pi quantity, helps to get the greater chance to detect this activity in the experiment. Predicting the probability of substance manifestation of specific types of biological activity determines which tests are the most appropriate for studying the biological activity of specific chemical substances and which substances of those that are available to the researcher likely will show the desired effect. With theoretical prediction the most likely basic structures of new compounds with desired biological effect, which best suits the task will be selected. Results. Analysis of computer prediction demonstrates the promising search of antineoplastic, antibiotic, analgesic and other types of activity in some of these compounds. An important instant of prediction of these substances is

  6. Central Nervous System Infection with Borna Disease Virus Causes Kynurenine Pathway Dysregulation and Neurotoxic Quinolinic Acid Production.

    Science.gov (United States)

    Formisano, Simone; Hornig, Mady; Yaddanapudi, Kavitha; Vasishtha, Mansi; Parsons, Loren H; Briese, Thomas; Lipkin, W Ian; Williams, Brent L

    2017-07-15

    Central nervous system infection of neonatal and adult rats with Borna disease virus (BDV) results in neuronal destruction and behavioral abnormalities with differential immune-mediated involvement. Neuroactive metabolites generated from the kynurenine pathway of tryptophan degradation have been implicated in several human neurodegenerative disorders. Here, we report that brain expression of key enzymes in the kynurenine pathway are significantly, but differentially, altered in neonatal and adult rats with BDV infection. Gene expression analysis of rat brains following neonatal infection showed increased expression of kynurenine amino transferase II (KATII) and kynurenine-3-monooxygenase (KMO) enzymes. Additionally, indoleamine 2,3-dioxygenase (IDO) expression was only modestly increased in a brain region- and time-dependent manner in neonatally infected rats; however, its expression was highly increased in adult infected rats. The most dramatic impact on gene expression was seen for KMO, whose activity promotes the production of neurotoxic quinolinic acid. KMO expression was persistently elevated in brain regions of both newborn and adult BDV-infected rats, with increases reaching up to 86-fold. KMO protein levels were increased in neonatally infected rats and colocalized with neurons, the primary target cells of BDV infection. Furthermore, quinolinic acid was elevated in neonatally infected rat brains. We further demonstrate increased expression of KATII and KMO, but not IDO, in vitro in BDV-infected C6 astroglioma cells. Our results suggest that BDV directly impacts the kynurenine pathway, an effect that may be exacerbated by inflammatory responses in immunocompetent hosts. Thus, experimental models of BDV infection may provide new tools for discriminating virus-mediated from immune-mediated impacts on the kynurenine pathway and their relative contribution to neurodegeneration. IMPORTANCE BDV causes persistent, noncytopathic infection in vitro yet still elicits

  7. Crosslinked wholly aromatic polyether membranes based on quinoline derivatives and their application in high temperature polymer electrolyte membrane fuel cells

    Science.gov (United States)

    Kallitsis, K. J.; Nannou, R.; Andreopoulou, A. K.; Daletou, M. K.; Papaioannou, D.; Neophytides, S. G.; Kallitsis, J. K.

    2018-03-01

    An AB type difunctional quinoline based monomer bearing a pentafluorophenyl unit combined with a phenol functionality is being synthesized and homopolymerized to create linear aromatic polyethers as polymer electrolytes for HT-PEM FCs applications. Several conditions are tested for the optimized synthesis of the monomer and homopolymer. Additionally, covalent crosslinking through aromatic polyether bond formation enables the creation of wholly aromatic crosslinked polymeric electrolyte membranes. More specifically, the perfluorophenyl units are crosslinked with other hydroxyl end functionalized moieties, providing membranes with enhanced chemical and mechanical properties that are moreover easily doped with phosphoric acid even at ambient temperatures. All membranes are evaluated for their structural and thermal characteristics and their doping ability with phosphoric acid. Selected crosslinked membranes are further tested in terms of their single cell performance at the temperature range 160 °C-200 °C showing promising performance and high conductivity values even up to 0.2 S cm-1 in some cases.

  8. Synthesis in aqueous medium and organic praseodymium complexes with ligands derived from Schiff base quinolinic. Characterization and physicochemical study

    International Nuclear Information System (INIS)

    Garcia G, A.

    2015-01-01

    It was investigated the coordination ability of the quinolinic Schiff base organic tetradentate quinolinic ligand (Q Schiff-(OH) 2 ) towards the trivalent praseodymium by UV/Vis spectrophotometric titration (St). By St, was studied the formed species between the Q Schiff-(OH) 2 ligand and the praseodymium nitrate salt in equimolar concentrations (5.86 x 10 -4 M: 5.22 x 10 -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) 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 32 H 20 N 4 O 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 48 H 33 N 6 O 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) 2 Na for the pure coordination compound from the aqueous-organic medium and the minimum formula Pr(Q Schiff) 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 evaluated by emission and excitation luminescence (fluorescence and

  9. A spectroscopic study of the hydrogen bonding and pi-pi stacking interactions of harmane with quinoline.

    Science.gov (United States)

    Balón, M; Guardado, P; Muñoz, M A; Carmona, C

    1998-01-01

    A spectroscopic (UV-vis, Fourier transform IR, steady state, and time-resolved fluorescence) study of the interactions of the ground and excited singlet states of harmane (1-methyl-9H-pyrido/3,4-b/indole) with quinoline has been carried out in cyclohexane, toluene, and buffered pH=8.7 aqueous solutions. To analyze how the number of rings in the substrate influences these interactions, pyridine and phenanthridine have also been included in this study. In cyclohexane and toluene 1:1 stoichiometric hydrogen-bonded complexes are formed in both the ground and the excited singlet states. As the number of rings of the benzopyridines and the solvent polarity increase hydrogen-bonding interactions weaken and pi-pi van der Waals interactions become apparent.

  10. 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)

    2015-03-14

    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.

  11. 3,3′-Bis(quinolin-8-yl-1,1′-[4,4′-methylenebis(4,1-phenylene]diurea

    Directory of Open Access Journals (Sweden)

    Avijit Pramanik

    2012-01-01

    Full Text Available The title compound, C33H26N6O2, contains two 3-(quinolin-8-ylurea groups linked to a diphenylmethane. The asymmetric unit contains two molecules, A and B. Each quinoline plane is essentially parallel to the attached urea unit [dihedral angles = 8.97 (18 and 8.81 (19 in molecule A and 18.47 (18 and 4.09 (19° in molecule B]. The two benzene rings are twisted, making dihedral angles of 81.36 (8° in A and 87.20 (9° in B. The molecular structures are stabilized by intramolecular N—H...N hydrogen bonds. In the crystal, each urea O atom is involved in two N—H...O hydrogen bonds, generating two interpenetrating three-dimensional sets of molecules.

  12. Potent, nonsteroidal selective androgen receptor modulators (SARMs) based on 8H-[1,4]oxazino[2,3-f]quinolin-8-ones.

    Science.gov (United States)

    Higuchi, Robert I; Thompson, Anthony W; Chen, Jyun-Hung; Caferro, Thomas R; Cummings, Marquis L; Deckhut, Charlotte P; Adams, Mark E; Tegley, Christopher M; Edwards, James P; López, Francisco J; Kallel, E Adam; Karanewsky, Donald S; Schrader, William T; Marschke, Keith B; Zhi, Lin

    2007-10-01

    A series of androgen receptor modulators based on 8H-[1,4]oxazino[2,3-f]quinolin-8-ones was synthesized and evaluated in an androgen receptor transcriptional activation assay. The most potent analogues from the series exhibited single-digit nanomolar potency in vitro. Compound 18h demonstrated full efficacy in the maintenance of muscle weight, at 10 mg/kg, with reduced activity in prostate weight in an in vivo model of androgen action.

  13. Synthesis and antimicrobial activity of some new substituted 9-(1H-Pyrazolo [3, 4-b] Quinolin-1-YL) Acridines

    International Nuclear Information System (INIS)

    Thakor, S.; Parmar, P.; Patel, M.; Patel, R.

    2008-01-01

    2-chloro-6-methyl/methoxy-3-formylquinoline upon condensation with substituted 9-hydrazino-acridine afforded corresponding hydrazones which were cyclized under alkaline condition to give 9-(6-substituted-1H-pyrazolo [3, 4-b] quinolin-1-yl) acridine analoges. All of the synthesized compounds were characterized by their elemental analysis, IR and NMR spectral studies. Biological screenings of the prepared compounds have been screened on some strain of bacteria and fungus. (author)

  14. Synthesis, radiosynthesis and biological evaluation of quinoline carboxamide analogues of Talnetant (SB 223412) to study by PET or SPECT imaging the NK-3 receptor

    International Nuclear Information System (INIS)

    Bennacef, Idriss

    2003-01-01

    With the aim of visualizing NK-3 receptors in vivo by medical imaging techniques (positron emission tomography and single photon emission computed tomography), the synthesis of novel 2-phenylquinoline-4-carboxamides, derived from SB 223412 or SB 222 200, two non peptide potent (hNK-3-CHO: K i = 1.0 nM; K i = 4.4 nM respectively) and selective (NK-3/NK-1 ≥10 5 ) human NK-3 receptor antagonists, has been studied. The compounds obtained are characterized by the presence, on the quinoline moiety, of an atom of carbon, fluorine or iodine that can be substituted by their β + emitter (carbon-11, t(1/2) = 20 min; fluorine-18, t(1/2) = 110 min) or γ emitter (iodine-123, t(1/2) = 13 h) radio-isotopes. Monohalogenated (fluorinated or iodinated) quinolines were prepared using an efficient synthesis based on the Pfitzinger reaction. Di-halogenated analogues, bearing both an iodine and a fluorine atom, were obtained via a regioselective ortho-metalation reaction. Biological evaluation of these compounds led to the determination of potent and selective structures towards the NK-3 receptor, for which labeling will be envisaged. Functionalization in position 3 of quinoline-4-carboxamides, using a directed metalation reaction, allowed the introduction of various (hetero)elements (chlorine, bromine, iodine, trialkystannyle or silyle moiety). This research allowed to perform the radiosynthesis of [ 11 C]SB 222200 using a Stille coupling with [ 11 C]iodomethane. (author) [fr

  15. Pharmacological effects of a synthetic quinoline, a hybrid of tomoxiprole and naproxen, against acute pain and inflammation in mice: a behavioral and docking study

    Directory of Open Access Journals (Sweden)

    Hossein Hosseinzadeh

    2017-04-01

    Full Text Available Objective(s: In the present study, we investigated the potential anti-nociceptive activity and acute anti-inflammatory effect of a synthetic quinoline compound (2-(4-Methoxyphenylbenzo[h]quinoline-4-carboxylic acid, QC, possessing structural elements of both naproxen and tomoxiprole drugs. Materials and Methods: The anti-nociceptive activity of QC was evaluated using chemical- and thermal-induced nociception models and its acute anti-inflammatory effect was evaluated by xylene-induced ear edema test in mice. Results: QC displayed a dose dependent effect in both acute anti-nociceptive tests (writhing and hot plate. This compound at dose of 6.562 mg/kg showed a high anti-nociceptive effect near equal to  diclofenac 5 mg/kg. It also showed high anti-inflammatory effects (less than 6.562 mg/kg comparable to those of reference drugs diclofenac (5 mg/kg and celecoxib (100 mg/kg. Docking study showed that this quinoline derivative could inhibit COX-2 enzyme strongly. Conclusion: QC showed high anti-nociceptive and anti-inflammatory effects comparable to reference drugs and can exert its anti-nociceptive and anti-inflammatory activities through COX-2 inhibition.

  16. Hemin potentiates nitric oxide-mediated nitrosation of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to 2-nitrosoamino-3-methylimidazo[4,5-f]quinoline.

    Science.gov (United States)

    Lakshmi, Vijaya M; Clapper, Margie L; Chang, Wen-Chi; Zenser, Terry V

    2005-03-01

    Heme has been reported to be an important contributor to endogenous N-nitrosation within the colon and to the enhanced incidence of colon cancer observed with increased intake of red meat. This study uses the heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) as a target to evaluate hemin potentiation of nitric oxide (NO)-mediated nitrosation. Formation of 14C-2-nitrosoamino-3-methylimidazo[4,5-f]quinoline (N-NO-IQ) was monitored by HPLC following incubation of 10 microM IQ with the NO donor spermine NONOate (1.2 microM NO/min) at pH 7.4 in the presence or absence of hemin. N-NO-IQ formation due to autoxidation of NO was at the limit of detection (0.1 microM) and increased 22-fold in the presence of 10 microM hemin and an in situ system for generating H2O2 (glucose oxidase/glucose). A linear increase in N-NO-IQ formation was observed from 1 to 10 microM hemin. Significant nitrosamine formation occurred at fluxes of NO and H2O2 as low as 0.024 and 0.25 microM/min, respectively. Potentiation by hemin was not affected by a 400-fold excess flux of H2O2 over NO or a 4.8-fold excess flux of NO over H2O2. Reactive nitrogen species produced by hemin potentiation had a 46-fold greater affinity for IQ than those produced by autoxidation. Azide inhibited autoxidation, suggesting involvement of the nitrosonium ion, NO+. Hemin potentiation was inhibited by NADH, but not azide, suggesting oxidative nitrosylation with NO2* or a NO2*-like species. IQ and 2,3-diaminonaphthylene were much better targets for nitrosation than the secondary amine morpholine. Apc(min) mice with dextran sulfate sodium-induced colitis demonstrated increased levels of urinary nitrite and nitrate consistent with increased expression of iNOS and NO synthesis. As reported previously, identical conditions increased fecal N-nitroso compounds. Thus, hemin potentiation of NO-mediated nitrosation of heterocyclic amines provides a testable mechanism by which red meat consumption can generate N

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

    Directory of Open Access Journals (Sweden)

    Chan-on W

    2015-04-01

    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

  18. Excitation dynamics of dye doped tris(8-hydroxy quinoline) aluminum films studied using time-resolved photoelectron spectroscopy

    International Nuclear Information System (INIS)

    Read, K.; Karlsson, H. S.; Murnane, M. M.; Kapteyn, H. C.; Haight, R.

    2001-01-01

    In this work, we use excite-probe photoelectron spectroscopy to study the decay of electronic excitation in tris(8-hydroxy quinoline) aluminum (Alq) doped with the organic dye 4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (DCM). Ultrashort laser pulses are used to photoexcite electrons into unoccupied molecular orbitals, and the ensuing decay rate is directly observed using photoelectron spectroscopy. Decay of the electronic excitation is studied as a function of DCM doping percentage and excitation intensity. The decay rate is seen to increase with both doping percentage and excitation intensity. These data are explained using a model including Foerster transfer, stimulated emission, concentration quenching, and bimolecular singlet - singlet exciton annihilation. In this model, we find that it is necessary to include a very fast (faster than predicted in standard Foerster transfer theory) excitation transfer of a fraction of the excitation from the Alq to the DCM, where that fraction corresponds to the approximate nearest-neighbor population. [copyright] 2001 American Institute of Physics

  19. Profiling the Interaction Mechanism of Quinoline/Quinazoline Derivatives as MCHR1 Antagonists: An in Silico Method

    Directory of Open Access Journals (Sweden)

    Mingwei Wu

    2014-09-01

    Full Text Available 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.

  20. Sharp green electroluminescence from 1H-pyrazolo[3,4-b]quinoline-based light-emitting diodes

    Science.gov (United States)

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

    2000-09-01

    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.

  1. Essential fatty acid-rich diets protect against striatal oxidative damage induced by quinolinic acid in rats.

    Science.gov (United States)

    Morales-Martínez, Adriana; Sánchez-Mendoza, Alicia; Martínez-Lazcano, Juan Carlos; Pineda-Farías, Jorge Baruch; Montes, Sergio; El-Hafidi, Mohammed; Martínez-Gopar, Pablo Eliasib; Tristán-López, Luis; Pérez-Neri, Iván; Zamorano-Carrillo, Absalom; Castro, Nelly; Ríos, Camilo; Pérez-Severiano, Francisca

    2017-09-01

    Essential fatty acids have an important effect on oxidative stress-related diseases. The Huntington's disease (HD) is a hereditary neurologic disorder in which oxidative stress caused by free radicals is an important damage mechanism. The HD experimental model induced by quinolinic acid (QUIN) has been widely used to evaluate therapeutic effects of antioxidant compounds. The aim of this study was to test whether the fatty acid content in olive- or fish-oil-rich diet prevents against QUIN-related oxidative damage in rats. Rats were fed during 20 days with an olive- or a fish-oil-rich diet (15% w/w). Posterior to diet period, rats were striatally microinjected with QUIN (240 nmol/µl) or saline solution. Then, we evaluated the neurological damage, oxidative status, and gamma isoform of the peroxisome proliferator-activated receptor (PPARγ) expression. Results showed that fatty acid-rich diet, mainly by fish oil, reduced circling behavior, prevented the fall in GABA levels, increased PPARγ expression, and prevented oxidative damage in striatal tissue. In addition none of the enriched diets exerted changes neither on triglycerides or cholesterol blood levels, nor or hepatic function. This study suggests that olive- and fish-oil-rich diets exert neuroprotective effects.

  2. 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

    2011-01-01

    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.

  3. Insight into the effects of modifying chromophores on the performance of quinoline-based dye-sensitized solar cells

    Science.gov (United States)

    Mao, Mao; Wang, Jian-Bo; Liu, Xiu-Lin; Wu, Guo-Hua; Fang, Xia-Qin; Song, Qin-Hua

    2018-02-01

    A series of organic dyes based on quinoline as an electron-deficient π-linker, were designed and synthesized for dye sensitized solar cells (DSSC) application. These push-pull conjugated dyes, sharing same anchoring group with distinctive electron-rich donating groups such as N,N-diethyl (DEA-Q), 3,6-dimethoxy carbazole (CBZ-Q), bis(4-butoxyphenyl)amine (BPA-Q), were synthesized by Riley oxidation of sbnd CH3 followed by Knoevenagel condensation of the corresponding aldehyde precursors 2a-c with cyanoacrylic acid. The optical, electrochemical, theoretical calculation and photovoltaic properties with these three dyes were systematically investigated. Compared to DEA-Q and CBZ-Q, BPA-Q possesses better light harvesting properties with regard to extended conjugate length, red-shifted intramolecular charge transfer band absorption and broaden light-responsive IPCE spectrum, resulting in a greater short circuit photocurrent density output. BPA-Q also has improved open-circuit voltage due to the apparent large charge recombination resistance. Consequently, assembled with iodine redox electrolytes, the device with BPA-Q achieved the best overall conversion efficiency value of 3.07% among three dyes under AM 1.5G standard conditions. This present investigation demonstrates the importance of various N-substituent chromophores in the prevalent D-π-A type organic sensitizers for tuning the photovoltaic performance of their DSSCs.

  4. Protonated MIL-125-NH2: Remarkable Adsorbent for the Removal of Quinoline and Indole from Liquid Fuel.

    Science.gov (United States)

    Ahmed, Imteaz; Khan, Nazmul Abedin; Yoon, Ji Woong; Chang, Jong-San; Jhung, Sung Hwa

    2017-06-21

    The removal of nitrogen-containing compounds (NCCs) from fossil fuels prior to combustion is currently of particular importance, and so we investigated an adsorptive method using metal-organic frameworks (MOFs) for the removal of indole (IND) and quinoline (QUI), which are two of the main NCCs present in fossil fuels. We herein employed an amino (-NH 2 )-functionalized MIL-125 (MIL-125-NH 2 ) MOF, which was further modified by protonation (P-MIL-125-NH 2 ). These modified MOFs exhibited extraordinary performance in the adsorption of both IND (as representative neutral NCC) and QUI (as representative basic NCC). These MOFs were one of the most efficient adsorbents for the removal of NCCs. For example, P-MIL-125-NH 2 showed the highest adsorption capacity for QUI among ever reported adsorbent. The improved adsorption of IND was explained by H-bonding and cation-π interactions for MIL-125-NH 2 and P-MIL-125-NH 2 , respectively, while the mechanisms for QUI were H-bonding and acid-base interactions, respectively. This is a rare phenomenon for a single material (especially not with very high porosity) to exhibit such remarkable performances in the adsorption of both basic QUI and neutral IND. The adsorption results obtained using regenerated MIL-125-NH 2 and P-MIL-125-NH 2 also showed that these materials can be used several times without any severe degradation.

  5. Di-?-cyanido-tetra?cyanido(5,5,7,12,12,14-hexa?methyl-1,4,8,11-tetra?aza?cyclo?tetra?decane)[N-(quinolin-8-yl)quinoline-2-carboxamidato]diiron(III)nickel(II) 2.07-hydrate

    OpenAIRE

    Yang, Yuqi; Zhou, Hongbo; Shen, Xiaoping

    2013-01-01

    The asymmetric unit of the title complex, [Fe2Ni(C19H12N3O)2(CN)6(C16H36N4)]?2.07H2O, contains one [Fe(qcq)(CN)3]? anion, half a [Ni(teta)]2+ cation and two partially occupied inter?stitial water mol?ecules [qcq? is the N-(quinolin-8-yl)quinoline-2-carboxamidate anion and teta is 5,5,7,12,12,14-hexa?methyl-1,4,8,11-tetra?aza?cyclo?tetra?deca?ne]. In the complex mol?ecule, two [Fe(qcq)(CN)3]? anions additionally coordinate the central [Ni(teta)]2+ cation through cyanide groups in a trans mode,...

  6. 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

    2011-11-01

    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.

  7. 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.

    Science.gov (United States)

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

    2011-01-01

    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.

  8. An Efficient One-Pot Synthesis of Pyrano[3,2-c]quinolin-2,5-dione Derivatives Catalyzed by L-Proline

    Directory of Open Access Journals (Sweden)

    Jing Wang

    2012-11-01

    Full Text Available A series of 4-aryl-6-methyl-3,4-dihydro-2H-pyrano[3,2-c]quinolin-2,5(6H-diones were synthesized via the three-component reactions of aromatic aldehydes, 4-hydroxy-1-methylquinolin-2(1H-one, and Meldrum’s acid catalyzed by L-proline. The structures of the products were identified by spectroscopic analysis. A mechanism for this three-component reaction catalyzed by L-proline was proposed.

  9. Tandem Reduction/Cyclization of O-Nitrophenyl Propargyl Alcohols-A Novel Synthesis of 2- & 2,4-Disubstituted Quinolines and Application to the Synthesis of Streptonigrin

    Science.gov (United States)

    2008-01-01

    useful quinoline alkaloids from both plant and marine animal sources each year.10-20 N OH OMe OMe Me COOH H2N N O O H2N MeO N N N O O O OH OH OH N...the synthesis of an inhibitor of HMG-CoA (the rate-limiting enzyme in sterol biosynthesis in animals and plants ) was conducted by Suzuki, using a...less commonly identified in the literature. An early example was reported by Pelletier in his synthesis of three monoterpene pheromones (22, 23, and

  10. Discovery of a novel, CNS penetrant M4 PAM chemotype based on a 6-fluoro-4-(piperidin-1-yl)quinoline-3-carbonitrile core.

    Science.gov (United States)

    Bewley, Blake R; Spearing, Paul K; Weiner, Rebecca L; Luscombe, Vincent B; Zhan, Xiaoyan; Chang, Sichen; Cho, Hyekyung P; Rodriguez, Alice L; Niswender, Colleen M; Conn, P Jeffrey; Bridges, Thomas M; Engers, Darren W; Lindsley, Craig W

    2017-09-15

    This Letter details the discovery and subsequent optimization of a novel M 4 PAM scaffold based on an 6-fluoro-4-(piperidin-1-yl)quinoline-3-carbonitrile core, which represents a distinct departure from the classical M 4 PAM chemotypes. Optimized compounds in this series demonstrated improved M 4 PAM potency on both human and rat M 4 (4 to 5-fold relative to HTS hit), and displayed attractive physicochemical and DMPK profiles, including good CNS penetration (rat brain:plasma K p =5.3, K p,uu =2.4; MDCK-MDR1 (P-gp) ER=1.1). Copyright © 2017 Elsevier Ltd. All rights reserved.

  11. N-{4-[(2E-3-(2H-1,3-Benzodioxol-5-ylprop-2-enoyl]phenyl}quinoline-3-carboxamide

    Directory of Open Access Journals (Sweden)

    Efrain Polo

    2017-10-01

    Full Text Available An amide chalconehas been synthesized in a two-step reaction. First, N-(4-acetylphenylquinoline-3-carboxamide 2 was synthesized by the reaction of quinoline-3-carboxylic acid 1 and thionyl chloride (SOCl2, following the addition of 4-aminoacetophenone. Then, a typical Claisen–Schmidtreactionwas made between 2 and piperonal using KOH solution as a catalystin ethanol, under ultrasonic irradiation. The structure of the target compound was established by FTIR (Fourier-transform infrared spectroscopy, HRMS, 1H and 13C-NMR.

  12. New quinoline derivatives demonstrate a promising antimalarial activity against Plasmodium falciparum in vitro and Plasmodium berghei in vivo.

    Science.gov (United States)

    Soares, Roberta Reis; da Silva, José Marcio Fernandes; Carlos, Bianca Cecheto; da Fonseca, Camila Campos; de Souza, Laila Salomé Araújo; Lopes, Fernanda Valério; de Paula Dias, Rafael Mafra; Moreira, Paulo Otávio Lourenço; Abramo, Clarice; Viana, Gustavo Henrique Ribeiro; de Pila Varotti, Fernando; da Silva, Adilson David; Scopel, Kézia Katiani Gorza

    2015-06-01

    Malaria continues to be an important public health problem in the world. Nowadays, the widespread parasite resistance to many drugs used in antimalarial therapy has made the effective treatment of cases and control of the disease a constant challenge. Therefore, the discovery of new molecules with good antimalarial activity and tolerance to human use can be really important in the further treatment of the disease. In this study we have investigated the antiplasmodial activity of 10 synthetic compounds derived from quinoline, five of them combined to sulfonamide and five to the hydrazine or hydrazide group. The compounds were evaluated according to their cytotoxicity against HepG2 and HeLa cell lines, their antimalarial activity against CQ-sensitive and CQ-resistant Plasmodium falciparum strains and, finally, their schizonticide blood action in mice infected with Plasmodium berghei NK65. The compounds exhibited no cytotoxic action in HepG2 and HeLa cell lines when tested up to a concentration of 100 μg/mL. In addition, the hydrazine or hydrazide derivative compounds were less cytotoxic against cell lines and more active against CQ-sensitive and CQ-resistant P. falciparum strains, showing high SI (>1000 when SI was calculated using the CC50 from the 3D7 strain as reference). When tested in vivo, the hydrazine derivative 1f compound showed activity against the development of blood parasites similar to that observed with CQ, the reference drug. Interestingly, the 1f compound demonstrated the best LipE value (4.84) among all those tested in vivo. Considering the in vitro and in vivo activities of the compounds studied here and the LipE values, we believe the 1f compound to be the most promising molecule for further studies in antimalarial chemotherapy. Copyright © 2015 Elsevier Ltd. All rights reserved.

  13. New donor-acceptor-donor molecules based on quinoline acceptor unit with Schiff base bridge: synthesis and characterization

    Energy Technology Data Exchange (ETDEWEB)

    Kotowicz, Sonia [Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice (Poland); Siwy, Mariola [Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze (Poland); Filapek, Michal; Malecki, Jan G. [Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice (Poland); Smolarek, Karolina; Grzelak, Justyna; Mackowski, Sebastian [Institute of Physics, Faculty of Physics, Astronomy and Informatics, Nicolaus Copernicus University, 5 Grudziadzka Str., 87-100 Torun (Poland); Slodek, Aneta, E-mail: aneta.slodek@us.edu.pl [Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice (Poland); Schab-Balcerzak, Ewa, E-mail: ewa.schab-balcerzak@us.edu.pl [Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice (Poland); Centre of Polymer and Carbon Materials, Polish Academy of Sciences, 34 M. Curie-Sklodowska Str., 41-819 Zabrze (Poland)

    2017-03-15

    Three solution-processable small organic molecules bearing quinoline as electron-accepting moiety were synthesized via condensation reaction of novel 6-amino-2-(2,2’-bithiophen-5-yl)-4-phenylquinoline with 2,2’-bithiophene-5-carboxaldehyde, 9-ethyl-9H-carbazole-3-carbaldehyde and 9-phenanthrenecarboxaldehyde. The presence of alternating electron-donating and accepting units results in a donor-acceptor-donor architecture of these molecular systems. Thermal, photophysical, and electrochemical properties of these small molecules were examined and the experimental results were supported by the density functional theory calculations. The obtained molecular systems exhibited high thermal stability with decomposition temperatures (5% weight loss) exceeding 330 °C in nitrogen atmosphere. It was found, based on DSC measurements, that investigated Schiff bases form amorphous material with glass transition temperatures between 88 and 190 °C. They also showed a UV–vis absorption in the range of 250–500 nm both in solution and in solid state as film and blend with PMMA and PVK. Photoluminescence measurements revealed moderately strong blue-light emission of the imines in solution as well as in PMMA blend with quantum yields in the range of 2–26%. In the case of imines dispersed in PVK matrix the emission of green light was mainly observed. In addition, when mixed with plasmonically active silver nanowires, the compounds exhibit relatively strong electroluminescence signal, associated with plasmonics enhancement, as evidenced by high-resolution photoluminescence imaging. The energy band gap estimated based on cyclic voltammetry was between 2.38 and 2.61 eV. - Highlights: • New Schiff bases possess donor-acceptor-imine-bridge-donor architecture were synthesized and examined. • Thorough characterization of optical and electrochemical properties of novel Schiff bases has been carried out. • Optical and electrochemical measurements were compared with DFT

  14. Quinolinic Carboxylic Acid Derivatives as Potential Multi-target Compounds for Neurodegeneration: Monoamine Oxidase and Cholinesterase Inhibition.

    Science.gov (United States)

    Khan, Nehal A; Khan, Imtiaz; Abid, Syed M A; Zaib, Sumera; Ibrar, Aliya; Andleeb, Hina; Hameed, Shahid; Iqbal, Jamshed

    2018-01-01

    Parkinson's disease (PD), a debilitating and progressive disorder, is among the most challenging and devastating neurodegenerative diseases predominantly affecting the people over 60 years of age. To confront PD, an advanced and operational strategy is to design single chemical functionality able to control more than one target instantaneously. In this endeavor, for the exploration of new and efficient inhibitors of Parkinson's disease, we synthesized a series of quinoline carboxylic acids (3a-j) and evaluated their in vitro monoamine oxidase and cholinesterase inhibitory activities. The molecular docking and in silico studies of the most potent inhibitors were performed to identify the probable binding modes in the active site of the monoamine oxidase enzymes. Moreover, molecular properties were calculated to evaluate the druglikeness of the compounds. The biological evaluation results revealed that the tested compounds were highly potent against monoamine oxidase (A & B), 3c targeted both the isoforms of MAO with IC50 values of 0.51 ± 0.12 and 0.51 ± 0.03 µM, respectively. The tested compounds also demonstrated high and completely selective inhibitory action against acetylcholinesterase (AChE) with IC50 values ranging from 4.36 to 89.24 µM. Among the examined derivatives, 3i was recognized as the most potent inhibitor of AChE with an IC50 value of 4.36 ± 0.12 ±µM. The compounds appear to be promising inhibitors and could be used for the future development of drugs targeting neurodegenerative disorders. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  15. Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

    Directory of Open Access Journals (Sweden)

    Kyohei Yonekura

    2018-04-01

    Full Text Available We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs with structural diversity, which include tricyclic and tetracyclic structures with (benzothienyl, (benzofuranyl, and indolyl rings. The target HA[b]Q is addressed by the annulation of o-acylanilines and MeO–heteroarenes with the aid of an indium Lewis acid that effectively works to make two different types of the N–C and C–C bonds in one batch. A series of indolo[3,2-b]quinolines prepared here can be subsequently transformed to structurally unprecedented cryptolepine derivatives. Mechanistic studies showed that the N–C bond formation is followed by the C–C bond formation. The indium-catalyzed annulation reaction thus starts with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion, and thereby the N–C bond is formed. The resulting intermediate then cyclizes to make the C–C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, providing the HA[b]Q after aromatizing dehydration.

  16. Quinoline-Flanked Diketopyrrolopyrrole Copolymers Breaking through Electron Mobility over 6 cm2 V-1 s-1 in Flexible Thin Film Devices.

    Science.gov (United States)

    Ni, Zhenjie; Dong, Huanli; Wang, Hanlin; Ding, Shang; Zou, Ye; Zhao, Qiang; Zhen, Yonggang; Liu, Feng; Jiang, Lang; Hu, Wenping

    2018-03-01

    Herein, the design and synthesis of novel π-extended quinoline-flanked diketopyrrolopyrrole (DPP) [abbreviated as QDPP] motifs and corresponding copolymers named PQDPP-T and PQDPP-2FT for high performing n-type organic field-effect transistors (OFETs) in flexible organic thin film devices are reported. Serving as DPP-flankers in backbones, quinoline is found to effectively tune copolymer optoelectric properties. Compared with TDPP and pyridine-flanked DPP (PyDPP) analogs, widened bandgaps and strengthened electron deficiency are achieved. Moreover, both hole and electron mobility are improved two orders of magnitude compared to those of PyDPP analogs (PPyDPP-T and PPyDPP-2FT). Notably, featuring an all-acceptor-incorporated backbone, PQDPP-2FT exhibits electron mobility of 6.04 cm 2 V -1 s -1 , among the highest value in OFETs fabricated on flexible substrates to date. Moreover, due to the widened bandgap and strengthened electron deficiency of PQDPP, n-channel on/off ratio over 10 5 with suppressed hole transport is first realized in the ambipolar DPP-based copolymers. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  17. 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

    2017-09-01

    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.

  18. Ruthenium(II) bipyridine complexes bearing quinoline-azoimine (NN'N″) tridentate ligands: synthesis, spectral characterization, electrochemical properties and single-crystal X-ray structure analysis.

    Science.gov (United States)

    Al-Noaimi, Mousa; Abdel-Rahman, Obadah S; Fasfous, Ismail I; El-khateeb, Mohammad; Awwadi, Firas F; Warad, Ismail

    2014-05-05

    Four octahedral ruthenium(II) azoimine-quinoline complexes having the general molecular formula [Ru(II)(L-Y)(bpy)Cl](PF6) {L-Y=YC6H4N=NC(COCH3)=NC9H6N, Y=H (1), CH3 (2), Br (3), NO2 (4) and bpy=2,2'-bipyrdine} were synthesized. The azoimine-quinoline based ligands behave as NN'N″ tridentate donors and coordinated to ruthenium via azo-N', imine-N' and quinolone-N″ nitrogen atoms. The composition of the complexes has been established by elemental analysis, spectral methods (FT-IR, electronic, (1)H NMR, UV/Vis and electrochemical (cyclic voltammetry) techniques. The crystal structure of complex 1 is reported. The Ru(II) oxidation state is greatly stabilized by the novel tridentate ligands, showing Ru(III/II) couples ranging from 0.93-1.27 V vs. Cp2Fe/Cp2Fe(+). The absorption spectrum of 1 in dichloromethane was modeled by time-dependent density functional theory (TD-DFT). Copyright © 2014 Elsevier B.V. All rights reserved.

  19. 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

    2012-07-01

    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.)

  20. 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

    2003-01-01

    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...

  1. Synthesis and crystal structure of bis(1-{[(quinolin-8-ylimino]methyl}pyrene-κ2N,N′silver(I trifluoromethanesulfonate

    Directory of Open Access Journals (Sweden)

    Miguel Pinto

    2016-10-01

    Full Text Available The title compound, [Ag(qPyr2]CF3SO3 where qPyr = 1-(quinoline-2-ylmethyleneaminopyrene, C26H16N2, was synthesized from a reaction of silver trifluoromethanesulfonate and qPyr in dichloromethane–methanol mixed media. In this design, the qPyr ligand was chosen for its characteristic excitation and emission profiles, which could enable the tracking of the silver complex within biological targets. The AgI atom resides in a distorted tetrahedral N4 coordination sphere. Analysis of the packing pattern revealed significant intra- and intermolecular π–π stacking interactions between the [Ag(qPyr2]+ cations. In addition, a weak C—H...O hydrogen bond consolidates the packing between cations and anions.

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

    International Nuclear Information System (INIS)

    Laayoun, A.; Coulombeau, C.; Constant, J.F.; Lhomme, J.; Berger, M.; Cadet, J.

    1994-01-01

    In a search for more active radioprotective compounds, we have prepared and examined a series of model molecules in which the radioprotective β-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 γ-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 β-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)

  3. Synthesis and characterization of a new photoluminescent material (8-hydroxy quinoline) bis (2-2’bipyridine) lanthanum La(Bpy)2q

    International Nuclear Information System (INIS)

    Kumar, Rahul; Bhargava, Parag

    2016-01-01

    A new photoluminescence material, (8-hydroxy quinoline) bis (2-2’bipyridine) lanthanum has been synthesized and characterized by different techniques. The prepared material La(Bpy) 2 q was characterized for structural, thermal and photoluminescence analysis. Structural analysis of this material was done by Fourier transformed infrared spectroscopy (FTIR) and mass spectroscopy. Thermal analysis of this material was done by thermal gravimetric analysis (TGA) shows the thermal stability up to 190°C.Absorption and emission spectra of the material was measured by UV-visible spectroscopy and photoluminescence spectroscopy. Solution of this material La(Bpy) 2 q in ethanol showed absorption peak at 385nm, which may be attributed due to (π – π*) transitions. The photoluminescence spectra of La(Bpy) 2 q in ethanol solution showed intense peak at 490 nm

  4. Synthesis and characterization of a new photoluminescent material (8-hydroxy quinoline) bis (2-2’bipyridine) lanthanum La(Bpy)2q

    Energy Technology Data Exchange (ETDEWEB)

    Kumar, Rahul, E-mail: id-kumarrahul003@gmail.com; Bhargava, Parag [Department of Metallurgical Engineering and Materials Science, Indian Institute of Technology-Bombay, Mumbai-400076 (India)

    2016-05-06

    A new photoluminescence material, (8-hydroxy quinoline) bis (2-2’bipyridine) lanthanum has been synthesized and characterized by different techniques. The prepared material La(Bpy){sub 2}q was characterized for structural, thermal and photoluminescence analysis. Structural analysis of this material was done by Fourier transformed infrared spectroscopy (FTIR) and mass spectroscopy. Thermal analysis of this material was done by thermal gravimetric analysis (TGA) shows the thermal stability up to 190°C.Absorption and emission spectra of the material was measured by UV-visible spectroscopy and photoluminescence spectroscopy. Solution of this material La(Bpy){sub 2}q in ethanol showed absorption peak at 385nm, which may be attributed due to (π – π*) transitions. The photoluminescence spectra of La(Bpy){sub 2}q in ethanol solution showed intense peak at 490 nm.

  5. Synthesis and characterization of lanthanum complex (5-choloro-8-hydroxy quinoline) bis (2-2'bipyridine) lanthanum La(Bpy)2(5-Clq)

    Science.gov (United States)

    Kumar, Rahul; Soam, Ankur; Bhargava, Parag

    2017-05-01

    Lanthanum complex, (5-choloro 8-hydroxy quinoline) bis (2-2'bipyridine) has been synthesized and characterized by different techniques. Lanthanum complex, La(Bpy)2(5-Clq) was characterized for structural, thermal and photoluminescence analysis. Structural analysis of this material was done by Fourier transformed infrared spectroscopy (FTIR) and mass spectroscopy. Thermal analysis of this material was done by thermal gravimetric analysis (TGA) and material shows the thermal stability up to 400°C. Absorption and emission spectra of the material was measured by UV-visible spectroscopy and photoluminescence spectroscopy. Solution of this material La(Bpy)2(5-Clq) in ethanol showed absorption peak at 332 nm, which may be attributed due to (π - π*) transitions. The photoluminescence spectra of La(Bpy)2(5-Clq) in ethanol solution showed intense peak at 505 nm.

  6. Synthesis and characterization of a new photoluminescent material (8-hydroxy quinoline) bis (2-2'bipyridine) lanthanum La(Bpy)2q

    Science.gov (United States)

    Kumar, Rahul; Bhargava, Parag

    2016-05-01

    A new photoluminescence material, (8-hydroxy quinoline) bis (2-2'bipyridine) lanthanum has been synthesized and characterized by different techniques. The prepared material La(Bpy)2q was characterized for structural, thermal and photoluminescence analysis. Structural analysis of this material was done by Fourier transformed infrared spectroscopy (FTIR) and mass spectroscopy. Thermal analysis of this material was done by thermal gravimetric analysis (TGA) shows the thermal stability up to 190°C.Absorption and emission spectra of the material was measured by UV-visible spectroscopy and photoluminescence spectroscopy. Solution of this material La(Bpy)2q in ethanol showed absorption peak at 385nm, which may be attributed due to (π - π*) transitions. The photoluminescence spectra of La(Bpy)2q in ethanol solution showed intense peak at 490 nm

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

    Science.gov (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

    2007-05-17

    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.

  8. Sertraline and venlafaxine improves motor performance and neurobehavioral deficit in quinolinic acid induced Huntington's like symptoms in rats: Possible neurotransmitters modulation.

    Science.gov (United States)

    Gill, Jaskamal Singh; Jamwal, Sumit; Kumar, Puneet; Deshmukh, Rahul

    2017-04-01

    Huntington Disease is autosomal, fatal and progressive neurodegenerative disorder for which clinically available drugs offer only symptomatic relief. Emerging strides have indicated that antidepressants improve motor performance, restore neurotransmitters level, ameliorates striatal atrophy, increases BDNF level and may enhance neurogenesis. Therefore, we investigated sertraline and venlafaxine, clinically available drugs for depression with numerous neuroprotective properties, for their beneficial effects, if any, in quinolinic acid induced Huntington's like symptoms in rats. Rats were administered quinolinic acid (QA) (200 nmol/2μl saline) intrastriatal bilaterally on 0day. Sertraline and venlafaxine (10 and 20mg/kg, po) each were administered for 21days once a day. Motor performance was assessed using rotarod test, grip strength test, narrow beam walk test on weekly basis. On day 22, animals were sacrificed and rat striatum was isolated for biochemical (LPO, GSH and Nitrite), neuroinflammation (TNF-α, IL-1β and IL-6) and neurochemical analysis (GABA, glutamate, norepinephrine, dopamine, serotonin, DOPAC, HVA and 5-HIAA). QA treatment significantly altered body weight, motor performance, oxidative defense (increased LPO, nitrite and decreased GSH), pro-inflammatory cytokines levels (TNF-α, IL-6 and IL-1β), neurochemical level (GABA, glutamate, nor-epinephrine, dopamine, serotonin, HVA, DOPAC, 5-HIAA). Sertraline and venlafaxine at selected doses significantly attenuated QA induced alterations in striatum. The present study suggests that modulation of monoamines level, normalization of GABA and glutamatergic signaling, anti-oxidant and anti-inflammatory properties could underlie the neuroprotective effect of sertraline and venlafaxine in QA induced Huntington's like symptoms. Copyright © 2016. Published by Elsevier Urban & Partner Sp. z o.o.

  9. Di-μ-cyanido-tetra­cyanido(5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane)[N-(quinolin-8-yl)quinoline-2-carboxamidato]diiron(III)nickel(II) 2.07-hydrate

    Science.gov (United States)

    Yang, Yuqi; Zhou, Hongbo; Shen, Xiaoping

    2013-01-01

    The asymmetric unit of the title complex, [Fe2Ni(C19H12N3O)2(CN)6(C16H36N4)]·2.07H2O, contains one [Fe(qcq)(CN)3]− anion, half a [Ni(teta)]2+ cation and two partially occupied inter­stitial water mol­ecules [qcq− is the N-(quinolin-8-yl)quinoline-2-carboxamidate anion and teta is 5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­deca­ne]. In the complex mol­ecule, two [Fe(qcq)(CN)3]− anions additionally coordinate the central [Ni(teta)]2+ cation through cyanide groups in a trans mode, resulting in a trinuclear structure with the Ni2+ cation lying on an inversion centre. The two inter­stitial water mol­ecules are partially occupied, with occupancy factors of 0.528 (10) and 0.506 (9). O—H⋯O and O—H⋯N hydrogen bonding involving the two lattice water molecules and the carbonyl function and a teta N atom in an adjacent cluster leads to the formation of layers extending parallel to (010). PMID:23723777

  10. Di-μ-cyanido-tetra-cyanido(5,5,7,12,12,14-hexa-methyl-1,4,8,11-tetra-aza-cyclo-tetra-decane)[N-(quinolin-8-yl)quinoline-2-carboxamidato]diiron(III)nickel(II) 2.07-hydrate.

    Science.gov (United States)

    Yang, Yuqi; Zhou, Hongbo; Shen, Xiaoping

    2013-05-01

    The asymmetric unit of the title complex, [Fe2Ni(C19H12N3O)2(CN)6(C16H36N4)]·2.07H2O, contains one [Fe(qcq)(CN)3](-) anion, half a [Ni(teta)](2+) cation and two partially occupied inter-stitial water mol-ecules [qcq(-) is the N-(quinolin-8-yl)quinoline-2-carboxamidate anion and teta is 5,5,7,12,12,14-hexa-methyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-ne]. In the complex mol-ecule, two [Fe(qcq)(CN)3](-) anions additionally coordinate the central [Ni(teta)](2+) cation through cyanide groups in a trans mode, resulting in a trinuclear structure with the Ni(2+) cation lying on an inversion centre. The two inter-stitial water mol-ecules are partially occupied, with occupancy factors of 0.528 (10) and 0.506 (9). O-H⋯O and O-H⋯N hydrogen bonding involving the two lattice water molecules and the carbonyl function and a teta N atom in an adjacent cluster leads to the formation of layers extending parallel to (010).

  11. Crystal structure of {(R-N2-[(benzo[h]quinolin-2-ylmethyl]-N2′-[(benzo[h]quinolin-2-ylmethylidene]-1,1′-binaphthyl-2,2′-diamine-κ4N,N′,N′′,N′′′}(trifluoromethanesulfonato-κOzinc(II} trifluoromethanesulfonate dichloromethane 1.5-solvate

    Directory of Open Access Journals (Sweden)

    Shayna R. Skokan

    2017-07-01

    Full Text Available The zinc(II atom in the title compound, [Zn(C48H31N4(CF3SO3](CF3SO3·1.5CH2Cl2, adopts a distorted five-coordinate square-pyramidal geometry. It is coordinated by one trifluoromethanesulfonate ligand and four N atoms of the N2-[(benzo[h]quinolin-2-ylmethyl]-N2′-[(benzo[h]quinolin-2-ylmethylidene]-1,1′-binaphthyl-2,2′-diamine ligand. The complex is present as a single-stranded P-helimer monohelical structure incorporating π–π and/or σ–π interactions. One of the imine bonds present in the original ligand framework is reduced, leading to variations in bond lengths and torsion angles for each side of the ligand motif. The imine-bond reduction also affects the bond lengths involving the metal atom with the N-donor atoms located on the imine bond. There are two molecules of the complex in the asymmetric unit. One of the molecules exhibits positional disorder within the coordinating trifluoromethanesulfonate ion making the molecules symmetrically non-equivalent.

  12. 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

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    Mohammad Saadatmandzadeh

    2014-09-01

    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.

  13. 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

    2016-09-01

    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.

  14. Synthesis of (R)-5-(Di[2,3-3H2]propylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one-([3H]U-86170) and (R)-5-([2,3-3H2]propylamino)-5,6-dihydro-4H-imidazo(4,5,1-ij) quinolin-2(1H)-one ([3H]U-91356)

    International Nuclear Information System (INIS)

    Moon, M.W.; Hsi, R.S.P.

    1992-01-01

    (R)-5-(diallylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (12b) was prepared in 9% overall yield from 3-aminoquinoline. Reaction of 12b in ethyl acetate with tritium gas in presence of a 5% platinum on carbon catalyst afforded a mixture of (R)-5-(di[2,3- 3 H 2 ]propylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one ([ 3 H]U-86170, 69 Ci/mmol) and (R)-5-([2,3- 3 H 2 ]-propylamino)5,6-dihydro-4H-imidazo-[4,5,1-ij]quinolin-2(1H)-one ( [ 3 H]U-91356, 34 Ci/mmol) which was separated by preparative reverse-phase chromatography. U-86170 and U-91356 are potent dopamine D2 agonists. The labelled compounds are useful for drug disposition studies. [ 3 H]U-86170 is also useful as a dopamine D2 agonist radioligand for receptor binding studies. (author)

  15. 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

    2016-06-01

    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

  16. 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

    2004-01-01

    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...

  17. 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.

    2001-01-01

    associated with enhanced development of ACF and colorectal cancer in humans. The present study was designed as an integrated part of our earlier published ACF study and follows the animals until tumour development. The aim of the study was to investigate (1) the effect of a refined carbohydrate-rich diet...... 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......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...

  18. Synthesis and biological evaluation of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives as inhibitors of colon cancer cell growth

    Directory of Open Access Journals (Sweden)

    Tie-Ling Li

    2015-08-01

    Full Text Available A convenient synthesis of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives was reported using 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with different aromatic amines using silica sulfuric acid. The compounds were tested for their anticancer activity against colon (HCT-116 and S1-MI-80, prostate (PC3 and DU-145, breast (MCF-7 and MDAMB-231 cancer cells. These com-pounds showed more selectivity and potent cytotoxic activity against colon cancer cells. 3c was tested against five other colon cancer cell lines (HT-29, HCT-15, LS-180, LS-174, and LoVo, which had similar cytotoxicity and selectivity. 3c did not induce PXR-regulated ABCB1 or ABCG2 transporters. In fact, 3c induced cytotoxicity in HEK293 cells over expressing ABCB1 or ABCG2 to the same extent as in normal HEK293 cells. It was cytotoxic approximately 3- and 5-fold to resistant colon carcinoma S1-MI-80 cells. 3c also produced concentration-dependent changes in HCT-116 colon cancer cells, in mitochondrial membrane potential, leading to apoptosis, and sub-micromolar concentrations caused chromosomal DNA fragmentation.

  19. DMH1 (4-[6-(4-isopropoxyphenylpyrazolo[1,5-a]pyrimidin-3-yl]quinoline inhibits chemotherapeutic drug-induced autophagy

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    Yue Sheng

    2015-07-01

    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.

  20. Quinolinic acid induced neurodegeneration in the striatum: a combined in vivo and in vitro analysis of receptor changes and microglia activation

    International Nuclear Information System (INIS)

    Moresco, R.M.; Lavazza, T.; Belloli, S.; Todde, S.; Matarrese, M.; Carpinelli, A.; Turolla, E.; Fazio, F.; Lecchi, M.; Pezzola, A.; Popoli, P.; Zimarino, V.; Malgaroli, A.

    2008-01-01

    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 2A and dopamine D 2 receptors) together with the degree of microglia activation. Both approaches showed a loss of adenosine A 2A and dopamine D 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.)

  1. Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

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    Martina Tireli

    2017-11-01

    Full Text Available Copper-catalyzed mechanochemical click reactions using Cu(II, Cu(I and Cu(0 catalysts have been successfully implemented to provide novel 6-phenyl-2-(trifluoromethylquinolines with a phenyl-1,2,3-triazole moiety at O-4 of the quinoline core. Milling procedures proved to be significantly more efficient than the corresponding solution reactions, with up to a 15-fold gain in yield. Efficiency of both solution and milling procedures depended on the p-substituent in the azide reactant, resulting in H < Cl < Br < I reactivity bias. Solid-state catalysis using Cu(II and Cu(I catalysts entailed the direct involvement of the copper species in the reaction and generation of highly luminescent compounds which hindered in situ monitoring by Raman spectroscopy. However, in situ monitoring of the milling processes was enabled by using Cu(0 catalysts in the form of brass milling media which offered a direct insight into the reaction pathway of mechanochemical CuAAC reactions, indicating that the catalysis is most likely conducted on the surface of milling balls. Electron spin resonance spectroscopy was used to determine the oxidation and spin states of the respective copper catalysts in bulk products obtained by milling procedures.

  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: wlya@lynu.edu.cn [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)

    2015-10-15

    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. Synthesis, DNA binding and cytotoxic activity of pyrimido[4',5':4,5]thieno(2,3-b)quinoline with 9-hydroxy-4-(3-diethylaminopropylamino) and 8-methoxy-4-(3-diethylaminopropylamino) substitutions.

    Science.gov (United States)

    KiranKumar, Hulihalli N; RohitKumar, Heggodu G; Advirao, Gopal M

    2018-01-01

    Two new derivatives of pyrimido[4',5';4,5]thieno(2,3-b)quinoline (PTQ), 9-hydroxy-4-(3-diethylaminopropylamino)pyrimido[4',5';4,5]thieno(2,3-b)quinoline (Hydroxy-DPTQ) and 8-methoxy-4-(3-diethylaminopropylamino)pyrimido[4',5';4,5]thieno(2,3-b)quinoline (Methoxy-DPTQ) were synthesized and their DNA binding ability was analyzed using spectroscopy (UV-visible, fluorescence and circular dichroism), ethidium bromide dye displacement assay, melting temperature (T m ) analysis and computational docking studies. The hypochromism in UV-visible spectrum and increased fluorescence emission of Hydroxy-DPTQ and Methoxy-DPTQ in the presence of DNA suggested the molecule-DNA interaction. The association constants calculated from UV-visible and spectral titrations were of the order 10 4 to 10 6 M -1 . Circular dichroism studies corroborated the induced conformational changes in DNA upon addition of molecules. The change in the ellipticity was observed both in negative and positive peak of DNA, thus, suggesting the intercalation of molecules. The observed displacement of ethidium bromide from the DNA and increased T m , upon addition of DNA confirmed the intercalative mode of binding. This was further validated by computational docking, which showed clear intercalation of molecules into the d(GpC)-d(CpG) site of the receptor DNA. Anticancer activities of these molecules are evaluated by using MTT assay. Both molecules showed antiproliferative activity against all the three cancer cells studied, with Hydroxy-DPTQ being more potential molecule among the two. IC 50 value of Hydroxy-DPTQ and Methoxy-DPTQ were in the range of 3-5μM and 130-250μM, respectively. Copyright © 2017 Elsevier B.V. All rights reserved.

  4. Effect of quinolinic acid-induced lesions of the nucleus accumbens core on performance on a progressive ratio schedule of reinforcement: implications for inter-temporal choice.

    Science.gov (United States)

    Bezzina, G; Body, S; Cheung, T H C; Hampson, C L; Deakin, J F W; Anderson, I M; Szabadi, E; Bradshaw, C M

    2008-04-01

    The nucleus accumbens core (AcbC) is believed to contribute to the control of operant behaviour by reinforcers. Recent evidence suggests that it is not crucial for determining the incentive value of immediately available reinforcers, but is important for maintaining the values of delayed reinforcers. This study aims to examine the effect of AcbC lesions on performance on a progressive-ratio schedule using a quantitative model that dissociates effects of interventions on motor and motivational processes (Killeen 1994 Mathematical principles of reinforcement. Behav Brain Sci 17:105-172). Rats with bilateral quinolinic acid-induced lesions of the AcbC (n = 15) or sham lesions (n = 14) were trained to lever-press for food-pellet reinforcers under a progressive-ratio schedule. In Phase 1 (90 sessions) the reinforcer was one pellet; in Phase 2 (30 sessions), it was two pellets; in Phase 3, (30 sessions) it was one pellet. The performance of both groups conformed to the model of progressive-ratio performance (group mean data: r2 > 0.92). The motor parameter, delta, was significantly higher in the AcbC-lesioned than the sham-lesioned group, reflecting lower overall response rates in the lesioned group. The motivational parameter, a, was sensitive to changes in reinforcer size, but did not differ significantly between the two groups. The AcbC-lesioned group showed longer post-reinforcement pauses and lower running response rates than the sham-lesioned group. The results suggest that destruction of the AcbC impairs response capacity but does not alter the efficacy of food reinforcers. The results are consistent with recent findings that AcbC lesions do not alter sensitivity to reinforcer size in inter-temporal choice schedules.

  5. 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

    2011-08-01

    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.

  6. 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

    2010-05-01

    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.

  7. Synthesis and antimalarial testing of neocryptolepine analogues: addition of ester function in SAR study of 2,11-disubstituted indolo[2,3-b]quinolines.

    Science.gov (United States)

    Lu, Wen-Jie; Wicht, Kathryn J; Wang, Li; Imai, Kento; Mei, Zhen-Wu; Kaiser, Marcel; El Sayed, Ibrahim El Tantawy; Egan, Timothy J; Inokuchi, Tsutomu

    2013-06-01

    This report describes the synthesis, and in vitro and in vivo antimalarial evaluations of certain ester-modified neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives. The modifications were carried out by introducing ester groups at the C2 and/or C9 position on the neocryptolepine core and the terminal amino group of the 3-aminopropylamine substituents at the C11 position with a urea/thiourea unit. The antiplasmodial activities of our derivative agents against two different strains (CQS: NF54, and CQR: K1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that the ester modified neocryptolepine derivatives have higher antiplasmodial activities against both strains and a low cytotoxic activity against normal cells. The best results were achieved by compounds 9c and 12b against the NF54 strain with the IC50/SI value as 2.27 nM/361 and 1.81 nM/321, respectively. While against K1 strain, all the tested compounds showed higher activity than the well-known antimalarial drug chloroquine. Furthermore, the compounds were tested for β-haematin inhibition and 12 were found to be more active than chloroquine (IC50 = 18 μM). Structure activity relationship studies exposed an interesting linear correlation between polar surface area of the molecule and β-haematin inhibition for this series. In vivo testing of compounds 7 and 8a against NF54 strain on Plasmodium berghei female mice showed that the introduction of the ester group increased the antiplasmodial activity of the neocryptolepine core substantially. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

  8. Gold(I) complex of 1,1'-bis(diphenylphosphino) ferrocene-quinoline conjugate: a virostatic agent against HIV-1.

    Science.gov (United States)

    Gama, Ntombenhle; Kumar, Kamlesh; Ekengard, Erik; Haukka, Matti; Darkwa, James; Nordlander, Ebbe; Meyer, Debra

    2016-06-01

    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.

  9. Type 1 cannabinoid receptor mapping with [18F]MK-9470 PET in the rat brain after quinolinic acid lesion: a comparison to dopamine receptors and glucose metabolism

    International Nuclear Information System (INIS)

    Casteels, Cindy; Martinez, Emili; Camon, Lluisa; Vera, Nuria de; Planas, Anna M.; Bormans, Guy; Baekelandt, Veerle; Laere, Koen van

    2010-01-01

    Several lines of evidence imply early alterations in metabolic, dopaminergic and endocannabinoid neurotransmission in Huntington's disease (HD). Using [ 18 F]MK-9470 and small animal PET, we investigated cerebral changes in type 1 cannabinoid (CB 1 ) receptor binding in the quinolinic acid (QA) rat model of HD in relation to glucose metabolism, dopamine D 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 [ 18 F]MK-9470, [ 18 F]FDG and [ 11 C]raclopride. Relative glucose metabolism and parametric CB 1 receptor and D 2 binding images were anatomically standardized to Paxinos space and analysed voxel-wise using Statistical Parametric Mapping (SPM2). In the QA model, [ 18 F]MK-9470 uptake, glucose metabolism and D 2 receptor binding were reduced in the ipsilateral caudate-putamen by 7, 35 and 77%, respectively (all p -5 ), while an increase for these markers was observed on the contralateral side (>5%, all p -4 ). [ 18 F]MK-9470 binding was also increased in the cerebellum (p = 2.10 -5 ), where it was inversely correlated to the number of ipsiversive turnings (p = 7.10 -6 ), suggesting that CB 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 -6 ). These data point to in vivo changes in endocannabinoid transmission, specifically for CB 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 2 and CB 1 neurotransmission in the contralateral hemisphere. (orig.)

  10. 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

    2002-11-01

    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)

  11. Modification of oxidative status in Plasmodium berghei-infected erythrocytes by E-2-chloro-8-methyl-3-[(4'-methoxy-1'-indanoyl-2'-methyliden]-quinoline compared to chloroquine

    Directory of Open Access Journals (Sweden)

    Juan Rodrigues

    2009-09-01

    Full Text Available E-2-chloro-8-methyl-3-[(4'-methoxy-1'-indanoyl-2'-methyliden]-quinoline (IQ is a new quinoline derivative which has been reported as a haemoglobin degradation and ß-haematin formation inhibitor. The haemoglobin proteolysis induced by Plasmodium parasites represents a source of amino acids and haeme, leading to oxidative stress in infected cells. In this paper, we evaluated oxidative status in Plasmodium berghei-infected erythrocytes in the presence of IQ using chloroquine (CQ as a control. After haemolysis, superoxide dismutase (SOD, catalase, glutathione cycle and NADPH + H+-dependent dehydrogenase enzyme activities were investigated. Lipid peroxidation was also assayed to evaluate lipid damage. The results showed that the overall activities of glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase were significantly diminished by IQ (by 53.5% and 100%, respectively. Glutathione peroxidase activity was also lowered (31% in conjunction with a higher GSSG/GSH ratio. As a compensatory response, overall SOD activity increased and lipid peroxidation decreased, protecting the cells from the haemolysis caused by the infection. CQ shared most of the effects showed by IQ; however it was able to inhibit the activity of isocitrate dehydrogenase and glutathione-S-transferase. In conclusion, IQ could be a candidate for further studies in malaria research interfering with the oxidative status in Plasmodium berghei infection.

  12. Effect of Mentha pulegium extract and 8-hydroxy quinoline sulphate to extend the quality and vase life of rose (Rosa hybrid) cut flower.

    Science.gov (United States)

    Hashemabadi, Davood; Torkashvand, Ali Mohammadi; Kaviani, Behzad; Bagherzadeh, Maryam; Rezaalipour, Mohaddeseh; Zarchini, Mohammad

    2015-01-01

    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

  13. The anti-tumor effect of the quinoline-3-carboxamide tasquinimod: blockade of recruitment of CD11b+ Ly6Chi cells to tumor tissue reduces tumor growth

    International Nuclear Information System (INIS)

    Deronic, Adnan; Leanderson, Tomas; Ivars, Fredrik

    2016-01-01

    Previous work has demonstrated immunomodulatory, anti-tumor, anti-metastatic and anti-angiogenic effects of the small molecule quinoline-3-carboxamide tasquinimod in pre-clinical cancer models. To better understand the anti-tumor effects of tasquinimod in transplantable tumor models, we have evaluated the impact of the compound both on recruitment of myeloid cells to tumor tissue and on tumor-induced myeloid cell expansion as these cells are known to promote tumor development. Mice bearing subcutaneous 4 T1 mammary carcinoma tumors were treated with tasquinimod in the drinking water. A BrdU-based flow cytometry assay was utilized to assess the impact of short-term tasquinimod treatment on myeloid cell recruitment to tumors. Additionally, long-term treatment was performed to study the anti-tumor effect of tasquinimod as well as its effects on splenic myeloid cells and their progenitors. Myeloid cell populations were also immune-depleted by in vivo antibody treatment. Short-term tasquinimod treatment did not influence the proliferation of splenic Ly6C hi and Ly6G hi cells, but instead reduced the influx of Ly6C hi cells to the tumor. Treatment with tasquinimod for various periods of time after tumor inoculation revealed that the anti-tumor effect of this compound mainly operated during the first few days of tumor growth. Similar to tasquinimod treatment, antibody-mediated depletion of Ly6C hi cells within that same time frame, caused reduced tumor growth, thereby confirming a significant role for these cells in tumor development. Additionally, long-term tasquinimod treatment reduced the splenomegaly and expansion of splenic myeloid cells during a later phase of tumor development. In this phase, tasquinimod normalized the tumor-induced alterations in myeloerythroid progenitor cells in the spleen but had only limited impact on the same populations in the bone marrow. Our results indicate that tasquinimod treatment reduces tumor growth by operating early after tumor

  14. IND-2, a pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline derivative, circumvents multi-drug resistance and causes apoptosis in colon cancer cells.

    Science.gov (United States)

    Karthikeyan, Chandrabose; Lee, Crystal; Moore, Joshua; Mittal, Roopali; Suswam, Esther A; Abbott, Kodye L; Pondugula, Satyanarayana R; Manne, Upender; Narayanan, Narayanan K; Trivedi, Piyush; Tiwari, Amit K

    2015-02-01

    Naturally occurring condensed quinolines have anticancer properties. In efforts to find active analogues, we designed and synthesized eight polycyclic heterocycles with a pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline framework (IND series). The compounds were evaluated for activity against colon (HCT-116 and S1-MI-80), prostate (PC3 and DU-145), breast (MCF-7 and MDAMB-231), ovarian (ov2008 and A2780), and hepatocellular (HepG2) cancer cells and against non-cancerous Madin Darby canine kidney (MDCK), mouse embryonic fibroblast (NIH/3T3), and human embryonic kidney cells (HEK293). IND-2, a 4-chloro-2-methyl pyrimido[1″,2″:1,5]pyrazolo[3,4-b]quinoline, exhibited more than ten-fold selectivity and potent cytotoxic activity against colon cancer cells relative to the other cancer and non-cancer cells. With five additional colon cancer cell lines (HT-29, HCT-15, LS-180, LS-174, and LoVo), IND-2 had similar cytotoxicity and selectivity, and sub-micromolar concentrations caused changes in the morphology of HCT-116 and HCT-15 cells. IND-2 did not activate the transactivating function of the pregnane X receptor (PXR), indicating that it does not induce PXR-regulated ABCB1 or ABCG2 transporters. Indeed, IND-2 was not a substrate of ABCB1 or ABCG2, and it induced cytotoxicity in HEK293 cells overexpressing ABCB1 or ABCG2 to the same extent as in normal HEK293 cells. IND-2 was cytotoxic to resistant colon carcinoma S1-MI-80 cells, approximately three- and five-fold more than SN-38 and topotecan, respectively. In HCT-116 colon cancer cells, IND-2 produced concentration-dependent changes in mitochondrial membrane potential, leading to apoptosis, and sub-micromolar concentrations caused chromosomal DNA fragmentation. These findings suggest that, by increasing apoptosis, IND-2 has potential therapeutic efficacy for colorectal cancer. Copyright © 2014 Elsevier Ltd. All rights reserved.

  15. Molecular Iodine: A Versatile Catalyst for the Synthesis of 4-Aryl-3-methyl-1-phenyl-1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-diones in Water

    International Nuclear Information System (INIS)

    Wu, Liqiang; Yang, Limin; Yan, Fulin; Yang, Chunguang; Fang, Lizhen

    2010-01-01

    An efficient methodology for the synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-diones has been developed. To our best knowledge, this is the first report for the synthesis of these compounds by multicomponent condensation of 3-methyl-1-phenyl-1H-pyrazol-5-amine, aldehydes and 2-hydroxynaphthalene-1,4-dione in the presence of molecular iodine as a catalyst in water. The simple experimental procedure, utilization of an inexpensive and readily available catalyst, and excellent yields are the advantages of the present method. Multicomponent reactions (MCRs) have attracted considerable attention since they are performed without need to isolate any intermediate during their processes; may reduce time and save both energy and raw materials. They have merits over two-component reactions in several aspects including the simplicity of a one-pot procedure, possible structural variations and building up complex molecules

  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.

    1996-01-01

    ,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......The aberrant crypt foci (ACF) bioassay has been used extensively to study the early effects of different dietary components on the colonic mucosa of laboratory rodents. ACF are proposed to represent preneoplastic lesions of colon cancer. Compared to the normally used initiators 1....... 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. 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

    2015-01-01

    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.

  18. PEG1000-Based Dicationic Acidic Ionic Liquid Catalyzed One-Pot Synthesis of 4-Aryl-3-Methyl-1-Phenyl-1H-Benzo[h]pyrazolo [3,4-b]quinoline-5,10-Diones via Multicomponent Reactions

    Directory of Open Access Journals (Sweden)

    Yi-Ming Ren

    2015-09-01

    Full Text Available A novel and green approach for efficient and rapid synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[h]pyrazolo[3,4-b]quinoline-5,10-diones has been accomplished by the one-pot condensation reaction of aromatic aldehydes, 3-methyl-1-phenyl-1H-pyrazol-5-amine and 2-hydroxynaphthalene-1,4-dione using PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL as a catalyst was reported. Recycling studies have shown that the PEG1000-DAIL can be readily recovered and reused several times without significant loss of activity. The key advantages are the short reaction time, high yields, simple workup, and recovered catalyst.

  19. Synthesis, Characterization and Biological Evaluation of Mononuclear Dichloro-bis[2-(2-chloro-6,7-substituted Quinolin-3-yl-1H-benzo[d]imidazole]Co(II Complexes

    Directory of Open Access Journals (Sweden)

    Minaxi Samatbhai Maru

    2015-06-01

    Full Text Available A series of Co(II complexes 3¢a-g of 2-(2-chloro-6,7-substituted quinolin-3-yl-1H-benzo[d]imidazole ligands 3a-g were prepared and characterized by various spectroscopic and physico-chemical methods viz. FT-IR, ESI mass, 1H NMR, 13C NMR and UV-Visible spectroscopy, Thermogravimetric analysis, Magnetic susceptibility, Molar conductance and Elemental analysis. The 2-(2-chloro-6,7-substituted quinolin-3-yl-1H-benzo[d]imidazole ligands 3a-g have been synthesized by cyclocondensation of benzene-1,2-diamine with 2-chloroquinoline-3-carbaldehydes by using ceric ammonium nitrate as a catalyst in presence of hydrogen peroxide as an oxidant. The structures of all ligands were confirmed by IR, Mass, UV-Visible, 1H NMR and 13C NMR spectroscopy. All ligands 3a-g and their Co(II complexes 3¢a-g were screened for their in vitro antimicrobial activity using twofold serial dilution technique against standard MTCC strains of two Gram-positive Staphylococcus aureus and Streptococcus pyogenes, two Gram-negative Escherichia coli and Pseudomonas aeruginosa bacteria and three Candida albicans, Aspergillus niger and Aspergillus clavatus fungus in comparison with standard drugs. All ligands 3a-g and complexes 3¢a-g also evaluated for antimycobacterial activity against standard Mycobacterium tuberculosis H37Rv strain. DOI: http://dx.doi.org/10.17807/orbital.v7i2.530

  20. 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.

    Science.gov (United States)

    Nowak, Adriana; Czyżowska, Agata; Huben, Krzysztof; Sójka, Michał; Kuberski, Sławomir; Otlewska, Anna; Śliżewska, Katarzyna

    2016-06-01

    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. Copyright © 2016 Elsevier Ltd. All rights reserved.

  1. TD-DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

    International Nuclear Information System (INIS)

    Paul, Bijan Kumar; Guchhait, Nikhil

    2011-01-01

    Here, we report a Density Functional Theoretical (DFT) study on the photophysics of a potent Excited-State Intramolecular Proton Transfer (ESIPT) molecular system, viz., 10-hydroxybenzo[h]quinoline (HBQ). Particular emphasis has been rendered on the assessment of the proton transfer reaction in HBQ in the ground and excited-states through elucidation and a careful perusal of the potential energy surfaces (PES). The non-viability of Ground-State Intramolecular Proton Transfer (GSIPT) process is dictated by a high-energy barrier coupled with no energy minimum for the proton transferred (K-form) form at the ground-state (S 0 ) PES. Remarkable reduction of the barrier along with thermodynamic stability inversion between the enol (E-form) and the keto forms (K-form) of HBQ upon photoexcitation from S 0 to the S 1 -state advocate for the operation of ESIPT process. These findings have been cross-validated on the lexicon of analysis of optimized geometry parameters, Mulliken's charge distribution on the heavy atoms, and molecular orbitals (MO) of the E- and the K-forms of HBQ. Our computational results also corroborate to experimental observations. From the modulations in optimized geometry parameters in course of the PT process a critical assessment has been endeavoured to delve into the movement of the proton during the process. Additional stress has been placed on the analysis of the intramolecular hydrogen bonding (IMHB) interaction in HBQ. The IMHB interaction has been explored by calculation of electron density ρ(r) and the Laplacian ∇ 2 ρ(r) at the bond critical point (BCP) using Atoms-In-Molecule (AIM) method and by calculation of interaction between σ* of OH with the lone pair of the nitrogen atom using Natural Bond Orbital (NBO) analysis. - Highlights: → Theoretical modelling of the photophysics of an ESIPT probe 10-hydroxybenzo[h]quinoline (HBQ). → Calculation of intramolecular hydrogen bond (IMHB) energy. → Role of hyperconjugative charge transfer

  2. Tandem pseudopericyclic reactions: [1,5]-X sigmatropic shift/6pi-electrocyclic ring closure converting N-(2-X-carbonyl)phenyl ketenimines into 2-X-quinolin-4(3H)-ones.

    Science.gov (United States)

    Alajarín, Mateo; Ortín, María-Mar; Sanchez-Andrada, Pilar; Vidal, Angel

    2006-10-13

    N-(2-X-Carbonyl)phenyl ketenimines undergo, under mild thermal conditions, [1,5]-migration of the X group from the carbonyl carbon to the electron-deficient central carbon atom of the ketenimine fragment, followed by a 6pi-electrocyclic ring closure of the resulting ketene to provide 2-X-substituted quinolin-4(3H)-ones in a sequential one-pot manner. The X groups tested are electron-donor groups, such as alkylthio, arylthio, arylseleno, aryloxy, and amino. When involving alkylthio, arylthio, and arylseleno groups, the complete transformation takes place in refluxing toluene, whereas for aryloxy and amino groups the starting ketenimines must be heated at 230 degrees C in a sealed tube in the absence of solvent. The mechanism for the conversion of these ketenimines into quinolin-4(3H)-ones has been studied by ab initio and DFT calculations, using as model compounds N-(2-X-carbonyl)vinyl ketenimines bearing different X groups (X = F, Cl, OH, SH, NH(2), and PH(2)) converting into 4(3H)-pyridones. This computational study afforded two general reaction pathways for the first step of the sequence, the [1,5]-X shift, depending on the nature of X. When X is F, Cl, OH, or SH, the migration occurs in a concerted mode, whereas when X is NH(2) or PH(2), it involves a two-step sequence. The order of migratory aptitudes of the X substituents at the acyl group is predicted to be PH(2) > Cl > SH > NH(2) > F> OH. The second step of the full transformation, the 6pi-electrocyclic ring closure, is calculated to be concerted and with low energy barriers in all the cases. We have included in the calculations an alternative mode of cyclization of the N-(2-X-carbonyl)vinyl ketenimines, the 6pi-electrocyclic ring closure leading to 1,3-oxazines that involves its 1-oxo-5-aza-1,3,5-hexatrienic system. Additionally, the pseudopericyclic topology of the transition states for some of the [1,5]-X migrations (X = F, Cl, OH, SH), for the 6pi-electrocyclization of the ketene intermediates to the 4

  3. Structural, Optical, Electrical and Photoelectrical Properties of 2-Amino-4-(5-bromothiophen-2-yl)-5,6-dihydro-6-methyl-5-oxo-4 H-pyrano[3,2-c] quinoline-3-carbonitrile Films

    Science.gov (United States)

    Mansour, A. M.; El-Taweel, F. M. A.; Abu El-Enein, R. A. N.; El-Menyawy, E. M.

    2017-12-01

    2-Amino-4-(5-bromothiophen-2-yl)-5,6-dihydro-6-methyl-5-oxo-4 H-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.

  4. 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.

    1996-01-01

    The usefulness of transgenic E mu-pim-1 mice over-expressing the pim-1 oncogene in lymphoid tissues, as sensitive test organisms was studied in a short-term carcinogenicity study. The mice were fed standard diet Altromin 1314 supplemented either with 0.03% 2-amino-1-methyl-6-phenylimidazo[4,5-b......]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...... 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...

  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

    2011-03-01

    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. Crystal structure of ({(1R,2R-N,N′-bis[(quinolin-2-ylmethyl]cyclohexane-1,2-diamine}chloridoiron(III-μ-oxido-[trichloridoferrate(III] chloroform monosolvate

    Directory of Open Access Journals (Sweden)

    Hannah Swift

    2017-07-01

    Full Text Available The first FeIII atom in the solvated title compound, [Fe2Cl4O(C26H28N4]·CHCl3, adopts a distorted six-coordinate octahedral geometry. It is coordinated by one chloride ligand, four N atoms from the (1R,2R-N,N′-bis[(quinolin-2-ylmethyl]cyclohexane-1,2-diamine ligand, and a bridging oxido ligand attached to the second FeIII atom, which is also bonded to three chloride ions. A very weak intramolecular N—H...Cl hydrogen bond occurs. In the crystal, the coordination complexes stack in columns, and a grouping of six such columns create channels, which are populated by disordered chloroform solvent molecules. Although the Fe—Cl bond lengths for the two metal atoms are comparable to the mean Fe—Cl bond lengths as derived from the Cambridge Structural Database, the Fe—O bond lengths are notably shorter. The solvent chloroform molecule exhibits `flip' disorder of the C—H moiety in a 0.544 (3:0.456 (3 ratio. The only directional interaction noted is a weak C—H...Cl hydrogen bond.

  7. 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

    International Nuclear Information System (INIS)

    Ferguson, Lynnette R.; Harris, Philip J.; Kestell, Philip; Zhu, Shuotun; Munday, Rex; Munday, Christine M.

    2011-01-01

    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 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.

  8. Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11.

    Science.gov (United States)

    Wang, Ning; Wicht, Kathryn J; Imai, Kento; Wang, Ming-Qi; Anh Ngoc, Tran; Kiguchi, Ryo; Kaiser, Marcel; Egan, Timothy J; Inokuchi, Tsutomu

    2014-05-01

    A series of indolo[3,2-c]quinolines were synthesized by modifying the side chains of the ω-aminoalkylamines at the C6 position and introducing substituents at the C2 position, such as F, Cl, Br, Me, MeO and NO2, and a methyl group at the N11 position for an SAR study. The in vitro antiplasmodial activities of the derivative agents against two different strains (CQS: NF54 and CQR: K1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that compounds 6k and 6l containing the branched methyl groups of 3-aminopropylamino at C6 with a Cl atom at C2 exhibited a very low cytotoxicity with IC50 values above 4000 nM, high antimalarial activities with IC50 values of about 11 nM for CQS (NF54), IC50 values of about 17 nM for CQR (K1), and RI resistance indices of 1.6. Furthermore, the compounds were tested for β-haematic inhibition, and QSAR revealed an interesting linear correlation between the biological activity of CQS (NF54) and three contributing factors, namely solubility, hydrophilic surface area, and β-haematin inhibition for this series. In vivo testing of 6l showed a reduction in parasitaemia on day 4 with an activity of 38%. Copyright © 2014 Elsevier Ltd. All rights reserved.

  9. The synthesis of 1,2,7,11b-Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and 1,3,3a,9b-tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones

    OpenAIRE

    Heaney, Frances; Bourke, Sharon

    1995-01-01

    The reaction of various ethyl 3-[[2-(1-hydroxyiminoalkyl)phenyl]carbamoyl]acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolo[2,3-d][1,4]benzodiazepin-6(5H)-ones and tetrahydroisoxazolo[4,3-c]quinolin-4(5H)-ones (4) and (6). The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.

  10. (E)-4-Methyl-N-((quinolin-2-yl)ethylidene)aniline as ligand for IIB supramolecular complexes: synthesis, structure, aggregation-induced emission enhancement and application in PMMA-doped hybrid material.

    Science.gov (United States)

    Wang, Ani; Fan, Ruiqing; Dong, Yuwei; Chen, Wei; Song, Yang; Wang, Ping; Hao, Sue; Liu, Zhigang; Yang, Yulin

    2016-12-20

    Judicious structural design employing 2-quinolinecarboxaldehyde and 4-methylaniline was used to generate the Schiff base ligand (E)-4-methyl-N-((quinolin-2-yl)ethylidene)aniline (L). Five IIB complexes, namely, [ZnLCl 2 ] (1), [ZnL(NO 3 ) 2 ] (2), [ZnL(OAc) 2 ] 3 (3), [CdL(OAc) 2 ] 3 (4), and [HgLCl 2 ] (5) have been synthesized based on L. Single-crystal X-ray diffraction analysis indicates that complexes 1, 3 and 4 exhibit 3D networks, whereas 2 and 5 form 2D layers and 1D chains, respectively. TD-DFT calculations show a good correlation with the UV-vis absorption assigned to π → π* intraligand transitions. Furthermore, complexes 1-5 displayed strong greenish luminescent emissions (518-524 nm) in the aggregate state but weak emissions in solution (aggregation-induced emission enhancement), which may be due to the existence of C-HCl/O hydrogen bonding and ππ stacking interactions, resulting in restriction of intramolecular rotation (RIR). Variable-concentration 1 H NMR studies suggested that the aggregates undergo intramolecular changes in conformation due to intermolecular interactions. Moreover, the emission intensity and lifetime exhibited obvious increases induced by mechanical grinding and temperature reduction, which were also attributed to AIEE properties. Subsequently, complex 1 was incorporated into poly(methyl methacrylate) (PMMA), whereby 1-PMMA exhibited enhanced emission intensity (20-fold increase in comparison with that of 1), which offers opportunities for use in plastic greenhouses to increase leaf photosynthesis.

  11. 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)

    International Nuclear Information System (INIS)

    Ferk, Franziska; Huber, Wolfgang W.; Filipic, Metka; Bichler, Julia; Haslinger, Elisabeth; Misik, Miroslav; Nersesyan, Armen; Grasl-Kraupp, Bettina; Zegura, Bojana; Knasmueller, Siegfried

    2010-01-01

    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 μg/kg b.w.) before and during carcinogen treatment led to a significant reduction of the number of GST-p + 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.

  12. Oxovanadium(IV), cerium(III), thorium(IV) and dioxouranium(VI) complexes of 1-ethyl-4-hydroxy-3-(nitroacetyl)quinolin-2(1H)-one: Synthesis, spectral, thermal, fluorescence, DFT calculations, antimicrobial and antitumor studies

    Science.gov (United States)

    El-Shafiy, H. F.; Shebl, Magdy

    2018-03-01

    A new series of mononuclear oxovanadium(IV), cerium(III), thorium(IV) and dioxouranium(VI) complexes of a quinolinone ligand; 1-ethyl-4-hydroxy-3-(nitroacetyl)quinolin-2(1H)-one (H2L) have been synthesized. The metal complexes were characterized by different techniques such as elemental and thermal analyses, IR, 1H NMR, electronic, ESR, mass spectra and powder XRD, TEM in addition to magnetic susceptibility and conductivity measurements. The quinolinone ligand acts as a dibasic bidentate ligand forming mononuclear complexes, which can be formulated as: [(L)VO(H2O)2]·0.5H2O, [(L)M(NO3)x(H2O)y]·nH2O; M = Ce or Th, x = 1 or 2, y = 3 or 4 and n = 2 or 7 and [(L)UO2(H2O)x(MeOH)y]·nH2O; x = 2 or 3, y = 0 or 1 and n = 0.5 or 2.5. The photoluminescent properties of the prepared complexes were studied. The ligand and its thorium(IV) complex are characterized by an intense green emission. Kinetic parameters (Ea, A, ΔH, ΔS and ΔG) of the thermal decomposition stages have been evaluated using Coats-Redfern equations. The geometry of the ligand and its oxovanadium(IV) complex has been optimized using density functional theory (DFT). Total energy, energy of HOMO and LUMO, dipole moment and structure activity relationship were performed and confirmed practical antimicrobial and antitumor results. The antimicrobial activity of the ligand and its metal complexes was conducted against the microorganisms S. aureus, K. pnemonia, E. coli, P. vulgaris and C. albicans and the MIC values were determined. The antitumor activity of the ligand and its metal complexes was investigated against human Hepatocelluar carcinoma and human breast cancer cell lines.

  13. Synthesis of samarium complexes with the derivative binder of Schiff Quinolinic base. Characterization and photophysical study; Sintesis de complejos de samario con el ligante derivado de base de Schiff Quinolinica. Caracterizacion y estudio fotofisico

    Energy Technology Data Exchange (ETDEWEB)

    Lucas H, J.

    2016-07-01

    In this work we determined the metal: binder stoichiometry of the species formed during the UV/Vis spectrophotometric titration of the derivative binder of Schiff quinolinic base, L1 with the samarium nitrate pentahydrate in methanol. Statistical analysis of the data allowed proposing the metal: binder stoichiometry for the synthesis of the complexes which was one mole of samarium salt by 2.5 moles of binder and thus favor the formation of complexes with 1M: 1L and 1M: 2L stoichiometries. They were synthesized in aqueous-organic medium (water-ethanol), isolated and purified two complexes with stoichiometry 1 Sm: 1 L1, complex 1 and 1 Sm: 2 L1, complex 2. The overall yield of the reaction was 76%. The characterization of the formed complexes was performed by visible ultraviolet spectrometry (UV/Vis), nuclear magnetic resonance, X-ray photoelectron spectroscopy (XP S), thermal gravimetric analysis with differential scanning calorimetry (TGA/DSC), and radial distribution function. These complexes were studied by fluorescence and emission phosphorescence at variable temperature. Spectroscopic techniques used in both solution and solid demonstrated the formation and stability of these complexes. In addition XP S indicated that in both complexes the samarium retains its oxidation state 3+. Luminescence studies indicated that there is intra-binding charge transfer which decreases the transfer of light energy from the binder to the samarium. Based on the experimental results, L1 binder molecules and complexes 1 and 2 were modeled that demonstrated the proposed Nc for each complex, as well as allowed to visualize the structural arrangement of the molecules, complexes and binder. (Author)

  14. 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)

    2017-03-24

    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.

  15. 7-Chloro-6-piperidin-1-yl-quinoline-5,8-dione (PT-262), a novel synthetic compound induces lung carcinoma cell death associated with inhibiting ERK and CDC2 phosphorylation via a p53-independent pathway.

    Science.gov (United States)

    Hsu, Tzu-Sheng; Chen, Chinpiao; Lee, Pei-Ting; Chiu, Shu-Jun; Liu, Huei-Fang; Tsai, Chih-Chien; Chao, Jui-I

    2008-10-01

    The derivatives of 5,8-quinolinedione have been shown to exert anticancer activities. A new synthetic compound 7-chloro-6-piperidin-1-yl-quinoline-5,8-dione (designed as PT-262) derived from 6,7-dichloroquinoline-5,8-dione on its anticancer activity was investigated in this study. PT-262 was synthesized as the following: triethylamine (0.56 ml, 5.1 mmol) was added dropwise to a solution of 6,7-dichloroquinoline-5,8-dione (1.00 g, 4.4 mmol) and piperidine (0.50 ml, 5.1 mmol) in 150 ml of benzene with stirring at room temperature for 5 min, and the solvent was removed using rotary evaporator to give a dark brown solid. PT-262 was purified by flash chromatography using 50% ethyl acetate/hexanes to elute that displayed as brown solids. To examine the induction of apoptosis following PT-262 treatment, the lung cancer cells were subjected to apoptotic cell observation, caspase activation, and mitochondrial functional assays. The protein levels of phosphorylated ERK and CDC2 after treatment with PT-262 were analyzed by Western blot. Treatment with 1-20 microM PT-262 for 24 h induced cytotoxicity via a concentration-dependent manner in human lung cancer cells. PT-262 induced the loss of mitochondrial membrane potential and elevated the caspase-3 activation and apoptosis. Interestingly, the phosphorylation of ERK was inhibited by PT-262. The IC50 value of ERK phosphorylation inhibition was approximate around 5 microM. Treatment with a specific MEK1/2 (the upstream of ERK) inhibitor, PD98059, increased the PT-262-induced cytotoxicity in lung cancer cells. Moreover, PT-262 did not alter the protein expression of tumor suppressor p53. PT-262 elicited the cytotoxicity and accumulated the G2/M fractions in both the p53-wild type and p53-null lung cancer cells. The mitosis-regulated protein levels of cyclin B1 and phospho-CDC2 at Thr14, Tyr15, and Thr161 were repressed by PT-262 in these cells. PT-262 suppresses the phosphorylation of ERK and CDC2 associated with proliferation

  16. A new and general method for the preparation of novel II-heterocyclic derivatives of ruthenium [C5Me5Ru (η6-arene)]X (arene = benzene, thiophene, 3-methylthiophene, benzothiophene, pyridine, 2.6 and 3.5-lutidine, quinoline, acridine). X-ray crystal structure of [(C5Me5)2Ru2Cl2(pyridine)2] PF6

    International Nuclear Information System (INIS)

    Chaudret, B.; Jalon, F.; Perez-Manrique, M.; Lahoz, F.; Plou, F.J.

    1990-01-01

    Zinc reduction of (Cp*RuCl 2 ) n (Cp* = C 5 Me 5 ) in acetone or THF followed by addition of 1 equivalent of an arene or aromatic heterocycle leads to compounds of general formulation [Cp* Ru(arene)]X (X = Cl, BF 4 ). Coordination of benzene is rapid and competes successfully with any other arene. Thiophene and 3-methylthiophene give stable π adducts whereas benzothiophene is coordinated through the benzene not through the heterocyclic ring. 2.6 and 3.5-lutidine coordinate through the ring, thus demonstrating an electronic rather than steric stabilization. Again, quinoline and acridine coordinate through the benzene ring. Pyridine gives an unstable π adduct in THF. A paramagnetic mixed-valence species, byproduct of the reaction in THF, has been characterized by an X-ray crystal structure determination. Crystals are triclinic, space group P-1

  17. 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.

    2015-07-01

    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

  18. SYNTHESIS OF SUBSTITUTED QUINOLINE-3-CARBALDEHYDES

    Directory of Open Access Journals (Sweden)

    L. G. Klad'ko

    2015-12-01

    Full Text Available Dehalogenation of а series substituted 2-chloroquinoline-3-carbaldehydes was investigated. It was found that zinc dust in alkali ethanol practically do not react with 2-chloro-3-(1,3-dioxolan-2-yl-7-methylquinolines for a 5 day at ambient temperature. Increase temperature to boiling point of reaction mixture lead to increase yield 7-methylquinoline-3-carbaldehyde to 12.5%. This reaction with 2-chloro-3-dimetoxymetyl-7-methylquinoline give 26.5 above aldehyde. Replacement of ethanol to methanol give only traces of desired aldehyde. Neither 2-chloro-7-methylquinoline-3-carbaldehyde, nor his acetals do not react with sodium dithionite. Furthermore for activation of halogen we replaced chloraldehydes to iodoaldehydes by Finkelstein reaction, then protect aldehyde function by formation of dimethylacetals and treatment his by sodium dithionite in mixture pyridine-water. Desired aldehydes was obtained with poor to moderate yields. Increasing yields of this reaction is goal our further investigations.

  19. synthesis and characterisation of quinoline functionalised

    African Journals Online (AJOL)

    DR. AMINU

    . Accepted: ... Department of Chemistry, Kano University of Science and Technology Wudil. Email: aahmedte64@yahoo.com, ... Keywords: Nucleophilic heterocyclic carbene (NHC), Imidazolium salt, ligand, ring closure. Barf. INTRODUCTION.

  20. Solventless Synthesis of Quinoline Derivatives: Acceleration of ...

    African Journals Online (AJOL)

    NICO

    bKermanshah Oil Refining Company, Kermanshah, Iran. Received 25 October ... formation of polymers that combine enhanced electronic, opto- electronic, or ..... 960/85. Long reaction time, difficulties in the catalyst synthesis and. 41 recovery.

  1. Pharmacokinetics and pharmacodynamics of LGD-3303 [9-chloro-2-ethyl-1-methyl-3-(2,2,2-trifluoroethyl)-3H-pyrrolo-[3,2-f]quinolin-7(6H)-one], an orally available nonsteroidal-selective androgen receptor modulator.

    Science.gov (United States)

    Vajda, Eric G; López, Francisco J; Rix, Peter; Hill, Robert; Chen, Yanling; Lee, Kyoung-Jin; O'Brien, Z; Chang, William Y; Meglasson, Martin D; Lee, Yong-Hee

    2009-02-01

    Selective androgen receptor modulators (SARMs) are a new class of molecules in development to treat a variety of diseases. SARMs maintain the beneficial effects of androgens, including increased muscle mass and bone density, while having reduced activity on unwanted side effects. The mechanisms responsible for the tissue-selective activity of SARMs are not fully understood, and the pharmacokinetic (PK)/pharmacodynamic (PD) relationships are poorly described. Tissue-specific compound distribution potentially could be a mechanism responsible for apparent tissue selectivity. We examined the PK/PD relationship of a novel SARM, LGD-3303 [9-chloro-2-ethyl-1-methyl-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[3,2-f]quinolin-7(6H)-one], in a castrated rat model of androgen deficiency. LGD-3303 has potent activity on levator ani muscle but is a partial agonist on the preputial gland and ventral prostate. LGD-3303 never stimulated ventral prostate above intact levels despite increasing plasma concentrations of compound. Tissue-selective activity was maintained when LGD-3303 was dosed orally or by continuous infusion, two routes of administration with markedly different time versus exposure profiles. Despite the greater muscle activity relative to prostate activity, local tissue concentrations of LGD-3303 were higher in the prostate than in the levator ani muscle. LGD-3303 has SARM properties that are independent of its pharmacokinetic profile, suggesting that the principle mechanism for tissue-selective activity is the result of altered molecular interactions at the level of the androgen receptor.

  2. An asymmetric synthesis of (R)-5-(methylamino)-5,6-dihydro-4H-imidazo-[4,5,1-ij]quinolin-2(1H) -one (1) and its [2-14C]-and [6,7-3H2]-labeled forms

    International Nuclear Information System (INIS)

    Heier, R.F.; Moon, M.W.; Stolle, W.T.; Easter, J.A.; Hsi, R.S.P.

    1996-01-01

    (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo [4,5,1-ij)quinolin-2(1H)-one (1) is a dopamine agonist which shows selectivity for the D2 receptor subtype, and is of interest as a potential drug for the treatment of Parkinson's disease. An asymmetric epoxidation approach has been used to prepare 1 in eleven steps (15% overall yield) from 8-nitroquinoline. An advanced intermediate in this synthesis, tert-butyl (R)-methyl(8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate, has been reacted with [ 14 C]phosgene to provide a two-step synthesis of 1 labeled with carbon-14 at the C-2 position (236 μCi/mg). Bromination of 1 gave the dibromo analogue which was reduced in the presence of tritium gas to give 1 labeled with tritium at the C-6 and C-7 positions (28.5 Ci/mmol). In addition to providing syntheses for labeled forms of the drug which are useful in drug disposition and receptor binding studies, this approach also provides a convenient synthesis for the unlabeled form of drug. (author)

  3. Comparative DNA adduct formation and induction of colonic aberrant crypt foci in mice exposed to 2-amino-9H-pyrido[2,3-b]indole, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline and azoxymethane

    Science.gov (United States)

    Kim, Sangyub; Guo, Jingshu; O’Sullivan, M. Gerald; Gallaher, Daniel D.; Turesky, Robert J.

    2015-01-01

    Considerable evidence suggests that environmental factors, including diet and cigarette smoke, are involved in the pathogenesis of colon cancer. Carcinogenic nitroso compounds (NOC), such as N-nitrosodimethylamine (NDMA), are present in tobacco and processed red meat, and NOC have been implicated in colon cancer. Azoxymethane (AOM), commonly used for experimental colon carcinogenesis, is an isomer of NDMA, and it produces the same DNA adducts as does NDMA. Heterocyclic aromatic amines (HAAs) formed during the combustion of tobacco and high-temperature cooking of meats are also associated with an elevated risk of colon cancer. The most abundant carcinogenic HAA formed in tobacco smoke is 2-amino-9H-pyrido[2,3-b]indole (AαC), whereas 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ) is the most potent carcinogenic HAA formed during the cooking of meat and fish. However, the comparative tumor-initiating potential of AαC, MeIQ, and AOM is unknown. In this report, we evaluate the formation of DNA adducts as a measure of genotoxicity, and the induction of colonic aberrant crypt foci (ACF) and dysplastic ACF, as an early measure of carcinogenic potency of these compounds in the colon of male A/J mice. Both AαC and AOM induced a greater number of DNA adducts than MeIQ in the liver and colon. AOM induced a greater number of ACF and dysplastic ACF than either AαC or MeIQ. Conversely, based on adduct levels, MeIQ-DNA adducts were more potent than AαC- and AOM-DNA adducts at inducing ACF. Long-term feeding studies are required to relate levels of DNA adducts, induction of ACF, and colon cancer by these colon genotoxicants. PMID:26734915

  4. Development and Structure/Property Relationship of New Electron Accepting Polymers Based on Thieno[2',3':4,5]pyrido[2,3- g ]thieno[3,2- c ]quinoline-4,10-dione for All-Polymer Solar Cells

    Energy Technology Data Exchange (ETDEWEB)

    Jung, In Hwan; Zhao, Donglin; Jang, Jaeyoung; Chen, Wei; Landry, Erik S.; Lu, Luyao; Talapin, Dmitri V.; Yu, Luping

    2015-09-08

    Several electron accepting polymers having weak accepting–strong accepting (WA-SA) and strong accepting–strong accepting (SA-SA) monomer alternation were synthesized for studies of structure/property relationship in all-polymer solar cells. Two kinds of cyclic amide monomers, 4,10-bis(2-butyloctyl)-thieno[2',3':5,6]pyrido[3,4-g]thieno-[3,2-c]isoquinoline-5,11-dione (TPTI) and 5,11-bis(2-butyloctyl)-thieno[2',3':4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10-dione (TPTQ), were synthesized as weak accepting monomers (WA). Difluorinated TPTQ (FTPTQ) and well-known perylene diimide (PDI) monomers were synthesized as strong electron accepting monomers (SA). By using 1-chloronaphthalene (CN) as a cosolvent, the morphology of the polymer blended films can be finely tuned to achieve better ordering toward face-on mode and favorable phase separation between electron donor and acceptor, resulting in significant enhancement of short circuit current (Jsc) and fill factor (FF). The fluorination in the TPTQ unit reduced the dipole moment of the D–A complex and gave a negative effect on a polymer system. PFP showed worse electron accepting property with lower electron mobility than PQP. It is reasoned that the internal polarization plays an important role in the design of electron accepting polymers. As a result, PQP having TPTQ monomer exhibited the best photovoltaic performance with power conversion efficiency (PCE) of 3.52% (Voc = 0.71 V, Jsc = 8.57 mA/cm2, FF = 0.58) at a weight ratio of PTB7-Th:PQP = 1:1, under AM 1.5G.

  5. Development and Structure/Property Relationship of New Electron Accepting Polymers Based on Thieno[2',3':4,5]pyrido[2,3- g ]thieno[3,2- c ]quinoline-4,10-dione for All-Polymer Solar Cells

    Energy Technology Data Exchange (ETDEWEB)

    Jung, In Hwan; Zhao, Donglin; Jang, Jaeyoung; Chen, Wei; Landry, Erik S.; Lu, Luyao; Talapin, Dmitri V.; Yu, Luping

    2015-09-08

    Several electron accepting polymers having weak accepting–strong accepting (WA-SA) and strong accepting–strong accepting (SA-SA) monomer alternation were synthesized for studies of structure/property relationship in all-polymer solar cells. Two kinds of cyclic amide monomers, 4,10-bis(2-butyloctyl)-thieno[2',3':5,6]pyrido[3,4-g]thieno-[3,2-c]isoquinoline-5,11-dione (TPTI) and 5,11-bis(2-butyloctyl)-thieno[2',3':4,5]pyrido[2,3-g]thieno[3,2-c]quinoline-4,10-dione (TPTQ), were synthesized as weak accepting monomers (WA). Difluorinated TPTQ (FTPTQ) and well-known perylene diimide (PDI) monomers were synthesized as strong electron accepting monomers (SA). By using 1-chloronaphthalene (CN) as a cosolvent, the morphology of the polymer blended films can be finely tuned to achieve better ordering toward face-on mode and favorable phase separation between electron donor and acceptor, resulting in significant enhancement of short circuit current (Jsc) and fill factor (FF). The fluorination in the TPTQ unit reduced the dipole moment of the D–A complex and gave a negative effect on a polymer system. PFP showed worse electron accepting property with lower electron mobility than PQP. It is reasoned that the internal polarization plays an important role in the design of electron accepting polymers. As a result, PQP having TPTQ monomer exhibited the best photovoltaic performance with power conversion efficiency (PCE) of 3.52% (Voc = 0.71 V, Jsc = 8.57 mA/cm2, FF = 0.58) at a weight ratio of PTB7-Th:PQP = 1:1, under AM 1.5G.

  6. Disposition and metabolism of benzo[f]quinoline

    International Nuclear Information System (INIS)

    1982-01-01

    5,6-( 14 C) Benzoquinoline (BQ) administered orally as a single dose was very rapidly absorbed in the rat; the extent of absorption, however, was not determined. 14 C-derived radioactivity appeared to be extensively distributed in all the tissues studied, albeit at levels which represented minute fractions of the administered dose. None of the tissue studies appeared to accumulate significant levels of 14 C-BQ-derived radioactivity although the level of radioactivity in the adrenals at the termination of the experiment (168 h) suggested a slight accumulating potential for this organ. The diarrhea encountered in the elimination studies precluded a meaningful analysis of the data on elimination. HPLC analysis of the plasma from rats dosed with radioactive BQ revealed that metabolites appear in plasma starting a short time after administration of BQ and remain in detectable but progressively decreasing amounts for 24 hours. Analysis of urine collected over 48 hours post dosing reveals that 30 to 35% of radioactivity is extractable as free metabolites. The kinetics of endogenous hepatic DNA, RNA or protein adducts with 14 C-BQ derivatives were studied during a course of 96 hours following a single oral dose (20 mg/kg) of 14 C-BQ in rats. Peak adduct formation appeared at the same time in all three macromolecules although the highest level of adducts was observed in DNA. The data suggest DNA to be a target macromolecule for BQ and/or its derivatives in vivo

  7. Crystal structure of N-(quinolin-6-ylhydroxylamine

    Directory of Open Access Journals (Sweden)

    Anuruddha Rajapakse

    2014-11-01

    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.

  8. Synthesis of some quinoline-pyrazoline-based naphthalenyl ...

    African Journals Online (AJOL)

    Compound 5d (R = 4-F, naphthalen-1-yl derivative) displayed higher antifungal activity than ketoconazole against C. albicans (MIC = 25 μg/mL, p <0.0001). Conclusion: The naphthalen-2-yl derivatives (6a-6e) are superior antimicrobial agents as compared to the naphthalen-1-yl derivatives (5a-5e) and the presence of 4-F ...

  9. A quinoline based pH sensitive ratiometric fluorescent sensor ...

    Indian Academy of Sciences (India)

    1637–1643. c Indian Academy of Sciences. ... of research. Various photophysical properties can be exploited for ... few drops of methanolic 1N KOH to the solution of 1. (scheme 1). ..... detected by naked eye and ratiometric measurements.

  10. Synthesis of some quinoline-pyrazoline-based naphthalenyl ...

    African Journals Online (AJOL)

    naphthalenyl thiazole derivatives and their evaluation as ... naphthalen-2-yl derivative) exhibited antimicrobial activities that were higher than those of the ...... Asia. J Patient Saf Infec Cont 2013; 1(1): 19-21. 10. Brandt C, Makarewicz O, Fischer T, Stein C, Pfeifer Y,. Werner G, Pletz MW. The bigger picture: the history of.

  11. Synthesis of new biphenyl-substituted quinoline derivatives ...

    Indian Academy of Sciences (India)

    with 10 mL of water and dried in an oven under reduced pressure for 5 h at 50. ◦. C. .... Structures of the obtained products were confirmed by elemental analysis, IR, 1H ..... the active pockets of β-tubulin(PDB ID: 1OJ0). Molec- ular docking of ...

  12. A review on transition-metal mediated synthesis of quinolines

    Indian Academy of Sciences (India)

    Rashmi Sharma

    2018-06-14

    Jun 14, 2018 ... Special Section on Transition Metal Catalyzed Synthesis of Medicinally Relevant Molecules. A review on ...... iron(III) chloride and TEMPO oxoammonium salt as an .... propyl-3-ethylquinoline (209) in presence of platinum.

  13. Inhibitory activity of benzo[h]quinoline and benzo[h]chromene in ...

    African Journals Online (AJOL)

    Street, Dokki, Cairo 12622, Egypt, 2Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University,. Riyadh 11451, Saudi Arabia, 3Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura. 35516, 4Department of Chemistry, Faculty of Science, Cairo University, ...

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

    Indian Academy of Sciences (India)

    Reactions of zinc halides with 8-hydroxyquinoline (hydroxQ) in equimolar ratio were carried out in different solvents. ... determination of surface area. We prepared a ..... resulted in the formation of de-solvated complex, which on standing at ...

  15. Photo-physics study of an hydroxy-quinoline derivative as inhibitor of Pim-1 kinase

    DEFF Research Database (Denmark)

    Lamhasni, T.; Aitlyazidi, S.; Hnach, M.

    2013-01-01

    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...

  16. (quinolin-5-yl)urea as a host for distinction of phthalic acid and ...

    Indian Academy of Sciences (India)

    Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781 039, India e-mail: ... well-known in both in solid and in solution state.1–5. Hosts having urea ..... References. 1. Byrne P, Turner D R, Lloyd G O, Clarke N and Steed ... 2002 In Handbook of pharmaceutical salts (New-York: Wiley-VCH). 9.

  17. Aqua[N-phenyl-2-(quinolin-8-yloxyacetamide]dinitratozinc(II

    Directory of Open Access Journals (Sweden)

    Qiu-Fen Wang

    2010-03-01

    Full Text Available In the title complex, [Zn(NO32(C17H14N2O2(H2O], the six-coordinated Zn atom is in a distorted octahedral geometry, the donor centers being two O atoms and one N atom from the tridentate organic ligand, a water O atom and two O atoms from two monodentate nitrate ions. In the crystal, O—H...O hydrogen bonds between the coordinated water molecules and nitrate O atoms and N—H...O hydrogen bonds between the main ligand and nitrate O atoms consolidate the three-dimensional network.

  18. trans-Bis(methanol-κObis(quinoline-2-carboxylato-κ2N,Omanganese(II

    Directory of Open Access Journals (Sweden)

    Lucjan B. Jerzykiewicz

    2008-11-01

    Full Text Available The title compound, [Mn(C10H6NO22(CH4O2], was obtained unintentionally as the product of an attempt to synthesize a polynuclear carboxylate bridged manganese(III/IV complex, using methanol to reduce the permanganate ion. The molecule is centrosymmetric; the pairs of equivalent ligands coordinate trans to each other in a distorted octahedral geometry. Intramolecular C—H...O bonds lying in the equatorial plane stabilize the molecule. In the crystal, molecules are linked by O—H...O and C—H...O hydrogen bonds, creating a three-dimensional supramolecular structure. π–π and C—H...π interactions are also observed. The dihedral angle and centroid-to-centroid distance between the pyridine ring (A and the benzene ring (Bi of a symmetrically related molecule [symmetry code: (i −1 − x, −y, −z] are 1.27 (11° and 3.974 (2 Å, respectively. For the C—H...π interactions, the relevant distances and angles are: C...Cg[Aii] = 3.643 (2 Å, H...Cg[Aii] = 2.750 (2 Å and C—H...Cg[Aii] = 155 (1° [symmetry code: (ii x, −1 + y, z].

  19. Inhibitory activity of benzo[h]quinoline and benzo[h]chromene in ...

    African Journals Online (AJOL)

    tetramethylsilane (TMS) as an internal standard. Coupling constants are given in Hz. The mass spectra were recorded on GCMC-QP 1000 EX. Shimadzo. Gas ... Statistical analysis. Data were analyzed using Prism 5.0 software. (GraphPad Software, LaJolla, CA, USA). Statistical significance was assessed by one-way.

  20. Synthesis, characterization and in vitro antitrypanosomal activities of new carboxamides bearing quinoline moiety.

    Directory of Open Access Journals (Sweden)

    David Izuchukwu Ugwu

    Full Text Available The reported toxicities of current antitrypanosomal drugs and the emergence of drug resistant trypanosomes underscore the need for the development of new antitrypanosomal agents. We report herein the synthesis and antitrypanosomal activity of 24 new amide derivatives of 3-aminoquinoline, bearing substituted benzenesulphonamide. Nine of the new derivatives showed comparable antitrypanosomal activities at IC50 range of 1-6 nM (melarsoprol 5 nM. Compound 11n and 11v are more promising antitrypanosomal agents with IC50 1.0 nM than the rest of the reported derivatives. The novel compounds showed satisfactory predicted physico-chemical properties including oral bioavailability, permeability and transport properties.

  1. 3-Chloro-4-methyl­quinolin-2(1H)-one

    Science.gov (United States)

    Kassem, Mohamed G.; Ghabbour, Hazem A.; Abdel-Aziz, Hatem A.; Fun, Hoong-Kun; Ooi, Chin Wei

    2012-01-01

    The title compound, C10H8ClNO, is almost planar (r.m.s. deviation for the 13 non-H atoms = 0.023 Å). In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) rings. Weak aromatic π–π stacking inter­actions [centroid–centroid distance = 3.7622 (12) Å] also occur. PMID:22589913

  2. Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

    KAUST Repository

    Xu, Jun

    2016-01-12

    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.

  3. 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: mmartins@base.ufsm.br [Nucleo de Quimica de Heterociclos (NUQUIMHE), Departamento de Quimica, Universidade Federal de Santa Maria (UFSM), Santa Maria, RS (Brazil)

    2012-09-15

    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)

  4. Thermal, dielectric characteristics and conduction mechanism of azodyes derived from quinoline and their copper complexes.

    Science.gov (United States)

    El-Ghamaz, N A; Diab, M A; El-Bindary, A A; El-Sonbati, A Z; Nozha, S G

    2015-05-15

    A novel series of (5-(4'-derivatives phenyl azo)-8-hydroxy-7-quinolinecarboxaldehyde) (AQLn) (n=1, p-OCH3; n=2, R=H; and n=3; p-NO2) and their complexes [Cu(AQLn)2]·5H2O are synthesized and investigated. The optimized bond lengths, bond angles and the calculated quantum chemical parameters for AQLn are investigated. HOMO-LUMO energy gap, absolute electronegativities, chemical potentials, and absolute hardness are also calculated. The thermal properties, dielectric properties, alternating current conductivity (σac) and conduction mechanism are investigated in the frequency range 0.1-100kHz and temperature range 293-568K for AQL1-3 and 318-693K for [Cu(AQL1-3)2]·5H2O complexes. The thermal properties are of ligands (AQLn) and their Cu(II) complexes investigated by thermogravimetric analysis (TGA). The temperature and frequency dependence of the real and the imaginary part of the dielectric constant are studied. The values of the thermal activation energy of conduction mechanism for AQLn and their complexes [Cu(AQLn)2]·5H2O under investigation are calculated at different test frequencies. The values of thermal activation energies ΔE1 and ΔE2 for AQLn and [Cu(AQLn)2]·5H2O decrease with increasing the values of frequency. The ac conductivity is found to be depending on the chemical structure of the compounds. Different conduction mechanisms have been proposed to explain the obtained experimental data. The small polaron tunneling (SPT) is the dominant conduction mechanism for AQL1 and its complex [Cu(AQL1)2]·5H2O. The quantum mechanical tunneling (QMT) is the dominant conduction mechanism for AQL2 and its complex [Cu(AQL2)2]·5H2O. The correlated barrier hopping (CBH) is the dominant conduction mechanism for AQL3 and its complex [Cu(AQL3)2]·5H2O, and the values of the maximum barrier height (Wm) are calculated. Copyright © 2015 Elsevier B.V. All rights reserved.

  5. A fluorescent sensor based on binaphthol-quinoline Schiff base for ...

    Indian Academy of Sciences (India)

    est in developing selective and sensitive Zn2+ sensors to recognize the physiological ... tion of oxalate has received substantial attention due to its simplicity and waiver .... and isophthalate caused no significant fluorescence spectrum changes ...

  6. Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

    KAUST Repository

    Xu, Jun; Shen, Chao; Zhu, Xiaolei; Zhang, Pengfei; Ajitha, Manjaly John; Huang, Kuo-Wei; An, Zhongfu; Liu, Xiaogang

    2016-01-01

    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

  7. Synthesis of quinolines via Friedlander reaction catalyzed by CuBTC metal-organic-framework

    Czech Academy of Sciences Publication Activity Database

    Pérez-Mayoral, E.; Musilová, Zuzana; Gil, B.; Marszalek, B.; Položij, M.; Nachtigall, P.; Čejka, Jiří

    2012-01-01

    Roč. 41, č. 14 (2012), s. 4036-4044 ISSN 1477-9226 Institutional research plan: CEZ:AV0Z40400503 Keywords : EFFICIENT HETEROGENEOUS CATALYST * AUGMENTED-WAVE METHOD * SOLID ACID CATALYSTS Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 3.806, year: 2012

  8. CCDC 1419405: Experimental Crystal Structure Determination : (benzo[h]quinolin-10-ylmethylene)-dichloro-(tricyclohexylphosphine)-ruthenium dichloromethane solvate

    KAUST Repository

    Pump, Eva

    2015-01-01

    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.

  9. Chemistry, photophysics, and ultrafast kinetics of two structurally related Schiff bases containing the naphthalene or quinoline ring

    Science.gov (United States)

    Fita, P.; Luzina, E.; Dziembowska, T.; Radzewicz, Cz.; Grabowska, A.

    2006-11-01

    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.

  10. CCDC 1041995: Experimental Crystal Structure Determination : N-(5-((4-methylphenyl)sulfonyl)quinolin-8-yl)benzamide

    KAUST Repository

    Xu, Jun; Shen, Chao; Zhu, Xiaolei; Zhang, Pengfei; Ajitha, Manjaly John; Huang, Kuo-Wei; An, Zhongfu; Liu, Xiaogang

    2016-01-01

    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.

  11. A highly selective turn-on fluorescent probe for Al3+ in aqueous solution based on quinoline Schiff-base

    Science.gov (United States)

    Huang, Peng-Cheng; Fang, Hao; Xiong, Jing-Jing; Wu, Fang-Ying

    2017-06-01

    A new Al3+-specific fluorescent probe NQ was designed and synthesized from 2-hydroxy-1-naphthaldehyde and 2-aminoquinoline. Upon the addition of Al3+, the fluorescent intensity of NQ was significantly enhanced compared with other examined metal ions in aqueous solution. The result of a Job’s plot indicated the formation of a 1:1 complex between the probe and Al3+, and the possible binding mode of the system between NQ and Al3+ was clarified by IR analysis and 1H NMR titration. Moreover, other metal ions examined had little effect on the detection of Al3+. The detection limit of NQ for Al3+ detection was 1.98 μM, which is lower than the level (7.4 μM) in drinking water defined by the World Health Organization. In addition, the fluorescent probe NQ could be recyclable simply through treatment with a proper reagent such as F-, and could also be used for the detection of Al3+ in real samples.

  12. EFFECTS OF QUINOLINE ON ULTRASTRUCTURE IN PARAMECIUM CAUDATUM AND THE PROTECTIVE EFFECTS OF DISSOLVED CALCIUM. (R825513C004)

    Science.gov (United States)

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  13. LOW TEMPERATURE FORMATION OF NITROGEN-SUBSTITUTED POLYCYCLIC AROMATIC HYDROCARBONS (PANHs)—BARRIERLESS ROUTES TO DIHYDRO(iso)QUINOLINES

    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: ralfk@hawaii.edu, E-mail: Timothy.J.Lee@nasa.gov [Space Science and Astrobiology Division, NASA Ames Research Center, Moffett Field, Mountain View, CA 94035 (United States)

    2015-12-20

    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.

  14. Quinolinic Acid - Iron(II) Complexes: Slow Autoxidation, but Enhanced Hydroxyl Radical Production in the Fenton Reaction

    Czech Academy of Sciences Publication Activity Database

    Pláteník, J.; Stopka, Pavel; Vejražka, M.; Štípek, S.

    2001-01-01

    Roč. 34, č. 5 (2001), s. 445-459 ISSN 1071-5762 R&D Projects: GA ČR GA203/97/0642; GA ČR GA309/99/0211 Institutional research plan: CEZ:AV0Z4032918 Keywords : iron chelator * reactive oxygen species * excitotoxicity Subject RIV: CA - Inorganic Chemistry Impact factor: 2.735, year: 2001

  15. Quinoline-8-ol-immobilized Amberlite XAD-4: Synthesis, characterization, and uranyl ion uptake properties suitable for analytical applications

    International Nuclear Information System (INIS)

    Gladis, Mary J.; Prasada Rao, T.

    2002-01-01

    Amberlite XAD-4 has been functionalized by coupling it with 5-aminoquinoline-8-ol after acetylation. The resulting resin has been characterized by elemental analysis and IR spectra and has been used for preconcentrating uranyl ions prior to its determination by spectrophotometry. The optimum pH value for quantitative sorption is 4-6, and desorption can be achieved by using 5 mL of 1 mol L -1 HCl. The sorption capacity of the resin is 11.5 mmol g -1 . The effect of various cations and anions on the preconcentration of uranium in conjunction with the determination procedure has been studied and we have found that none of the ions interfere except thorium. The enrichment factor for preconcentration of uranium was found to be 200. Ten replicate determinations of 40 μg of uranium present in 1 L of sample gave a mean absorbance of 0.185 with a relative standard deviation of 2.64%. The detection limit corresponding to three times the standard deviation of the bank was found to be 2 μg L -1 . The validation of the developed preconcentration procedure was carried out by successfully analyzing standard marine sediment reference material. The uranyl content of sediment and soils is estimated by spectrophotometry after its preconcentration with the above chelating resin. (orig.)

  16. Production of 9-thioxo-2,3,4,9-tetrahydro-pyrrolo[3,4-b]quinolin-1

    African Journals Online (AJOL)

    ated using SHELXTL and PLATON.10. Crystal data for 3a. C17H19N3OS, M = 313.41, monoclinic, space group C2/c (No. 15), a = 18.581(3), b = 13.760(2), c = 14.272(2) Å,. $ = 117.518(3)°, V = 3236.1(9) Å3, Z = 8, Dx = 1.287 Mg m–3,µ= 0.205 mm–1, T = 293(2) K, 10970 reflections collected for 1.93 <. 2 < 28.33° of which ...

  17. Transgenic mice expressing a Huntington s disease mutation are resistant to quinolinic acid-induced striatal excitotoxicity

    OpenAIRE

    Hansson, Oskar; Petersén, Åsa; Leist, Marcel; Nicotera, Pierluigi; Castilho, Roger F.; Brundin, Patrik

    1999-01-01

    Huntington’s disease (HD) is a hereditary neurodegenerative disorder presenting with chorea, dementia, and extensive striatal neuronal death. The mechanism through which the widely expressed mutant HD gene mediates a slowly progressing striatal neurotoxicity is unknown. Glutamate receptor-mediated excitotoxicity has been hypothesized to contribute to the pathogenesis of HD. Here we show that transgenic HD mice expressing exon 1 of a human HD gene with an expanded number of CAG repeats (line R...

  18. Quinolinic acid neurotoxicity: Differential roles of astrocytes and microglia via FGF-2-mediated signaling in redox-linked cytoskeletal changes.

    Science.gov (United States)

    Pierozan, Paula; Biasibetti, Helena; Schmitz, Felipe; Ávila, Helena; Parisi, Mariana M; Barbe-Tuana, Florencia; Wyse, Angela T S; Pessoa-Pureur, Regina

    2016-12-01

    QUIN is a glutamate agonist playing a role in the misregulation of the cytoskeleton, which is associated with neurodegeneration in rats. In this study, we focused on microglial activation, FGF2/Erk signaling, gap junctions (GJs), inflammatory parameters and redox imbalance acting on cytoskeletal dynamics of the in QUIN-treated neural cells of rat striatum. FGF-2/Erk signaling was not altered in QUIN-treated primary astrocytes or neurons, however cytoskeleton was disrupted. In co-cultured astrocytes and neurons, QUIN-activated FGF2/Erk signaling prevented the cytoskeleton from remodeling. In mixed cultures (astrocyte, neuron, microglia), QUIN-induced FGF-2 increased level failed to activate Erk and promoted cytoskeletal destabilization. The effects of QUIN in mixed cultures involved redox imbalance upstream of Erk activation. Decreased connexin 43 (Cx43) immunocontent and functional GJs, was also coincident with disruption of the cytoskeleton in primary astrocytes and mixed cultures. We postulate that in interacting astrocytes and neurons the cytoskeleton is preserved against the insult of QUIN by activation of FGF-2/Erk signaling and proper cell-cell interaction through GJs. In mixed cultures, the FGF-2/Erk signaling is blocked by the redox imbalance associated with microglial activation and disturbed cell communication, disrupting the cytoskeleton. Thus, QUIN signal activates differential mechanisms that could stabilize or destabilize the cytoskeleton of striatal astrocytes and neurons in culture, and glial cells play a pivotal role in these responses preserving or disrupting a combination of signaling pathways and cell-cell interactions. Taken together, our findings shed light into the complex role of the active interaction of astrocytes, neurons and microglia in the neurotoxicity of QUIN. Copyright © 2016 Elsevier B.V. All rights reserved.

  19. 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

    2015-01-01

    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.

  20. CCDC 1419407: Experimental Crystal Structure Determination : (benzo[h]quinolin-10-ylmethylene)-dichloro-(1,3-dimesitylimidazolidin-2-ylidene)-ruthenium dichloromethane solvate

    KAUST Repository

    Pump, Eva

    2015-01-01

    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.

  1. CCDC 1419408: Experimental Crystal Structure Determination : (benzo[h]quinolin-10-ylmethylene)-dichloro-(1,3-bis(2,5-dimethylphenyl)imidazolidin-2-ylidene)-ruthenium

    KAUST Repository

    Pump, Eva

    2015-01-01

    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.

  2. Severe depression is associated with increased microglial quinolinic acid in subregions of the anterior cingulate gyrus: Evidence for an immune-modulated glutamatergic neurotransmission?

    OpenAIRE

    Steiner, Johann; Walter, Martin; Gos, Tomasz; Guillemin, Gilles J; Bernstein, Hans-Gert; Sarnyai, Zoltán; Mawrin, Christian; Brisch, Ralf; Bielau, Hendrik; zu Schwabedissen, Louise Meyer; Bogerts, Bernhard; Myint, Aye-Mu

    2011-01-01

    RIGHTS : This article is licensed under the BioMed Central licence at http://www.biomedcentral.com/about/license which is similar to the 'Creative Commons Attribution Licence'. In brief you may : copy, distribute, and display the work; make derivative works; or make commercial use of the work - under the following conditions: the original author must be given credit; for any reuse or distribution, it must be made clear to others what the license terms of this work are. Abstract Backgrou...

  3. Correction: Severe depression is associated with increased microglial quinolinic acid in subregions of the anterior cingulate gyrus: evidence for an immune-modulated glutamatergic neurotransmission?

    OpenAIRE

    Steiner, Johann; Walter, Martin; Gos, Tomasz; Guillemin, Gilles J.; Bernstein, Hans-Gert; Sarnyai, Zoltán; Mawrin, Christian; Brisch, Ralf; Bielau, Hendrik; zu Schwabedissen, Louise M.; Bogerts, Bernhard; Myint, Aye-Mu

    2013-01-01

    RIGHTS : This article is licensed under the BioMed Central licence at http://www.biomedcentral.com/about/license which is similar to the 'Creative Commons Attribution Licence'. In brief you may : copy, distribute, and display the work; make derivative works; or make commercial use of the work - under the following conditions: the original author must be given credit; for any reuse or distribution, it must be made clear to others what the license terms of this work are. AbstractN/a

  4. Evolution from a natural flavones nucleus to obtain 2-(4-Propoxyphenyl)quinoline derivatives as potent inhibitors of the S. aureus NorA efflux pump.

    Science.gov (United States)

    Sabatini, Stefano; Gosetto, Francesca; Manfroni, Giuseppe; Tabarrini, Oriana; Kaatz, Glenn W; Patel, Diixa; Cecchetti, Violetta

    2011-08-25

    Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resistance mechanism. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, resulting in a multidrug resistant phenotype. In this work, a series of 2-phenyl-4(1H)-quinolone and 2-phenyl-4-hydroxyquinoline derivatives, obtained by modifying the flavone nucleus of known efflux pump inhibitors (EPIs), were synthesized in an effort to identify more potent S. aureus NorA EPIs. The 2-phenyl-4-hydroxyquinoline derivatives 28f and 29f display potent EPI activity against SA-1199B, a strain that overexpresses norA, in an ethidium bromide efflux inhibition assay. The same compounds, in combination with ciprofloxacin, were able to completely restore its antibacterial activity against both S. aureus SA-K2378 and SA-1199B, norA-overexpressing strains. © 2011 American Chemical Society

  5. 2-Ethyl-6-(2-pyridyl-5,6,6a,11b-tetrahydro-7H-indeno[2,1-c]quinoline

    Directory of Open Access Journals (Sweden)

    Alexander Briceño

    2010-03-01

    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.

  6. Photo-physics study of an hydroxy-quinoline derivative as inhibitor of Pim-1 kinase: ultraviolet-visible linear dichroism spectroscopy and quantum chemical calculations.

    Science.gov (United States)

    Lamhasni, T; Ait Lyazidi, S; Hnach, M; Haddad, M; Desmaële, D; Spanget-Larsen, J; Nguyen, D D; Ducasse, L

    2013-09-01

    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. Copyright © 2013 Elsevier B.V. All rights reserved.

  7. 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

    2009-01-01

    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.

  8. Fluorescent sensors based on quinoline-containing styrylcyanine: determination of ferric ions, hydrogen peroxide, and glucose, pH-sensitive properties and bioimaging.

    Science.gov (United States)

    Yang, Xiaodong; Zhao, Peiliang; Qu, Jinqing; Liu, Ruiyuan

    2015-08-01

    A novel styrylcyanine-based fluorescent probe 1 was designed and synthesized via facile methods. Ferric ions quenched the fluorescence of probe 1, whereas the addition of ferrous ions led to only small changes in the fluorescence signal. When hydrogen peroxide was introduced into the solution containing probe 1 and Fe(2+) , Fe(2+) was oxidized to Fe(3+), resulting in the quenching of the fluorescence. The probe 1/Fe(2+) solution fluorescence could also be quenched by H2 O2 released from glucose oxidation by glucose oxidase (GOD), which means that probe 1/Fe(2+) platform could be used to detect glucose. Probe 1 is fluorescent in basic and neutral media but almost non-fluorescent in strong acidic environments. Such behaviour enables it to work as a fluorescent pH sensor in both the solution and solid states and as a chemosensor for detecting volatile organic compounds with high acidity and basicity. Subsequently, the fluorescence microscopic images of probe 1 in live cells and in zebrafish were achieved successfully, suggesting that the probe has good cell membrane permeability and a potential application for imaging in living cells and living organisms. Copyright © 2014 John Wiley & Sons, Ltd.

  9. Bis(8-hy?droxy-1-methyl?quinolin-1-ium) bis?(1,2-dicyano?ethene-1,2-dithiol?ato)nickelate(II) dihydrate

    OpenAIRE

    Guan, Zhi-Heng; Jiang, Zhang; Wang, Fang-Ming

    2011-01-01

    In the title ion-pair complex, (C10H10NO)2[Ni(C4N2S2)2]·2H2O, the anion has crystallographically imposed centre of symmetry. The NiII atom exhibits a slightly distorted square-planar coordination geometry. In the crystal, the water molecule links anions and cations into a three-dimensional network via O—H...N, O—H...S and O—H...O hydrogen bonds. The structure is further stabilized by weak S...π contacts [S...centroid = 3.8047 (9)&#...

  10. Bis(8-hy-droxy-1-methyl-quinolin-1-ium) bis-(1,2-dicyano-ethene-1,2-dithiol-ato)nickelate(II) dihydrate.

    Science.gov (United States)

    Guan, Zhi-Heng; Jiang, Zhang; Wang, Fang-Ming

    2011-12-01

    In the title ion-pair complex, (C(10)H(10)NO)(2)[Ni(C(4)N(2)S(2))(2)]·2H(2)O, the anion has crystallographically imposed centre of symmetry. The Ni(II) atom exhibits a slightly distorted square-planar coordination geometry. In the crystal, the water mol-ecule links anions and cations into a three-dimensional network via O-H⋯N, O-H⋯S and O-H⋯O hydrogen bonds. The structure is further stabilized by weak S⋯π contacts [S⋯centroid = 3.8047 (9) Å] and π-π stacking inter-actions [centriod-centroid distance = 3.8653 (7) Å].

  11. 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

    2011-01-01

    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.

  12. Simultaneous regioselective synthesis of trifluoromethyl-containing 1,7-phenanthrolines and quinolines from cyclocondensation reaction of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines

    Energy Technology Data Exchange (ETDEWEB)

    Bonacorso, Helio G.; Andrighetto, Rosalia; Krueger, Nicolas; Martins, Marcos A.P.; Zanatta, Nilo [Universidade Federal de Santa Maria (NUQUIMHE/UFSM), RS (Brazil). Dept. de Quimica. Nucleo de Quimica de Heterociclos

    2011-08-15

    This paper reports interesting results of the conventional synthesis of a new series of 2,10-dialkyl(aryl)-4,8-bis(trifluoromethyl)-1,7-phenanthrolines, in 22-40% yields, from cyclization reactions of N,N'-bis(oxotrifluoroalkenyl)-1,3-phenylenediamines [1,3-C{sub 6}H{sub 4}-(NHCR=CHC(O)CF{sub 3}){sub 2}] in a strongly acidic medium and absence of solvent. The synthetic route also allowed the isolation of a new series of 2-alkyl(aryl/heteroaryl)-4-trifluoromethyl-7-aminoquinolines, in 20-73% yields, simultaneously. The enaminone precursors were obtained from the reaction of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF{sub 3}C(O)CH=C(R)OR1, where R = H, Me, Ph, 4-MePh, 4-OMePh, 4-ClPh, 4-FPh, 4-BrPh, 4-NO{sub 2}Ph, 2-furyl and R1 = Me, Et] with 1,3-phenylenediamine under mild conditions, in 47-91% yields. (author)

  13. 3-[4-(10H-Indolo[3,2-b]quinolin-11-ylpiperazin-1-yl]propan-1-ol

    Directory of Open Access Journals (Sweden)

    Gary S. Nichol

    2011-12-01

    Full Text Available In the title compound, C22H24N4O, the aromatic moiety is essentially planar (r.m.s. deviation of a least-squares plane fitted through all non-H atoms = 0.0386 Å and is rotated by 89.98 (4° from the piperazine ring, which adopts the expected chair conformation. The propanol chain is not fully extended away from the piperazine ring. In the crystal, there are two unique hydrogen-bonding interactions. One is an O—H...N interaction which, together with an inversion-related symmetry equivalent, forms a ring motif. The second is an N—H...N interaction which links adjacent molecules by means of a chain motif which propagates in the c-axis direction. Overall, a two-dimensional hydrogen-bonded structure is formed.

  14. Synthesis and Study of Chemical and Photo-physical Properties of Quinolinate Aluminum and Zinc Complexes in Organic Light Emitting Diodes (OLEDs)

    Science.gov (United States)

    Rawat, Madhu; Prakash, Sattey; Singh, C.; Anand, R. S.

    2011-10-01

    Two well known electroluminescent (EL) compounds, aluminum and zinc metallo-8-hydroxyquinolates have been synthesized. Their chemical and physical properties like NMR, FTIR, Cyclic Voltammetry, absorption and EL are studied. Organic LEDs are fabricated using both the material as emissive layers. Electroluminescence spectra of the complexes are measured. 2Alq3 and Znq2 give peak emission in yellow-green region at wavelengths 527nm and 540nm respectively. Znq2 is slightly red shifted compared to Alq3 because metal to ligand charge transfer is more in Znq2. A study of ON voltage, luminance efficiency and stability of OLEDs using both materials is made.

  15. Quinoline derivative containing monomeric and polymeric metal carboxylates: Synthesis, crystal structure and gas adsorption study over a 2D layered framework

    Science.gov (United States)

    Gayen, Saikat; Saha, Debraj; Koner, Subratanath

    2018-06-01

    A new supramolecular metal-carboxylate framework [Co(mqc)2]n (1), and another monomeric compound [Zn (mqc)2(H2O)] (2) (mqcH = 4-methoxy 2-quinolinecarboxylic acid) have been synthesized solvothermally and characterized by single crystal X-ray diffraction, elemental analysis, IR spectra, UV-vis spectra, powdered X-ray diffraction (PXRD) and thermogravimetric analysis. Compound 1 is a 2D coordination polymer, extended to a 3D porous supramolecular network having void space in between 2D layers. Compound 1 exhibits gas uptake capacity of N2, H2, CO2 and CH4 like small gas molecules in which moderately high uptake of H2 and CO2 takes place among the 2D MOFs. While the Zn variety, compound 2 features a one-dimensional chain like structure through strong intermolecular hydrogen-bonding.

  16. 11-[Bis(trimethylsilylamino]-2,4-bis(trimethylsilyl-7,8,9,10-tetrahydro-6H-cyclohepta[1,2-b]quinoline

    Directory of Open Access Journals (Sweden)

    Ísmail Çelik

    2017-06-01

    Full Text Available In the title compound, C26H48N2Si4, the cycloheptane ring adopts a chair conformation, while the quinolinyl ring system is almost planar [maximum deviation = 0.040 (3 Å for one of the C atoms carrying a Me3Si group]. In the crystal, in the absence of classical hydrogen bonding, the packing is dominated by van der Waals forces. One of the N-bound trimethylsilyl groups is disordered by rotation about the C—SiMe3 bond, and was modelled over two sets of sites in the ratio 0.873 (8:0.127 (8.

  17. A quinoline-based Cu2 + ion complex fluorescence probe for selective detection of inorganic phosphate anion in aqueous solution and its application to living cells

    Science.gov (United States)

    Dai, Yanpeng; Wang, Peng; Fu, Jiaxin; Yao, Kun; Xu, Kuoxi; Pang, Xiaobin

    2017-08-01

    A quinaldine functionalized probe QP has been designed and synthesized. It exhibited selective turn-off fluorescence response toward Cu2 + ion over most of the biologically important ions at physiological pH. The binding ratio of the probe QP and Cu2 + ion was determined to be 1:1 through fluorescence titration, Job's plot and ESI-MS. The binding constant (K) of Cu2 + to probe QP was found to be 2.12 × 104 M- 1. Further, the Cu2 + ensemble of probe QP was found to respond H2PO4- and HPO42 - among other important biological anions via fluorescence turn-on response at physiological pH. Fluorescence microscopy imaging using living Hela cells showed that probe QP could be used as an effective fluorescent probe for detecting Cu2 + cation and H2PO4- and HPO42 - anions in living cells.

  18. 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).

    Science.gov (United States)

    1983-08-01

    through opacity .................. 4 IRIS Normal ............................................................... I Markedly deepened rugae , congestion...of the rugae or light hyperemia of circumcorneal blood vessels), or obvious swelling of the eyelids were considered to be signs of Positive eye

  19. 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

    the concern with respect to genotoxicity in vitro and accordingly the substance is not evaluated through the Procedure. For 21 substances [FL-no: 13.134, 14.001, 14.004, 14.007, 14.030, 14.038, 14.039, 14.041, 14.045, 14.046, 14.047, 14.058, 14.059, 14.060, 14.061, 14.065, 14.066, 14.068, 14.071, 14...

  20. CCDC 1419406: Experimental Crystal Structure Determination : (benzo[h]quinolin-10-ylmethylene)-dichloro-(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene)-ruthenium dichloromethane solvate

    KAUST Repository

    Pump, Eva

    2015-01-01

    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.

  1. Design, synthesis, docking study and biological evaluation of some novel tetrahydrochromeno [3',4':5,6]pyrano[2,3-b]quinolin-6(7H)-one derivatives against acetyl- and butyrylcholinesterase.

    Science.gov (United States)

    Khoobi, Mehdi; Alipour, Masoumeh; Moradi, Alireza; Sakhteman, Amirhossein; Nadri, Hamid; Razavi, Seyyede Faeze; Ghandi, Mehdi; Foroumadi, Alireza; Shafiee, Abbas

    2013-10-01

    Novel hybrid derivatives of two known scaffolds; tetrahydroaminoquinoline and coumarin were synthesized and evaluated for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities. By means of an efficient nanocatalyst, the reaction time for the syntheses of the target compounds was reduced. Subsequently, Ellman's modified method was used to evaluate the enzyme inhibitory activity of the synthesized structures. It was observed that most hybrid structures were moderate to potent inhibitors of AChE compared to Tacrine as the reference drug among which 7f with 4-fluorophenyl substituent was the most active compound (IC50=5 nM). Copyright © 2013 Elsevier Masson SAS. All rights reserved.

  2. 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.

    2004-01-01

    HMGCR/mtsl t9579 transgenic mice were designed to direct the expression of metastasis-promoting mts 1 (S100A4) gene to all the tissues. In order to test the usefulness of this mouse model for carcinogenicity tests shorter than that recommended by OECD guideline mr. 451, HMGCR/mtsl tg579 transgenic...

  3. 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

    2016-01-01

    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.

  4. 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

    2002-01-01

    , 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...

  5. 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.

    2002-01-01

    , 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...

  6. The synthesis of (-)-4-methyl-8-chloro-trans-1,2,3,4,4a,5,6,10b-octahydrobenzo-[f]-quinolin-3-one-[3-14C] (LY300502-[14C]) via a circuitous route

    International Nuclear Information System (INIS)

    Fengjiun Kuo; Wheeler, W.J.

    1994-01-01

    The synthesis of the C-14 labeled isotopomer of LY300502, a potent 5α-reductase inhibitor has been accomplished in four radiochemical steps. The route involves the synthesis of LY300502-[ 14 C] from LY300502 via a circuitous route; the label was introduced with ethyl chloroformate-[carbonyl- 14 C]. (author)

  7. 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

    2014-09-01

    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

  8. Quinoline compound KM11073 enhances BMP-2-dependent osteogenic differentiation of C2C12 cells via activation of p38 signaling and exhibits in vivo bone forming activity.

    Directory of Open Access Journals (Sweden)

    Seung-hwa Baek

    Full Text Available Recombinant human bone morphogenetic protein (rhBMP-2 has been approved by the FDA for clinical application, but its use is limited due to high cost and a supra-physiological dose for therapeutic efficacy. Therefore, recent studies have focused on the generation of new therapeutic small molecules to induce bone formation or potentiate the osteogenic activity of BMP-2. Here, we show that [4-(7-chloroquinolin-4-yl piperazino][1-phenyl-5-(trifluoromethyl-1H-pyrazol-4-yl]methanone (KM11073 strongly enhances the BMP-2-stimulated induction of alkaline phosphatase (ALP, an early phase biomarker of osteoblast differentiation, in bi-potential mesenchymal progenitor C2C12 cells. The KM11073-mediated ALP induction was inhibited by the BMP antagonist noggin, suggesting that its osteogenic activity occurs via BMP signaling. In addition, a pharmacological inhibition study suggested the involvement of p38 activation in the osteogenic action of KM11073 accompanied by enhanced expression of BMP-2, -6, and -7 mRNA. Furthermore, the in vivo osteogenic activity of KM11073 was confirmed in zebrafish and mouse calvarial bone formation models, suggesting the possibility of its single use for bone formation. In conclusion, the combination of rhBMP-2 with osteogenic small molecules could reduce the use of expensive rhBMP-2, mitigating the undesirable side effects of its supra-physiological dose for therapeutic efficacy. Moreover, due to their inherent physical properties, small molecules could represent the next generation of regenerative medicine.

  9. 8-{(E-[(4-Chlorophenylimino]methyl}-1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-ol

    Directory of Open Access Journals (Sweden)

    Esen Nur Kantar

    2013-06-01

    Full Text Available The title Schiff base, C23H27ClN2O adopts the phenol–imine tautomeric form, with an intramolecular O—H...N hydrogen bond, which generates an S(6 ring motif. Three C atoms of the heterocyclic moiety of the hexahydropyridoquinoline unit, as well as the two methyl groups bonded to one of these C atoms, are disordered over two set of sites, with anoccupancy ratio of 0.740 (4:0.260 (4.

  10. Preparation of Chemicals and Bulk Drug Substances for the U.S. Army Drug Development Program

    National Research Council Canada - National Science Library

    Blumbergs, Peter

    1997-01-01

    .... Types of compounds delivered include substituted quinolines, pyridines, oxazolidines, N-arylpropenamides, carboxylic acids, disulfides, sulfones, thiols and thiol ethers, benzimidazoles, benzoxazoles...

  11. ORF Alignment: NC_002755 [GENIUS II[Archive

    Lifescience Database Archive (English)

    Full Text Available osphoribosyltransferase (Qaprtase) From ... Mycobacterium Tuberculosis In Complex With Phthalate And ...b|1QPR|D Chain D, Quinolinate ... Phosphoribosyltransferase (Qaprtase) From Mycobacterium ... Tuberculosis...horibosyltransferase (Qaprtase) From Mycobacterium ... Tuberculosis In Com...e (Qaprtase) From Mycobacterium ... Tuberculosis In Complex With Phthalate And Prpcp ... pdb|1...cture Of Quinolinic Acid ... Phosphoribosyltransferase From Mycobacterium ... Tuberculosis: A

  12. ORF Alignment: NC_002945 [GENIUS II[Archive

    Lifescience Database Archive (English)

    Full Text Available osphoribosyltransferase (Qaprtase) From ... Mycobacterium Tuberculosis In Complex With Phthalate And ...b|1QPR|D Chain D, Quinolinate ... Phosphoribosyltransferase (Qaprtase) From Mycobacterium ... Tuberculosis...horibosyltransferase (Qaprtase) From Mycobacterium ... Tuberculosis In Com...e (Qaprtase) From Mycobacterium ... Tuberculosis In Complex With Phthalate And Prpcp ... pdb|1...cture Of Quinolinic Acid ... Phosphoribosyltransferase From Mycobacterium ... Tuberculosis: A

  13. ORF Alignment: NC_000962 [GENIUS II[Archive

    Lifescience Database Archive (English)

    Full Text Available osphoribosyltransferase (Qaprtase) From ... Mycobacterium Tuberculosis In Complex With Phthalate And ...b|1QPR|D Chain D, Quinolinate ... Phosphoribosyltransferase (Qaprtase) From Mycobacterium ... Tuberculosis...horibosyltransferase (Qaprtase) From Mycobacterium ... Tuberculosis In Com...e (Qaprtase) From Mycobacterium ... Tuberculosis In Complex With Phthalate And Prpcp ... pdb|1...cture Of Quinolinic Acid ... Phosphoribosyltransferase From Mycobacterium ... Tuberculosis: A

  14. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    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 ...

  15. UV IRRADIATION OF AROMATIC NITROGEN HETEROCYCLES IN INTERSTELLAR ICE ANALOGS

    Science.gov (United States)

    Elsila, J. E.; Bernstein, M. P.; Sanford, S. A.

    2005-01-01

    Here, we present information on the properties of the ANH quinoline frozen in interstellar water-ice analogs. Quinoline is a two-ring compound structurally analogous to the PAH naphthalene. In this work, binary mixtures of water and quinoline were frozen to create interstellar ice analogs, which were then subjected to ultraviolet photolysis. We will present the infrared spectra of the resulting ices at various temperatures, as well as chromatographic analysis of the residues remaining upon warm-up of these ices to room temperature.

  16. Effects of Electron Acceptors, Reducing Agents, and Toxic Metabolites on Anaerobic Degradation of Heterocyclic Compounds

    DEFF Research Database (Denmark)

    Licht, Dorthe; Ahring, Birgitte Kiær; Arvin, Erik

    1996-01-01

    Degradation of four heterocyclic compounds was examined under nitrate-reducing, sulphate-reducing and methanogenic conditions. Soil samples from a creosote-polluted site in Denmark were used as inoculum. Indole and quinoline were degraded under all redox conditions with the highest degradation...... of quinoline under sulphate-reducing conditions which was inhibited by sulphide at concentrations above 0.8 mM. Degradation of quinoline under methanogenic conditions was also inhibited by 3.2 mM sulphide used as a reducing agent, but sulphide had no inhibitory effect on the degradation of indole...... in methanogenic and sulphate-reducing soil slurries...

  17. Photo-induced antimicrobial and DNA cleavage studies of ...

    Indian Academy of Sciences (India)

    of quinoline derivatives has led to their successful use in different fields ... cally produces cell damage that inactivates the microor- ... bioactivity against bacteria upon UV irradiation. The ... were visualized by shortwave UV light and iodine.

  18. IJS v10 n1.cdr

    African Journals Online (AJOL)

    De Don

    2-dicarbonyl derivatives under different reaction conditions) have been reported to show various biological properties. The quinoxaline ring system has been described as bioisoster of aromatic rings, including quinoline, naphthalene,.

  19. Synergic Adsorption–Biodegradation by an Advanced Carrier for Enhanced Removal of High-Strength Nitrogen and Refractory Organics

    KAUST Repository

    Ahmad, Muhammad; Liu, Sitong; Mahmood, Nasir; Mahmood, Asif; Ali, Muhammad; Zheng, Maosheng; Ni, Jinren

    2017-01-01

    Coking wastewater contains not only high-strength nitrogen but also toxic biorefractory organics. This study presents simultaneous removal of high-strength quinoline, carbon, and ammonium in coking wastewater by immobilized bacterial communities

  20. PEG-SO3H as a catalyst in aqueous media: A simple, proficient and ...

    Indian Academy of Sciences (India)

    cants, and a myriad of other value added products essential to ... purchased from Merck Chemical Companies. Purity .... A selected reaction model for the synthesis of quinoline. ... diketones took place faster than open chain analogues.

  1. Augmentation of the Differentiation Response to Antitumor Antimalarials

    National Research Council Canada - National Science Library

    Rahim, Rayhana

    2003-01-01

    .... We have shown that the quinoline antimalarials chloroquine (CO) and hydroxychioroquine (HCQ) inhibit proliferation and induce differentiation in breast cancer cell lines without toxicity to normal MCF-10A cells...

  2. Ugi-Smiles couplings of 4-substituted pyridine derivatives : a fast access to chloroquine analogues

    NARCIS (Netherlands)

    El Kaïm, Laurent; Grimaud, Laurence; Pravin, Patil; Patil, Pravin

    2012-01-01

    4-Hydroxy and mercapto pyridines were successfully tested in Ugi-Smiles couplings. Such multicomponent reactions applied to quinoline derivatives afford a very convenient and short synthesis of antimalarial analogues.

  3. Ugi-Smiles couplings of 4-substituted pyridine derivatives: a fast access to chloroquine analogues.

    Science.gov (United States)

    El Kaïm, Laurent; Grimaud, Laurence; Pravin, Patil

    2012-01-20

    4-Hydroxy and mercapto pyridines were successfully tested in Ugi-Smiles couplings. Such multicomponent reactions applied to quinoline derivatives afford a very convenient and short synthesis of antimalarial analogues. © 2011 American Chemical Society

  4. Heterocycles [h]-Fused Onto 4-Oxoquinoline-3-Carboxylic Acid, Part VIII [1]. Convenient Synthesis and Antimicrobial Properties of Substituted Hexahydro[1,4]diazepino[2,3-h]quinoline-9-carboxylic acid and Its Tetrahydroquino[7,8-b]benzodiazepine Analog

    Directory of Open Access Journals (Sweden)

    Yusuf M. Al-Hiari

    2008-11-01

    Full Text Available [1,4]Diazepino[2,3-h]quinolone carboxylic acid 3 and its benzo-homolog tetrahydroquino[7,8-b]benzodiazepine-3-carboxylic acid 5 were prepared via PPAcatalyzed thermal lactamization of the respective 8-amino-7-substituted-1,4-dihydroquinoline-3-carboxylic acid derivatives 8, 10. The latter compounds were obtained by reduction of their 8-nitro-7-substituted-1,4-dihydroquinoline-3-carboxylic acid precursors 7, 9 which, in turn, were prepared by reaction of 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydroquinoline-3-carboxylic acid (6 with each of β-alanine and anthranilic acid. All intermediates and target compounds were characterized using elemental analysis, NMR, IR and MS spectral data. The prepared targets and the intermediates have shown interesting antibacterial activity mainly against Gram positive strains. In particular, compound 8 showed good activity against S. aureus (MIC = 0.39 μg/mL and B. subtilis (MIC = 0.78 μg/mL. Compounds 5a and 9 have also displayed good antifungal activity against C. albicans (MIC = 1.56 μg/mL and 0.78 μg/mL, respectively. None of the compounds tested showed any anticancer activity against solid breast cancer cell line MCF-7 cells or a human breast adenocarcinoma cell line.

  5. 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

    for isoquinoline [FL-no: 14.001], pyrrole [FL-no: 14.041] and 2-acetylpyrrole [FL-no: 14.047]. The toxicity data on 2-acetylpyrrole should also cover 2-propionylpyrrole [FL-no: 14.068]. Further, additional genotoxicity data on 6-methylquinoline [FL-no: 14.042] have become available. The Panel concluded that for 6......-methylquinoline [FL-no: 14.042], the new genotoxicity data did not clear the concern with respect to genotoxicity in vitro and accordingly the substance is not evaluated through the Procedure. For 18 substances [FL-no: 14.001, 14.004, 14.007, 14.030, 14.038, 14.039, 14.041, 14.047, 14.058, 14.059, 14.060, 14...

  6. NMR of 1,2-dioxiquinolines

    International Nuclear Information System (INIS)

    Figueroa Villar, Jose Daniel; Santos, N.L. dos

    1993-01-01

    Several derivates of quinoline are known for presenting pharmacological activity as antibiotics and anti-parasites, from which an important group are the antibiotics for the treatment of malaria and infections of the urinary tract. This work presents the structures and the NMR spectra of three new derivates of quinoline. These compounds are being tested as possible antibiotics for the treatment of urinary infections caused by Escherichia coli which are extremely resistant to other types of antibiotics

  7. Synthesis and tritium labeling of the food mutagens IQ and methyl-IQ

    International Nuclear Information System (INIS)

    Waterhouse, A.L.; Rapoport, H.

    1985-01-01

    The mutagens found in cooked meat, 2-amino-3-methylimidazo[4,5-f]-quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (Methyl-IQ), have been synthesized by unambiguous methods that allow for the preparation of sufficient quantities of material for biological studies. These methods avoid difficult separations of regioisomeric mixtures of products and incorporate specific high level tritium labeling, effected by hydrogenolysis of the appropriately substituted 5-bromo precursors. (author)

  8. Reactions of model compounds in the presence of pyrene and MoS sub 2 to simulate coprocessing

    Energy Technology Data Exchange (ETDEWEB)

    Ting, P.-S.; Curtis, C.W.; Cronauer, D.C. (Auburn University, Auburn, AL (USA). Chemical Engineering Dept.)

    Catalytic reactions of pyrene using in situ generated MoS{sub 2} from molybdenum naphthenate and excess sulfur were evaluated in the presence of added model species, both hydrocarbons and heteroatomic species. The added hydrocarbons and heteroatomic compounds containing oxygen and sulfur had little effect on the hydrogenation of pyrene at either 400 or 425{degree}C, but quinoline at 400{degree}C reduced the hydrogenation of pyrene by half. Reactions at 425{degree}C also reduced the hydrogenation of pyrene by half regardless of the added model species. The added model species underwent different degrees of reaction: the hydrocarbons underwent little or no reaction, dibenzofuran showed little hydrodeoxygenation, dibenzothiophene yielded substantial hydrodesulfurization and quinoline was almost totally hydrodenitrogenated. The addition of quinoline at increasing concentration resulted in substantial lowering of pyrene hydrogenation and quinoline hydrodenitrogenation. Introduction of quinoline at a low concentration of 0.4 wt% gave a pyrene hydrogenation rate constant of 0.073 min{sup -1} at 400{degree}C while an increase in quinoline to 10.0 wt% yielded a rate constant of 0.020 min{sup -1}. 21 refs., 7 figs., 6 tabs.

  9. [New-type electrodeless excilamp for advanced treatment on nitrogen-heterocyclic compounds (NHCs) in aqueous solution].

    Science.gov (United States)

    Ye, Zhao-Lian; Wang, Bin; Lu, Juan-Juan; Li, Feng; Zhang, Ren-Xi

    2012-03-01

    A novel 206 nm excilamp generated by microwave-driven Kr/I2 mixtures was employed for nitrogen-heterocyclic compounds (NHCs) degradation in aqueous solution. The photodissociation efficiencies of indole and quinoline with 206 nm excilamp were estimated on the basis of removal efficiency of targeted compounds and the loss of total organic carbon (TOC). The results indicated that removal efficiency of 20 mg x L(-1) indole was as high as 62.0% after 80 min and TOC loss efficiency of 50.7% for 150 min. The irradiation time, initial concentration and pH value had some influences on quinoline degradation. Indole removal efficiency and TOC loss was markedly higher than that of quinoline under the same condition. The intermediates were identified qualitatively by gas chromatography/mass spectrum (GC/MS) with headspace sampling after they were extracted by rotary evaporator. GC/MS analysis indicated that indole and quinoline underwent ring-open dissociation under 206 nm irradiation, as a result, benzene, xylene, acetate, aldehyde, as well as ester compounds were formed, while indole aggregation reaction occurred during indole photodegradation. At last, degradation mechanisms of quinoline and indole in aqueous media with 206 nm excilamp were proposed on the basis of intermediates.

  10. Basic nitrogen-heterocyclic compounds in the Murchison meteorite

    International Nuclear Information System (INIS)

    Stoks, P.G.; Schwartz, A.W.

    1982-01-01

    A fragment of the Murchison (C2) carbonaceous meteorite was analyzed for basic, N-heterocyclic compounds, by dual detector capillary gas chromatography as well as capillary gas chromatography/mass spectrometry, using two columns of different polarity. In the formic acid extract 2,4,6-trimethylpyridine, quinoline, isoquinoline, 2-methylquinoline and 4-methylquinoline were positively identified. In addition, a suite of alkylpyridines and quinolines and/or isoquinolines was tentatively identified from their mass spectra. The (iso)quinolines were found to contain methyl substituents exclusively. The distribution of the pyridines observed reveals a similarity to that observed from catalytic reactions of ammonia and simple aldehydes under conditions similar to those applied in Fischer-Tropsch type reactions. (author)

  11. Phytochemical and chemosystematic studies of Conchocarpus marginatus and C. inopinatus (Rutaceae)

    International Nuclear Information System (INIS)

    Bellete, Barbara Sayuri; Sa, Israel Civico Gil de; Mafezoli, Jair; Cerqueira, Cristovam do Nascimento; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista; Vieira, Paulo Cezar; Zukerman-Schpector, Julio; Pirani, Jose Rubens

    2012-01-01

    Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methylarborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus. (author)

  12. Oligoquinolines under Solvent-free Microwave Irradiation

    Energy Technology Data Exchange (ETDEWEB)

    Park, Kwi-Jeon; Kwon, Tae-Woo [Kyungsung University, Busan (Korea, Republic of)

    2015-01-15

    Quinolines are thermally stable and can be used as an excellent n-type semiconducting materials. Since quinolines are also known to be electron acceptor molecules, combination of various electron donor building blocks can be utilized in photonic and electronic organic light-emitting diode (OLED) applications. For example, donor.acceptor systems with phenothiazine (or carbazole) molecules as electron donors and the phenylquinoline group as an electron acceptor provide an efficient approach for the design of new materials exhibiting highly efficient charge-transfer photophysics and electroluminescence in OLEDs. We have described the Friedlander quinoline synthesis between aminobenzophenones and symmetrical diacetyl compounds having phenothiazine, carbazole, biphenyl, and phenyl moieties under solvent-free microwave irradiation in 12.98% isolated yields.

  13. Fitoquímica e quimiossistemática de Conchocarpus marginatus e C. inopinatus (Rutaceae

    Directory of Open Access Journals (Sweden)

    Barbara Sayuri Bellete

    2012-01-01

    Full Text Available Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methyl-arborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus.

  14. Phytochemical and chemosystematic studies of Conchocarpus marginatus and C. inopinatus (Rutaceae); Fitoquimica e quimiossistematica de Conchocarpus marginatus e C. inopinatus (Rutaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Bellete, Barbara Sayuri; Sa, Israel Civico Gil de; Mafezoli, Jair; Cerqueira, Cristovam do Nascimento; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista; Vieira, Paulo Cezar; Zukerman-Schpector, Julio [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Pirani, Jose Rubens, E-mail: dmfs@ufscar.br [Universidade de Sao Paulo (USP), Sao Paulo, SP (Brazil). Inst. de Biociencias

    2012-07-01

    Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methylarborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus. (author)

  15. Quinine conjugates and quinine analogues as potential antimalarial agents.

    Science.gov (United States)

    Jones, Rachel A; Panda, Siva S; Hall, C Dennis

    2015-06-05

    Malaria is a tropical disease, prevalent in Southeast Asia and Africa, resulting in over half a million deaths annually; efforts to develop new antimalarial agents are therefore particularly important. Quinine continues to play a role in the fight against malaria, but quinoline derivatives are more widely used. Drugs based on the quinoline scaffold include chloroquine and primaquine, which are able to act against the blood and liver stages of the parasite's life cycle. The purpose of this review is to discuss reported biologically active compounds based on either the quinine or quinoline scaffold that may have enhanced antimalarial activity. The review emphasises hybrid molecules, and covers advances made in the last five years. The review is divided into three sections: modifications to the quinine scaffold, modifications to aminoquinolines and finally metal-containing antimalarial compounds. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

  16. Bis(μ-2-methylquinolin-8-olato-κ3N,O:O;κ3O:N,O-bis[(methanol-κO(nitrato-κ2O,O′lead(II

    Directory of Open Access Journals (Sweden)

    2009-03-01

    Full Text Available The molecule of the title compound, [Pb2(C10H8NO2(NO32(CH3OH2], lies about a centre of inversion. The Pb atom is chelated by nitrate and substituted quinolin-8-olate anions. The O atom of the quinolin-8-olate also bridges, to confer a six-coordinate status on the metal centre. When a longer Pb...O interaction is considered, the geometry approximates a Ψ-cube in which one of the sites is occupied by a stereochemically active lone pair.

  17. Synthesis of some new heterocyclic compounds bearing a sulfonamide moiety and studying their combined anticancer effect with γ-radiation

    International Nuclear Information System (INIS)

    El-Hossary, E.M.M.

    2010-01-01

    In search for new cytotoxic agents with improved anticancer profile, some new halogen-containing quinoline and pyrimido[4,5-b]quinoline derivatives bearing a free sulfonamide moiety were synthesized. All the newly synthesized target compounds were subjected to in vitro anticancer screening against human breast cancer cell line (MCF7). The most potent compounds, as concluded from the in vitro anticancer screening, were selected to be evaluated again for their in vitro anticancer activity in combination with radiation. Also, the newly synthesized compounds were docked in the active site of the carbonic anhydrase enzyme

  18. Ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

    Directory of Open Access Journals (Sweden)

    De-Cai Wang

    2008-11-01

    Full Text Available In the title compound, C16H15F2NO4, the dihedral angle between the three-membered ring and the quinoline ring system is 64.3 (3°. In the crystal structure, intermolecular C—H...O hydrogen bonds link the molecules, forming a column running along [101].

  19. An efficient one-pot synthesis of carbazole fused benzoquinolines ...

    Indian Academy of Sciences (India)

    KRIPALAYA RATHEESH ARYA

    2018-03-28

    org/ 10.1007/ ..... 1(a-d). 2. 3(a-d). 120°C. 1,3 a: R1 = R2 = R3 = H b: R1 = CH3, R2 = R3 = H c: R1 = R2 = H ..... moted green Friedländer synthesis: a versatile new malic ... and Curini M 2011 An alternative quinoline synthesis by.

  20. Dimethylurea/citric acid as a highly efficient deep eutectic solvent

    Indian Academy of Sciences (India)

    Dimethylurea/citric acid deep eutectic solvent was used as a dual catalyst and a green reaction medium for the efficient synthesis of bis(indolyl)methanes, quinolines and aryl-4, 5-diphenyl-1H-imidazoles. Ease of recovery and reusability of DES with high activity makes this method efficient and eco-friendly.

  1. Variation of the Sterical Properties of the N-Heterocyclic Carbene Coligand in Thermally Triggerable Ruthenium-Based Olefin Metathesis Precatalysts/Initiators

    KAUST Repository

    Pump, Eva; Leitgeb, Anita; Kozłowska, Anna; Torvisco, Ana; Falivene, Laura; Cavallo, Luigi; Grela, Karol; Slugovc, Christian

    2015-01-01

    A series of ruthenium complexes based on the κ(C,N)-(2-(benzo[h]quinolin-10-yl)methylidene ruthenium dichloride fragment featuring different neutral coligands L (L = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene (SIPr), 1,3-bis(2

  2. Fulltext PDF

    Indian Academy of Sciences (India)

    Computational study of ethanol complexes with H2O, H2S and HF molecules has been carried .... A fluorescent sensor based on binaphthol-quinoline Schiff base for ... functionality in DMSO-H2O (1/1, v/v, HEPES 10 mM, pH = 7.4) solution. iv.

  3. Two Novel Thermal Biradical Cyclizations of Enyne-Ketenimines: Theory, Experiment, and Synthetic Potential.

    Science.gov (United States)

    Schmittel, Michael; Steffen, Jens-Peter; Wencesla Ángel, Miguel Á; Engels, Bernd; Lennartz, Christian; Hanrath, Michael

    1998-06-19

    Both benzocarbazoles and quinolines can be synthesized from enyne ketenimines 1 generated in situ via biradical intermediates (see reaction below). Which of the heterocyclic ring systems is formed depends on the choice of the substituent R 1 at the alkyne terminus. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

  4. Preparation, one- and two-photon properties of carbazole derivatives containing nitrogen heterocyclic ring

    Science.gov (United States)

    Zhang, Yichi; Wang, Ping; Li, Liang; Chen, Zhimin; He, Chunying; Wu, Yiqun

    Preparation of recording materials with high two-photon absorption activities is one of the important issues to superhigh- density two-photon absorption (TPA) three-dimensional (3D) optical data storage. In this paper, three new carbazole derivatives containing nitrogen heterocyclic ring with symmetric and asymmetric structures are prepared using ethylene as the π bridge between the carbazole unit and nitrogen heterocyclic ring, namely, 9-butyl-3-(2-(1,8- naphthyridin)vinyl)-carbazole (material 1), 9-butyl-3,6-bis(2-(1,8-naphthyl)vinyl)-carbazole (material 2) and 9-butyl-3,6- bis(2-(quinolin)vinyl)-carbazole (material 3). Their one photon properties including linear absorption spectra, fluorescence emission spectra, and fluorescence quantum yields are studied. The fluorescence excited by 120 fs pulse at 800 nm Ti: sapphire laser operating at 1 kHz repetition rate with different incident powers of 9-butyl-3-(2-(quinolin) vinyl)-carbazole (material 3) was investigated, and two-photon absorption cross-sections has been obtained. It is shown that material 3 containing quinoline rings as electron acceptor with symmetric structure exhibit high two-photon absorption activity. The result implies that material 3 (9-butyl-3-(2-(quinolin) vinyl)-carbazole) is a good candidate as a promising recording material for super-high-density two-photon absorption (TPA) three-dimensional (3D) optical data storage. The influence of chemical structure of the materials on the optical properties is discussed.

  5. Unraveling the Mechanism of a Reversible Photoactivated Molecular Proton Crane

    NARCIS (Netherlands)

    van der Loop, T.H.; Ruesink, F.; Amirjalayer, S.; Sanders, H. J.; Buma, W.J.; Woutersen, S.

    2014-01-01

    Structural dynamics of the photoactivated mol. proton crane 7-​hydroxy-​8-​(morpholinomethyl)​quinoline has been studied using femtosecond UV-​pump IR-​probe spectroscopy. Upon electronic excitation, a proton is transferred from the hydroxy to the amine group located on the rotatable morpholino side

  6. Protein regulation of induced pluripotent stem cells by transplanting in a Huntington's animal model.

    Science.gov (United States)

    Mu, S; Han, L; Zhou, G; Mo, C; Duan, J; He, Z; Wang, Z; Ren, L; Zhang, J

    2016-10-01

    The purpose of this study was to determine the functional recovery and protein regulation by transplanted induced pluripotent stem cells in a rat model of Huntington's disease (HD). In a quinolinic acid-induced rat model of striatal degeneration, induced pluripotent stem cells were transplanted into the ipsilateral lateral ventricle 10 days after the quinolinic acid injection. At 8 weeks after transplantation, fluorodeoxyglucose-PET/CT scan and balance-beam test were performed to evaluate the functional recovery of experimental rats. In addition, immunofluorescence and protein array analysis were used to investigate the regulation of stimulated protein expression in the striatum. At 8 weeks after induced pluripotent stem cell transplantation, motor function was improved in comparison with the quinolinic acid-treated rats. High fluorodeoxyglucose accumulation in the injured striatum was also observed by PET/CT scans. In addition, immunofluorescence analysis demonstrated that implanted cells migrated from the lateral ventricle into the lesioned striatum and differentiated into striatal projection neurons. Array analysis showed a significant upregulation of GFR (Glial cell line-derived neurotrophic factor receptor) alpha-1, Adiponectin/Acrp30, basic-fibroblast growth factors, MIP-1 (Macrophage-inflammatory protein) alpha and leptin, as well as downregulation of cytokine-induced neutrophil chemoattractant-3 in striatum after transplantatation of induced pluripotent stem cells in comparison with the quinolinic acid -treated rats. The findings in this work indicate that transplantation of induced pluripotent stem cells is a promising therapeutic candidate for HD. © 2016 British Neuropathological Society.

  7. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    Cyclodiphosphazanes as synthetic probes: P-C/P-N bond formation from the reaction ... Studies on cluster, salt and molecular complex of zinc-quinolinate ..... lithium iminophosphonamides and homoleptic bis-chelates of Co(II), Ni(II) and Cu(II).

  8. Fulltext PDF

    Indian Academy of Sciences (India)

    2,4]triazolo[4,3-a]quinolines; cytotoxic agents; antiviral agents. 1. Introduction. During our ongoing studies aimed at the discovery of new structure leads endowed with diverse chemother- apeutic activities,1–9 much concern has been given to.

  9. Redox reactions of copper(II) upon electrospray ionization in the presence of acridine ligands with an amide side chain

    Czech Academy of Sciences Publication Activity Database

    Tintaru, A.; Charles, L.; Milko, Petr; Roithová, J.; Schröder, Detlef

    2009-01-01

    Roč. 22, č. 3 (2009), s. 229-233 ISSN 0894-3230 R&D Projects: GA AV ČR KJB400550704; GA ČR GA203/08/1487 Institutional research plan: CEZ:AV0Z40550506 Keywords : acridine * copper * electrospray ionization * mass spectrometry * quinoline Subject RIV: CC - Organic Chemistry Impact factor: 1.602, year: 2009

  10. Synthesis of a novel class of some biquinoline pyridine hybrids via

    Indian Academy of Sciences (India)

    A small library of novel class of biquinoline containing pyridine moiety were synthesized by a one-pot cyclocondensation of 2-chloro-3-formyl quinoline, active methylene compounds and 3-(pyridine-3- ylamino)cyclohex-2-enone in the presence of catalytic amount of sodium hydroxide. The protocol offers rapid synthesis of ...

  11. Carbonic anhydrase inhibitors: Design, synthesis and structural characterization of new heteroaryl-N-carbonylbenzenesulfonamides targeting druggable human carbonic anhydrase isoforms

    Czech Academy of Sciences Publication Activity Database

    Buemi, M. R.; De Luca, L.; Ferro, S.; Bruno, E.; Ceruso, M.; Supuran, C. T.; Pospíšilová, K.; Brynda, Jiří; Řezáčová, Pavlína; Gitto, R.

    2015-01-01

    Roč. 102, Sep 18 (2015), s. 223-232 ISSN 0223-5234 Institutional support: RVO:61388963 Keywords : human carbonic anhydrase * isoquinoline * quinoline * X-ray * molecular docking Subject RIV: CE - Biochemistry Impact factor: 3.902, year: 2015

  12. Bulletin of Materials Science | News

    Indian Academy of Sciences (India)

    Effect of aligned carbon nanotubes on electrical conductivity behaviour in ... hydrophobic drugs effectively (intravenous) with desired pharmacokinetic profile for breast ... Influence of pH on ZnO nanocrystalline thin films prepared by sol–gel dip ..... on corrosion inhibition performance of quinoline derivatives for MS in 1N HCl.

  13. An environmentally benign one pot synthesis of substituted ...

    Indian Academy of Sciences (India)

    Instance of Plagiarism in Journal of Chemical Sci- ences and withdrawal of published article. The Journal of Chemical Sciences office received a complaint from an alert reader to the effect that the paper 'An environmentally benign one pot syn- thesis of substituted quinolines catalysed by fluo- roboric acid based ionic ...

  14. Fe (III) complex of mefloquine hydrochloride: Synthesis ...

    African Journals Online (AJOL)

    As part of the ongoing research for more effective antimalarial drug, Fe (III) complex of mefloquine hydrochloride (antimalarial drug) was synthesized using template method. Mefloquine was tentatively found to have coordinated through the hydroxyl and the two nitrogen atoms in the quinoline and piperidine in the structure, ...

  15. Iodine catalyzed one-pot synthesis of chloro-substituted linear and angular indoloquinolines and in vitro antiproliferative activity study of different indoloquinolines

    Digital Repository Service at National Institute of Oceanography (India)

    Parvatkar, P.T.; Ajay, A.K.; Bhat, M.K.; Parameswaran, P.S.; Tilve, S.G.

    ) and some indolo[2,3-b]quinolines (3a–d) against human hepatocellular carcinoma HepG2 and human breast carcinoma MCF-7 cells. Anti-proliferative assay against human hepatocellular carcinoma HepG2 and human breast carcinoma MCF-7 cells indicated methyl...

  16. Visible light- and radiation-induced alkylation of pyridine ring with alkanoic acid

    International Nuclear Information System (INIS)

    Sugimori, Akira; Yamada, Tetsuo

    1986-01-01

    Quinoline and 4-methylquinoline are efficiently alkylated with alkanoic acid in the presence of iron(III) sulfate upon visible light-irradiation. Iron(III) sulfate not only accelerates the photoreaction but also increases the yield of alkylation. Gamma-irradiation also brings about the alkylation. In the photo- and radiation-induced alkylation with alkanoic acid, alkyl radicals play important roles. (author)

  17. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    ... corresponding quinoline carboxylic acid derivatives 12 and 13, respectively. Volume 125 Issue 3 May 2013 pp 555-560. Application of chalcones in heterocycles synthesis: Synthesis of 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues of 1,4-benzodiazepin-5-carboxamides linked through an oxyphenyl bridge.

  18. Design, Synthesis and In Vitro Activity of Anticancer Styrylquinolines. The p53 Independent Mechanism of Action

    Czech Academy of Sciences Publication Activity Database

    Mrozek-Wilczkiewicz, A.; Spaczynska, E.; Malarz, K.; Cieslik, W.; Rams-Baron, M.; Kryštof, Vladimír; Musiol, R.

    2015-01-01

    Roč. 10, č. 11 (2015), e0142678 E-ISSN 1932-6203 R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : BIOLOGICAL-ACTIVITY SPECTRUM * MUTANT P53 * QUINOLINE DERIVATIVES Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 3.057, year: 2015

  19. Biosynthesis of quinoxaline antibiotics: Purification and characterization of the quinoxaline-2-carboxylic acid activating enzyme from Streptomyces triostinicus

    International Nuclear Information System (INIS)

    Glund, K.; Schlumbohm, W.; Bapat, M.; Keller, U.

    1990-01-01

    A quinoxaline-2-carboxylic acid activating enzyme was purified to homogeneity from triostin-producing Streptomyces triostinicus. It could also be purified from quinomycin-producing Streptomyces echinatus. Triostins and quinomycins are peptide lactones that contain quinoxaline-2-carboxylic acid as chromophoric moiety. The enzyme catalyzes the ATP-pyrophosphate exchange reaction dependent on quinoxaline-2-carboxylic acid and the formation of the corresponding adenylate. Besides quinoxaline-2-carboxylic acid, the enzyme also catalyzes the formation of adenylates from quinoline-2-carboxylic acid and thieno[3,2-b]pyridine-5-carboxylic acid. No adenylates were seen from quinoline-3-carboxylic acid, quinoline-4-carboxylic acid, pyridine-2-carboxylic acid, and 2-pyrazinecarboxylic acid. Previous work revealed that quinoline-2-carboxylic acid and thieno[3,2-b]pyridine-5-carboxylic acid became efficiently incorporated into the corresponding quinoxaline antibiotic analogues in vivo. Together with the data described here, this suggests that the enzyme is part of the quinoxaline antibiotics synthesizing enzyme system. The enzyme displays a native molecular weight of 42,000, whereas in its denatured form it is a polypeptide of Mr 52,000-53,000. It resembles in its behavior actinomycin synthetase I, the chromophore activating enzyme involved in actinomycin biosynthesis

  20. Spectroscopic effects in 1H and 13C NMR spectra of 4,4'-di-substituted 3,3'-diquinolines sulfides

    International Nuclear Information System (INIS)

    Pluta, K.

    1994-01-01

    The 1 H and 13 C NMR spectra of 4,4'-disubstituted sulfides of 3,3'-quinolines have been studied in CDCl 3 solutions. The observed spectroscopic effects have been interpreted in terms of molecule structure and configuration. The factors being responsible for the value of spectroscopic effects have been discussed

  1. Interferon-alpha induced depressive-like behavior in rats

    DEFF Research Database (Denmark)

    Fischer, C. W.; Liebenberg, N.; Elfving, B.

    2013-01-01

    to link inflammation and depression, such as increased levels of the neurotoxic tryptophan metabolite, quinolinic acid (QUIN), and decreased brain-derived neurotrophic factor (BDNF), a protein that plays an important role in survival, differentiation and growth of neurons. The successful development...

  2. The European standard series. European Environmental and Contact Dermatitis Research Group (EECDRG)

    DEFF Research Database (Denmark)

    Bruynzeel, D P; Andersen, Klaus Ejner; Camarasa, J G

    1995-01-01

    Changes to the European standard series which have taken place since the last officially recommended alterations in 1988, are explained. New to the series is the sesquiterpene lactone mix. The PPD black rubber mix and the quinoline mix have been replaced by single components; one of the p-hydroxy...

  3. Synthesis of novel precursors of Pfitzinger reaction: A facile one-pot ...

    Indian Academy of Sciences (India)

    strategy to the synthesis of quinoline carboxylic acid derivatives of ... solution of sodium nitrite (0.7g in 2ml water) while ... sodium acetate trihydrate (1.80 g) in methanol (10 ml) ... the aqueous layer was acidified with acetic acid till neu-.

  4. Reaction of Titanocene Alkyls with Pyridines; A Novel Type of Cyclometallation Reaction

    NARCIS (Netherlands)

    Klei, E.; Teuben, J.H.

    1981-01-01

    Reaction of Cp2TiR (R = alkyl) with 2-substituted-pyridines and with quinolines leads to α-metallation of these ligands with formation of triangular titanocycles containing TiIII. Proof of the metallation at the α-position comes from reactions of the complexes formed with I2 and D2O/DCl which yield

  5. 77 FR 20034 - Harmful and Potentially Harmful Constituents in Tobacco Products and Tobacco Smoke; Established List

    Science.gov (United States)

    2012-04-03

    ...]pyridine). Polonium-210 CA Propionaldehyde RT, CT Propylene oxide CA, RT Quinoline CA Selenium RT Styrene... DEPARTMENT OF HEALTH AND HUMAN SERVICES Food and Drug Administration [Docket No. FDA-2012-N-0143... AGENCY: Food and Drug Administration, HHS. ACTION: Notice; establishment of a list. SUMMARY: The Food and...

  6. High coking value pitch

    Science.gov (United States)

    Miller, Douglas J.; Chang, Ching-Feng; Lewis, Irwin C.; Lewis, Richard T.

    2014-06-10

    A high coking value pitch prepared from coal tar distillate and has a low softening point and a high carbon value while containing substantially no quinoline insolubles is disclosed. The pitch can be used as an impregnant or binder for producing carbon and graphite articles.

  7. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    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 ...

  8. CNS adverse events associated with antimalarial agents. Fact or fiction?

    NARCIS (Netherlands)

    Phillips-Howard, P. A.; ter Kuile, F. O.

    1995-01-01

    CNS adverse drug events are dramatic, and case reports have influenced clinical opinion on the use of antimalarials. Malaria also causes CNS symptoms, thus establishing causality is difficult. CNS events are associated with the quinoline and artemisinin derivatives. Chloroquine, once considered too

  9. Ligand-Enabled γ-C–H Olefination and Carbonylation: Construction of β-Quaternary Carbon Centers

    Science.gov (United States)

    2015-01-01

    Monoselective γ-C–H olefination and carbonylation of aliphatic acids has been accomplished by using a combination of a quinoline-based ligand and a weakly coordinating amide directing group. The reaction provides a new route for constructing richly functionalized all-carbon quaternary carbon centers at the β-position of aliphatic acids. PMID:24666182

  10. Browse Title Index

    African Journals Online (AJOL)

    Items 301 - 350 of 444 ... Vol 64 (2011), Solventless Synthesis of Quinoline Derivatives: ... and Some Transition Metal Complexes, Abstract PDF. A Tavman ... Vol 60 (2007), Synthesis & Spectral Characterization of Some New Carbacylamidophosphate Derivatives. ... 1,3,4-Thiadiazole and 1,2,4-Triazole Moieties, Abstract PDF.

  11. Water quality criteria for colored smokes: Solvent Yellow 33, Final report. [Contains glossary

    Energy Technology Data Exchange (ETDEWEB)

    Davidson, K.A.; Hovatter, P.S.

    1987-11-01

    The available data on the environmental fate, aquatic toxicity, and mammalian toxicity of Solvent Yellow 33, a quinoline dye used in colored smoke grenades, were reviewed. The US Environmental Protection Agency (USEPA) guidelines were used in an attempt to generate water quality criteria for the protection of aquatic life and its use and of human health. 87 refs., 2 figs., 13 tabs.

  12. Journal of Chemical Sciences | Indian Academy of Sciences

    Indian Academy of Sciences (India)

    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+ ...

  13. Bikash Kumar Panda

    Indian Academy of Sciences (India)

    Home; Journals; Journal of Chemical Sciences. Bikash Kumar Panda. Articles written in Journal of Chemical Sciences. Volume 116 Issue 5 August 2004 pp 245-250. Synthesis, characterization and emission properties of quinolin-8-olato chelated ruthenium organometallics · Bikash Kumar Panda · More Details Abstract ...

  14. 4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethylphenyl]-1,2-dihydroquinoline-3-carboxamide

    Directory of Open Access Journals (Sweden)

    Emmanuel S. Akinboye

    2014-03-01

    Full Text Available 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-(trifluoromethylphenyl 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-hydroxy H atom acts as a double proton donor in an intramolecular hydrogen bond to the 5-position methoxy O atom and in an intermolecular contact to the 2-oxo group, generating a chain along [010] in the crystal structure.

  15. Toxicokinetics of the food-toxin IQ in human placental perfusion is not affected by ABCG2 or xenobiotic metabolism

    DEFF Research Database (Denmark)

    Immonen, E; Kummu, M; Petsalo, A

    2010-01-01

    Metabolizing enzymes and transporters affect toxicokinetics of foreign compounds (e.g. drugs and carcinogens) in human placenta. The heterocyclic amine, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) is a food-borne carcinogen being metabolically activated by cytochrome P450 (CYP) enzymes, especial...

  16. Biotransformation of Food Dyes by Human Intestinal Bacteria ...

    African Journals Online (AJOL)

    Biotransformation of food dyes (Tartrazine and Quinoline yellow) by Streptococcus faecalis and Escherichia coli isolated from human intestinal microflora was investigated. Decolourisation of the media containing the dyes was used as an index of biotransformation. Biotransformation was higher under aerobic than under ...

  17. Kynurenine pathway metabolic balance influences microglia activity: Targeting kynurenine monooxygenase to dampen neuroinflammation.

    Science.gov (United States)

    Garrison, Allison M; Parrott, Jennifer M; Tuñon, Arnulfo; Delgado, Jennifer; Redus, Laney; O'Connor, Jason C

    2018-08-01

    Chronic stress or inflammation increases tryptophan metabolism along the kynurenine pathway (KP), and the generation of neuroactive kynurenine metabolites contributes to subsequent depressive-like behaviors. Microglia regulate KP balance by preferentially producing oxidative metabolites, including quinolinic acid. Research has focused on the interplay between cytokines and HPA axis-derived corticosteroids in regulating microglial activity and effects of KP metabolites directly on neurons; however, the potential role that KP metabolites have directly on microglial activity is unknown. Here, murine microglia were stimulated with lipopolysaccharide(LPS). After 6 h, mRNA expression of interleukin(IL)-1β, IL-6, tumor necrosis factor(TNF)-α and inducible nitric oxide synthase(iNOS) was dose-dependently increased along with the rate-limiting enzymes for oxidative KP metabolism, indoleamine-2,3-dioxygenase(IDO)-1 and kynurenine 3-monooxygenase(KMO). By 24 h post-LPS, kynurenine and quinolinic acid in the media was elevated. Inhibiting KMO with Ro 61-8048 during LPS challenge attenuated extracellular nitrite accumulation and expression of KMO and TNF-α in response to LPS. Similarly, primary microglia isolated from KMO -/- mice exhibited a significantly reduced pro-inflammatory response to LPS compared to WT controls. To determine whether the substrate (kynurenine) or end product (quinolinic acid) of KMO-dependent metabolism modulates the LPS response, microglia were treated with increasing concentrations of L-kynurenine or quinolinic acid in combination with LPS or saline. Interestingly, quinolinic acid did not impact the microglial LPS response. However, L-kynurenine had dose-dependent inhibitory effect on the LPS response. These data are the first to show an anti-inflammatory effect of KMO inhibition on microglia during immune challenge and suggest that KP metabolic balance may play a direct role in regulating microglia activity. Published by Elsevier Ltd.

  18. Quinolinone and pyridopyrimidinone inhibitors of DNA-dependent protein kinase.

    Science.gov (United States)

    Barbeau, Olivier R; Cano-Soumillac, Celine; Griffin, Roger J; Hardcastle, Ian R; Smith, Graeme C M; Richardson, Caroline; Clegg, William; Harrington, Ross W; Golding, Bernard T

    2007-08-21

    8-Substituted 2-morpholin-4-yl-quinolin-4-ones and 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones with selected aryl and heteroaryl groups as the substituent have been synthesised as potential inhibitors of DNA-dependent protein kinase. A multiple-parallel approach, employing Suzuki cross-coupling methodology, was utilised in the preparation of 8-substituted 2-morpholin-4-yl-quinolin-4-ones. For this purpose 8-bromo-2-morpholin-4-yl-quinolin-4-one was required as an intermediate. This compound was obtained by adapting a literature route in which thermal cyclocondensation of (2-bromoanilino)-morpholin-4-yl-5-methylene-2,2-dimethyl[1,3]dioxane-4,6-dione afforded 8-bromo-2-morpholin-4-yl-quinolin-4-one. A multiple-parallel approach, employing Suzuki cross-coupling methodology, was also utilised to prepare 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones using 9-hydroxy-2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-one O-trifluoromethanesulfonate as an intermediate. 8-Substituted 2-morpholin-4-yl-quinolin-4-ones and 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones were both inhibitors of DNA-dependent protein kinase. When the substituent was dibenzothiophen-4-yl, dibenzofuran-4-yl or biphen-3-yl, IC50 values in the low nanomolar range were observed. Interestingly, the pyridopyrimidinones and quinolinones were essentially equipotent with the corresponding 8-substituted 2-morpholin-4-yl-chromen-4-ones previously reported (I. R. Hardcastle, X. Cockcroft, N. J. Curtin, M. Desage El-Murr, J. J. J. Leahy, M. Stockley, B. T. Golding, L. Rigoreau, C. Richardson, G. C. M. Smith and R. J. Griffin, J. Med. Chem., 2005, 48, 7829-7846).

  19. Investigation of the Biological Properties of (HeteroAromatic Thiosemicarbazones

    Directory of Open Access Journals (Sweden)

    Jaroslaw Polanski

    2012-11-01

    Full Text Available Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E-2-(quinolin-2-ylvinyl-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116. Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET in spinach (Spinacia oleracea L. chloroplasts. The structure-activity relationships are discussed for all of the compounds.

  20. Stable isotope dilution quantification of mutagens in cooked foods by combined liquid chromatography-thermospray mass spectrometry

    International Nuclear Information System (INIS)

    Yamaizumi, Ziro; Kasai, Hiroshi; Nishimura, Susumu; Edmonds, C.G.; McCloskey, J.A.

    1986-01-01

    A method of general applicability for the detection and quantification of mutagens in cooked foods at the ppb level is presented. A minimal sample prefractionation is employed and [Me- 2 H 3 ]-labeled analogs of the compounds of interest are added for identification and quantification of mutagens by accurate measurement of chromatographic retention (K') in reverse-phase high-performance liquid chromatography (HPLC), and by measurement of the ratio of response of the protonated molecular ions of analyte and internal standard by directly coupled liquid chromatography-mass spectrometry (LC/MS). Initial application is demonstrated in the analysis of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MelQ) in broiled salmon. (Auth.)

  1. Determination of selected azaarenes in water by bonded-phase extraction and liquid chromatography

    Science.gov (United States)

    Steinheimer, T.R.; Ondrus, M.G.

    1986-01-01

    A method for the rapid and simple quantitative determination of quinoline, isoquinoline, and five selected three-ring azaarenes in water has been developed. The azaarene fraction is separated from its carbon analogues on n-octadecyl packing material by edition with acidified water/acetonitrile. Concentration as great as 1000-fold is achieved readily. Instrumental analysis involves high-speed liquid chromatography on flexible-walled, wide-bore columns with fluorescence and ultraviolet detection at several wavelengths employing filter photometers in series. Method-validation data is provided as azaarene recovery efficiency from fortified samples. Distilled water, river water, contaminated ground water, and secondary-treatment effluent have been tested. Recoveries at part-per-billion levels are nearly quantitative for the three-ring compounds, but they decrease for quinoline and isoquinoline. ?? 1986 American Chemical Society.

  2. NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

    KAUST Repository

    Gurinov, Andrei A.; Denisov, Gleb S.; Borissova, Alexandra O.; Goloveshkin, Alexander S.; Greindl, Julian; Limbach, Hans-Heinrich; Shenderovich, Ilya G.

    2017-01-01

    Hydrogen bond geometries in the proton-bound homodimers of quinoline and acridine derivatives in an aprotic polar solution have been experimentally studied using 1H NMR at 120 K. The reported results show that increase of the dielec-tric permittivity of the medium results in contraction of the N…N distance. The degree of contraction depends on the homodimer's size and its substituent-specific solvation features. Neither of these effects can be reproduced using conven-tional implicit solvent models employed in computational studies. In general, the N…N distance in the homodimers of pyridine, quinoline, and acridine derivatives decreases in the sequence gas phase > solid state > polar solvent.

  3. NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

    KAUST Repository

    Gurinov, Andrei A.

    2017-10-24

    Hydrogen bond geometries in the proton-bound homodimers of quinoline and acridine derivatives in an aprotic polar solution have been experimentally studied using 1H NMR at 120 K. The reported results show that increase of the dielec-tric permittivity of the medium results in contraction of the N…N distance. The degree of contraction depends on the homodimer\\'s size and its substituent-specific solvation features. Neither of these effects can be reproduced using conven-tional implicit solvent models employed in computational studies. In general, the N…N distance in the homodimers of pyridine, quinoline, and acridine derivatives decreases in the sequence gas phase > solid state > polar solvent.

  4. Binding of 14C-labeled food mutagens (IQ, MeIQ, MeIQx) by dietary fiber in vitro

    International Nuclear Information System (INIS)

    Sjoedin, P.B.; Nyman, M.E.; Nilsson, L.; Asp, N.L.; Jaegerstad, M.

    1985-01-01

    Binding of three mutagens, known to occur in fried or broiled foods, by thirteen different types of dietary fiber was investigated in vitro. Nonspecific binding by other food polymers was minimized by using protease and amylase treatment. Water-insoluble fiber components were responsible for most of the binding capacity. Generally, a slightly larger proportion of 2-amino-3,4-dimethylimidazo [4,5-f]quinoline (MeIQ) than of 2-amino-3-methylimidazo [4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo] -4,5-f]quinoxaline (MeIQx) was bound. There was a significant correlation between Klason lignin content and binding of mutagens. Optimum pH for binding was between 4 and 6. Dietary fiber from sorghum had the highest binding capacity, which could be due to the presence of a large Klason lignin fraction

  5. 6-Chloro-3-[5-(3-methoxy-8-methyl-4-quinolyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4-phenylquinoline

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2009-11-01

    Full Text Available In the title compound, C36H29ClN4O, the dihydropyrazole ring adopts an envelope conformation. The two quinoline ring systems (r.m.s. deviations = 0.029 and 0.018 Å are oriented at a dihedral angle of 71.43 (4°. One of the quinoline rings makes a dihedral angle of 65.40 (7° with the phenyl substituent. In the crystal, molecules are linked into chains along the b axis by intermolecular C—H...N hydrogen bonds. In addition, C—H...π and π–π [centroid–centroid distance = 3.7325 (8 Å] interactions are observed.

  6. Analysis of recovered solvents from coal liquefaction in a flowing-solvent reactor by SEC and UV-fluorescence

    Energy Technology Data Exchange (ETDEWEB)

    Li, W.Y.; Feng, J.; Xie, K.C.; Kandiyoti, R. [Taiyuan University of Technology, Taiyuan (China)

    2005-08-01

    Point of Ayr coal has been extracted using three solvents: tetralin, quinoline and 1-methyl-2-pyrrolidinone (NMP); at two temperatures: 350 {sup o}C and 450{sup o}C, corresponding approximately to before and after the onset of massive covalent bond scission by pyrolysis. These solvents differ in solvent power and the ability to donate hydrogen atoms to stabilize free radicals produced by pyrolysis of the coal. Analysis of the fresh solvents and recovered solvents from coal liquefaction was achieved by size exclusion chromatography and UV-fluorescence spectroscopy. In the blank run, it was testified that the filling material sand and the steel powder did not react with solvent with increasing reaction temperature. The role of hydrogen donation in the tetralin extracts was to increase the proportion of large molecules with increasing extraction temperature. Quinoline and NMP both have the powerful extracting capability to get more materials out of coal with increasing extraction temperature.

  7. Analysis of recovered solvents from coal liquefaction in a flowing-solvent reactor by SEC and UV-fluorescence

    Energy Technology Data Exchange (ETDEWEB)

    Wen-Ying Li; Jie Feng; Ke-Chang Xie; R. Kandiyoti [Taiyuan University of Technology, Taiyuan (China). Key Laboratory of Coal Science and Technology for Ministry of Education and Shanxi Province

    2005-08-01

    Point of Ayr coal has been extracted using three solvents: tetralin, quinoline and 1-methyl-2-pyrrolidinone (NMP); at two temperatures: 350{sup o}C and 450{sup o}C, corresponding approximately to before and after the onset of massive covalent bond scission by pyrolysis. These solvents differ in solvent power and the ability to donate hydrogen atoms to stabilize free radicals produced by pyrolysis of the coal. Analysis of the fresh solvents and recovered solvents from coal liquefaction was achieved by size exclusion chromatography and UV-fluorescence spectroscopy. In the blank run, it was testified that the filling material sand and the steel powder did not react with solvent with increasing reaction temperature. The role of hydrogen donation in the tetralin extracts was to increase the proportion of large molecules with increasing extraction temperature. Quinoline and NMP both have the powerful extracting capability to get more materials out of coal with increasing extraction temperature.

  8. Phosphoribosyl diphosphate synthetase-independent NAD de novo synthesis in Escherichia coli: a new phenotype of phosphate regulon mutants

    DEFF Research Database (Denmark)

    Hove-Jensen, Bjarne

    1996-01-01

    Phosphoribosyl diphosphate-lacking (Δprs) mutant strains of Escherichia coli require NAD, guanosine, uridine, histidine, and tryptophan for growth. NAD is required by phosphoribosyl diphosphate-lacking mutants because of lack of one of the substrates for the quinolinate phosphoribosyltransferase...... reaction, an enzyme of the NAD de novo pathway. Several NAD-independent mutants of a host from which prs had been deleted were isolated; all of them were shown to have lesions in the pstSCAB-phoU operon, in which mutations lead to derepression of the Pho regulon. In addition NAD-independent growth...... was dependent on a functional quinolinate phosphoribosyltransferase. The prs suppressor mutations led to the synthesis of a new phosphoryl compound that may act as a precursor for a new NAD biosynthetic pathway. This compound may be synthesized by the product of an unknown phosphate starvation-inducible gene...

  9. Anoxic degradation of nitrogenous heterocyclic compounds by activated sludge and their active sites.

    Science.gov (United States)

    Xu, Peng; Han, Hongjun; Zhuang, Haifeng; Hou, Baolin; Jia, Shengyong; Wang, Dexin; Li, Kun; Zhao, Qian

    2015-05-01

    The potential for degradation of five nitrogenous heterocyclic compounds (NHCs), i.e., imidazole, pyridine, indole, quinoline, and carbazole, was investigated under anoxic conditions with acclimated activated sludge. Results showed that NHCs with initial concentration of 50 mg/L could be completely degraded within 60 hr. The degradation of five NHCs was dependent upon the chemical structures with the following sequence: imidazole>pyridine>indole>quinoline>carbazole in terms of their degradation rates. Quantitative structure-biodegradability relationship studies of the five NHCs showed that the anoxic degradation rates were correlated well with highest occupied molecular orbital. Additionally, the active sites of NHCs identified by calculation were confirmed by analysis of intermediates using gas chromatography and mass spectrometry. Copyright © 2015. Published by Elsevier B.V.

  10. New heterocyclic compounds: Synthesis and antitrypanosomal properties.

    Science.gov (United States)

    Pomel, S; Dubar, F; Forge, D; Loiseau, P M; Biot, C

    2015-08-15

    Three new series of quinoline, quinolone, and benzimidazole derivatives were synthesized and evaluated in vitro against Trypanosoma brucei gambiense. In the quinoline series, the metallo antimalarial drug candidate (ferroquine, FQ) and its ruthenium analogue (ruthenoquine, RQ, compound 13) showed the highest in vitro activities with IC50 values around 0.1 μM. Unfortunately, both compounds failed to cure Trypanosoma brucei brucei infected mice in vivo. The other heterocyclic compounds were active in vitro with IC50 values varying from 0.8 to 34 μM. One of the most interesting results was a fluoroquinolone derivative (compound 2) that was able to offer a survival time of 8 days after a treatment at the single dose of 100 μmol/kg by intraperitoneal route. Although no clear-cut structure-activity relationships emerged, further pharmacomodulations are worth to be developed in this series. Copyright © 2015 Elsevier Ltd. All rights reserved.

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

    International Nuclear Information System (INIS)

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

    2005-01-01

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

  12. Radiochemical investigations on the solubility of molybdatophosphate in phosphate determination

    International Nuclear Information System (INIS)

    Noack, S.

    1975-01-01

    The solubility of various molybdatophosphates was determined under the conditions of a gravimetric phosphate determination by radiochemical means by labelling PO 4 3- with P-32. Starting with various conditions for phosphate determination via the molybdatophosphate of quinoline, 8-hydroxyquinoline, dimorpholino ethane, N,N,N',N'-tetrakis-β-hydroxypropyl ethylene diamine and N,N,N',N'-tetrakis-β-hydroxybutyl ethylene diamine, a general working rule was developed to determine the solubility. Taking the example of quinoline molybdatophosphates, a series of influencing factors - work, concentration and measuring parameters - were investigated in order to be able to limit the reliability region of the gravimetric phosphate determination. Depending on the conditions, the measured solubilities were between 10 -10 and 10 -6 Mol/l, the corresponding degrees of precipitation between 99.0 and 99.9999%. Apparent solubility products were calculated for the different molybdatophosphates using computer programmes especially developed for this purpose. (orig./RB) [de

  13. Searching for Bio-Precursors and Complex Organic Molecules in Space using the GBT

    Science.gov (United States)

    Cordiner, M.; Charnley, S.; Kisiel, Z.

    2012-01-01

    Using the latest microwave receiver technology, large organic molecules with abundances as low as approx. 10(exp -11) times that of molecular hydrogen are detectable in cold interstellar clouds via their rotational emission line spectra. We report new observations to search for complex molecules, including molecules of possible pre-biotic importance, using the newly-commissioned Kband focal plane array (KFPA) of the NRAO Robert C. Byrd Green Bank Telescope. Spectra are presented of the dense molecular cloud TMC-1, showing strict upper limits on the level of emission from nitrogen-bearing rings pyrimidine, quinoline and iso-quinoline, carbon-chain oxides C60, C70, HC60 and HC70, and the carbon-chain anion C4H-. The typical RMS brightness temperature noise levels we achieved are approx. 1 mK at around 20 GHz.

  14. Positron annihilation studies of some charge transfer molecular complexes

    CERN Document Server

    El-Sayed, A; Boraei, A A A

    2000-01-01

    Positron annihilation lifetimes were measured for some solid charge transfer (CT) molecular complexes of quinoline compounds (2,6-dimethylquinoline, 6-methoxyquinoline, quinoline, 6-methylquinoline, 3-bromoquinoline and 2-chloro-4-methylquinoline) as electron donor and picric acid as an electron acceptor. The infrared spectra (IR) of the solid complexes clearly indicated the formation of the hydrogen-bonding CT-complexes. The annihilation spectra were analyzed into two lifetime components using PATFIT program. The values of the average and bulk lifetimes divide the complexes into two groups according to the non-bonding ionization potential of the donor (electron donating power) and the molecular weight of the complexes. Also, it is found that the ionization potential of the donors and molecular weight of the complexes have a conspicuous effect on the average and bulk lifetime values. The bulk lifetime values of the complexes are consistent with the formation of stable hydrogen-bonding CT-complexes as inferred...

  15. Role of non-ferrous coal minerals and by-product metallic wastes in coal liquefaction. Technical progress report, December 1, 1980-February 28, 1981

    Energy Technology Data Exchange (ETDEWEB)

    Garg, D.; Givens, E.N.; Schweighardt, F.K.; Curtis, C.W.; Guin, J.A.; Huang, W.J.; Shridharani, K.

    1981-04-01

    Results from screening studies showed that the pyrite samples separated from various coal seams had similar catalytic activity. The addition of all the pyrite samples to feed slurry increased conversion of coal and production of oil. A sample of fusinite was also tested for its liquefaction behavior with and without added pyrite. The addition of pyrite increased the conversion of fusinite and production of oil. These results show that pyrite catalyzes the conversion of fusinite and therefore improves overall coal conversion. Conversion of coal and oil production increased by impregnating coal with iron and molybdenum compounds. Coal conversion and oil production also increased with increasing concentration of both iron and molybdenum impregnated on coal. Addition of various transition metal sulfides increased coal conversion and oil production. Dramatic improvements were noted with nickel, vanadium, and tin sulfides. Addition of transition metal naphthenates produced mixed results; some of them improved coal conversion and others had no effect. The effect of metal concentration on coal conversion was also not clear. Deep cleaning of coal did not affect coal conversion, but it significantly reduced oil production. Addition of pyrite separated from coal to deep cleaned coal sample regained the oil production to the original value, i.e., oil produced from liquefaction of raw coal.Coal cleaned by oil agglomeration gave highest coal conversion and oil production. Basic and non-basic nitrogen compounds reduced the naphthalene hydrogenation activity of both Co-Mo-Al and sulfided Fe/sub 2/O/sub 3/. Sulfided Fe/sub 2/O/sub 3/ was inactive for denitrogenation of quinoline, and the reaction product mainly consisted of hydrogenated and hydrocracked quinoline. On the contrary, Co-Mo-Al was active for denitrogenation of quinoline, resulting in lower quinoline poisoning.

  16. Conformationally constrained farnesoid X receptor (FXR) agonists: heteroaryl replacements of the naphthalene.

    Science.gov (United States)

    Bass, Jonathan Y; Caravella, Justin A; Chen, Lihong; Creech, Katrina L; Deaton, David N; Madauss, Kevin P; Marr, Harry B; McFadyen, Robert B; Miller, Aaron B; Mills, Wendy Y; Navas, Frank; Parks, Derek J; Smalley, Terrence L; Spearing, Paul K; Todd, Dan; Williams, Shawn P; Wisely, G Bruce

    2011-02-15

    To improve on the drug properties of GSK8062 1b, a series of heteroaryl bicyclic naphthalene replacements were prepared. The quinoline 1c was an equipotent FXR agonist with improved drug developability parameters relative to 1b. In addition, analog 1c lowered body weight gain and serum glucose in a DIO mouse model of diabetes. Copyright © 2010 Elsevier Ltd. All rights reserved.

  17. Magnetoactive elastomeric composites: Cure, tensile, electrical and ...

    Indian Academy of Sciences (India)

    M/s Godrej Soap Ltd, India. N-(1,3-dimethylbutyl)-N-phenyl-P-phenylenediamene M/s Bayer India. 1,2-Dihydro-2,2,4-trimethyl quinoline. M/s Bayer India. Carbon black, FEF N 550. M/s Philips Carbon Black Ltd, Kochi. Carbon black, HAF N 330. M/s Philips Carbon Black Ltd, Kochi. Lead oxide (red lead). M/s Glaxo, Mumbai.

  18. CuI-catalyzed photochemical or thermal reactions of 3-(2-azidobenzylidene)lactams. Application to the synthesis of fused indoles.

    Science.gov (United States)

    Shi, Zongjun; Ren, Yuwei; Li, Bing; Lu, Shenci; Zhang, Wei

    2010-06-14

    Photochemical or thermal reactions of 3-(2-azidobenzylidene)-lactams afforded fused indoles such as indolo[3,2-c]quinolin-6-ones, pyrido[4,3-b]indol-1-ones and other similar compounds in moderate to high yields via cyclization-ring expansion reactions. The photolytic process was much more facile than the thermal process and could be further improved by addition of CuI.

  19. Secondary promoters in alumina-supported nickel-molybdenum hydroprocessing catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Lewis, J.M.

    1992-01-01

    Two secondary promoters, phosphorus and fluoride, have been investigated for their influences on the physicochemical properties of alumina-supported nickel-molybdenum hydroprocessing catalysts. Model compound reactions and infrared spectroscopy were used to probe the functionalities of the different catalysts, and the catalysts were tested in the hydroprocessing of a low-nitrogen and a high-nitrogen (quinoline-spiked) gas oil feed to assess the utility of the model compound reaction studies. Fluoride-promoted catalysts with high cumene hydrocracking activity and with comparable thiophene hydrodesulphurization (HDS) activity to Ni-Mo/Al[sub 2]O[sub 3] can be prepared by coimpregnation of the F, Ni and Mo additives. Fluoride promotes the hydrogenation (HYD) and HDS activity of Ni-Mo/Al[sub 2]O[sub 3] in the hydroprocessing (HYD) and HDS activity of Ni-Mo/Al[sub 2]O[sub 3] in the hydroprocessing of a low-nitrogen feed. Fluoride promotes the quinoline hydrodenitrogenation (HDN) activity of Ni-Mo/Al[sub 2]O[sub 3] catalysts. Impregnation of phosphorus prior to the metal additives results in catalysts which are more active in HDS. Phosphorus increases indirectly the Broensted acidity of the catalyst by increasing the activity of the MoS[sub 2]-associated acid sites. Phosphorus promotes the HDSW and HYD activities of Ni-Mo/Al[sub 2]O[sub 3] in the hydroprocessing of the low-N feed. A promotional effect of phosphorus is seen in quinoline HDN. P- and F-promoted Ni-MO/Al[sub 2]O[sub 3] catalysts are very active in quinoline HDN and maintain good activity in HDS and HYD of the high-N feed. Thiophene HDS was a good reaction for probing the activity of catalysts in the HDS of sterically-unhindered molecules, but an inaccurate probe for the HDS of hindered compounds.

  20. Distinctions in sensitivity and repair of cells of children with some hereditary diseases

    International Nuclear Information System (INIS)

    Zasukhina, G.D.; Barashnev, Yu.I.; Vasil'eva, I.M.; Sdirkova, N.I.; Semyachkina, A.N.

    1982-01-01

    A study was made of blood cell sensitivity of children, with some hereditary diseases, to ν-radiation and 4-nitro-quinoline-1-oxide. Using the host cell reactivation and chromatographic methods we revealed the increase in the sensitivity to the above mentioned agents and inhibition of the repair function in cells of patients with the following diseases: Marfan's disease, histidinemia, osteogenesis imperfecta, Sylvere-Russelle, Laurence, Franchescetti, and Losch-Nychane syndromes

  1. Comparative activities of ciprofloxacin, ticarcillin, and tobramycin against experimental Pseudomonas aeruginosa pneumonia.

    OpenAIRE

    Schiff, J B; Small, G J; Pennington, J E

    1984-01-01

    The therapeutic efficacy of ciprofloxacin, an investigational quinoline derivative, was compared with those of ticarcillin and tobramycin in guinea pigs with experimental Pseudomonas aeruginosa pneumonia. Guinea pigs challenged with tracheal instillations of 10(8) CFU of P. aeruginosa developed acute pneumonia, for which survival rates were: controls, 0%; ticarcillin treatment, 37%; ciprofloxacin treatment, 57%; and tobramycin treatment, 69%. Intrapulmonary killing of P. aeruginosa was greate...

  2. Lutetium-177 and iodine-131 loaded chelating polymer microparticles intended for radioembolization of liver malignancies

    Czech Academy of Sciences Publication Activity Database

    Hrubý, Martin; Škodová, Michaela; Macková, Hana; Skopal, Jan; Tomeš, Marek; Kropáček, Martin; Zimová, Jana; Kučka, Jan

    2011-01-01

    Roč. 71, č. 12 (2011), s. 1155-1159 ISSN 1381-5148 R&D Projects: GA ČR GPP207/10/P054; GA MŠk 1M0505 Institutional research plan: CEZ:AV0Z40500505; CEZ:AV0Z10480505 Keywords : macroporous chelating beads * radioembolization * quinoline-8-ol Subject RIV: CD - Macromolecular Chemistry Impact factor: 2.479, year: 2011

  3. Carbonic anhydrase inhibitors: Design, synthesis and structural characterization of new heteroaryl-N-carbonylbenzenesulfonamides targeting druggable human carbonic anhydrase isoforms

    Czech Academy of Sciences Publication Activity Database

    Buemi, M. R.; De Luca, L.; Ferro, S.; Bruno, E.; Ceruso, M.; Supuran, C. T.; Pospíšilová, K.; Brynda, Jiří; Řezáčová, Pavlína; Gitto, R.

    2015-01-01

    Roč. 102, SEP 18 (2015), s. 223-232 ISSN 0223-5234 R&D Projects: GA ČR GA15-05677S Grant - others:Fondo di Ateneo per la Ricerca (PRA)(IT) ORME09SPNC Institutional support: RVO:68378050 Keywords : Human carbonic anhydrase * Isoquinoline * Quinoline * X-ray * Molecular docking Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 3.902, year: 2015

  4. Use of promoters to enhance hydrodenitrogenation and hydrodeoxygenation catalysis

    Energy Technology Data Exchange (ETDEWEB)

    Hirschon, A.S.; Ackerman, L.L.; Laine, R.M.; Wilson, R.B. Jr. (SRI International, Menlo Park, CA (USA). Inorganic and Organometallic Chemistry Program)

    1989-10-01

    Results demonstrate that addition of an active transalkylation catalyst such as ruthenium to a CoMo catalyst greatly increased the HDN activity and selectivity to aromatic products, using quinoline as a model compound. Although the non-promoted CoMo was a better HDO catalyst, in the presence of both nitrogen and oxygen containing models, the RuCoMo was the superior HDO in terms of both activity and selectivity. 5 refs., 4 tabs.

  5. Crystal structure of ethyl 2,4-dichloroquinoline-3-carboxylate

    Directory of Open Access Journals (Sweden)

    Alberto Cabrera

    2015-12-01

    Full Text Available In the crystal structure of the title compound, C12H9Cl2NO2, the mean planes through the quinoline and carboxylate groups have r.m.s. deviations of 0.006 and 0.021 Å, respectively, and form a dihedral angle of 87.06 (19°. In the crystal, molecules are linked via very weak C—H...O hydrogen bonds, forming chains, which propagate along the c-axis direction.

  6. Microwave-Assisted Synthesis of Phenothiazine and Qinoline Derivatives

    Directory of Open Access Journals (Sweden)

    Ioan A. Silberg

    2007-02-01

    Full Text Available Application of a dynamic microwave power system in the chemical synthesis ofsome phenothiazine and quinoline derivatives is described. Heterocyclic ring formation,aromatic nucleophilic substitution and heterocyclic aldehydes/ketones condensationreactions were performed on solid support, or under solvent free reaction conditions. Themicrowave-assisted Duff formylation of phenothiazine was achieved. Comparison ofmicrowave-assisted synthesis with the conventional synthetic methods demonstratesadvantages related to shorter reaction times and in some cases better reaction yields.

  7. Distinctions in sensitivity and repair of cells of children with some hereditary diseases

    Energy Technology Data Exchange (ETDEWEB)

    Zasukhina, G.D.; Barashnev, Yu.I.; Vasil' eva, I.M.; Sdirkova, N.I.; Semyachkina, A.N. (AN SSSR, Moscow. Inst. Obshchej Genetiki)

    A study was made of blood cell sensitivity of children with some hereditary diseases, to ..gamma..-radiation and 4-nitro-quinoline-1-oxide. Using the host cell reactivation and chromatographic methods we revealed the increase in the sensitivity to the above mentioned agents and inhibition of the repair function in cells of patients with the following diseases: Marfan's disease, histidinemia, osteogenesis imperfecta, Sylvere-Russelle, Laurence, Franchescetti, and Losch-Nychane syndromes.

  8. Oxidative desulfurization of dibenzothiophene with hydrogen peroxide catalyzed by selenium(IV)-containing peroxotungstate.

    Science.gov (United States)

    Hu, Yiwen; He, Qihui; Zhang, Zheng; Ding, Naidong; Hu, Baixing

    2011-11-28

    With stoichiometric H(2)O(2) as oxidant, dibenzothiophene (DBT) is oxidized to its corresponding sulfone with high efficiency, catalyzed by a sub-valence heteronuclear peroxotungstate, [C(18)H(37)N(CH(3))(3)](4)[H(2)Se(IV)(3)W(6)O(34)], under mild biphase conditions and the catalyst shows remarkable selectivity of catalytic oxidation towards DBT, cinnamyl alcohol and quinoline.

  9. Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics

    DEFF Research Database (Denmark)

    Flagstad, Thomas; Petersen, Mette Terp; Hinnerfeldt, Daniel Michael

    2014-01-01

    A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81-85%. Halogenated quinoline building blocks have found much use in ...... in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds. © Georg Thieme Verlag....

  10. Preliminary assessment of medicinal plants used as antimalarials in the southeastern Venezuelan Amazon

    Directory of Open Access Journals (Sweden)

    Caraballo Alejandro

    2004-01-01

    Full Text Available Eighteen species of medicinal plants used in the treatment of malaria in Bolívar State, Venezuela were recorded and they belonged to Compositae, Meliaceae, Anacardiaceae, Bixaceae, Boraginaceae, Caricaceae, Cucurbitaceae, Euphorbiaceae, Leguminosae, Myrtaceae, Phytolaccaceae, Plantaginaceae, Scrophulariaceae, Solanaceae and Verbenaceae families. Antimalarial plant activities have been linked to a range of compounds including anthroquinones, berberine, flavonoids, limonoids, naphthquinones, sesquiterpenes, quassinoids, indol and quinoline alkaloids.

  11. Prenatal inhibition of the kynurenine pathway leads to structural changes in the hippocampus of adult rat offspring

    OpenAIRE

    Khalil, Omari S; Pisar, Mazura; Forrest, Caroline M; Vincenten, Maria C J; Darlington, L Gail; Stone, Trevor W

    2014-01-01

    Glutamate receptors for N-methyl-d-aspartate (NMDA) are involved in early brain development. The kynurenine pathway of tryptophan metabolism includes the NMDA receptor agonist quinolinic acid and the antagonist kynurenic acid. We now report that prenatal inhibition of the pathway in rats with 3,4-dimethoxy-N-[4-(3-nitrophenyl)thiazol-2-yl]benzenesulphonamide (Ro61-8048) produces marked changes in hippocampal neuron morphology, spine density and the immunocytochemical localisation of developme...

  12. Patofyziologický význam neuroinfekce v neurovývojovém modelu schizofrenie

    Czech Academy of Sciences Publication Activity Database

    Tejkalová, H.; Ruml, T.; Rumlová, M.; Lipovová, P.; Klaschka, Jan; Šťastný, František

    2007-01-01

    Roč. 11, Suppl. 1 (2007), s. 92-93 ISSN 1211-7579. [Celostátní konference biologické psychiatrie /13./. 06.06.2007-09.06.2007, Luhačovice] R&D Projects: GA MZd NR8797 Institutional research plan: CEZ:AV0Z10300504; CEZ:AV0Z50110509 Keywords : schizopfrenia * animal model * gp 120 * HIV-1 CA * quinolinic acid * behaviour

  13. Complexes of vanadium (V) oxotrichloride with amides and tertiary amines

    International Nuclear Information System (INIS)

    Paul, R.C.; Sharma, N.C.; Sahi, Y.P.; Chadha, S.L.; Sharma, A.K.

    1975-01-01

    Vanadium(V) oxotrichloride forms dark brown hygroscopic solid complexes of the composition VOCl 3 .3B and VOCl 3 .2B' where B represents pyridine, α-, β-, and γ-picolines, quinoline, isoquinoline, urea, N-methylformamide or acetanilide while B' represents N, N'-dimethylformamide, N-methylacetamide or dimethylacetamide. These complexes have been characterized on the basis of their analytical and IR spectral data. (author)

  14. N-(4-Chloro-2-nitrophenylmethanesulfonamide

    Directory of Open Access Journals (Sweden)

    Muhammad Nadeem Arshad

    2008-10-01

    Full Text Available The title compound, C7H7ClN2O4S, is of interest as a precursor to biologically active substituted quinolines. Its structure resembles those of the previously reported N-phenylmethane sulfonamide and its 4-nitro, 4-fluoro and 4-bromo derivatives, with slightly different geometric parameters. An intramolecular N—H...O hydrogen bond gives rise to a six-membered ring. Intermolecular C—H...O contacts stabilize the crystal packing.

  15. 8-Bromo-2-methylquinoline

    Directory of Open Access Journals (Sweden)

    Lin-Tao Yang

    2009-07-01

    Full Text Available In the crystal structure of the title compound, C10H8BrN, the dihedral angle between the two six-membered rings of the quinoline system is 0.49 (16°. The molecules are packed in a face-to-face arrangement fashion, with a centroid–centroid distance of 3.76 Å between the benzene and pyridine rings of adjacent molecules. No hydrogen bonding is found in the crystal structure.

  16. Recycling antimalarial leads for cancer: Antiproliferative properties of N-cinnamoyl chloroquine analogues

    OpenAIRE

    Bianca C Perez; Iva Fernandes; Nuno Mateus; Catia Teixeira; Paula Gomes

    2013-01-01

    Cinnamic acids and quinolines are known as useful scaffolds in the discovery of antitumor agents. Therefore, N-cinnamoylated analogues of chloroquine, recently reported as potent dual-action antimalarials, were evaluated against three different cancer cell lines: MKN-28, Caco-2, and MCF-7. All compounds display anti-proliferative activity in the micromolar range against the three cell lines tested, and most of them were more active than their parent drug, chloroquine, against all cell lines t...

  17. 4-N, 4-S & 4-O Chloroquine Analogues: Influence of Side Chain Length and Quinolyl Nitrogen pKa on Activity vs. Chloroquine Resistant Malaria+, #

    OpenAIRE

    Natarajan, Jayakumar K.; Alumasa, John; Yearick, Kimberly; Ekoue-Kovi, Kekeli A.; Casabianca, Leah B.; de Dios, Angel C.; Wolf, Christian; Roepe, Paul D.

    2008-01-01

    Using predictions from heme – quinoline antimalarial complex structures, previous modifications of chloroquine (CQ), and hypotheses for chloroquine resistance (CQR), we synthesize and assay CQ analogues that test structure – function principles. We vary side chain length for both monoethyl and diethyl 4N CQ derivatives. We alter the pKa of the quinolyl N by introducing alkylthio or alkoxy substituents into the 4 position, and vary side chain length for these analogues. We introduce an additio...

  18. Hexacoordinated mixed-ligand complexes of vanadium(IV) and copper(II)

    International Nuclear Information System (INIS)

    Islam, M.S.; Motahera Begum; Roy, H.N.; Haroon, S.A.Q.M.

    1996-01-01

    The literature reports simple complexes of metal ions with Schiff bases derived from amino acids. But their mixed-ligand complexes are very rare. Keeping this fact in mind, some new mixed ligand complexes of V IV and Cu II with tridentate Schiff bases derived from glycine, salicylaldehyde and amino bases, e.g. quinoline (Q), isoquinoline (IQ), 2-picoline (2-pic), 4-picoline (4-pic) and pyridine (Py) were prepared and studied. 6 refs., 1 tab

  19. Immunohistochemical Studies of the Kynurenine Pathway in Morphea

    Directory of Open Access Journals (Sweden)

    Rowland Noakes

    2013-01-01

    Full Text Available Cutaneous sclerosis, resembling that seen in subcutaneous morphea, is a feature of eosinophilic fasciitis and eosinophilia-myalgia syndrome, two conditions in which the kynurenine pathway is known to be activated. To investigate the possibility of activation of the kynurenine pathway in morphea, skin biopsies were taken from involved and non-involved sites in a series of three patients with morphea. Immunohistochemical stains for quinolinic acid and indoleamine 2,3-dioxygenase (IDO were performed.

  20. Immunohistochemical Studies of the Kynurenine Pathway in Morphea

    OpenAIRE

    Noakes, Rowland; Mellick, Nick

    2013-01-01

    Cutaneous sclerosis, resembling that seen in subcutaneous morphea, is a feature of eosinophilic fasciitis and eosinophilia-myalgia syndrome, two conditions in which the kynurenine pathway is known to be activated. To investigate the possibility of activation of the kynurenine pathway in morphea, skin biopsies were taken from involved and non-involved sites in a series of three patients with morphea. Immunohistochemical stains for quinolinic acid and indoleamine 2,3-dioxygenase (IDO) were perf...

  1. Recognition of thymine in DNA bulges by a Zn(II) macrocyclic complex.

    Science.gov (United States)

    del Mundo, Imee Marie A; Fountain, Matthew A; Morrow, Janet R

    2011-08-14

    A Zn(II) macrocyclic complex with appended quinoline is a bifunctional recognition agent that uses both the Zn(II) center and the pendent aromatic group to bind to thymine in bulges with good selectivity over DNA containing G, C or A bulges. Spectroscopic studies show that the stem containing the bulge stays largely intact in a DNA hairpin with the Zn(II) complex bound to the thymine bulge. This journal is © The Royal Society of Chemistry 2011

  2. Mitochondrial oxodicarboxylate carrier deficiency is associated with mitochondrial DNA depletion and spinal muscular atrophy-like disease.

    Science.gov (United States)

    Boczonadi, Veronika; King, Martin S; Smith, Anthony C; Olahova, Monika; Bansagi, Boglarka; Roos, Andreas; Eyassu, Filmon; Borchers, Christoph; Ramesh, Venkateswaran; Lochmüller, Hanns; Polvikoski, Tuomo; Whittaker, Roger G; Pyle, Angela; Griffin, Helen; Taylor, Robert W; Chinnery, Patrick F; Robinson, Alan J; Kunji, Edmund R S; Horvath, Rita

    2018-03-08

    PurposeTo understand the role of the mitochondrial oxodicarboxylate carrier (SLC25A21) in the development of spinal muscular atrophy-like disease.MethodsWe identified a novel pathogenic variant in a patient by whole-exome sequencing. The pathogenicity of the mutation was studied by transport assays, computer modeling, followed by targeted metabolic testing and in vitro studies in human fibroblasts and neurons.ResultsThe patient carries a homozygous pathogenic variant c.695A>G; p.(Lys232Arg) in the SLC25A21 gene, encoding the mitochondrial oxodicarboxylate carrier, and developed spinal muscular atrophy and mitochondrial myopathy. Transport assays show that the mutation renders SLC25A21 dysfunctional and 2-oxoadipate cannot be imported into the mitochondrial matrix. Computer models of central metabolism predicted that impaired transport of oxodicarboxylate disrupts the pathways of lysine and tryptophan degradation, and causes accumulation of 2-oxoadipate, pipecolic acid, and quinolinic acid, which was confirmed in the patient's urine by targeted metabolomics. Exposure to 2-oxoadipate and quinolinic acid decreased the level of mitochondrial complexes in neuronal cells (SH-SY5Y) and induced apoptosis.ConclusionMitochondrial oxodicarboxylate carrier deficiency leads to mitochondrial dysfunction and the accumulation of oxoadipate and quinolinic acid, which in turn cause toxicity in spinal motor neurons leading to spinal muscular atrophy-like disease.GENETICS in MEDICINE advance online publication, 8 March 2018; doi:10.1038/gim.2017.251.

  3. Synthesis, characterization of some novel 1,3,4-oxadiazole compounds containing 8-hydroxy quinolone moiety as potential antibacterial and anticancer agents

    Directory of Open Access Journals (Sweden)

    Vinayak Mahadev Adimule

    2014-12-01

    Full Text Available In the present work a series of novel derivatives of 8-hydroxy quinolone substituted 1,3,4-oxadiazole compounds were synthesized by convergent synthetic method and studied for their antibacterial and anticancer properties. The cell lines used for cytotoxic evaluation were HeLa, Caco-2 and MCF7. The synthetic chemistry involved conversion of various substituted aromatic acids into ethyl ester 2a-e. The ethyl ester was converted into corresponding carbohydrazide 3a-e. Carbohydrazides are reacted with chloroacetic acid, phosphorous oxytrichloride and irradiated with microwave in order to obtain the various key intermediates 2-(chloromethyl-5-(substituted phenyl-1,3,4-oxadiazole 4a-e. The 2-(chloromethyl-5-(substituted phenyl-1,3,4-oxadiazole was reacted with 8-hydroxy quinolone in presence of sodium hydride and obtained a series of 8-hydroxy quinoline substituted 1,3,4-oxadiazoles 5a-e. Among the synthesised compounds, the cytotoxicity of the compound 5b i.e. 8-{[5-(2,4-dichlorophenyl-1,3,4-oxadiazol-2-yl]methoxy}quinoline against MCF7 with IC50 of 5.3µM and the compound 5e i.e. 8-{[5-(4-bromophenyl-1,3,4-oxadiazol-2-yl]methoxy}quinoline showed MIC of < 6.25µg/mL against Staphylococcus aureus which is comparable with the known standards. The standards used for cytotoxic evaluation was 5-fluorouracil and for antibacterial was nitrofurazone

  4. Formation of nitrogen compounds from nitrogen-containing rings during oxidative regeneration of spent hydroprocessing catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Furimsky, E.; Nielsen, M.; Jurasek, P. [CANMET, Ottawa, ON (Canada). Energy Research Laboratories

    1995-05-01

    Commercial CoMo and NiMo catalysts in an oxidic and sulfided form and a {gamma}-alumina were deposited with pyrrole, pyridine, and quinoline. The deposited catalysts and two spent hydroprocessing catalysts were pyrolyzed and oxidized under conditions typical of regeneration of hydroprocessing catalysts. The formation of NH{sub 3} and HCN, as well as selected cases of N{sub 2}O and NO, was monitored during the experiments. NH{sub 3} and HCN were formed during pyrolysis of pyrrole-deposited catalysts whereas only NH{sub 3} was formed during that of pyridine-and quinoline-deposited catalysts. For all deposited catalysts, both NH{sub 3} and HCN were formed during temperature programmed oxidation in 2% O{sub 2}. For spent catalysts, a small amount of N{sub 2}O was formed in 2 and 4% O{sub 2}. For pyrrole-deposited catalysts, large yields of N{sub 2}O were formed in 4% O{sub 2}. Under the same conditions, N{sub 2}O yields for pyridine- and quinoline-deposited catalysts were very small. 13 refs., 12 figs., 6 tabs.

  5. Analysis of solvent extracts from coal liquefaction in a flowing solvent reactor

    Energy Technology Data Exchange (ETDEWEB)

    Li, Wen-Ying; Feng, Jie; Xie, Ke-Chang [Key Laboratory of Coal Science and Technology, Taiyuan University of Technology, Ministry of Education and Shanxi Province, No. 79 Yingze West Street, Taiyuan 030024 (China); Kandiyoti, R. [Department of Chemical Engineering and Chemical Technology, Imperial College, University of London, London SW7 2BY (United Kingdom)

    2004-10-15

    Point of Ayr coal has been extracted using three solvents, tetralin, quinoline and 1-methyl-2-pyrrolidinone (NMP) at two temperatures 350 and 450 C, corresponding approximately to before and after the onset of massive covalent bond scission by pyrolysis. The three solvents differ in solvent power and the ability to donate hydrogen atoms to stabilise free radicals produced by pyrolysis of the coal. The extracts were prepared in a flowing solvent reactor to minimise secondary thermal degradation of the primary extracts. Analysis of the pentane-insoluble fractions of the extracts was achieved by size exclusion chromatography, UV-fluorescence spectroscopy in NMP solvent and probe mass. With increasing extraction temperature, the ratio of the amount having big molecular weight to that having small molecular weight in tetralin extracts was increased; the tetralin extract yield increased from 12.8% to 75.9%; in quinoline, increasing extraction temperature did not have an effect on the molecular weight of products but there was a big increase in extract yield. The extracts in NMP showed the enhanced solvent extraction power at both temperatures, with a shift in the ratio of larger molecules to smaller molecules with increasing extraction temperature and with the highest conversion of Point of Ayr coal among these three solvents at both temperatures. Solvent adducts were detected in the tetralin and quinoline extracts by probe mass spectrometry; solvent products were formed from NMP at both temperatures.

  6. Biodegradation of Various Aromatic Compounds by Enriched Bacterial Cultures: Part B--Nitrogen-, Sulfur-, and Oxygen-Containing Heterocyclic Aromatic Compounds.

    Science.gov (United States)

    Oberoi, Akashdeep Singh; Philip, Ligy; Bhallamudi, S Murty

    2015-07-01

    Present study focused on the biodegradation of various heterocyclic nitrogen, sulfur, and oxygen (NSO) compounds using naphthalene-enriched culture. Target compounds in the study were pyridine, quinoline, benzothiophene, and benzofuran. Screening studies were carried out using different microbial consortia enriched with specific polycyclic aromatic hydrocarbon (PAH) and NSO compounds. Among different microbial consortia, naphthalene-enriched culture was the most efficient consortium based on high substrate degradation rate. Substrate degradation rate with naphthalene-enriched culture followed the order pyridine > quinoline > benzofuran > benzothiophene. Benzothiophene and benzofuran were found to be highly recalcitrant pollutants. Benzothiophene could not be biodegraded when concentration was above 50 mg/l. It was observed that 2-(1H)-quinolinone, benzothiophene-2-one, and benzofuran-2,3-dione were formed as metabolic intermediates during biodegradation of quinoline, benzothiophene, and benzofuran, respectively. Quinoline-N and pyridine-N were transformed into free ammonium ions during the biodegradation process. Biodegradation pathways for various NSO compounds are proposed. Monod inhibition model was able to simulate single substrate biodegradation kinetics satisfactorily. Benzothiophene and benzofuran biodegradation kinetics, in presence of acetone, was simulated using a generalized multi-substrate model.

  7. M. tuberculosis induces potent activation of IDO-1, but this is not essential for the immunological control of infection.

    Directory of Open Access Journals (Sweden)

    Antje Blumenthal

    Full Text Available Indoleamine 2,3-dioxygenesae-1 (IDO-1 catalyses the initial, rate-limiting step in tryptophan metabolism, thereby regulating tryptophan availability and the formation of downstream metabolites, including picolinic and quinolinic acid. We found that Mycobacterium tuberculosis infection induced marked upregulation of IDO-1 expression in both human and murine macrophages in vitro and in the lungs of mice following aerosol challenge with M. tuberculosis. The absence of IDO-1 in dendritic cells enhanced the activation of mycobacteria-specific T cells in vitro. Interestingly, IDO-1-deficiency during M. tuberculosis infection in mice was not associated with altered mycobacteria-specific T cell responses in vivo. The bacterial burden of infected organs, pulmonary inflammatory responses, and survival were also comparable in M. tuberculosis-infected IDO-1 deficient and wild type animals. Tryptophan is metabolised into either picolinic acid or quinolinic acid, but only picolinic acid inhibited the growth of M. tuberculosis in vitro. By contrast macrophages infected with pathogenic mycobacteria, produced quinolinic, rather than picolinic acid, which did not reduce M. tuberculosis growth in vitro. Therefore, although M. tuberculosis induces robust expression of IDO-1 and activation of tryptophan metabolism, IDO-1-deficiency fails to impact on the immune control and the outcome of the infection in the mouse model of tuberculosis.

  8. Spectral and time-resolved properties of photoinduced hydroxyquinolines doped thin polymer films

    Science.gov (United States)

    Mehata, Mohan Singh

    2018-01-01

    Quinoline and its derivatives have a wide range of biological and pharmacological activities. Quinoline ring is used to design functional materials (quinoline derivatives) for OLEDs and field-induce electrooptics. It possesses antibacterial, antifungal, antimalarial, cardiotonic, anthelmintic, anti-inflammatory, anticonvulsant and analgesic activity. Here, we have examined photoexcitation dynamics of 6-hydroxyquinoline (6-HQ) doped in polymer films of polymethyl methacrylate (PMMA), polyvinyl alcohol (PVA) and cellulose acetate (CA) at atmospheric conditions. The absorption maximum of 6-HQ in polymer films was observed at 333 ± 1 nm, whereas fluorescence (FL) maximum fell in the range of 365-371 nm. In PVA film, in addition to the typical FL, a band maximum at 432 nm appeared as a result of an excited-state intermolecular proton transfer (ESIPT) reaction facilitated in the hydrogen-bonded complex formed in the ground state between 6-HQ:PVA. The multi-exponential decay behavior of 6-HQ in all the three polymer films indicates a nanoscale heterogeneity of the polymer environments.

  9. Neuroprotective actions of the synthetic estrogen 17alpha-ethynylestradiol in the hippocampus.

    Science.gov (United States)

    Picazo, Ofir; Becerril-Montes, Adriana; Huidobro-Perez, Delia; Garcia-Segura, Luis M

    2010-07-01

    17alpha-ethynylestradiol (EE2), a major constituent of many oral contraceptives, is similar in structure to 17beta-estradiol, which has neuroprotective properties in several animal models. This study explored the potential neuroprotective actions of EE2 against kainic and quinolinic acid toxicity in the hippocampus of adult ovariectomized Wistar rats. A decrease in the number of Nissl-stained neurons and the induction of vimentin immunoreactivity in astrocytes was observed in the hilus of the dentate gyrus of the hippocampus after the administration of either kainic acid or quinolinic acid. EE2 prevented the neuronal loss and the induction of vimentin immunoreactivity induced by kainic acid at low (1 microg/rat) and high (10-100 microg/rat) doses and exerted a protection against quinolinic acid toxicity at a low dose (1 microg/rat) only. These observations demonstrate that EE2 exerts neuroprotective actions against excitotoxic insults. This finding is relevant for the design of new neuroprotective estrogenic compounds.

  10. Biologically active perspective synthesis of heteroannulated 8-nitroquinolines with green chemistry approach.

    Science.gov (United States)

    Arasakumar, Thangaraj; Mathusalini, Sadasivam; Gopalan, Subashini; Shyamsivappan, Selvaraj; Ata, Athar; Mohan, Palathurai Subramaniam

    2017-04-01

    A new class of pyrazolo[4,3-c]quinoline (5a-i, 7a-b) and pyrano[3,2-c]quinoline (9a-i) derivatives were designed and synthesized in moderate to good yields by microwave conditions. To enhance the yield of pyrano[3,2-c]quinoline derivatives, multicomponent one-pot synthesis has been developed. The synthesized compounds were identified by spectral and elemental analyses. Compounds 9a and 9i showed good antibacterial activity against Gram-positive and Gram-negative bacterial strains. All of the new compounds exhibited weak to moderate antioxidant activity, compound 9d exerted significant antioxidant power. The cytotoxicity of these compounds were also evaluated against MCF-7 (breast) and A549 (Lung) cancer cell lines. Most of the compounds displayed moderate to good cytotoxic activity against these cell lines. Compound 9i was found to be significantly active in this assay and also induced cell death by apoptosis. Molecular docking studies were carried out using EGFR inhibitor in order to determine the molecular interactions. Copyright © 2017 Elsevier Ltd. All rights reserved.

  11. Structural-based differences in ecotoxicity of benzoquinoline isomers to the zebra mussel (Dreissena polymorpha)

    Energy Technology Data Exchange (ETDEWEB)

    Kraak, M.H.S.; Wijnands, P.; Govers, H.A.J.; Admiraal, W.; Voogt, P. de [Univ. of Amsterdam (Netherlands)

    1997-10-01

    Effects of four benzoquinoline isomers on the filtration rate of the zebra mussel (Dreissena polymorpha) were analyzed, to study the effect of minor differences in chemical structure on adverse biological effects. Filtration rates were measured after 48 h of exposure to different concentrations of acridine, phenanthridine, benzo[f]quinoline, and benzo[h]quinoline in the water. The 50% effective concentration (EC50) values for filtration rate of the four isomers differed significantly. Effects increased in the order benzo[f], -[h], -[b], and -[c]quinoline, and the difference between the most toxic isomer and the least toxic isomer amounted to a factor of 30. Attempts were made to relate these differences in toxicity to the structure of the isomers. Size- or topology-related molecular descriptors provided insufficient resolution to distinguish between the benzoquinoline isomers, and none of the electronic descriptors separately provided a significant correlation with the observed effects. In an alternative approach, molecular shape, accessibility, and minimum agent-macromolecule distance were used to represent repulsive and attractive forces between the benzoquinoline isomers and biological membranes. This approach could tentatively explain the observed effects and is supported by a high correlation between the EC50 data and the reversed-phase C18-HPLC behavior of the benzoquinolines (k{sub 0}), which is likely to be governed by similar processes.

  12. Metal coordination by sterically hindered heterocyclic ligands, including 2-vinylpyridine, assessed by investigation of cobaloximes.

    Science.gov (United States)

    Siega, Patrizia; Randaccio, Lucio; Marzilli, Patricia A; Marzilli, Luigi G

    2006-04-17

    Structural and 1H NMR data have been obtained for cobaloximes with the bulkiest substituted pyridines reported so far. We have isolated in noncoordinating solvents the complexes CH3Co(DH)2L (methylcobaloxime, where DH = the monoanion of dimethylglyoxime) with L = sterically hindered N-donor ligands: quinoline, 4-CH3quinoline, 2,4-(CH3)2pyridine, and 2-R-pyridine (R = CH3, OCH3, CH2CH3, CH=CH2). We have found that the Co-N(ax) bond is very long in the structurally characterized complexes. In particular, CH3Co(DH)2(4-CH3quinoline) has a longer Co-N(ax) bond (2.193(3) A) than any reported for methylcobaloximes. The main cause of the long bonds is unambiguously identified as the steric bulk of L by the fairly linear relationship found for Co-N(ax) distance vs CCA (calculated cone angle, CCA, a computed measure of bulk) over an extensive series of methylcobaloximes. The linear relationship improves if L basicity (quantified by pKa) is taken into account. In anhydrous CDCl3 at 25 degrees C, all complexes except the 2-aminopyridine adduct exhibit 1H NMR spectra consistent with partial dissociation of L to form the methylcobaloxime dimer. 1H NMR experiments at -20 degrees C allowed us to assess qualitatively the relative binding ability of L as follows: 2,4-(CH3)2pyridine > 4-CH3quinoline approximately = quinoline approximately = 2-CH3pyridine > 2-CH3Opyridine > 2-CH3CH2pyridine > 2-CH2=CHpyridine. The broadness of the 1H NMR signals at 25 degrees C suggests a similar order for the ligand exchange rate. The lack of dissociation by 2-aminopyridine is attributed to an intramolecular hydrogen bond between the NH2 group and an oxime O atom. The weaker than expected binding of 2-vinylpyridine relative to the Co-N(ax) bond length is attributed to rotation of the 2-vinyl group required for this bulky ligand to bind to the metal center, a conclusion supported by pronounced changes in 2-vinylpyridine signals upon coordination.

  13. Molecular modeling of the voltammetric oxidation at a glassy carbon electrode of the antimalarial drug primaquine and its prodrugs succinylprimaquine and maleylprimaquine

    Energy Technology Data Exchange (ETDEWEB)

    La-Scalea, Mauro A [Lapen, Laboratorio de Planejamento e Sintese de Quimioterapicos Potencialmente Ativos Contra Endemias Tropicais, Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, 580 Bl. 13 sup., 05508-900 Sao Paulo (Brazil); Menezes, Carla M.S. [Lapen, Laboratorio de Planejamento e Sintese de Quimioterapicos Potencialmente Ativos Contra Endemias Tropicais, Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, 580 Bl. 13 sup., 05508-900 Sao Paulo (Brazil); Matsutami, Guilherme C [Lapen, Laboratorio de Planejamento e Sintese de Quimioterapicos Potencialmente Ativos Contra Endemias Tropicais, Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, 580 Bl. 13 sup., 05508-900 Sao Paulo (Brazil); Polli, Michelle C [Lapen, Laboratorio de Planejamento e Sintese de Quimioterapicos Potencialmente Ativos Contra Endemias Tropicais, Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, 580 Bl. 13 sup., 05508-900 Sao Paulo (Brazil); Serrano, Silvia H.P. [Departamento de Quimica Fundamental, Instituto de Quimica, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, 748 Bl. 2 sup., 05508-90 Sao Paulo (Brazil); Ferreira, Elizabeth I [Lapen, Laboratorio de Planejamento e Sintese de Quimioterapicos Potencialmente Ativos Contra Endemias Tropicais, Departamento de Farmacia, Faculdade de Ciencias Farmaceuticas, Universidade de Sao Paulo, Av. Prof. Lineu Prestes, 580 Bl. 13 sup., 05508-900 Sao Paulo (Brazil)

    2006-07-15

    The 8-aminoquinoline primaquine (PQ) is the only antimalarial drug used as tissue schizonticide and relapsing malaria. Antichagasic activity was also reported. Nevertheless, as it also shows serious side effects, prodrugs such as succinyl and maleyl derivatives have been proposed to decrease its toxicity. Although PQ mechanism of action has not been completely elucidated, the promotion of oxidative stress is an advanced hypothesis that could explain its activity in both plasmodia and trypanosome parasites. The oxidation of PQ and its prodrugs, maleylprimaquine (MPQ) and succinylprimaquine (SPQ), was studied by cyclic voltammetry using glassy carbon electrode. All compounds were oxidized in aqueous medium, with the charge transfer process being pH-dependent in acidic medium and pH-independent in a weak basic medium, being the neutral form more easily oxidized. This indicated that the protonation of the nitrogen atoms displays a determinant role in the voltammetric oxidation, being both prodrugs more easily oxidized than PQ protonated forms, in the order: SPQ < MPQ < PQ. For a better understanding of this behavior, a molecular modeling study was performed using the AM1 semi-empirical method from Spartan 04 for Linux (v.119, Wavefunction Inc.). The medium pH showed to be fundamental not only to the electronic density of the quinoline ring but also to the rearrangement of the nitrogen side chain. The electronic density of primaquine non-protonated quinoline ring is higher than that in its protonated and diprotonated species. Also, the use of prodrugs and the degree of saturation of the carriers (maleic or succinic acid) interfere with this feature. SPQ and MPQ have a slight increase in the quinoline electronic density in comparison to PQ. Nevertheless, the carrier in the side chain of SPQ is closer to the quinoline ring than it is in MPQ, which accounts for the higher electronic density in the former. The most significant effect occurs in the correspondent protonated

  14. Molecular modeling of the voltammetric oxidation at a glassy carbon electrode of the antimalarial drug primaquine and its prodrugs succinylprimaquine and maleylprimaquine

    International Nuclear Information System (INIS)

    La-Scalea, Mauro A.; Menezes, Carla M.S.; Matsutami, Guilherme C.; Polli, Michelle C.; Serrano, Silvia H.P.; Ferreira, Elizabeth I.

    2006-01-01

    The 8-aminoquinoline primaquine (PQ) is the only antimalarial drug used as tissue schizonticide and relapsing malaria. Antichagasic activity was also reported. Nevertheless, as it also shows serious side effects, prodrugs such as succinyl and maleyl derivatives have been proposed to decrease its toxicity. Although PQ mechanism of action has not been completely elucidated, the promotion of oxidative stress is an advanced hypothesis that could explain its activity in both plasmodia and trypanosome parasites. The oxidation of PQ and its prodrugs, maleylprimaquine (MPQ) and succinylprimaquine (SPQ), was studied by cyclic voltammetry using glassy carbon electrode. All compounds were oxidized in aqueous medium, with the charge transfer process being pH-dependent in acidic medium and pH-independent in a weak basic medium, being the neutral form more easily oxidized. This indicated that the protonation of the nitrogen atoms displays a determinant role in the voltammetric oxidation, being both prodrugs more easily oxidized than PQ protonated forms, in the order: SPQ < MPQ < PQ. For a better understanding of this behavior, a molecular modeling study was performed using the AM1 semi-empirical method from Spartan 04 for Linux (v.119, Wavefunction Inc.). The medium pH showed to be fundamental not only to the electronic density of the quinoline ring but also to the rearrangement of the nitrogen side chain. The electronic density of primaquine non-protonated quinoline ring is higher than that in its protonated and diprotonated species. Also, the use of prodrugs and the degree of saturation of the carriers (maleic or succinic acid) interfere with this feature. SPQ and MPQ have a slight increase in the quinoline electronic density in comparison to PQ. Nevertheless, the carrier in the side chain of SPQ is closer to the quinoline ring than it is in MPQ, which accounts for the higher electronic density in the former. The most significant effect occurs in the correspondent protonated

  15. Formation of methemoglobin and metmyoglobin using 8-aminoquinoline derivatives or sodium nitrite and subsequent reaction with cyanide.

    Science.gov (United States)

    Steinhaus, R K; Baskin, S I; Clark, J H; Kirby, S D

    1990-10-01

    The kinetics of the oxidation of hemoglobin (Hb) and myoglobin (Mb) by sodium nitrite, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-quinoline diphosphate (primaquine), 6-methoxy-8-(6-diethylaminohexylamino)-4-methyl-quinoline dihydrochloride (WR6026) and 8-[(4-amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl- 5-[(3-trifluoromethyl)phenoxy]quinoline succinate (WR238,605) were studied at pH values ranging from 7.4 to 7.6 and at 37 +/- 1 degrees C. The reaction between Hb and primaquine, WR6026 and WR238,605 resulted in precipitation, as did the reaction between Mb and WR238,605. The reaction between nitrite ion (NO2-) and Hb showed a lag period followed by an autocatalytic phase. The data in this study are consistent with and substantiate the proposed mechanism for the Hb-NO2- oxidation reaction. The reaction between Mb and NO2- at higher NO2- concentrations also showed a lag period followed by an autocatalytic period, while at lower NO2- concentrations no lag period was seen. The data suggest a shift in rate constant at these lower NO2- concentrations. The reaction between Mb and both WR6026 and primaquine followed a two-term rate law with oxidant-dependent and -independent terms. Concentration-effect curve data, along with these results, suggest the presence of a catalytic pathway. The rates of formation of cyanomethemoglobin and cyanometmyoglobin complexes from cyanide ion and methemoglobin (MHb) and metmyoglobin (MMb), respectively, were followed in the presence of the heme oxidants. The rate constants were all within a narrow range and suggest that complexation of cyanide by MHb and MMb is not affected by the presence of oxidants.

  16. Investigation of the effect of cucurbit[7]uril complexation on the photophysical and acid-base properties of the antimalarial drug quinine.

    Science.gov (United States)

    Mallick, Suman; Pal, Kaushik; Chandra, Falguni; Koner, Apurba L

    2016-11-09

    Host-guest complexation of mono and dicationic quinine with cucurbit[7]uril (CB7), a water-soluble macrocyclic host molecule, has been investigated. Job's plot, time-resolved anisotropy as well as concentration dependent NMR titration confirm the binding of two CB7 macrocycles with one quinine molecule. The binding affinity of dicationic quinine with CB7 is one order of magnitude higher than the binding constant of mono-cationic quinine. Such preferential binding results in one unit pK a shift in the ground-state of the quinoline ring. However, using fluorescence spectroscopy we have obtained two acid-dissociation constants, one for quinoline ring nitrogen and the other for the nitrogen of the quinuclidine moiety. In the excited state, CB7 complexation causes one unit pK a shift for the quinoline ring and 1.9 unit shift for the quinuclidine moiety. Interestingly, a large enhancement of fluorescence lifetime and anisotropy of quinine at pH 2.7 and pH 9.0 upon CB7 complexation was observed due to the restriction of conformational flexibility. Moreover, at pH 3.0, a large fluorescence enhancement of quinine due to CB7 complexation was observed and it was quite significant as compared to that of quinine in 0.1 (M) HCl without CB7. We believe that this study of quinine complexation with CB7 will reduce phototoxicity, increase bioavailability and offer an alternative standard for quantum yield measurements in an amiable condition.

  17. Enantiomeric separation of some demethylated analogues of clofibric acid by capillary zone electrophoresis and nano-liquid chromatography.

    Science.gov (United States)

    Fantacuzzi, Marialuigia; Bettoni, Giancarlo; D'Orazio, Giovanni; Fanali, Salvatore

    2006-03-01

    The enantiomeric separation of some demethylated analogues of clofibric acid, namely 2-(6-chloro-benzothiazol-2-ylsulfanyl)-, 2-(6-methoxy-benzothiazol-2-ylsulfanyl)-, 2-(quinolin-2-yloxy)-, 2-(6-chloro-quinolin-2-yloxy)-, 2-(7-chloro-quinolin-4-yloxy)-propionic acid (compounds A-E, respectively), has been studied by CZE and nano-LC using for the first technique two beta-CD derivatives and vancomycin added to the BGE and vancomycin-modified silica particles for the second one, with the aim to find the optimum experimental conditions for the baseline resolution. The type and the concentration of the chiral selector added to the BGE, the buffer pH, the type of organic modifier and its concentration, the capillary temperature and the applied voltage played a very important role in the enantioresolution of the analysed compounds. The use of 6-monodeoxy-6-monoamino-beta-CD allowed to achieve baseline resolution of four of five clofibric acid derivatives in less than 10 min while heptakis-(2,3,6-tri-O-methyl)-beta-CD partially resolved the same compounds in their enantiomers. Employing vancomycin as the chiral selector in CZE, the counter-current partial filling method was chosen achieving baseline resolution of four analytes. All the studied compounds were enantioresolved employing a capillary column packed with vancomycin stationary phase by nano-LC, and the resolution was strongly influenced by the concentration of the organic modifier and by the pH of the mobile phase. The best results were achieved at pH 4.5 in presence of 60% of methanol (MeOH). However, longer analysis times were observed in the experiments carried out by nano-LC.

  18. Biodegradation of NSO-compounds under different redox-conditions

    DEFF Research Database (Denmark)

    Dyreborg, S.; Arvin, E.; Broholm, K.

    1997-01-01

    Laboratory experiments were carried out to investigate the potential of groundwater microorganisms to degrade selected heterocyclic aromatic compounds containing nitrogen, sulphur, or oxygen (NSO-compounds) under four redox-conditions over a period of 846 days. Eight compounds (pyrrole, 1...... anaerobic conditions, even though the microorganisms present in the anaerobic microcosms were active throughout the incubation period. A high variability in the lag period among the NSO-compounds was observed under aerobic conditions. While quinoline, indole, and carbazole were degraded with a lag period...

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

    Science.gov (United States)

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

    2013-11-01

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

  20. From ketenimines to ketenes to quinolones: two consecutive pseudopericyclic events.

    Science.gov (United States)

    Alajarín, Mateo; Ortín, María-Mar; Sánchez-Andrada, Pilar; Vidal, Angel; Bautista, Delia

    2005-11-10

    [reaction: see text] N-[2-(Alkyl- or arylthio)carbonyl]phenyl ketenimines undergo cyclization under mild thermal conditions to afford 2-alkyl(aryl)thio-3H-quinolin-4-ones by means of the 1,5-migration of the alkyl(aryl)thio group from the carbonyl carbon to the central carbon atom of the ketenimine fragment followed by the 6pi-electrocyclization of the resulting vinyliminoketene. These 1,5-migration and electrocyclization processes occur via transition states whose pseudopericyclic characteristics have been established on the basis of their magnetic properties, geometries, and NBO analyses.

  1. Crystal structure of 1-[(6-chloropyridin-3-ylsulfonyl]-1,2,3,4-tetrahydroquinoline

    Directory of Open Access Journals (Sweden)

    S. Jeyaseelan

    2015-06-01

    Full Text Available The tetrahydropyridine ring of the quinoline system in the title compound, C14H13ClN2O2S, adopts a half-chair conformation with the bond-angle sum at the N atom being 350.0°. The dihedral angle between the least-squares planes of the two aromatic rings is 50.13 (11°. In the crystal, inversion dimers linked by pairs of C—H...O hydrogen bonds generate R22(10 loops. Additional intermolecular C—H...O hydrogen bonds generate C(7 chains along [100].

  2. Glia: the not so innocent bystanders.

    Science.gov (United States)

    Chao, C C; Hu, S; Peterson, P K

    1996-08-01

    Activated glial cells (microglia and astrocytes) are a hallmark of a variety of neurodegenerative diseases. Recent in vitro studies have suggested that mediators derived from reactive glial cells (eg, cytokines, reactive oxygen intermediates, nitric oxide, glutamate or quinolinic acids, and neurotoxins) contribute to neuronal injury. Several of these mediators have been implicated in the neuropathogenesis of HIV-1. Although the precise role of glial cell-mediated neurotoxicity in viral infections of the central nervous system has not been established, it is hoped that research in this field will yield new therapies for these infections as well as for immune-mediated neurodegenerative diseases.

  3. Application of adsorption analysis to the investigation of phenols and bases in low-temperature tar

    Energy Technology Data Exchange (ETDEWEB)

    Kalechts, I V; Salimgareeva, F G; Tumbusova, Z P

    1955-01-01

    The use of chromatographic adsorption for the separation of mono- and bicyclic phenols and bases from coal tar and from its hydrogenation products were studied with o-cresol, ..beta..-naphthol, pyridine, and quinoline. Experimental data show that Al/sub 2/O/sub 3/ was preferable for separating phenols, but that silica gel was better for the bases. The best order of use of the developers was as follows: C/sub 6/H/sub 6/, Et/sub 2/O, EtOH. The data show that the destructive hydrogenation process degrades the higher series phenols to lower ones.

  4. Components of Stem Barks of Winchia calophylla A. DC. and Their Bronchodilator Activities

    Institute of Scientific and Technical Information of China (English)

    Wei-Ming ZHU; Hong-Ping HE; Li-Ming FAN; Yue-Mao SHEN; Jun ZHOU; Xiao-Jiang HAO

    2005-01-01

    The Dai medicinal plant Winchia calophylla A. DC. (Apocynaceae) has efficacy as an anticough and anti-asthmatic medication. In order to investigate its relative bioactive components, we studied the chemical constituents of this plant. Using repeated column chromatography, 28 compounds, including loganin, six phenolic compounds, 17 indole alkaloids, three pyridine alkaloids, and a quinoline alkaloid,were isolated from the stem barks of W. calophylla. Loganin, paeonol, N (4)-methyl akuammicine, and cantleyine exhibited a moderate relaxation effect on isolated smooth muscles of guinea-pig tracheal spirals and lung strips and may be the bioactive components responsible for the bronchodilation produced by W. calophylla.

  5. Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or Modifications via Silver Tetrafluoroborate Mediation

    Directory of Open Access Journals (Sweden)

    Matthew C. Achilonu

    2015-01-01

    Full Text Available This review provides an overview of the biological activities, natural occurrences, and the silver tetrafluoroborate- (AgBF4- mediated synthesis of proanthocyanidins, glycosides, N-heterocyclic alkaloid analogues (of pyrrole, morphine, quinoline, isoquinoline, and indole, furan analogues, and halocompounds. AgBF4 has been reviewed as an effective reaction promoter, used extensively in the synthesis of relevant biologically active compounds via carbon-carbon and carbon-heteroatom bonds formation. The literatures from 1979 to April 2014 were reviewed.

  6. Radical C-H functionalization to construct heterocyclic compounds.

    Science.gov (United States)

    Yu, Jin-Tao; Pan, Changduo

    2016-02-07

    Heterocyclic compounds are widely present in natural products, pharmaceuticals and bioactive molecules. Thus, organic and pharmaceutical chemists have been making extensive efforts to construct those heterocyclic frameworks through developing versatile and efficient synthetic strategies. The direct C-H functionalization via the radical pathway has emerged as a promising and dramatic approach towards heterocycles with high atom- and step-economy. Heterocyclic compounds such as coumarins, furans, benzofurans, xanthones, benzothiazoles, indoles, indolines, oxindoles, quinolines, isoquinolines, quinoxaline, and phenanthridines have been successfully synthesized by C-H functionalization through the radical pathway. In this review, recent advances on radical C-H functionalization to construct heterocyclic compounds are highlighted with discussions.

  7. The use of phosphite-type ligands in the Ir-catalyzed asymmetric hydrogenation of heterocyclic compounds.

    Science.gov (United States)

    Lyubimov, Sergey E; Ozolin, Dmitry V; Ivanov, Pavel Yu; Melman, Artem; Velezheva, Valeriya S; Davankov, Vadim A

    2014-01-01

    A series of chiral phosphite-type ligands was tested in asymmetric Ir-catalyzed hydrogenation of quinolines and 2,4,5,6-tetrahydro-1H-pyrazino(3,2,1-j,k)carbazole. Hydrogenation of quinaldine hydrochloride provided superior enantioselectivity up to 65% ee compared to quinaldine free base. The ligands were tested for the first time in the asymmetric Ir-Ircatalyzed hydrogenation of 2,4,5,6-tetrahydro-1H-pyrazino(3,2,1-j,k)carbazole yielding the antidepressant drug, pirlindole. © 2013 Wiley Periodicals, Inc.

  8. Vibrational spectroscopy and structural analysis of complex uranium compounds (review)

    International Nuclear Information System (INIS)

    Umreiko, D.S.; Nikanovich, M.V.

    1985-01-01

    The paper reports on the combined application of experimental and theoretical methods of vibrational spectroscopy together with low-temperature luminescence data to determine the characteristic features of the formation and structure of complex systems, not only containing ligands directly coordinated to the CA uranium, but also associated with the extraspherical polyatomic electrically charged particles: organic cations. These include uranyl complexes and heterocyclical amines. Studied here were compounds of tetra-halouranylates with pyridine and its derivates, as well as dipyridyl, quinoline and phenanthroline. Structural schemes are also proposed for other uranyl complexes with protonated heterocyclical amines with a more complicated composition, which correctly reflect their spectroscopic properties

  9. 4-Nitro-N-(8-quinolylbenzamide

    Directory of Open Access Journals (Sweden)

    Li Zhou

    2008-12-01

    Full Text Available In the title compound, C16H11N3O3, the amide group is twisted away from the plane of the quinoline benzene ring by 3.93 (5°, but is twisted away from the nitrobenzene ring by 22.68 (4°. A weak intramolecular C—H...O hydrogen bond is observed. In the crystal structure, molecules are linked into a chain along the a axis by intermolecular C—H...O hydrogen bonds.

  10. Property-based design and synthesis of new chloroquine hybrids via simple incorporation of 2-imino-thiazolidine-4-one or 1h-pyrrol-2, 5-dione fragments on the 4-amino-7-chloroquinoline side chain

    International Nuclear Information System (INIS)

    Rojas, Fernando A.; Kouznetsov, Vladimir V.

    2011-01-01

    In the present work, the syntheses of new 4-amino-7-chloroquinoline N-derivatives were performed by selective modification of the side chain amino group of N-(7-chloroquinoline-4-yl) alkyldiamines, basis framework of chloroquine (CQ) drug through the incorporation of heterocyclic 2-imino-thiazolidine-4-one and 1 H-pyrrol-2,5-dione systems. These potential activity modulators were selected thanks to their characteristic properties, and evaluated by virtual screening employing the OSIRIS and Molinspirations platforms. Designed and synthesized quinolinic derivatives could increase the antimalarial activity of CQ analogues without affecting the lipophilicity as described in literature, suggesting them as candidates for further biological assessments. (author)

  11. Property-based design and synthesis of new chloroquine hybrids via simple incorporation of 2-imino-thiazolidine-4-one or 1h-pyrrol-2, 5-dione fragments on the 4-amino-7-chloroquinoline side chain

    Energy Technology Data Exchange (ETDEWEB)

    Rojas, Fernando A; Kouznetsov, Vladimir V., E-mail: kouznet@uis.edu.co [Laboratorio de Quimica Organica y Biomolecular, Escuela de Quimica, Universidad Industrial de Santander, Bucaramanga (Colombia)

    2011-09-15

    In the present work, the syntheses of new 4-amino-7-chloroquinoline N-derivatives were performed by selective modification of the side chain amino group of N-(7-chloroquinoline-4-yl) alkyldiamines, basis framework of chloroquine (CQ) drug through the incorporation of heterocyclic 2-imino-thiazolidine-4-one and {sup 1}H-pyrrol-2,5-dione systems. These potential activity modulators were selected thanks to their characteristic properties, and evaluated by virtual screening employing the OSIRIS and Molinspirations platforms. Designed and synthesized quinolinic derivatives could increase the antimalarial activity of CQ analogues without affecting the lipophilicity as described in literature, suggesting them as candidates for further biological assessments. (author)

  12. Synthesis,crystal structure and properties of inorganic-organic hybrid polymers based on 8-hydroxylquinoline-5-sulfonic acid

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    Two new inorganic-organic hybrid polymers, Mn(QS)(H2O) (1) and Co(QS)(H2O)2 (2) (H2QS=8-hydroxyl-quinoline-5-sulfonic acid), based on 8-hydroxylquinoline-5-sulfonate ligand, have been synthesized under solvothermal conditions and their structures were solved by single-crystal X-ray diffraction analysis. Compound 1 is a three-dimensional open framework with rutile topology structure, and compound 2 is a three-dimensional supramolecular structure. These compounds were characterized by powder XRD, infrared spectroscopy, thermogravimetric analysis, fluorescence properties and magnetism properties.

  13. Metallocene-based antimalarials: an exploration into the influence of the ferrocenyl moiety on in vitro antimalarial activity in chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum.

    Science.gov (United States)

    Blackie, Margaret A L; Beagley, Paul; Croft, Simon L; Kendrick, Howard; Moss, John R; Chibale, Kelly

    2007-10-15

    To establish the role of the ferrocenyl moiety in the antiplasmodial activity of ferroquine, compounds in which this moiety is replaced by the corresponding ruthenium-based moieties were synthesized and evaluated. In both the sensitive (D10) and resistant (K1) strains of Plasmodium falciparum, ruthenoquine analogues showed comparable potency to ferroquine. This suggests that a probable role of the ferrocenyl fragment is to serve simply as a hydrophobic spacer group. In addition, ferroquine analogues with different aromatic substituents were synthesized and evaluated. Unexpectedly high activity for quinoline compounds lacking the 7-chloro substituent suggests the ferrocenyl moiety may have an additive and/or synergistic effect.

  14. Recycling antimalarial leads for cancer: Antiproliferative properties of N-cinnamoyl chloroquine analogues.

    Science.gov (United States)

    Pérez, Bianca C; Fernandes, Iva; Mateus, Nuno; Teixeira, Cátia; Gomes, Paula

    2013-12-15

    Cinnamic acids and quinolines are known as useful scaffolds in the discovery of antitumor agents. Therefore, N-cinnamoylated analogues of chloroquine, recently reported as potent dual-action antimalarials, were evaluated against three different cancer cell lines: MKN-28, Caco-2, and MCF-7. All compounds display anti-proliferative activity in the micromolar range against the three cell lines tested, and most of them were more active than their parent drug, chloroquine, against all cell lines tested. Hence, N-cinnamoyl-chloroquine analogues are a good start towards development of affordable antitumor leads. Copyright © 2013 Elsevier Ltd. All rights reserved.

  15. 1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl-3-(3-methoxyphenylprop-2-en-1-one

    Directory of Open Access Journals (Sweden)

    Wan-Sin Loh

    2010-01-01

    Full Text Available In the title compound, C26H20ClNO2, the quinoline ring system is approximately planar with a maximum deviation of 0.028 (2 Å and forms a dihedral angle of 73.84 (5° with the phenyl ring. Two neighbouring molecules are arranged into a centrosymmetric dimer through a pair of intermolecular C—H...Cl interactions. A pair of intermolecular C—H...O hydrogen bonds link two methoxyphenyl groups into another centrosymmetric dimer, generating an R22(8 ring motif. The structure is further stabilized by C—H...π interactions.

  16. Atmospheric oxidation of N-PAC and nitro substituted N-PAC in water droplets

    DEFF Research Database (Denmark)

    Feilberg, A.; Holcman, J.; Nielsen, T.

    1999-01-01

    A pulse radiolysis technique was used to study the formation of OH-adducts of quinoline (Q) and 5-nitroquinoline (5NQ) and the subsequent reactions of the OH-adducts with O-2 in both acidic and alkaline aqueous solution. The rate constants in alkaline solution were: k(Q+OH) = (9.0+/-1.0)lozenge 10...... with OH in water droplets in the atmosphere is less than 1 hour. It is estimated that the degradation of Q is accelerated in the presence of aqueous droplets with comparable contributions from aqueous and gas phase chemistry at neutral pH. Under acidic conditions the aqueous phase degradation is predicted...

  17. ACCERBATIN, a small molecule at the intersection of auxin and reactive oxygen species homeostasis with herbicidal properties

    Czech Academy of Sciences Publication Activity Database

    Hu, Y.; Depaepe, T.; Smet, D.; Hoyerová, Klára; Klíma, Petr; Cuypers, J.; Cutler, S.; Buyst, D.; Morreel, K.; Boerjan, W.; Martins, J.; Petrášek, Jan; Vandenbussche, F.; Van Der Straeten, D.

    2017-01-01

    Roč. 68, č. 15 (2017), s. 4185-4203 ISSN 0022-0957 R&D Projects: GA MŠk LD15137 Institutional support: RVO:61389030 Keywords : apical hook development * root hair development * arabidopsis-thaliana seedlings * ethylene biosynthesis * shoot gravitropism * cell elongation * abiotic stress * abscisic-acid * plant-growth * gene family * Arabidopsis * auxin homeostasis * chemical genetics * ethylene signaling * herbicide * quinoline carboxamide * reactive oxygen species * triple response Subject RIV: EA - Cell Biology OBOR OECD: Plant sciences, botany Impact factor: 5.830, year: 2016

  18. Electron Transfer Mediators for Photoelectrochemical Cells Based on Cu(I Metal Complexes

    Directory of Open Access Journals (Sweden)

    Michele Brugnati

    2007-01-01

    Full Text Available The preparation and the photoelectrochemical characterization of a series of bipyridine and pyridyl-quinoline Cu(I complexes, used as electron transfer mediators in regenerative photoelectrochemical cells, are reported. The best performing mediators produced maximum IPCEs of the order of 35–40%. The J-V curves recorded under monochromatic light showed that the selected Cu(I/(II couples generated higher Vocs and fill factors compared to an equivalent I-/I3- cell, due to a decreased dark current.

  19. Crystal structure and tautomerism of Pigment Yellow 138 determined by X-ray powder diffraction and solid-state NMR

    DEFF Research Database (Denmark)

    Gumbert, Silke D.; Körbitzer, Meike; Alig, Edith

    2016-01-01

    The crystal structure of C.I. Pigment Yellow 138 was determined from X-ray powder diffraction data using real-space methods with subsequent Rietveld refinements. The tautomeric state was investigated by solid-state 1D and 2D multinuclear NMR experiments. In the crystals, the compound exhibits...... the NH-tautomer with a hydrogen atom situated at the nitrogen of the quinoline moiety. Direct evidence of the presence of the NH-tautomer is provided by 1H–14N HMQC solid-state NMR at very fast MAS. Solid-state dispersion-corrected density functional theory calculations with BLYP-D3 confirm...

  20. 5,7-Dibromo-8-methoxyquinoline

    Directory of Open Access Journals (Sweden)

    Ísmail Çelik

    2017-05-01

    Full Text Available In the title compound, C10H7Br2NO, the methoxy C atom deviates from the quinoline ring system (r.m.s deviation = 0.003 Å by 1.204 (4 Å. In the crystal, C—H...O hydrogen bonds link the molecules into infinite chains along the b-axis direction. Aromatic π–π stacking interactions [centroid-to-centroid distance = 3.7659 (19 Å] are also observed.

  1. Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines.

    Science.gov (United States)

    Jiang, Heng; He, Jian; Liu, Tao; Yu, Jin-Quan

    2016-02-17

    Pd(II)-catalyzed olefination of γ-C(sp(3))-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp(3))-H olefination reactions. The use of Ns protecting group to direct C(sp(3))-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines.

  2. Preparation of tritiated polystyrene and its application in radio luminescent paints

    International Nuclear Information System (INIS)

    Ravi, S.; Mathewy, K.M.; Seshadri, N.K.; Subramanian, T.K.

    2001-01-01

    Beta radiation emanating from tritiated polystyrene in close proximity with copper activated zinc sulphide phosphor will provide self-sustained light sources and are used for nocturnal illumination of watches and clocks, product advertisements, telephone numbers, exit signs etc. Phenylacetylene was partially reduced in diethyl ether medium with tritium using 5% Pd/C poisoned with quinoline to give styrene. Styrene formed was polymerised to polystyrene by subjecting it to irradiation with γ-radiation (20 mega rad dose). Copper activated zinc sulphide phosphor was coated with tritiated polystyrene to give self-sustained light sources. (author)

  3. Determination of trace amounts of lead by chelating ion exchange and on-line preconcentration in flow-injection atomic absorption spectrometry

    International Nuclear Information System (INIS)

    Purohit, Rajesh; Devi, Surekha

    1992-01-01

    Resins synthesized from quinolin-8-ol and resorcinol or hydro-quinone, with furfuraldehyde, formaldehyde or benzaldehyde as cross-linking agent, were used for the preconcentration of nanogram amounts of lead. The rate of exchange and activation energy of lead exchange were calculated. Column separations of lead-copper and lead-zinc did not show any cross-contamination. A continuous flow manifold using resin microcolumns was developed for the preconcentration and determination of lead. (author). 24 refs.; 5 figs.; 3 tabs

  4. New Copolymers Containing Charge Carriers for Organic Devices with ITO Films Treated by UV-Ozone Using High Intensity Discharge Lamp

    Directory of Open Access Journals (Sweden)

    Emerson Roberto SANTOS

    2009-02-01

    Full Text Available For electroluminescent devices new copolymers were synthesized using a Suzuki cross-coupling reaction based on monomers (fluorine-alt-phenylene in conjugation with quinoline-alt-phenylene units. They were characterized by 1H NMR, 13C NMR and FTIR. TGA measurements indicated that the copolymers have good thermal properties and no weight loss was observed up to 250 °C. The UV-Vis spectra were characterized by absorptions from the fluorene-alt-phenylene and quinoline-alt-phenylene segments in the backbone, while their photoluminescence (PL spectra dominated by emissions from the fluorene excimer. For devices assembly ITO films were treated using a High Intensity Discharge Lamp (HPMVL without outer bulb presenting high ozone concentration than that conventional germicidal lamp. The device with ITO treated revealed significant decrease of threshold voltage (or turn-on voltage compared by untreated with I-V curves. This decrease can be related by water and carbon dioxide extracted on surface after UV-Ozone treatment revealed by DRIFT measurements.

  5. Synthesis and Electrical and Gas Sensing Properties of Some 5-(Quinolinylmethylene-2-thioxodihydropyrimidine-4,6(1H,5H-dione and 5-(Quinolinylmethylenepyrimidine-2,4,6(1H,3H,5H-trione Derivatives

    Directory of Open Access Journals (Sweden)

    H. Kerim Beker

    2013-01-01

    Full Text Available Eight new 5-(quinolinylmethylenebarbituric acid derivatives were synthesized by the reaction of 1,3-dimethylbarbituric acid and 1,3-diethyl-2-thiobarbituric acid with quinoline-4-carboxaldehydes and several quinoline-2-carboxaldehydes via Knoevenagel condensation. The novel compounds were characterized by 1H NMR, 13C NMR, mass, IR, and UV-visible spectral data and elemental analyses. d.c. and a.c. conduction properties of the compounds were investigated in the frequency range of 40–105 Hz and temperature range 295–440 K. The d.c. results showed an activated conductivity dependence on temperature for all films. Obtained data reveal that a.c. conductivity obeys the relation and exponent is found to decrease by increasing temperature. The analysis of the a.c. conduction data showed that the CBH model is the dominant conduction mechanism for the electron transport in the films. Gas sensing properties of the films for the volatile organic compounds (VOCs were also investigated in the same temperature range. Maximum sensitivity to VOCs was observed at around 360 K for compound 6.

  6. Crystal Structure of the Homo sapiens Kynureninase-3-Hydroxyhippuric Acid Inhibitor Complex: Insights into the Molecular Basis Of Kynureninase Substrate Specificity

    Energy Technology Data Exchange (ETDEWEB)

    Lima,Santiago; Kumar,Sunil; Gawandi,Vijay; Momany,Cory; Phillips,Robert S.; (Georgia)

    2009-02-23

    Homo sapiens kynureninase is a pyridoxal-5'-phosphate dependent enzyme that catalyzes the hydrolytic cleavage of 3-hydroxykynurenine to yield 3-hydroxyanthranilate and L-alanine as part of the tryptophan catabolic pathway leading to the de novo biosynthesis of NAD{sup +}. This pathway results in quinolinate, an excitotoxin that is an NMDA receptor agonist. High levels of quinolinate have been correlated with the etiology of neurodegenerative disorders such as AIDS-related dementia and Alzheimer's disease. We have synthesized a novel kynureninase inhibitor, 3-hydroxyhippurate, cocrystallized it with human kynureninase, and solved the atomic structure. On the basis of an analysis of the complex, we designed a series of His-102, Ser-332, and Asn-333 mutants. The H102W/N333T and H102W/S332G/N333T mutants showed complete reversal of substrate specificity between 3-hydroxykynurenine and L-kynurenine, thus defining the primary residues contributing to substrate specificity in kynureninases.

  7. Phase Behaviour of 1-Ethyl-3-methylimidazolium Thiocyanate Ionic Liquid with Catalytic Deactivated Compounds and Water at Several Temperatures: Experiments and Theoretical Predictions

    Directory of Open Access Journals (Sweden)

    Ramalingam Anantharaj

    2011-01-01

    Full Text Available Density, surface tension and refractive index were determined for the binary mixture of catalytic deactivated compounds with 1-ethyl-3-methylimidazolium thiocyanate {[EMIM][SCN]} at temperature of (298.15 to 323.15 K. For all the compounds with ILs, the densities varied linearly in the entire mole fraction with increasing temperature. From the obtained data, the excess molar volume and deviation of surface tension and refractive index have been calculated. A strong interaction was found between similar (cation-thiophene or cation-pyrrole compounds. The interaction of IL with dissimilar compounds such as indoline and quinoline and other multiple ring compounds was found to strongly depend on the composition of IL at any temperatures. For the mixtures, the surface tension decreases in the order of: thiophene > quinoline > pyridine > indoline > pyrrole > water. In general from the excess volume studies, the IL-sulphur/nitrogen mixture has stronger interaction as compared to IL-IL, thiophene-thiophene or pyrrole-pyrrole interaction. The deviation of surface tension was found to be inversely proportional to deviation of refractive index. The quantum chemical based COSMO-RS was used to predict the non-ideal liquid phase activity coefficient for all mixtures. It indicated an inverse relation between activity coefficient and excess molar volumes.

  8. Changes in pyridine metabolism profile during growth of trigonelline-forming Lotus japonicus cell cultures.

    Science.gov (United States)

    Yin, Yuling; Matsui, Ayu; Sakuta, Masaaki; Ashihara, Hiroshi

    2008-12-01

    Changes in the profile of pyridine metabolism during growth of cells were investigated using trigonelline-forming suspension-cultured cells of Lotus japonicus. Activity of the de novo and salvage pathways of NAD biosynthesis was estimated from the in situ metabolism of [(3)H] quinolinic acid and [(14)C] nicotinamide. Maximum activity of the de novo pathway for NAD synthesis was found in the exponential growth phase, whereas activity of the salvage pathway was increased in the lag phase of cell growth. Expression profiles of some genes related to pyridine metabolism were examined using the expression sequence tags obtained from the L. japonicus database. Transcript levels of NaPRT and NIC, encoding salvage enzymes, were enhanced in the lag phase of cell growth, whereas the maximum expression of NADS was found in the exponential growth phase. Correspondingly, the activities of the salvage enzymes, nicotinate phosphoribosyltransferase (EC 2.4.2.11) and nicotinamidase (EC 3.5.1.19), increased one day after transfer of the stationary phase cells to the fresh medium. The greatest in situ trigonelline synthesis, both from [(3)H] quinolinic acid and [(14)C] nicotinamide, was found in the stationary phase of cell growth. The role of trigonelline in leguminous plants is discussed.

  9. Pseudo-stir bar hollow fiber solid/liquid phase microextraction combined with anodic stripping voltammetry for determination of lead and cadmium in water samples

    Directory of Open Access Journals (Sweden)

    Zarrin Es’haghi

    2014-11-01

    Full Text Available A new procedure is presented for the determination of low concentrations of lead and cadmium in water samples. Ligand assisted pseudo-stir bar hollow fiber solid/liquid phase microextraction using sol–gel sorbent reinforced with carbon nanotubes was combined with differential pulse anodic stripping voltammetry for simultaneous determination of cadmium and lead in tap water, and Darongar river water samples. In the present work, differential pulse anodic stripping voltammetry (DPASV using a hanging mercury drop electrode (HMDE was used in order to determine the ultra trace level of lead and cadmium ions in real samples. This method is based on accumulation of lead and cadmium ions on the electrode using different ligands; Quinolin-8-ol, 5,7-diiodo quinoline-8-ol, 4,5-diphenyl-1H-imidazole-2(3H-one and 2-{[2-(2-Hydroxy-ethylamino-ethylamino]-methyl}-phenol as the complexing agent. The optimized conditions were obtained. The relationship between the peak current versus concentration was linear over the range of 0.05–500 ng mL−1 for Cd (II and Pb (II. The limits of detection for lead and cadmium were 0.015 ng mL−1 and 0.012 ng mL−1, respectively. Under the optimized conditions, the pre-concentration factors are 2440 and 3710 for Cd (II and Pb (II in 5 mL of water sample, respectively.

  10. Hypothalamic digoxin, hemispheric chemical dominance, and creativity.

    Science.gov (United States)

    Kurup, Ravi Kumar; Kurup, Parameswara Achutha

    2003-04-01

    The human hypothalamus produces an endogenous membrane Na(+)-K+ ATPase inhibitor, digoxin, which regulates neuronal transmission. The digoxin status and neurotransmitter patterns were studied in creative and non-creative individuals, as well as in individuals with differing hemispheric dominance, in order to find out the role of cerebral dominance in this respect. The activity of HMG CoA reductase and serum levels of digoxin, magnesium, tryptophan catabolites, and tyrosine catabolites were measured in creative/non-creative individuals, and in individuals with differing hemispheric dominance. In creative individuals there was increased digoxin synthesis, decreased membrane Na(+)-K+ ATPase activity, increased tryptophan catabolites (serotonin, quinolinic acid, and nicotine), and decreased tyrosine catabolites (dopamine, noradrenaline, and morphine). The pattern in creative individuals correlated with right hemispheric dominance. In non-creative individuals there was decreased digoxin synthesis, increased membrane Na(+)-K+ ATPase activity, decreased tryptophan catabolites (serotonin, quinolinic acid, and nicotine), and increased tyrosine catabolites (dopamine, noradrenaline, and morphine). This pattern in non-creative individuals correlated with that obtained in left hemispheric chemical dominance. Hemispheric chemical dominance and hypothalamic digoxin could regulate the predisposition to creative tendency.

  11. Directory of Open Access Journals (Sweden)

    Kamal M. El-Gamal

    2016-12-01

    Full Text Available A series of 3-substituted 6-methoxy-1H-pyrazolo [3,4-b]quinoline derivatives was synthesized by treating 6-methoxy-1H-pyrazolo[3,4-b]quinolin-3-amine (6 with different acid anhydrides including succinic anhydride, maleic anhydride and phthalic anhydride. Also, a series of 3-heteroaryl-2-chloro-6-methoxyquinolines was prepared through 1,3-dipolar cycloaddition of different bi-nucleophiles including hydrazine hydrate, hydroxylamine hydrochloride, thiourea, guanidine hydrochloride, urea and metformin hydrochloride to the chalcone derivative 3-(2-chloro-6-methoxyquinolin-3-yl-1-(4-methoxyphenylprop-2-en-1-one. Structural identifications of all products were reported and the new compounds were screened for their in vitro antimicrobial activity against Streptococcus pneumonia and Bacillus subtilis as examples for Gram-positive bacteria, Pseudomonas aeruginosa and Escherichia coli as examples for Gram-negative bacteria, and Aspergillus fumigatus, Syncephalastrum racemosum, Geotriucum candidum and Candida albicans as representative examples of fungi. The majority of tested compounds showed moderate activities against a wide range of the selected organisms. Among the tested compounds, pyrimidine derivatives 16 and 17 showed the highest antimicrobial activity against gram-positive strains while the highest activity against E. coli as example for Gram-negative strains was observed in the case of 11 and 17. Compounds 14 and 17 were found to be extremely potent against three of the selected fungal strains.

  12. Mutagenicity of food-derived carcinogens and the effect of antioxidant vitamins.

    Science.gov (United States)

    Montgomery, Beverly A; Murphy, Jessica; Chen, James J; Desai, Varsha G; McGarrity, Lynda; Morris, Suzanne M; Casciano, Daniel A; Aidoo, Anane

    2002-01-01

    The food-derived heterocyclic amines (HCAs) 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) are mutagenic in the Ames test and produce tumors in laboratory animals, including monkeys. These HCAs have also been shown to induce gene mutations in vivo. To assess the antimutagenic effects of dietary antioxidant vitamins, beta-carotene, ascorbic acid (vitamin C), and alpha-tocopherol (vitamin E), on food-borne mutagenes/carcinogens, we evaluated the mutagenic activity of the compounds alone or combined with antioxidant vitamins. We utilized the rat lymphocyte mutation assay at the hypoxanthine guanine phosphoribosyl transferase (Hprt) locus. Female Fischer 344 rats treated with different doses (0, 2.5, 5.0, 25.0, and 50.0 mg/kg) of the carcinogens were sacrificed 5 wk after mutagen treatment. Although IQ and MeIQ slightly increased mutation frequency (MF) at some doses, a significant (P carcinogen metabolism would be affected by ingestion of vitamins. The activities of endogenous detoxification enzymes, glutathione S-transferase and glutathione peroxidase (GPx), were thus examined. Intake of beta-carotene and vitamin C without the carcinogen resulted in an increase (P food or taken as supplements could, in part, counteract such mutagenic activities.

  13. Covalent binding of food carcinogens MeIQx, MeIQ and IQ to DNA and protein in microsomal incubations and isolated rat hepatocytes

    International Nuclear Information System (INIS)

    Wallin, H.; Holme, J.A.; Alexander, J.

    1992-01-01

    The metabolic activation of 14 C-labelled food carcinogens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx),2-amino-3,4-dimethylimidazo[4,5-f]quinoline(MeIQ) and 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to macromolecular bound species was studied in microsomal and hepatocellular incubations. Several data indicated that the covalent binding was dependent on P450 enzymes: It was dependent on NADPH, it was induced many times by the P450 IA1 and IA2 upregulators β-naphthoflavone and polychlorinated biphenyls, and was inhibited by the P450 IA1 and IA2 inhibitor α-naphtoflavone. In both hepatocellular and microsomal incubations the three compounds bound with similar efficiency, with IQ being somewhat more potent compared to MeIQx and MeIQ. The binding appeared to follow saturation kinetics with K m values less than 20 μM. In incubations with hepatocytes the compounds bound to both cellular DNA and to bovine serum albumin in the medium. The fact that 13-26% of total adducts were formed with bovine serum albumin, indicates that reactive metabolites of the compounds may be transported and react at distant sites from their formation without any further activation. (au)

  14. Inhibition of Cholinesterases and Some Pro-Oxidant induced Oxidative Stress in Rats Brain by Two Tomato (Lycopersicon Esculentum) Varieties

    Science.gov (United States)

    Oboh, G.; Bakare, O.O.; Ademosun, A.O.; Akinyemi, A.J.; Olasehinde, T.A.

    2015-01-01

    This study sought to investigate the effects of two tomato varieties [Lycopersicon esculentum Mill. var. esculentum (ESC) and Lycopersicon esculentum Mill. var. cerasiforme (CER)] on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities in vitro. Phenolics content, carotenoids characterisation, inhibition of Fe2+ and quinolinic acid-induced malondialdehyde (MDA) production in rats brain homogenate and NO* scavenging abilities were also assesed in addition to the AChE and BChE inhibition assays. There was no significant difference in the AChE inhibitory ability of the samples, while CER had significantly higher BChE inhibitory activity. Furthermore, the tomatoes inhibited Fe2+ and quinolinic acid-induced MDA production and further exhibited antioxidant activities through their NO* scavenging abilities. There was no significant difference in the phenolic content of the samples, while significantly high amounts of lycopene were detected in the tomatoes. The cholinesterase-inhibition and antioxidant properties of the “tomatoes” could make them good dietary means for the management of neurodegenerative disorders.

  15. Photostabilizers for azadirachtin-A (a neem-based pesticide).

    Science.gov (United States)

    Johnson, Sapna; Dureja, P; Dhingra, S

    2003-07-01

    Photostability of azadirachtin-A (a neem based pesticide) has been studied without and with adding stabilizers such as ter. butyl-p-cresol, 8-hydroxy quinoline and ter. butyl hydroquinone as thin film on glass surface and on leaf surface under sunlight and UV light. Half-life of azadirachtin has been found to be 48 min and 3.98 days as thin film under UV light and sunlight and 2.47 days on leaf surface, respectively. 8-Hydroxy quinoline and ter. butyl hydroquinone have been found effective in controlling degradation of azadirachtin under both sunlight and UV light with half-life of 44.42 and 35.90 days under sunlight, and 55.80 and 48.50 h under UV light, respectively. Whereas ter. butyl-p-cresol has been found effective A only under sunlight. Significant decreases in antifeedant and insect growth regulatory activity against third instar larvae of Spodopterra litura has been observed with azadirachtin when exposed to sunlight and UV light. However, by the addition of above stabilizers, the biological activity of azadirachtin-A has been retained even after 24 h of irradiation under UV light and up to 30 days of exposure to sunlight.

  16. Two 8-Hydroxyquinolinate Based Supramolecular Coordination Compounds: Synthesis, Structures and Spectral Properties

    Directory of Open Access Journals (Sweden)

    Chengfeng Zhu

    2017-03-01

    Full Text Available Two new Cr(III complexes based on 2-substituted 8-hydroxyquinoline ligands, namely [Cr(L13] (1, (HL1=(E-2-[2-(4-nitro-phenyl-vinyl]-8-hydroxy-quinoline and [Cr(L23] (2, (HL2=(E-2-[2-(4-chloro-phenylvinyl]-8-hydroxy-quinoline, were prepared by a facile hydrothermal method and characterized thoroughly by single crystal X-ray diffraction, powder X-ray diffraction, FTIR, TGA, ESI-MS, UV-Visible absorption spectra and fluorescence emission spectra. Single crystal X-ray diffraction analyses showed that the two compounds featured 3D supramolecular architectures constructed from noncovalent interactions, such as π···π stacking, C-H···π, C-H···O, C-Cl···π, C-H···Cl interactions. The thermogravimetric analysis and ESI-MS study of compounds 1 and 2 suggested that the Cr(III complexes possessed good stability both in solid and solution. In addition, the ultraviolet and fluorescence response of the HL1 and HL2 shown marked changes upon their complexation with Cr(III ion, which indicated that the two 8-hydroxyquinolinate based ligand are promising heavy metal chelating agent for Cr3+.

  17. Synthesis and SAR study of a novel series of dopamine receptor agonists

    DEFF Research Database (Denmark)

    Risgaard, R.; Jensen, M.; Jørgensen, M.

    2014-01-01

    The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D and D receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinolin-6-ol (PHBQ) and resulted in the ...... in the synthesis of (2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol (compound 27), which has a D and D receptor profile similar to that of the most recently approved drug for Parkinson's disease, rotigotine.......The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D and D receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinolin-6-ol (PHBQ) and resulted...

  18. Crystal structure of 1-[(2S*,4R*-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one

    Directory of Open Access Journals (Sweden)

    P. S. Pradeep

    2014-09-01

    Full Text Available In the title compound, C14H17FN2O, the 1,2,3,4-tetrahydropyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methylene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9°. The bridging N—C bond distance [1.349 (3 Å] is substantially shorter than the sum of the covalent radii (dcov: C—N = 1.47 Å and C=N = 1.27 Å, which indicates partial double-bond character for this bond, resulting in a certain degree of charge delocalization. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds, forming sheets lying parallel to (10-1. These two-dimensional networks are linked via C—H...F hydrogen bonds and C—H...π interactions, forming a three-dimensional structure.

  19. Iron is a substrate of the Plasmodium falciparum chloroquine resistance transporter PfCRT in Xenopus oocytes.

    Science.gov (United States)

    Bakouh, Naziha; Bellanca, Sebastiano; Nyboer, Britta; Moliner Cubel, Sonia; Karim, Zoubida; Sanchez, Cecilia P; Stein, Wilfred D; Planelles, Gabrielle; Lanzer, Michael

    2017-09-29

    The chloroquine resistance transporter of the human malaria parasite Plasmodium falciparum , PfCRT, is an important determinant of resistance to several quinoline and quinoline-like antimalarial drugs. PfCRT also plays an essential role in the physiology of the parasite during development inside erythrocytes. However, the function of this transporter besides its role in drug resistance is still unclear. Using electrophysiological and flux experiments conducted on PfCRT-expressing Xenopus laevis oocytes, we show here that both wild-type PfCRT and a PfCRT variant associated with chloroquine resistance transport both ferrous and ferric iron, albeit with different kinetics. In particular, we found that the ability to transport ferrous iron is reduced by the specific polymorphisms acquired by the PfCRT variant as a result of chloroquine selection. We further show that iron and chloroquine transport via PfCRT is electrogenic. If these findings in the Xenopus model extend to P. falciparum in vivo , our data suggest that PfCRT might play a role in iron homeostasis, which is essential for the parasite's development in erythrocytes. © 2017 by The American Society for Biochemistry and Molecular Biology, Inc.

  20. Synthesis and characterisation of new Schiff base monomers containing N-(alkyl and phenyl) pyrrole moieties

    Science.gov (United States)

    Amer, Ahcene Ait; Ilikti, Hocine; Maschke, Ulrich

    2017-11-01

    This article deals with the synthesis and characterisation of seven new functional Schiff base monomers, such as: M1: 1-(3-Pyrrole-1-yl-propylimino-methyl)-naphtalen-2-ol; M2: 2-(3-Pyrrole-1-yl-phenylimino-methyl)-phenol; M3: 1-(3-Pyrrole-1-yl-phenylimino-methyl)-naphtalen-2-ol; M4: N-(pyridin-2-yl-methylene)-2-(pyrrol-1-yl)-benzenamine; M5: N-(pyridin-2-yl-methylene)-3-(pyrrol-1-yl)-propan-1-amine; M6: 2-(3-pyrrol-1-yl-propylimino-methyl)-quinolin-8-ol; M7: 2-(3-pyrrol-1-yl-phenylimino-methyl)-quinolin-8-ol. Two series of compounds emerged from this study, N-propyl pyrrole derivatives (M1, M5, M6) and N-phenyl pyrrole compounds (M2, M3, M4, M7). All monomers were elaborated by condensation reactions between appropriate amines and aldehydes, and their molecular structures were confirmed by spectroscopic analysis methods like FT-IR, 1H NMR, 13C NMR, and GC-MS.