Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents


TATAR E. , KÜÇÜKGÜZEL Ş. G. , KARAKUŞ S. , De Clercq E., Andrei G., Snoeck R., ...More

MARMARA PHARMACEUTICAL JOURNAL, vol.19, no.2, pp.88-102, 2015 (Journal Indexed in ESCI) identifier

  • Publication Type: Article / Article
  • Volume: 19 Issue: 2
  • Publication Date: 2015
  • Title of Journal : MARMARA PHARMACEUTICAL JOURNAL
  • Page Numbers: pp.88-102
  • Keywords: Thioureas, 1,3,4-thiadiazoles, 1,2,4-triazoles, antiviral activity, influenza, antituberculosis activity, HIV-1 REVERSE-TRANSCRIPTASE, HERPES-SIMPLEX-VIRUS, HUMAN-IMMUNODEFICIENCY-VIRUS, ANTIMYCOBACTERIAL ACTIVITY, IN-VITRO, THIOUREA COMPOUNDS, MYCOBACTERIUM-TUBERCULOSIS, NONNUCLEOSIDE INHIBITORS, ANTICANCER ACTIVITY, COLORIMETRIC ASSAY

Abstract

Some novel 1,3,4-thiadiazole [5-8] and 1,2,4-triazole [9-12] derivatives carrying amino acid moiety were synthesized starting from L-methionine. 1,3,4-Thiadiazole and 1,2,4-triazole scaffolds were prepared by cyclocondensation of the corresponding thiosemicarbazide and finally converted to their thiourea derivatives. Structures of the synthesized compounds [4-12] were confirmed by IR, H-1-NMR and C-13-NMR spectral data and elemental analysis. Synthesized compounds were evaluated for their antiviral and antibacterial activity. Of the screened compounds, N-{3-(methylsulfanyl)1-[5-(phenylamino)-1,3,4-thiadiazole-2-yl] propyl} benzamide 5] was identified as the most potent inhibitor of Influenza A H3N2 virus with an EC50 value of 31.4 mu M, which serves as a lead compound for prospective development. The antituberculosis activity screen of the synthesized compounds revealed