New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties
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Date
2010
Journal Title
Journal ISSN
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Publisher
Elsevier Masson SAS
Abstract
Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence,substituted aniline was cyclized to 4-hydroxy quinoline 1,which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3,obtained from the compound 2,was successfully converted to target quinoline derivatives,viz. hydrazones 4aet,ureas 5aee,thioureas 6aec and pyrazoles 7aed,in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli,Staphylococcus aureus,Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H<inf>37</inf>Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. © 2010 Elsevier Masson SAS. All rights reserved.
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Keywords
1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 (2 fluoro 4 methoxybenzylidene)hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 (3 hydroxy 4 methoxybenzylidene)hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 (cyclohexylmethylene)hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 2 [(benzo[c][1,2,5]oxadiazol 5 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 octylidenehydazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(1 methyl 1h benzo[d][1,2,3]triazol 5 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(1 methyl 1h pyrrol 2 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(2,3 dihydrobenzofuran 5 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(4 bromofuran 3 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(4 chloro 1 methyl 1h pyrazol 3 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(4 methyl 1h imidazol 5 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(5 (acetoxymethyl)furan 2 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(5 methoxy 1h indol 3 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(7 methyl 1h indol 3 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(pyridin 3 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [(thiophen 2 yl)methylene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 2 [3 (trifluoromethoxy)benzylidene]hydrazine, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 4 (3 cyanophenyl)semicarbazide, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl) 4 (4 fluorophenyl)semicarbazide, 1 (2,8 bis(trifluoromethyl)quinolin 4 yl)2 (3 (1,1,2,2 tetrafluoroethoxy)benzylidene)hydrazine, 2 [(1h imidazol 4 yl)methylene] 1 [2,8 bis(trifluoromethyl)quinolin 4 yl]hydrazine, 2 [[2 [2,8 bis(trifluoromethyl)quinolin 4 yl]hydrazinylidene]methyl] 5 fluorophenol, antiinfective agent, hydrazone derivative, pyrazole derivative, quinoline derivative, thiourea derivative, tuberculostatic agent, unclassified drug, unindexed drug, urea derivative, antibacterial activity, article, drug synthesis, Escherichia coli, in vitro study, Klebsiella pneumoniae, multidrug resistant tuberculosis, Mycobacterium tuberculosis, nonhuman, Pseudomonas aeruginosa, Staphylococcus aureus
Citation
European Journal of Medicinal Chemistry, 2010, 45, 8, pp. 3374-3383