New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents

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

Research output: Contribution to journalArticlepeer-review

91 Scopus citations

Abstract

Three new series of quinoline-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines were synthesized through multi-step reactions. The required intermediate, [1-(6-methoxy-2-methylquinolin-4-yl)-1H-1, 2,3-triazol-4-yl]methanol (2) was prepared by treating 4-azido-6-methoxy-2- methylquinoline (1) with propargyl alcohol. Three different series of compounds were synthesized from this intermediate. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 2 was confirmed by X-ray crystallographic study. Further, the title compounds were evaluated for their in vitro anti-bacterial activity against five different bacterial strains and antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis (ATCC 19420) and Mycobacterium fortuitum (ATCC 19542). Title compounds, 6a, 6d, 6i, 6j, 7e, 10a and 10i were found to be active against Mycobacterium tuberculosis H37Rv strain and could be lead molecules of interest.

Original languageEnglish (US)
Pages (from-to)2503-2512
Number of pages10
JournalEuropean journal of medicinal chemistry
Volume46
Issue number6
DOIs
StatePublished - Jun 2011
Externally publishedYes

Keywords

  • 1,2,3-triazole
  • Amidopiperazine
  • Antimycobacterial
  • Propargyl alcohol
  • Quinoline

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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