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
Neurotropic, neuroprotective and antioxidant actions of the enantiomers and the racemate of 2-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)-4-methylthiobutanoic acid were investigated. Only (+)-(S)-2-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)-4-methylthiobutanoic acid was found to have neuroprotective properties. A distereoselective synthesis of enantiomers and racemate was performed by condensations of (S), (R) and (R,S)-N-carbamoylmethionines with 4,5-dihydroxyimidazolidin-2-one (DHI), respectively. By the X-ray method, the major racemate was proved to crystallize from water as a conglomerate. No antioxidant activity was revealed.
Assuntos
Butiratos/química , Butiratos/síntese química , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/síntese química , Animais , Antioxidantes/síntese química , Antioxidantes/química , Antioxidantes/farmacologia , Butiratos/farmacologia , Masculino , Camundongos , Estrutura Molecular , Fármacos Neuroprotetores/farmacologiaRESUMO
Water-soluble sulfate polysalts of carboxymethyl cellulose and tertiary aminomethyl derivatives of 2-isobornyl-4-methylphenol was obtained. For the synthesized conjugates investigated in vivo anti-inflammatory activity in the test of acute formalin inflammation and analgesic activity in tests the "hot plate" and "vinegar cramps".
Assuntos
Carboximetilcelulose Sódica , Inflamação , Medição da Dor/efeitos dos fármacos , Dor , Animais , Carboximetilcelulose Sódica/análogos & derivados , Carboximetilcelulose Sódica/síntese química , Carboximetilcelulose Sódica/química , Carboximetilcelulose Sódica/farmacologia , Formaldeído/toxicidade , Inflamação/induzido quimicamente , Inflamação/tratamento farmacológico , Camundongos , Dor/tratamento farmacológico , Dor/patologia , Solubilidade , Sulfatos/síntese química , Sulfatos/química , Sulfatos/farmacologia , Água/químicaRESUMO
The immunotropic effect of the 2,3-seco derivatives of allobetulon, betulonic acid, and the methyl ester of betulonic acid were studied. It was found that the highest activity is shown by compounds with an oleanane fragment. The presence of a free C28-carboxyl group enhances the activity of lupeolic 2,3-seco derivatives. A significant contribution to the development of the immune response is introduced by a functional group at the C3 atom in the A ring - the C3-carboxy derivatives intensify the processes of antibody production and alter the number and ratio of leukocyte forms. It is shown that 2,3-seco-1-cyano-19beta,28-epoxy-18alpha-olean-3-oic acid stimulates humoral immunity with a positive influence on hematopoiesis.
Assuntos
Fatores Imunológicos/farmacologia , Triterpenos/farmacologia , Animais , Formação de Anticorpos/efeitos dos fármacos , Feminino , Imunidade Humoral/efeitos dos fármacos , Fatores Imunológicos/síntese química , Fatores Imunológicos/química , Camundongos , Ácido Oleanólico/síntese química , Ácido Oleanólico/química , Ácido Oleanólico/farmacologia , Relação Estrutura-Atividade , Triterpenos/síntese química , Triterpenos/químicaRESUMO
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.
Assuntos
Imunossupressores/síntese química , Triterpenos/síntese química , Animais , Formação de Anticorpos , Ésteres , Imunidade Celular , Imunossupressores/química , Imunossupressores/imunologia , Cetonas/síntese química , Cetonas/imunologia , Espectroscopia de Ressonância Magnética , Masculino , Camundongos , Espectrofotometria Infravermelho , Relação Estrutura-Atividade , Triterpenos/química , Triterpenos/imunologiaRESUMO
2-Alkylaminomethylene-19beta,28-epoxyolean-3-ones were obtained by interaction of 2-hydroxymethylene-19beta,28-epoxyolean-3-one with aliphatic amines. Some of the resulting substances exhibit immunotropic activity.
