In Vitro and In Silico Studies of Quinoline-2-Carbaldehyde Hydrazone Derivatives as Potent Antimicrobial Agents
İsmail Çeli̇kMeryem ErolMustafa Orhan PüsküllüEbru UzunhisarcıklıUfuk İnceGülcan KuyucukluSíbel Süzen
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Abstract:
We previously synthesized a series of quinoline-2-carbaldehyde hydrazone derivatives and evaluated their antioxidant activities. In this study, the antimicrobial activities of these quinoline-2-carbaldehyde hydrazone derivatives were evaluated antimicrobial activity by the microdilution method, and there cytotoxic effect was investigated in MCF-7 and A549 cells by MTT assay. When the activity results were examined, although the antimicrobial activity of quinoline derivatives were equal or better than standard drugs in general, compound 4 (2 µg/mL) and 8 (1 µg/mL) against E. faecalis and 5 (8 µg/mL) against P. aeruginosa are the most effective derivatives of the series. Besides, disk diffusion test was applied to these three compounds, and significant zone formation was observed at 8 (7 mm) compared to vancomycin (9 mm). Compounds showed no antiproliferative in A549 and MCF-7 cell lines, and compound 4, 5, and 8, which showed the most effective antimicrobial activity, were examined in healthy cells (Beas-2b) and no effect on cell viability was found. To understand the mechanism of this action of these compounds against E. faecalis, molecular docking studies were performed on 15 different proteins, and it was concluded that the compounds interacted with FabH and not enough with other protein structures. The theoretical ADME profiles of compounds comply with Lipinski and other limiting rules. Also, some theoretical quantum parameters (HOMO-LUMO) of compounds, and both MEP analysis and geometric optimization analysis of 8 were calculated with 6–311 G (d,p) base set and DFT/B3LYP theory, and the results were shown.Keywords:
Quinoline
Hydrazone
ADME
MTT assay
Docking (animal)
Phenanthridine
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1-Cyano-2-methoxy-1, 2-dihydroquinolines (I) were dissolved in chloroform or bromo-form, 50% sodium hydroxide solution was added in the presence of a small quantity of interphase transition catalyst, and the mixture was stirred at room temperature, by which the corresponding 3-cyano-1, 1-dichloro (or dibromo)-2-methoxy-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] quinoline derivatives (II) were obtained. I can be obtained easily in one step from the commercial quinoline derivative so that this reaction is a useful two-step synthesis of cyclopropa [c] quinoline derivatives (II) from commercial quinoline derivatives.
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Sodium hydroxide
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Two ω-mercaptoalkoxy quinoline compounds:6-(ω-mercaptodecoxy)-quinoline and 2-(ω-mercaptodecoxy)-4-methyl-quinoline were succesfully synthesized by reacting quinoline with 1,10- dibromodecane and thiourea in alkaline solution. The intermediates and products were characterized by IR, 1H NMR and MS.
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Aim To synthesize new self-assembed monolayers(SAMs) functional materials of mercaptoalkoxy quinoline compounds.Methods The new SAMs functional materials are synthesized by reacting quinoline with 1,10-dibromodecane and thiourea,the products are characterized by 1H NMR and MS.Results and Conclusion Two new ω-mercaptoalkoxy quinoline compounds:1-(10-mercaptodecyl)-4-methyl-1H-quinoline-2-one and 1-(10mercaptodecoxy)-1H-quinoline-2-one were successfully synthesized by reacting quinoline with 1,10-dibromodecane and thiourea in alkaline solution.The intermediates and products were characterized by 1H NMR and MS.
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Benzo[f]quinoline and benzo[h]quinoline are widespread environmental pollutants which have been found to be mutagenic. The metabolism of benzo[f]quinoline and benzo[h]quinoline was investigated using a liver homogenate from Aroclor-pretreated rats. The metabolites of benzo[f]quinoline which were identified were 7,8-dihydroxy-7,8-dihydrobenzo[f]quinoline, 9,10-dihydroxy-9,10-dihydrobenzo[f]quinoline, 7-hydroxybenzo[f]quinoline, and benzo[f]quinoline-N-oxide. Metabolism studies on benzo[f]quinoline performed in the presence of the epoxide hydratase inhibitor, 3,3,3-trichloropropylene oxide, demonstrated that the formation of both of these dihydrodiols can be inhibited. The major metabolites of benzo[h]quinoline were identified as 5,6-dihydroxy-5,6-dihydrobenzo[h]quinoline and 7,8-dihydroxy-7,8-dihydrobenzo[h]quinoline. Benzo[h]quinoline-N-oxide was not detected as a metabolite. In the presence of an epoxide hydratase inhibitor, the major metabolites of benzo[h]quinoline were 5,6-epoxybenzo[h]quinoline and 7-hydroxybenzo[h]quinoline. The difference in the metabolism to N-oxides observed between benzo[h]quinoline and benzo[f]quinoline is consistent with previous observations in which sterically hindered aromatic ring nitrogen compounds such as benzo[h]quinoline are more resistant to N-oxide formation. The nitrogen atom of these aza-arenes with its lone pair of electrons has a significant influence on sites at which dihydrodiols are formed. The data suggest that the aromatic ring nitrogen of these azaphenanthrenes has an effect similar to that of a methyl substituent in directing their metabolic oxidation.
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Thirteen isomers of the p-dimethylaminophenylazoquinolines and their corresponding N-oxides were investigated for hepatic carcinogenic activity in Sprague-Dawley rats. The dyes were all fed at the 0.03 percent level, and the more active isomers were also examined at the 0.01 percent level. The isomers are listed in order of decreasing activity, with semiquantitative values based on p-dimethylaminoazobenzene as 6: 6- (p- dimethylaminophenylazo)quinoline, 200+ ; 5-(p-dimethylaminophenylazo)quinoline-1-oxide, 200+; 5-(p-dimethylaminophenylazo)quinoline, 150; 6-(p-dimethylaminophenylazo)quinoline-1-oxide, 100; 4-(p-dimethylaminophenylazo)quinoline-1-oxide, 22; 4-(p-dimethylaminophenylazo)quinoline, 15; 3- (p-dimethylaminophenylazo)quinoline-1-oxide, 3-(p-dimethylaminophenylazo)quinoline, 7-(p-dimethylaminophenylazo)quinoline-1-oxide, 7-(p-dimethylaminophenylazo)quinoline, 8-(p-dimethylaminophenylazo)quinoline-1-oxide, 8-(p-dimethylaminophenylazo)quinoline, and 2-(p-dimethylaminophenylazo)quinoline-1-oxide, with all the latter less than 2.
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