Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme

Suzanne Senior; Petr Illarionov; Sudagar Gurcha; IB Campbell; ML Schaeffer; David Minnikin; Gurdyal Besra

doi:10.1016/j.bmcl.2003.08.015

Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme

Suzanne Senior
, Petr Illarionov
, Sudagar Gurcha
, IB Campbell
, ML Schaeffer
, David Minnikin
, Gurdyal Besra

Biosciences

Research output: Contribution to journal › Article

54 Citations (Scopus)

Abstract

Analogues of the antibiotic thiolactomycin, with biphenyl-based 5-substituents, were found to have excellent in vitro inhibitory activity against the recombinant Mycobacterium tuberculosis beta-ketoacyl-ACP synthase mtFabH condensing enzyme. In particular, 5-(4'-benzyloxy-biphen-4-ylmethyl)-4-hydroxy-3,5-dimethyl-5H-thiophen-2- one exhibited approximately a 4-fold increased potency against this key condensing enzyme involved in M. tuberculosis mycolic acid biosynthesis, compared to thiolactomycin. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3685-3688
Number of pages	4
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	13
DOIs	https://doi.org/10.1016/j.bmcl.2003.08.015
Publication status	Published - 3 Nov 2003

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10.1016/j.bmcl.2003.08.015

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title = "Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme",

abstract = "Analogues of the antibiotic thiolactomycin, with biphenyl-based 5-substituents, were found to have excellent in vitro inhibitory activity against the recombinant Mycobacterium tuberculosis beta-ketoacyl-ACP synthase mtFabH condensing enzyme. In particular, 5-(4'-benzyloxy-biphen-4-ylmethyl)-4-hydroxy-3,5-dimethyl-5H-thiophen-2- one exhibited approximately a 4-fold increased potency against this key condensing enzyme involved in M. tuberculosis mycolic acid biosynthesis, compared to thiolactomycin. (C) 2003 Elsevier Ltd. All rights reserved.",

author = "Suzanne Senior and Petr Illarionov and Sudagar Gurcha and IB Campbell and ML Schaeffer and David Minnikin and Gurdyal Besra",

year = "2003",

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doi = "10.1016/j.bmcl.2003.08.015",

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journal = "Bioorganic \& Medicinal Chemistry Letters",

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TY - JOUR

T1 - Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme

AU - Senior, Suzanne

AU - Illarionov, Petr

AU - Gurcha, Sudagar

AU - Campbell, IB

AU - Schaeffer, ML

AU - Minnikin, David

AU - Besra, Gurdyal

PY - 2003/11/3

Y1 - 2003/11/3

N2 - Analogues of the antibiotic thiolactomycin, with biphenyl-based 5-substituents, were found to have excellent in vitro inhibitory activity against the recombinant Mycobacterium tuberculosis beta-ketoacyl-ACP synthase mtFabH condensing enzyme. In particular, 5-(4'-benzyloxy-biphen-4-ylmethyl)-4-hydroxy-3,5-dimethyl-5H-thiophen-2- one exhibited approximately a 4-fold increased potency against this key condensing enzyme involved in M. tuberculosis mycolic acid biosynthesis, compared to thiolactomycin. (C) 2003 Elsevier Ltd. All rights reserved.

AB - Analogues of the antibiotic thiolactomycin, with biphenyl-based 5-substituents, were found to have excellent in vitro inhibitory activity against the recombinant Mycobacterium tuberculosis beta-ketoacyl-ACP synthase mtFabH condensing enzyme. In particular, 5-(4'-benzyloxy-biphen-4-ylmethyl)-4-hydroxy-3,5-dimethyl-5H-thiophen-2- one exhibited approximately a 4-fold increased potency against this key condensing enzyme involved in M. tuberculosis mycolic acid biosynthesis, compared to thiolactomycin. (C) 2003 Elsevier Ltd. All rights reserved.

UR - https://www.scopus.com/pages/publications/0141433395

U2 - 10.1016/j.bmcl.2003.08.015

DO - 10.1016/j.bmcl.2003.08.015

M3 - Article

C2 - 14552758

VL - 13

SP - 3685

EP - 3688

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

ER -

Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme

Abstract

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