Symmetrical and unsymmetrical analogues of isoxyl, active against Mycobacterium tuberculosis

Veemal Bhowruth, Alistair Brown, RC Reynolds, GD Coxon, SP Mackay, David Minnikin, Gurdyal Besra

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Symmetrical and unsymmetrical analogues of the antimycobacterial agent isoxyl have been synthesized and tested against Mycobacterium tuberculosis H37Rv and Mycobacterium bovis BCG, some showing an increased bactericidal effect. In particular, compounds 1-(p-n-butylphenyl)-3-(4-propoxy-phenyl) thiourea (10) and 1-(p-n-butylphenyl)-3-(4-n-butoxy-phenyl) thiourea (11) showed an approximate 10-fold increase in in vitro potency compared to isoxyl, paralleled by increased inhibition of mycolic acid biosynthesis in M. bovis BCG. Interestingly, these isoxyl analogues showed relatively poor inhibition of oleate production, suggesting that the modifications have changed the spectrum of biological activity.
Original languageEnglish
Pages (from-to)4743-4747
Number of pages5
JournalBioorganic & Medicinal Chemistry Letters
Volume16
DOIs
Publication statusPublished - 15 Sep 2006

Keywords

  • Mt
  • isoxyl
  • Mycobacterium bovis
  • mycolic acids
  • inhibitor
  • Mb
  • Mycobacterium tuberculosis

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