Some 3-thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials

Bioorg Med Chem Lett. 2001 Jul 9;11(13):1703-7. doi: 10.1016/s0960-894x(01)00283-9.

Abstract

A series of novel N-alkyl/aryl-N'-[4-(4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thione-5-yl)phenyl]thioureas 1-19 and three S-alkylated representatives of the former, N-alkyl/aryl-N'-[4-(3-aralkylthio-4-alkyl/aryl-4H-1,2,4-triazole-5-yl)phenyl]thioureas 20-22, were synthesized and tested for antimycobacterial activity against Mycobacterium tuberculosis H37Rv as well as Mycobacterium fortuitum ATCC 6841 which is a rapid growing opportunistic pathogen. Compounds 4 and 9-11 were found to possess the same MIC value with that of Tobramycin against M. fortuitum ATCC 6841 whereas 1-3 and 21 had positive response against M. tuberculosis H37Rv at varying degrees. Compound 21 was identified as the most potent derivative of the 1-22 series by an MIC value of 6.25 microg/mL and selectivity index of 1.6.

MeSH terms

  • Animals
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Chlorocebus aethiops
  • Microbial Sensitivity Tests
  • Mycobacterium fortuitum / drug effects*
  • Mycobacterium tuberculosis / drug effects*
  • Thiourea / chemistry*
  • Triazoles / chemistry
  • Triazoles / pharmacology*
  • Vero Cells

Substances

  • Antitubercular Agents
  • Triazoles
  • Thiourea