Design, syntheses, and SAR studies of carbocyclic analogues of sergliflozin as potent sodium-dependent glucose cotransporter 2 inhibitors

Tony K.M. Shing; Wai Lung Ng; Judy Y.W. Chan; Clara B.S. Lau

doi:10.1002/anie.201302543

Design, syntheses, and SAR studies of carbocyclic analogues of sergliflozin as potent sodium-dependent glucose cotransporter 2 inhibitors

Tony K.M. Shing, Wai Lung Ng, Judy Y.W. Chan, Clara B.S. Lau

Department of Chemistry

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

14 Citations (Scopus)

Abstract

Combating diabetes: A small-molecule carbohydrate mimic, pseudo-sergliflozin, was synthesized effectively by a regio- and stereoselective allylic substitution reaction. It was found to be a potent and selective inhibitor of a transporter protein - sodium-dependent glucose cotransporter 2 (SGLT2) - which is responsible for glucose reabsorption in the human body. It could be a lead compound for further development into an antidiabetic agent.

Original language	English
Pages (from-to)	8401-8405
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	32
DOIs	https://doi.org/10.1002/anie.201302543
Publication status	Published - 2013 Aug 5

Keywords

SGLT2
allylation
antidiabetics
carbohydrate mimics
diastereoselectivity

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201302543

Fingerprint Dive into the research topics of 'Design, syntheses, and SAR studies of carbocyclic analogues of sergliflozin as potent sodium-dependent glucose cotransporter 2 inhibitors'. Together they form a unique fingerprint.

Cite this

@article{207c145929d4436d8dbc2b13d8d6b2a8,

title = "Design, syntheses, and SAR studies of carbocyclic analogues of sergliflozin as potent sodium-dependent glucose cotransporter 2 inhibitors",

abstract = "Combating diabetes: A small-molecule carbohydrate mimic, pseudo-sergliflozin, was synthesized effectively by a regio- and stereoselective allylic substitution reaction. It was found to be a potent and selective inhibitor of a transporter protein - sodium-dependent glucose cotransporter 2 (SGLT2) - which is responsible for glucose reabsorption in the human body. It could be a lead compound for further development into an antidiabetic agent.",

keywords = "SGLT2, allylation, antidiabetics, carbohydrate mimics, diastereoselectivity",

author = "Shing, {Tony K.M.} and Ng, {Wai Lung} and Chan, {Judy Y.W.} and Lau, {Clara B.S.}",

year = "2013",

month = aug,

day = "5",

doi = "10.1002/anie.201302543",

language = "English",

volume = "52",

pages = "8401--8405",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "32",

}

TY - JOUR

T1 - Design, syntheses, and SAR studies of carbocyclic analogues of sergliflozin as potent sodium-dependent glucose cotransporter 2 inhibitors

AU - Shing, Tony K.M.

AU - Ng, Wai Lung

AU - Chan, Judy Y.W.

AU - Lau, Clara B.S.

PY - 2013/8/5

Y1 - 2013/8/5

N2 - Combating diabetes: A small-molecule carbohydrate mimic, pseudo-sergliflozin, was synthesized effectively by a regio- and stereoselective allylic substitution reaction. It was found to be a potent and selective inhibitor of a transporter protein - sodium-dependent glucose cotransporter 2 (SGLT2) - which is responsible for glucose reabsorption in the human body. It could be a lead compound for further development into an antidiabetic agent.

AB - Combating diabetes: A small-molecule carbohydrate mimic, pseudo-sergliflozin, was synthesized effectively by a regio- and stereoselective allylic substitution reaction. It was found to be a potent and selective inhibitor of a transporter protein - sodium-dependent glucose cotransporter 2 (SGLT2) - which is responsible for glucose reabsorption in the human body. It could be a lead compound for further development into an antidiabetic agent.

KW - SGLT2

KW - allylation

KW - antidiabetics

KW - carbohydrate mimics

KW - diastereoselectivity

UR - http://www.scopus.com/inward/record.url?scp=84882244111&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84882244111&partnerID=8YFLogxK

U2 - 10.1002/anie.201302543

DO - 10.1002/anie.201302543

M3 - Article

C2 - 23784919

AN - SCOPUS:84882244111

VL - 52

SP - 8401

EP - 8405

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 32

ER -