title: Diastereoselective synthesis of glycosylated prolines as alpha-glucosidase inhibitors and organocatalyst in asymmetric aldol reaction.
abstract: 1,3-Dipolar cycloaddition of azomethine ylides and glycosyl E-olefins in presence of LDA led to diastereoselective formation of C-glycosylated proline esters. The selected esters on regioselective hydrolysis with LiOH gave C-glycosyl prolines. Few of the proline esters exhibited very good alpha-glucosidase inhibitory activity. The organocatalytic activity of the proline derivatives in a prototype Aldol reaction has also been investigated.
authors.affiliation: Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226001, India.
authors.forename: Jyoti
authors.initials: J
authors.lastname: Pandey
authors.forename: Namrata
authors.initials: N
authors.lastname: Dwivedi
authors.forename: Nimisha
authors.initials: N
authors.lastname: Singh
authors.forename: A K
authors.initials: AK
authors.lastname: Srivastava
authors.forename: A
authors.initials: A
authors.lastname: Tamarkar
authors.forename: R P
authors.initials: RP
authors.lastname: Tripathi
mesh_terms: D000447:Aldehydes; D002384:Catalysis; D065089:Glycoside Hydrolase Inhibitors; D006031:Glycosylation; D011392:Proline / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000447:Aldehydes; D065089:Glycoside Hydrolase Inhibitors; C116609:3-hydroxybutanal; D011392:Proline