| Autor: |
Jia M; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Zhao R; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Xu B; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Yan W; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Chu F; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Gu H; Department of Pharmacology , Xuanwu Hospital of Capital Medical University , Key Laboratory for Neurodegenerative Diseases of Ministry of Education , Beijing 100053 , China., Xie T; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Xiang H; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Ren J; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Chen D; Beijing lam ze biological technology co, LTD , 102500 , China., Wang P; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com., Lei H; School of Chinese Pharmacy , Beijing University of Chinese Medicine , Beijing 100102 , China . Email: hm_lei@126.com ; Email: wpl581@126.com. |
| Abstrakt: |
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 LD 50 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. |
