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Open AccessArticle

Design, Synthesis and Biological Evaluation of Stilbene Derivatives as Novel Inhibitors of Protein Tyrosine Phosphatase 1B

by Haibing He 1, Yinghua Ge 2, Hong Dai 1,*, Song Cui 1, Fei Ye 1, Jia Jin 2,* and Yujun Shi 1,*
1
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China
2
College of Life Sciences, Zhejiang Sci-Tech University, Hangzhou 310018, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2016, 21(12), 1722; https://doi.org/10.3390/molecules21121722
Received: 26 October 2016 / Revised: 7 December 2016 / Accepted: 12 December 2016 / Published: 16 December 2016
(This article belongs to the Section Medicinal Chemistry)
By imitating the scaffold of lithocholic acid (LCA), a natural steroidal compound displaying Protein Tyrosine Phosphatase 1B (PTP1B) inhibitory activity, a series of stilbene derivatives containing phenyl-substituted isoxazoles were designed and synthesized. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Activities of the title compounds were evaluated on PTP1B and the homologous enzyme TCPTP by using a colorimetric assay. Most of the target compounds had good activities against PTP1B. Among them, compound 29 (IC50 = 0.91 ± 0.33 μM), characterized by a 5-(2,3-dichlorophenyl) isoxazole moiety, exhibited an activity about 14-fold higher than the lead compound LCA and a 4.2-fold selectivity over TCPTP. Compound 29 was identified as a competitive inhibitor of PTP1B with a Ki value of 0.78 μM in enzyme kinetic studies. View Full-Text
Keywords: protein tyrosine phosphatase 1B (PTP1B); lithocholic acid; stilbene; inhibitor protein tyrosine phosphatase 1B (PTP1B); lithocholic acid; stilbene; inhibitor
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MDPI and ACS Style

He, H.; Ge, Y.; Dai, H.; Cui, S.; Ye, F.; Jin, J.; Shi, Y. Design, Synthesis and Biological Evaluation of Stilbene Derivatives as Novel Inhibitors of Protein Tyrosine Phosphatase 1B. Molecules 2016, 21, 1722.

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