New quinoline derivatives: synthesis and investigation of antibacterial and antituberculosis properties.
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 4a-t, ureas 5a-e, thioureas 6a-c and pyrazoles 7a-d, 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(37)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.
Eswaran
Sumesh
S
Anthem Biosciences Pvt. Ltd, 49 Bommasandra Industrial Area, Bommasandra, Bangalore 560099, Karnataka, India.
Adhikari
Airody Vasudeva
AV
Chowdhury
Imran H
IH
Pal
Nishith K
NK
Thomas
K D
KD
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D018360:Crystallography, X-Ray; D008826:Microbial Sensitivity Tests; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000995:Antitubercular Agents; D011804:Quinolines; C037219:quinoline