Structure-activity relationships of 3-O-β-chacotriosyl ursolic acid derivatives as novel H5N1 entry inhibitors

European Journal of Medicinal Chemistry
Gaopeng SongShuwen Liu

Abstract

A series of methyl ursolate 3-O-β-chacotrioside analogs have been designed, synthesized and evaluated as H5N1 entry inhibitors based on a small molecule inhibitor saponin 3 previously discovered by us. Detailed structure-activity relationships (SARs) studies on the aglycone of compound 3 indicated that both the type of pentacyclic triterpene and the subtle modification of ursolic acid as an aglycon had key influences on the antiviral activity. These results suggested that either the introduction of a disubstituted amide structure at the 17-COOH of ursolic acid or alteration of the C-3 configuration of ursolic acid from 3β-to 3α-forms was helpful to significantly improve the selective index while keeping their antiviral activities.

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Citations

Jan 19, 2016·Life Sciences·Dharambir KashyapAnil K Sharma
Dec 6, 2016·Expert Opinion on Investigational Drugs·Li-Yan ZengShuwen Liu
Jul 18, 2020·Medicinal Research Reviews·Zhi-Jun ZhangRong-Tao Li
Oct 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yu-Pu Juang, Pi-Hui Liang
Aug 8, 2021·International Journal of Molecular Sciences·Muhammed Muhsin VarikkodanTzong-Yuan Wu
Feb 3, 2018·Journal of Natural Products·Christina E MairJudith M Rollinger

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