title: [Synthesis and biological activity of 2,3-secotriterpene acid mono- and diamides].
abstract: Four types of amide (C3; C28; C3-C28) conjugates based on 2,3-seco-18alphaH-oleanane and 2,3-secolupane mono- and dicarboxylic acids were synthesized. The range of diamide derivatives was supplemented with C3-C3' and C28-C28' dicondensed amides with two A-secotriterpene backbones educed by reacting monocarboxylic A-secoacids with biogenic amino acid lysine. Compounds with inhibitory action against herpes virus reproduction (EC50 8.7 and 4.1 McM) were found among the synthesized mono- and diamide derivatives containing an ethyl-beta-alaninate fragment. It has been ascertained that diamide with ethyl-beta-alaninate fragment combines anti-herpes virus properties and anti-HIV activity (EC50 5.1 McM). For active compounds, the maximum non-toxic concentration (MNTC)/EC50 ratios ranges from 9.7 to 40.8. The synthesized amide conjugates do not exhibit any marked cytotoxic effects against human tumor cell lines rabdomiosarcoma RD TE32, A549 lung carcinoma and melanoma MS.
authors: I A
authors: IA
authors: Tolmacheva
authors: E V
authors: EV
authors: Igosheva
authors: Iu B
authors: IuB
authors: Vikharev
authors: V V
authors: VV
authors: Grishko
authors: O V
authors: OV
authors: Savinova
authors: E I
authors: EI
authors: Boreko
authors: V F
authors: VF
authors: Eremin
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects; D000094062:Betulinic Acid
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009828:Oleanolic Acid; D014315:Triterpenes; C118308:betulonic acid; D000094062:Betulinic Acid