Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis

Brendan L Wilkinson; Hilary Long; Edith Sim; Antony J Fairbanks

doi:10.1016/j.bmcl.2008.09.082

Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis

Bioorg Med Chem Lett. 2008 Dec 1;18(23):6265-7. doi: 10.1016/j.bmcl.2008.09.082. Epub 2008 Sep 26.

Authors

Brendan L Wilkinson¹, Hilary Long, Edith Sim, Antony J Fairbanks

Affiliation

¹ Department of Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

PMID: 18926698
DOI: 10.1016/j.bmcl.2008.09.082

Abstract

A series of arabino glycosyl triazoles with varying hydrophobic groups were synthesised as putative mimics of decaprenolphosphoarabinose (DPA) as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity, with strong dependence on the identity of the hydrophobic side chain.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antitubercular Agents / chemical synthesis*
Antitubercular Agents / pharmacology*
Arabinose / analogs & derivatives
Arabinose / chemical synthesis*
Arabinose / pharmacology*
Cell Wall / drug effects
Cell Wall / metabolism
Glycosides / chemical synthesis*
Glycosides / chemistry
Glycosides / pharmacology*
Isoniazid / pharmacology
Microbial Sensitivity Tests
Molecular Structure
Mycobacterium bovis / drug effects*
Mycobacterium bovis / metabolism
Structure-Activity Relationship
Triazoles / chemical synthesis*
Triazoles / chemistry
Triazoles / pharmacology*

Substances

Antitubercular Agents
Glycosides
Triazoles
Arabinose
Isoniazid