title: Synthesis of isofagomine-pyrrolidine hybrid sugars and analogues of (-)-steviamine and (+)-hyacinthacine C5 using 1,3-dipolar cycloaddition reactions.
abstract: Highly regioselective 1,3-dipolar cycloadditions between d-arabinose-derived nitrones and d-mannitol-derived trans-olefins have been utilized to synthesize isofagomine-pyrrolidine hybrid sugars, hydroxymethylated analogues of (-)-steviamine and analogues of (+)-hyacinthacine C5. All of the new compounds were subsequently tested against several commercially available glycosidases, and some of them showed good and selective glycosidase inhibition.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur Kanpur 208016, India.
authors.forename: Rima
authors.initials: R
authors.lastname: Lahiri
authors.forename: Ashokkumar
authors.initials: A
authors.lastname: Palanivel
authors.forename: Sudhir A
authors.initials: SA
authors.lastname: Kulkarni
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D050112:Imino Pyranoses / Q000138:chemical synthesis* / Q000737:chemistry; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D050111:Imino Sugars; D054836:Indolizidines; D011759:Pyrrolidines; D011763:Pyrrolizidine Alkaloids; C000599344:hyacinthacine C5; C098432:isofagomine; C551370:steviamine; D006026:Glycoside Hydrolases; C032519:pyrrolidine