Novel Ester Derivatives of Lithocolic Acid-3-oxime and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B

doi:10.6023/cjoc201811020

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2106-2116.DOI: 10.6023/cjoc201811020 Previous Articles Next Articles

Notes

新型石胆酸-3-肟酯衍生物及其蛋白酪氨酸磷酸酯酶1B抑制活性

侍术智^a, 梁志鹏^b, 孙建勇^a, 石玉军^a

a 南通大学化学化工学院南通 226019;
b 南通大学分析测试中心南通 226019

收稿日期:2018-11-14 修回日期:2019-01-08 发布日期:2019-03-08
通讯作者: 石玉军 E-mail:ntushyj@163.com

Novel Ester Derivatives of Lithocolic Acid-3-oxime and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B

Shi shuzhi^a, Liang zhipeng^b, Sun jiangyong^a, Shi Yujun^a

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019

Received:2018-11-14 Revised:2019-01-08 Published:2019-03-08
Contact: 10.6023/cjoc201811020 E-mail:ntushyj@163.com

1. Novel Ester Derivatives of Lithocolic Acid-3-oxime and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B.PDF(2606KB)

Abstract

Protein tyrosine phosphatase-1B (PTP1B) is recognized as a potent target for the therapy of diabetes. Lithocolic acid (LCA), a kind of endogenic steroid, was reported as a moderate PTP1B inhibitor. In this paper, 3-hydroxyl of LCA was oxidized, followed by oximating and splicing with cinnamoyl to afford a novel series of derivatives, which were characterized by ¹H NMR, ¹³C NMR and HRMS spectra. The results of bioassays exhibited that most of the titled compounds were active to PTP1B. Among them, compound 12b, the most potent one, has an IC₅₀ of 0.79 µmol•L^-1, about 15-fold more potent than the lead compound. Besides, it also has a selectivity of about 4-fold over T-cell protein tyrosine phosphatase (TCPTP).

Key words: PTP1B Inhibitor, TCPTP, lithocolic acid-3-oxime, Synthesis

Cite this article

Shi shuzhi, Liang zhipeng, Sun jiangyong, Shi Yujun. Novel Ester Derivatives of Lithocolic Acid-3-oxime and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B[J]. Chin. J. Org. Chem., 2019, 39(7): 2106-2116.

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新型石胆酸-3-肟酯衍生物及其蛋白酪氨酸磷酸酯酶1B抑制活性

Novel Ester Derivatives of Lithocolic Acid-3-oxime and Their Inhibitory Activities against Protein Tyrosine Phosphatase 1B

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