Stereoselective synthesis of beta-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

Benjamin Ayers; Hilary Long; Edith Sim; Iain A Smellie; Brendan L Wilkinson; Antony J Fairbanks

doi:10.1016/j.carres.2009.02.006

Stereoselective synthesis of beta-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

Carbohydr Res. 2009 Apr 21;344(6):739-46. doi: 10.1016/j.carres.2009.02.006. Epub 2009 Feb 12.

Authors

Benjamin Ayers¹, Hilary Long, Edith Sim, Iain A Smellie, Brendan L Wilkinson, Antony J Fairbanks

Affiliation

¹ Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.

PMID: 19269629
DOI: 10.1016/j.carres.2009.02.006

Abstract

A series of beta-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain.

Publication types

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

MeSH terms

Antitubercular Agents / chemical synthesis*
Antitubercular Agents / chemistry
Antitubercular Agents / pharmacology*
Cell Wall / drug effects
Molecular Structure
Mycobacterium bovis / drug effects*
Mycobacterium bovis / metabolism*
Stereoisomerism
Structure-Activity Relationship
Sulfones / chemical synthesis*
Sulfones / chemistry
Sulfones / pharmacology*

Substances

Antitubercular Agents
Sulfones