title: Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors.
abstract: Herein we describe the synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-rhamnose. The key reactions involved are (i) Zn(OTf)2 catalyzed enantioselective alkynylation of L-rhamnose derived azidoaldehyde and (ii) deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols. Some compounds exhibit excellent sodium-glucose transporter (SGLT1 and SGLT2) inhibition activity.
authors.affiliation: Organic Chemistry Division-II (C P C Division), CSIR-Indian Institute of Chemical Technology, Hyderabad, India. kantevari@yahoo.com kantevari@gmail.com.
authors.forename: Siddamal Reddy
authors.initials: SR
authors.lastname: Putapatri
authors.forename: Abhinav
authors.initials: A
authors.lastname: Kanwal
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: Sanjay K
authors.initials: SK
authors.lastname: Banerjee
authors.forename: Srinivas
authors.initials: S
authors.lastname: Kantevari
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D057809:HEK293 Cells; D006801:Humans; D008958:Models, Molecular; D012210:Rhamnose / Q000737:chemistry*; D051247:Sodium-Glucose Transport Proteins / Q000037:antagonists & inhibitors*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D001643:Bridged Bicyclo Compounds; D051247:Sodium-Glucose Transport Proteins; D014230:Triazoles; D012210:Rhamnose