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

doi:10.1039/c4ob01319k

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

^*Corresponding author for this work

Department of Pharmacology, Manipal College of Pharmaceutical Sciences, Manipal

Research output: Contribution to journal › Article › peer-review

10 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 language	English
Pages (from-to)	8415-8421
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	42
DOIs	https://doi.org/10.1039/c4ob01319k
Publication status	Published - 14-11-2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Putapatri, Siddamal Reddy

AU - Kanwal, Abhinav

AU - Sridhar, Balasubramanian

AU - Banerjee, Sanjay K.

AU - Kantevari, Srinivas

N1 - Publisher Copyright: © the Partner Organisations 2014.

PY - 2014/11/14

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N2 - 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

AB - 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

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

Abstract

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