Citation: Wen Jing Zhao, Yong Heng Shi, Gui Long Zhao, Yu Li Wang, Hua Shao, Li Da Tang, Jian Wu Wang. Design, synthesis and in vivo anti-hyperglycemic activity of gem-dimethyl-bearing C-glucosides as SGLT2 inhibitors[J]. Chinese Chemical Letters, ;2011, 22(10): 1215-1218. doi: 10.1016/j.cclet.2011.05.022 shu

Design, synthesis and in vivo anti-hyperglycemic activity of gem-dimethyl-bearing C-glucosides as SGLT2 inhibitors

a School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China;
b Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China;
c School of Pharmacy, Tianjin Medical University, Tianjin 300070, China

Fund Project: The authors are very grateful to Key Projects of Tianjin Science and Technology Support Plan (No.10ZCKFSH01300) for financial support.

A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors, with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the key step. The in vivo anti-hyperglycemic activity was evaluated with mice oral glucose tolerance test (OGTT), and all the synthesized compounds showed significant but less potent anti-hyperglycemic activity than the positive control dapagliflozin.
- Synthesis,
- C-Glucoside,
- SGLT2 inhibitor,
- Anti-hyperglycemic activity,
- gem-Dimethyl
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
3. [3]
  Mengyu Wu , Kewei Ren , Chengyu Zou , Jiacheng Chen , Rui Ma , Chuan Zhu , Chao Feng . A general synthesis of gem–difluorobicyclo[2.1.1]hexanes. Chinese Chemical Letters, 2025, 36(5): 110213-. doi: 10.1016/j.cclet.2024.110213
4. [4]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
5. [5]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
6. [6]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
9. [9]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
10. [10]
  Jiyang Liu , Xiangzhang Tao , Zhenlei Zou , Jia Xu , Hui Shu , Yi Pan , Weigang Zhang , Shengyang Ni , Yi Wang . Modular and practical synthesis of gem-difluoroalkenes via consecutive Ni-catalyzed reductive cross-coupling. Chinese Chemical Letters, 2025, 36(7): 110461-. doi: 10.1016/j.cclet.2024.110461
11. [11]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
12. [12]
  Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
13. [13]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
14. [14]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
15. [15]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
16. [16]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
17. [17]
  Jiang Gong , Fengling Zheng , Hanqing Zhang , Weihan Shu , Hao Wang , Ni Zhang , Pengbing Huang , Chuancai Zhang , Bin Dai . The interfacial effect of SiO₂-Ni₃Mo₃N efficiently catalyzes the low-temperature hydrogenation of dimethyl oxalate to ethanol. Chinese Chemical Letters, 2025, 36(8): 111122-. doi: 10.1016/j.cclet.2025.111122
18. [18]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
19. [19]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
20. [20]
  Wen-Rui Li , Ru-Bing Wang , Huiqiang Wang , Jin-Yao Yong , Yu-Huan Li , Shi-Shan Yu , Shuang-Gang Ma . Ring-reorganization strategy for asymmetric synthesis of sesquiterpenoid illihenin A and its antiviral activity evaluation. Chinese Chemical Letters, 2025, 36(11): 110945-. doi: 10.1016/j.cclet.2025.110945

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1151)
HTML views(42)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return