Stereoselective synthesis of beta-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis.
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.
Ayers
Benjamin
B
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford, UK.
Long
Hilary
H
Sim
Edith
E
Smellie
Iain A
IA
Wilkinson
Brendan L
BL
Fairbanks
Antony J
AJ
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002473:Cell Wall / Q000187:drug effects; D015394:Molecular Structure; D009163:Mycobacterium bovis / Q000187:drug effects* / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000995:Antitubercular Agents; D013450:Sulfones