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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 12: 2888 - 2894

DOI: https://doi.org/10.6023/cjoc201611016

ARTICLE

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

  • He Haibing ,
  • Dai Hong ,
  • Ge Yinghua ,
  • Shi Lei ,
  • Zou Zheng ,
  • Ye Fei ,
  • Jin Jia ,
  • Shi Yujun
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
    b College of Life Sciences, Zhejiang Sci-Tech University, Hangzhou 310018

Received date: 2016-11-14

  Revised date: 2016-12-07

  Online 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).

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Abstract

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]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2888 -2894 . DOI: 10.6023/cjoc201611016

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