Betulin and ursolic acid synthetic derivatives as inhibitors of Papilloma virus

✍ Scribed by Oxana B. Kazakova; Gul’nara V. Giniyatullina; Emil Yu. Yamansarov; Genrikh A. Tolstikov

• Book ID: 104004464
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 187 KB
• Volume: 20
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/j.bmcl.2010.05.083

✦ Synopsis

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 cytotoxicite, the most remarkable activity was found for 3b,28-di-O-nicotinoylbetulin. 3b,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).