title: Functionalization, cyclization and antiviral activity of A-secotriterpenoids.
abstract: Triterpene derivatives with an α,β-alkenenitrile moiety in the five-membered ring A have been synthesized by nitrile anion cyclizations of 1-cyano-2,3-secotriterpenoids. Oxime-containing precursors, 2,3-secointermediates and five-membered ring A products of cyclizations were screened for in vitro antiviral activity against enveloped viruses - influenza A virus and human immunodeficiency virus type I (HIV-1). Lupane ketoxime and the 2,3-secolupane C-3 aldoxime which possess antiviral activities against both influenza A virus (EC50 12.9-18.2 μM) and HIV-1 (EC50 0.06 μM) were the most promising compounds.
authors.affiliation: Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 3 Akad. Korolev Str., 614013 Perm, Russia. Electronic address: grishvic@gmail.com.
authors.forename: Victoria V
authors.initials: VV
authors.lastname: Grishko
authors.affiliation: Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 3 Akad. Korolev Str., 614013 Perm, Russia.
authors.forename: Natalia V
authors.initials: NV
authors.lastname: Galaiko
authors.affiliation: Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 3 Akad. Korolev Str., 614013 Perm, Russia.
authors.forename: Irina A
authors.initials: IA
authors.lastname: Tolmacheva
authors.affiliation: The Republican Research and Practical Center for Epidemiology and Microbiology, 23 Filimonov Str., 220114 Minsk, Belarus.
authors.forename: Igor I
authors.initials: II
authors.lastname: Kucherov
authors.affiliation: The Republican Research and Practical Center for Epidemiology and Microbiology, 23 Filimonov Str., 220114 Minsk, Belarus.
authors.forename: Vladimir F
authors.initials: VF
authors.lastname: Eremin
authors.affiliation: The Republican Research and Practical Center for Epidemiology and Microbiology, 23 Filimonov Str., 220114 Minsk, Belarus.
authors.forename: Eugene I
authors.initials: EI
authors.lastname: Boreko
authors.affiliation: The Republican Research and Practical Center for Epidemiology and Microbiology, 23 Filimonov Str., 220114 Minsk, Belarus.
authors.forename: Olga V
authors.initials: OV
authors.lastname: Savinova
authors.affiliation: Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 20 Kovalevskaya Str., 620219 Ekaterinburg, Russia.
authors.forename: Pavel A
authors.initials: PA
authors.lastname: Slepukhin
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D003500:Cyclization; D015497:HIV-1 / Q000187:drug effects; D057916:Influenza A Virus, H7N1 Subtype / Q000187:drug effects; D008958:Models, Molecular; D008968:Molecular Conformation; D010091:Oximes / Q000737:chemistry; D013729:Terpenes / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000998:Antiviral Agents; D010091:Oximes; D013729:Terpenes
keywords: 18βH-Glycyrrhetinic acid; A-secotriterpenoids; Antiviral activity; Betulin; HIV-1; Influenza virus; Nitrile anion cyclizations