New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties

Sumesh Eswaran, Airody Vasudeva Adhikari, Imran H. Chowdhury, Nishith K. Pal, K. D. Thomas

Research output: Contribution to journalArticlepeer-review

170 Scopus citations

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 H37Rv 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.

Original languageEnglish (US)
Pages (from-to)3374-3383
Number of pages10
JournalEuropean journal of medicinal chemistry
Volume45
Issue number8
DOIs
StatePublished - Aug 2010
Externally publishedYes

Keywords

  • Antibacterial
  • Antituberculosis activity
  • Mefloquine
  • Quinoline
  • X-ray crystallography

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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