Synthesis and Hypoglycemic Activity of 3,6-Dideoxydapagliflozin
Author(s): Zhang Lingyu, Li Xiugang, Wang Yuli, Liu Yuqiang, Xie Yafei, Gao Zhigang, Wei Peng, Xu Weiren, Tang Lida, Zhao Guilong, Department of Material and Chemical Engineering, Tongren University, Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology
Pages: 638-643
Year: 2015 Issue: 7
Journal: Chemistry
Keyword: SGLT2 inhibitor; Dideoxy; Synthesis; Hypoglycemic activity;
Abstract: 3,6-Dideoxydapagliflozin( 9) was synthesized by two routes starting from dapagliflozin,and 3,6-dideoxy functionality of 9 was further confirmed by NOE. In vitro inhibitory assay against h SGLT2 and rat urinary glucose excretion test found that 9 was almost completely inactive against h SGLT2,indicating that deletion of both 3-OH and 6-OH in the glucose moiety of SGLT2 inhibitors cannot be tolerated and would lead to complete loss of bioactivity.
Pages: 638-643
Year: 2015 Issue: 7
Journal: Chemistry
Keyword: SGLT2 inhibitor; Dideoxy; Synthesis; Hypoglycemic activity;
Abstract: 3,6-Dideoxydapagliflozin( 9) was synthesized by two routes starting from dapagliflozin,and 3,6-dideoxy functionality of 9 was further confirmed by NOE. In vitro inhibitory assay against h SGLT2 and rat urinary glucose excretion test found that 9 was almost completely inactive against h SGLT2,indicating that deletion of both 3-OH and 6-OH in the glucose moiety of SGLT2 inhibitors cannot be tolerated and would lead to complete loss of bioactivity.
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