gem‐Dimethyl‐bearing C‐Glucosides as Sodium‐glucose Co‐transporter 2 (SGLT2) Inhibitors |
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| Authors: | Yongheng Shi Prof. Dr. Guilong Zhao Yuanyuan Lou Yuli Wang Hua Shao Wei Liu Weiren Xu Lida Tang |
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| Affiliation: | 1. School of Pharmacy, Tianjin Medical University, Tianjin 300070, China;2. Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China;3. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042, China |
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| Abstract: | Three novel gem‐dimethyl C‐glucosides were designed as sodium‐glucose co‐transporter 2 (SGLT2) inhibitors, and their syntheses started from D‐glucose and three 2‐substituted‐5‐bromobenzoic acids were achieved via a facile 8‐step protocol, with the key step being anhydrous aluminum chloride‐catalyzed Friedel‐Crafts alkylation of tertiary alcohols and phenetol. These three SGLT2 inhibitors were evaluated in vivo with a mice oral glucose tolerance test (OGTT), and the anti‐hyperglycemic activities of all these three compounds were comparable with that of the positive control Dapagliflozin. |
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| Keywords: | sodium‐glucose co‐transporter 2 (SGLT2) gem‐dimethyl, synthesis Friedel‐Crafts alkylation oral glucose tolerance test (OGTT) |
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