Synthesis and antimicrobial activity of N-[5-(4-t-amino-2-butynyl)thio-1,3,4-thiadiazol-2-yl]-2-carbamates

ME Zuhair, A. Abu-Al-Teman, FA Hussein, SR Salman, D. Al-Dujaili, Victoria F. Roche

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Abstract

Three series of 5-thio-1,3,4-thiadiazole carbamates containing alkynyl, aminoalkynyl, alkenyl or alkyl thio substituents have been synthesized as potential antimicrobial agents. The influence of both the alkynyl linkage and the various terminal nitrogen heterocyclic moieties on antimicrobial activity was assessed utilizing representative Gram-positive, Gram-negative and fungal species. Mannich base analogs containing a 2-ethyl carbamate group and a nitrogen heterocyclic of limited bulk provided the broadest spectrum of antimicrobial activity. The thiadiazole carbamates containing a 5-alkylthio substituent were consistently active against the Pseudomonas and Candida organisms studied. It is concluded that an acetylenic linkage is not an absolute requirement for potent antimicrobial activity in this molecular series, and that the binding sites of the organisms tested exhibit a steric requirement for lipophilic, but non-bulky, amine-containing heterocycles on Mannich base analogs.

Original languageEnglish
Pages (from-to)93-99
Number of pages7
JournalEuropean Journal of Medicinal Chemistry
Volume27
Issue number2
DOIs
Publication statusPublished - 1992

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All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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