Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis.
A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain.
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
Kajitha
K
Suthagar
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
Andrew J A
AJ
Watson
School of Chemistry, Monash University, Box 23, Victoria 3800, Australia.
Brendan L
BL
Wilkinson
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand; Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. Electronic address: antony.fairbanks@canterbury.ac.nz.
Antony J
AJ
Fairbanks
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001089:Arabinose / Q000737:chemistry / Q000494:pharmacology*; D002473:Cell Wall / Q000187:drug effects* / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000166:cytology* / Q000187:drug effects* / Q000378:metabolism; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D013449:Sulfonamides; D001089:Arabinose
Arabinose; Carbohydrates; Furanosides; Mycobacteria; Pyranosides; Sulfamides; Tuberculosis