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

Bhowruth, V. and Brown, A.K. and Reynolds, R.C. and Coxon, G.D. and Mackay, S.P. and Minnikin, D.E. and Besra, G.S. (2006) Symmetrical and unsymmetrical analogues of isoxyl; active agents against mycobacterium tuberculosis. Bioorganic and Medicinal Chemistry Letters, 16 (18). pp. 4743-4747. ISSN 0960-894X

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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.