Symmetrical and unsymmetrical analogues of isoxyl; active agents against mycobacterium tuberculosis

V. Bhowruth, A.K. Brown, R.C. Reynolds, G.D. Coxon, S.P. Mackay, D.E. Minnikin, G.S. Besra

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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 pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number18
DOIs
Publication statusPublished - 15 Sep 2006

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Keywords

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

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