Design, Synthesis of Betulin Derivatives Containing 5-Phenyl-3-isoxazole and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B

doi:10.6023/cjoc201611016

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (12): 2888-2894.DOI: 10.6023/cjoc201611016 Previous Articles Next Articles

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含取代异噁唑的白桦脂醇衍生物的设计、合成及其蛋白酪氨酸磷酸酯酶1B抑制活性

何海兵^a, 戴红^a, 葛英花^b, 施磊^a, 邹政^a, 叶飞^b, 金甲^b, 石玉军^a

a 南通大学化学化工学院南通 226019;
b 浙江理工大学生命科学学院杭州 310018

收稿日期:2016-11-14 修回日期:2016-12-07 发布日期:2016-12-12
通讯作者: 金甲, 石玉军 E-mail:aukaukauk@163.com;ntushyj@163.com
基金资助:
江苏省自然科学基金青年（No. BK20140425）、南通大学引进人才科研启动费（No. 03080694）资助项目.

Design, Synthesis of Betulin Derivatives Containing 5-Phenyl-3-isoxazole and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B

He Haibing^a, Dai Hong^a, Ge Yinghua^b, Shi Lei^a, Zou Zheng^a, Ye Fei^b, Jin Jia^b, Shi Yujun^a

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b College of Life Sciences, Zhejiang Sci-Tech University, Hangzhou 310018

Received:2016-11-14 Revised:2016-12-07 Published:2016-12-12
Supported by:
Project supported by the Science Fund for Young Scholar of Jiangsu Province (No. BK20140425) and the Initiating Fund for Introduced Talents of Nantong University (No. 03080694).

Protein tyrosine phosphatase-1B (PTP1B) is recognized as a potent target for the therapy of diabetes. By introducing substituted 5-phenyl-3-isoxazole ring to the 3-position of betulin, a series of novel compounds were designed, synthesized and characterized by ¹H NMR, ¹³C NMR and HRMS. The results of bioassays exhibited that most of the titled compounds were active to PTP1B. Among them, compound 15h has an IC₅₀ of 0.98 μmol·L^-1 against PTP1B and a 4-fold selectivity over T cell protein tyrosine phosphatase (TCPTP).

Key words: PTP1B Inhibitor, TCPTP, Betulin, Synthesis

Cite this article

He Haibing, Dai Hong, Ge Yinghua, Shi Lei, Zou Zheng, Ye Fei, Jin Jia, Shi Yujun. Design, Synthesis of Betulin Derivatives Containing 5-Phenyl-3-isoxazole and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B[J]. Chin. J. Org. Chem., 2016, 36(12): 2888-2894.

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含取代异噁唑的白桦脂醇衍生物的设计、合成及其蛋白酪氨酸磷酸酯酶1B抑制活性

Design, Synthesis of Betulin Derivatives Containing 5-Phenyl-3-isoxazole and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B

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