title: Betulin and ursolic acid synthetic derivatives as inhibitors of Papilloma virus.
abstract: 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).
authors.affiliation: Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71, Prospect Oktyabrya, 450054 Ufa, Russian Federation. obf@anrb.ru
authors.forename: Oxana B
authors.initials: OB
authors.lastname: Kazakova
authors.forename: Gul'nara V
authors.initials: GV
authors.lastname: Giniyatullina
authors.forename: Emil Yu
authors.initials: EY
authors.lastname: Yamansarov
authors.forename: Genrikh A
authors.initials: GA
authors.lastname: Tolstikov
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D027383:Papillomaviridae / Q000187:drug effects*; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology*; D000097245:Ursolic Acid; D000094062:Betulinic Acid
chemical_list: D000998:Antiviral Agents; D014315:Triterpenes; D000097245:Ursolic Acid; C002503:betulin; D000094062:Betulinic Acid