Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams. Issue 5 (11th January 2019)

• Record Type: Journal Article
• Authors: Santhanam, Venkatesan; Pant, Pradeep; Jayaram, B.; Ramesh, Namakkal G.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 5(2019)
• Page Start: 1130
• Page End: 1140
• Publication Date: 2019-01-11
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob03084g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Synthesis of novel triazole fused iminocyclitol-δ-lactams, from tri- O -benzyl-d -glucal, involving intermolecular [3 + 2]cycloaddition and intramolecular lactamisation reactions as key steps is described. Abstract : Synthesis of novel triazole fused iminocyclitol-δ-lactams is described. The synthetic sequence involves the intermolecular [3 + 2] cycloaddition reaction of five-membered iminocyclitol derived azides with diethylacetylene dicarboxylate followed by intramolecular lactamisation, decarboxylation/reduction and final deprotection. Compound3 is found to be a selective inhibitor of α-glucosidase from baker's yeast while two other compounds (2 and4 ) that possess an additional hydroxymethyl group in the triazole ring are selective against β-galactosidase from E. coli . Docking studies suggest the significance of the lactam carbonyl group for effective binding of these inhibitors with the active sites through hydrogen bonding.