Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents
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Date
2013
Journal Title
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Elsevier Masson SAS infos@masson.fr 62 rue Camille Desmoulins Issy les Moulineaux Cedex 92442
Abstract
Three series of new trifluoromethyl substituted quinolone derivatives were synthesized (4a-f, 6a-f and 8a-f) from corresponding substituted anilines by multi-step reactions. The regioselective alkylation with different alkyl halides were carried out by approaching two different routes to get the final products in good yield. Newly synthesized compounds were characterized by spectral study and also by C, H, N analyses. Three dimensional structure of 2b and 4b were also confirmed by single crystal X-ray studies. The final compounds (4a-f, 6a-f and 8a-f) were screened for their in-vitro antibacterial and antifungal activity by well plate method (zone of inhibition). The results revealed that, compounds 4a, 6b, 6c and 8e showed significant antibacterial activity as compared to the standard drug Ciprofloxacin. The compound 8a was found to be a potent antifungal agent. © 2013 Elsevier Masson SAS. All rights reserved.
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Keywords
1 (2,4 dichlorobenzyl) 4 oxo 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carbohydrazide, 1 (2,4 dichlorobenzyl) 4 oxo 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylic acid, 1 (2,4 dichlorobenzyl) 4 oxo 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carbohydrazide, 1 (2,4 dichlorobenzyl) 4 oxo 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylic acid, 1 (4 cyanobenzyl) 4 oxo 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carbohydrazide, 1 (4 cyanobenzyl) 4 oxo 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylic acid, 1 (4 cyanobenzyl) 4 oxo 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carbohydrazide, 1 (4 cyanobenzyl) 4 oxo 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylic acid, 4 oxo 1 (prop 2 yn 1 yl) 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carbohydrazide, 4 oxo 1 (prop 2 yn 1 yl) 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylic acid, 4 oxo 1 (prop 2 yn 1 yl) 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carbohydrazide, 4 oxo 1 (prop 2 yn 1 yl) 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylic acid, antifungal agent, ciprofloxacin, ethyl 1 (2,4 dichlorobenzyl) 4 oxo 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylate, ethyl 1 (2,4 dichlorobenzyl) 4 oxo 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylate, ethyl 1 (4 cyanobenzyl) 4 oxo 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylate, ethyl 1 (4 cyanobenzyl) 4 oxo 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylate, ethyl 4 oxo 1 (prop 2 yn 1 yl) 7 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylate, ethyl 4 oxo 1 (prop 2 yn 1 yl) 8 (trifluoromethyl) 1,4 dihydroquinoline 3 carboxylate, quinolone derivative, trifluoromethylquinolone derivative, unclassified drug, alkylation, antibacterial activity, antifungal activity, article, bacterial strain, controlled study, crystal structure, drug design, drug screening, drug selectivity, drug synthesis, in vitro study, minimum inhibitory concentration, nonhuman, X ray crystallography, Antibacterial study, Antifungal study, Regioselective synthesis, Trifluoromethylquinolone derivative, Anti-Infective Agents, Bacteria, Candida albicans, Ciprofloxacin, Crystallography, X-Ray, Drug Design, Fluorine, Molecular Structure, Penicillium chrysogenum, Quinolines
Citation
European Journal of Medicinal Chemistry, 2013, 68, , pp. 422-432