| Betulin and ursolic acid synthetic derivatives as inhibitors of Papilloma virus. | |
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MedLine Citation:
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PMID: 20558062 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The synthesis of new betulin and ursolic acid derivatives and evaluation of their antiviral activity in vitro is reported. Betulin was modified at positions C-3, C-20 and C-28 to afford the derivatives with nicotinoyl-, methoxycynnamoyl-, alkyne and aminopropoxy-2-cyanoethyl-moieties. The two stage conversion of betulin to the new ursane-type triterpenoid by treatment of allobetulin with Ac(2)O-HClO(4) is suggested. Cyanoethylation of ursonic acid oxime led to cyanoethyloximinoderivative. According to the results of antiviral screening against human papillomavirus type 11 the selectivity index for tested triterpenoids has a range from 10 to 35 with no cellular cytotoxicity, the most remarkable activity was found for 3beta,28-di-O-nicotinoylbetulin. 3Beta,28-dihydroxy-29-norlup-20(30)-yne was also active against HCV replicon (EC(50) 1.32; EC(90) 16.82; IC(50) 12.41; IC(90) >20; SI(50) 9.4; SI(90) >1.19). 28-O-methoxycynnamoylbetulin was active against influenza type A virus (H1N1) (EC(50) 2; IC(50) >200; SI >100). |
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Authors:
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Oxana B Kazakova; Gul'nara V Giniyatullina; Emil Yu Yamansarov; Genrikh A Tolstikov |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-05-25 |
Journal Detail:
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Title: Bioorganic & medicinal chemistry letters Volume: 20 ISSN: 1464-3405 ISO Abbreviation: Bioorg. Med. Chem. Lett. Publication Date: 2010 Jul |
Date Detail:
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Created Date: 2010-07-08 Completed Date: 2010-12-07 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9107377 Medline TA: Bioorg Med Chem Lett Country: England |
Other Details:
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Languages: eng Pagination: 4088-90 Citation Subset: IM |
Copyright Information:
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2010 Elsevier Ltd. All rights reserved. |
Affiliation:
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Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71, Prospect Oktyabrya, 450054 Ufa, Russian Federation. obf@anrb.ru |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Antiviral Agents
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chemistry,
pharmacology* Microbial Sensitivity Tests Papillomaviridae / drug effects* Triterpenes / chemistry, pharmacology* |
| Chemical | |
Reg. No./Substance:
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0/Antiviral Agents; 0/Triterpenes; 473-98-3/betulin; 77-52-1/ursolic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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