Zwitterionic glycosidase inhibitors: salacinol and related analogues.
Natural products with interesting biological properties and structural diversity have often served as valuable lead drug candidates for the treatment of human diseases. Salacinol, a naturally occurring alpha-glucosidase inhibitor, was shown to be one of the active principles of the aqueous extract of a medicinal plant that has been prescribed traditionally as an Ayurvedic treatment for type II diabetes. Salacinol contains an intriguing zwitterionic sulfonium-sulfate structure that comprises a 1,4-anhydro-4-thio-D-arabinitol core and a polyhydroxylated acyclic chain. Due to the unique structural features and its potential to become a lead drug candidate in the treatment of type II diabetes, a great deal of attention has been focused on salacinol and its analogues. Since the isolation of salacinol, several papers describing various synthetic routes to salacinol and its analogues have appeared in the literature. This review is aimed at highlighting the synthetic aspects of salacinol and related compounds as well as their structure-activity relationship studies.
Mohan
Sankar
S
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6.
Pinto
B Mario
BM
D002236:Carbohydrate Conformation; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D007097:Imines / Q000494:pharmacology; D008958:Models, Molecular; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000737:chemistry / Q000494:pharmacology*; D013431:Sulfates / Q000737:chemistry / Q000494:pharmacology*
D004791:Enzyme Inhibitors; D007097:Imines; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol; D006026:Glycoside Hydrolases