Synthesis and Biological Evaluation of Phosphotyrosyl Mimetic as a Novel Protein Tyrosine Phosphatase 1B Inhibitor

doi:10.6023/cjoc201412027

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1363-1369.DOI: 10.6023/cjoc201412027 Previous Articles Next Articles

Notes

一种磷酸酪氨酸拟似物类蛋白酪氨酸磷酸酶1B 抑制剂的合成及体外活性评价

周晓伟^a, 唐延婷^b, 桑锋^c, 张秀利^a, 李立新^b, 周红刚^c, 刘伟^d, 戴玉洁^a

a 天津科技大学生物工程学院天津 300457;
b 天津国际生物医药联合研究院高通量药物筛选中心天津 300457;
c 南开大学药学院天津 300071;
d 天津科技大学理学院天津 300457

收稿日期:2014-12-16 修回日期:2015-01-26 发布日期:2015-02-05
通讯作者: 刘伟 E-mail:liuwei2006@tust.edu.cn
基金资助:
国家自然科学基金(Nos. 81102374, 21272171, 21302139)资助项目.

Synthesis and Biological Evaluation of Phosphotyrosyl Mimetic as a Novel Protein Tyrosine Phosphatase 1B Inhibitor

Zhou Xiaowei^a, Tang Yanting^b, Sang Feng^c, Zhang Xiuli^a, Li Lixin^b, Zhou Honggang^c, Liu Wei^d, Dai Yujie^a

a College of Biotechnology, Tianjin University of Science and Technology, Tianjin 300457;
b High Throughput Molecular Drug Discovery Center, Tianjin International Joint Academy of Biotechnology and Medicine, TEDA, Tianjin 300457;
c College of Pharmacy, Nankai University, Tianjin 300071;
d College of Sciences, Tianjin University of Science and Technology, Tianjin 300457

Received:2014-12-16 Revised:2015-01-26 Published:2015-02-05
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 81102374, 21272171, 21302139).

1. Synthesis and Biological Evaluation of Phosphotyrosyl Mimetic as a Novel Protein Tyrosine Phosphatase 1B Inhibitor.PDF(1924KB)

Abstract

Protein tyrosine phosphatase 1B (PTP1B) has been known to be a promising target for the treatment of type 2 diabetes and obesity. According to the reported phosphotyrosyl mimetics A, a new PTP1B inhibitor 1 was designed via computer-assisted drug design. The target compound 1 was achieved through eleven steps with Negishi cross-coupling reaction, diastereoselective sulfinylimine enolate addition reaction and the Dess-Martin oxidation as key steps. The compound 1 inhibited PTP1B competitively with an IC₅₀ value of 54.17 μmol·L^-1 in vitro.

Key words: protein tyrosine phosphatase 1B (PTP1B), phosphotyrosyl mimetics, inhibitors

Cite this article

Zhou Xiaowei, Tang Yanting, Sang Feng, Zhang Xiuli, Li Lixin, Zhou Honggang, Liu Wei, Dai Yujie. Synthesis and Biological Evaluation of Phosphotyrosyl Mimetic as a Novel Protein Tyrosine Phosphatase 1B Inhibitor[J]. Chin. J. Org. Chem., 2015, 35(6): 1363-1369.

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一种磷酸酪氨酸拟似物类蛋白酪氨酸磷酸酶1B 抑制剂的合成及体外活性评价

Synthesis and Biological Evaluation of Phosphotyrosyl Mimetic as a Novel Protein Tyrosine Phosphatase 1B Inhibitor

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