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Issue 1, 2017
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Synthesis and biological activity evaluation of novel peroxo-bridged derivatives as potential anti-hepatitis B virus agents

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Abstract

Previous studies have demonstrated that natural steroid compounds containing a peroxide bridge exhibited potential anti-hepatitis B virus activity. To continue our research, a simple and regioselective methodology, using Eosin Y as a clean photosensitized oxidation catalyst, was developed for the synthesis of a peroxide bridge in steroids. The method that using Eosin Y as the catalyst was exposed to visible light and furbished in high yields, did not involve tedious work-up or purification, and avoided using environmentally hazardous solvents. It can be regarded as a green protocol. Moreover, a series of cholesterol and β-sitosterol derivatives containing a peroxide bridge were synthesized using this method and screened for their anti-HBV activity. Among the compounds synthesized in this research, 5α,8α-cyclicobioxygen-6-vinyl-3-oxo-cholesterone (1f, 3.13 μg ml−1) had the most potent activity with inhibition rates of 77.45% ± 6.01% and 58.73% ± 8.64% on the secretion of HBsAg and HBeAg antigens, respectively, after 8 days. Further acute toxicity test showed that the LD50 value of compound 1f was 362.46 mg kg−1 after an intraperitoneal injection in mice. Moreover, structure–activity relationships of cholesterol and β-sitosterol derivatives were briefly discussed.

Graphical abstract: Synthesis and biological activity evaluation of novel peroxo-bridged derivatives as potential anti-hepatitis B virus agents

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Publication details

The article was received on 20 Jun 2016, accepted on 08 Oct 2016 and first published on 19 Oct 2016


Article type: Research Article
DOI: 10.1039/C6MD00344C
Citation: Med. Chem. Commun., 2017,8, 148-151
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    Synthesis and biological activity evaluation of novel peroxo-bridged derivatives as potential anti-hepatitis B virus agents

    M. Jia, R. Zhao, B. Xu, W. Yan, F. Chu, H. Gu, T. Xie, H. Xiang, J. Ren, D. Chen, P. Wang and H. Lei, Med. Chem. Commun., 2017, 8, 148
    DOI: 10.1039/C6MD00344C

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