RESUMO
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.
Assuntos
Amidas/síntese química , Antineoplásicos/síntese química , Antivirais/química , Ácido Oleanólico/análogos & derivados , Triterpenos/química , Amidas/química , Amidas/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Antivirais/síntese química , Antivirais/farmacologia , Linhagem Celular Tumoral , HIV-1/efeitos dos fármacos , Humanos , Ácido Oleanólico/síntese química , Ácido Oleanólico/química , Ácido Oleanólico/farmacologia , Simplexvirus/efeitos dos fármacos , Triterpenos/síntese química , Triterpenos/farmacologia , Replicação Viral/efeitos dos fármacosRESUMO
Novel 2,3-seco-triterpenic amides were prepared by the interaction of the chloride of 2,3-seco-l-cyano-19beta,28-epoxy-18alpha-oleane-3-oic acid with primary amines and synthetic and biogenic amino acids. A cytotoxic triterpenic conjugate with a residue of the ethyl ester of beta-alanine was found among the synthesized nitrogen-containing derivatives. Treatment with this conjugate in a concentration of 100 muM resulted in the 45.5% survival of melanoma cells in the medium.
Assuntos
Amidas/síntese química , Antineoplásicos/síntese química , Compostos de Epóxi/síntese química , Triterpenos/síntese química , Amidas/química , Amidas/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Compostos de Epóxi/química , Compostos de Epóxi/farmacologia , Humanos , Triterpenos/química , Triterpenos/farmacologiaRESUMO
New lupane beta-enaminoketones were synthesized by interaction of methyl 2-hydroxymethylene-3-oxolup-20(29)-en-28-oate with aliphatic amines. Immunotropic activity was found for some of these compounds.
