title: Synthesis of dihydroxymethyl dihydroxypyrrolidines and steviamine analogues from C-2 formyl glycals.
abstract: Synthesis of dihydroxymethyl dihydroxypyrrolidines from C-2 formyl D-glycals has been described via a common dicarbonyl intermediate. The hence obtained pyrrolidines have been further utilized for the synthesis of some steviamine analogues. The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, Uttar Pradesh 208 016, India.
authors.forename: Alafia A
authors.initials: AA
authors.lastname: Ansari
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar
mesh_terms: D000818:Animals; D002241:Carbohydrates / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006372:Helix, Snails / Q000201:enzymology; D050111:Imino Sugars / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D054836:Indolizidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D002241:Carbohydrates; D004791:Enzyme Inhibitors; D050111:Imino Sugars; D054836:Indolizidines; D011759:Pyrrolidines; C551370:steviamine; D001616:beta-Galactosidase