Citation: Yu Fei, Wang Qi, Wang Han, Si Long-Long, Liu Jia-Xin, Han Xu, Xiao Su-Long, Zhang Li-He, Zhou De-Min. Synthesis and biological evaluation of echinocystic acid derivatives as HCV entry inhibitors[J]. Chinese Chemical Letters, ;2016, 27(5): 711-713. doi: 10.1016/j.cclet.2016.01.050 shu

Synthesis and biological evaluation of echinocystic acid derivatives as HCV entry inhibitors

Yu Fei ^a,, ,
Wang Qi ^b ,
Wang Han ^b ,
Si Long-Long ^b ,
Liu Jia-Xin ^a ,
Han Xu ^b ,
Xiao Su-Long ^b ,
Zhang Li-He ^b ,
Zhou De-Min ^b,,

a.
Medical Faculty of Kunming University of Science and Technology, Kunming 650500, China
b.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China

Corresponding author: Yu Fei, feiyuz8@163.com Zhou De-Min, deminzhou@bjmu.edu.cn
Received Date: 26 June 2015
Revised Date: 14 December 2015
Accepted Date: 23 January 2016
Available Online: 6 May 2016

Figures(4)

A series of echinocystic acid (EA) 28-COOH derivatives was synthesized, and their anti-HCV entry activity was evaluated by HCVpp and VSVpp entry assay. It was found that some of them showed moderate anti-HCV entry activity, especially compound 12, and these modifications also removed the undesired hemolytic effect.
- Triterpene,
- Echinocystic acid,
- HCV entry inhibitors,
- Hemolysis
1. [1]
  Sy T., Jamal M.M.. Epidemiology of hepatitis C virus (HCV) infection[J]. Int. J. Med. Sci., 2006,3:41-46.
2. [2]
  Shepard C.W., Finelli L., Alter M.J.. Global epidemiology of hepatitis C virus infection[J]. Lancet Infect. Dis., 2005,5:558-567.
3. [3]
  Sheridan C.. New Merck and Vertex drugs raise standard of care in hepatitis C[J]. Nat. Biotechnol., 2011,29:553-554.
4. [4]
  Fried M., Shiffman M., Reddy K.. Peginterferon alfa-2a plus ribavirin for chronic hepatitis C virus infection[J]. New Engl. J. Med., 2002,347:975-982.
5. [5]
  Di Bisceglie A.M., McHutchison J., Rice C.M.. New therapeutic strategies for hepatitis C[J]. Hepatology, 2002,35:224-231.
6. [6]
  Thompson A., McHutchison J.. Antiviral resistance and specifically targeted therapy for HCV (STAT-C)[J]. J. Viral Hepatitis, 2009,16:377-387.
7. [7]
  Wong-Staal F., Syder A.J., McKelvy J.F.. Targeting HCV entry for development of therapeutics[J]. Viruses, 2010,2:1718-1733.
8. [8]
  Yu F., Wang Q., Zhang Z.. Development of oleanane-type triterpenes as a new class of HCV nntry inhibitors[J]. J. Med. Chem., 2013,56:4300-4319.
9. [9]
  Mittapalli G.K., Jackson A., Zhao F.. Discovery of highly potent small molecule hepatitis C virus entry inhibitors[J]. Bioorg. Med. Chem. Lett., 2011,21:6852-6855.
10. [10]
  Yu F., Peng Y., Wang Q.. Development of bivalent oleanane-type triterpenes as potent HCV entry inhibitors[J]. Eur. J. Med. Chem., 2014,77:258-268.
11. [11]
  Wang H., Wang Q., Xiao S.. Elucidation of the pharmacophore of echinocystic acid, a new lead for blocking HCV entry[J]. Eur. J. Med. Chem., 2013,64:160-168.
12. [12]
  Yang J., Zhou D., Wong-Staal F.. Screening of small-molecule compounds as inhibitors of HCV entry[J]. Meth. Mol. Biol., 2009,510:295-304.
13. [13]
  Bartosch B., Dubuisson J., Cosset F.. Infectious hepatitis C virus pseudo-particles containing functional E1-E2 envelope protein complexes[J]. J. Exp. Med., 2003,197:633-642.
14. [14]
  Hsu M., Zhang J., Flint M.. Hepatitis C virus glycoproteins mediate pHdependent cell entry of pseudotyped retroviral particles[J]. Proc. Natl. Acad. Sci. U.S.A., 2003,100:7271-7276.
15. [15]
  Francis G., Kerem Z., Makkar H.P.. The biological action of saponins in animal systems:a review[J]. Br. J. Nutr., 2002,88:587-605.
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