Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

Siddamal Reddy Putapatri, Abhinav Kanwal, Balasubramanian Sridhar, Sanjay K. Banerjee, Srinivas Kantevari

Research output: Contribution to journalArticle

6 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)8415-8421
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number42
DOIs
Publication statusPublished - 14-11-2014

Fingerprint

Sodium-Glucose Transport Proteins
Rhamnose
transporter
Triazoles
cycloaddition
sugars
glucose
inhibitors
Deoxy Sugars
sodium
acids
Cycloaddition
Cycloaddition Reaction
synthesis
Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Putapatri, Siddamal Reddy ; Kanwal, Abhinav ; Sridhar, Balasubramanian ; Banerjee, Sanjay K. ; Kantevari, Srinivas. / Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 42. pp. 8415-8421.
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Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors. / Putapatri, Siddamal Reddy; Kanwal, Abhinav; Sridhar, Balasubramanian; Banerjee, Sanjay K.; Kantevari, Srinivas.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 42, 14.11.2014, p. 8415-8421.

Research output: Contribution to journalArticle

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