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Synthesis and biological evaluation of benzocyclobutane-C-glycosides as potent and orally active SGLT1/SGLT2 dual inhibitors
Journal article   Peer reviewed

Synthesis and biological evaluation of benzocyclobutane-C-glycosides as potent and orally active SGLT1/SGLT2 dual inhibitors

Gee-Hong Kuo, Micheal D Gaul, Yin Liang, June Z Xu, Fuyong Du, Pamela Hornby, Guozhang Xu, Jenson Qi, Nathaniel Wallace, Seunghun Lee, …
Bioorganic & medicinal chemistry letters, v 28(7), pp 1182-1187
15 Apr 2018
PMID: 29523385
url
https://doi.org/10.7270/q2cj8h51View
Open

Abstract

Administration, Oral Animals Benzene Derivatives - administration & dosage Benzene Derivatives - chemistry Benzene Derivatives - pharmacology Cyclobutanes - administration & dosage Cyclobutanes - chemistry Cyclobutanes - pharmacology Dogs Dose-Response Relationship, Drug Glycosides - administration & dosage Glycosides - chemistry Glycosides - pharmacology Haplorhini Humans Mice Molecular Structure Rats Sodium-Glucose Transporter 1 - antagonists & inhibitors Sodium-Glucose Transporter 1 - metabolism Sodium-Glucose Transporter 2 - metabolism Sodium-Glucose Transporter 2 Inhibitors Structure-Activity Relationship
Synthesis and biological evaluation of benzocyclobutane-C-glycosides as potent and orally active SGLT1/SGLT2 dual inhibitors are described. Compound 19 showed high inhibitory potency at SGLT1 (IC  = 45 nM), and excellent potency at SGLT2 (IC  = 1 nM). It also displayed excellent PK profiles in mice, rats, dogs and monkeys (F = 78-107%). In SD rats, compound 19 treatments significantly reduced blood glucose levels in a dose-dependent manner. In ZDF rats, compound 19 displayed anti-hyperglycemic effect up to 24 h. Therefore, compound 19 may serve as valuable pharmacological tool, and potential use as a treatment for metabolic syndrome.

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Web of Science research areas
Chemistry, Medicinal
Chemistry, Organic
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