[Synthesis and biological activity of 2,3-secotriterpene acid mono- and diamides]

Autor: I A, Tolmacheva, E V, Igosheva, Iu B, Vikharev, V V, Grishko, O V, Savinova, E I, Boreko, V F, Eremin
Rok vydání: 2013
Předmět:
Zdroj: Bioorganicheskaia khimiia. 39(2)
ISSN: 0132-3423
Popis: 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.
Databáze: OpenAIRE