RESUMO
New potentially biologically active amidoethanesulfonamides of betulonic acid were synthesized by the acid chloride method via conjugation of betulonic acid with 2-aminoethanesulfonamides as the free bases.
RESUMO
Under the action of PCl(5), the Beckman rearrangement of a 3 : 1 mixture of Z- and E-ketoximes of 18beta-hydroxydihydroquinopimaric acid resulted in 5'-caprolactam and isomeric caprolactams containing fragments of cyclic ether. Z- and E-ketoximes were separated as acetates. Using a carrageenan inflammation model, we demonstrated that the anti-inflammatory activity of quinopimaric acid derivatives was comparable with that of diclofenac.
Assuntos
Abietanos/síntese química , Anti-Inflamatórios não Esteroides/síntese química , Abietanos/química , Abietanos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antivirais/síntese química , Antivirais/química , Antivirais/farmacologia , Carragenina , Edema/induzido quimicamente , Edema/tratamento farmacológico , Vírus da Influenza A/efeitos dos fármacos , Camundongos , Estereoisomerismo , Relação Estrutura-Atividade , Testes de Toxicidade AgudaRESUMO
The interaction of betulin diacetate with formaldehyde by the Prins reaction in various media was studied. As a result, 3beta,28-di-O-acetyl-30-hydroxymethyl-(20)29-lupene, 3beta-acetyl-28-hydroxy-(20)29-lupene, and 3beta,28-di-O-acetoxy-19-(5',6'-dihydro-2'H-pyran-4'-yl)-20,29,30-trinorlupane were obtained.
Assuntos
Acetatos/química , Formaldeído/química , Triterpenos/química , Ésteres , Espectroscopia de Ressonância Magnética , Espectrofotometria InfravermelhoRESUMO
A reductive transformation of the peroxide products of ozonolysis of derivatives of 3beta-O-acetyl-22(17-->28)-abeo-lupa-17(28),20(29)-diene and the subsequent intramolecular ketalization led to a compound with a trioxane fragment. This is a new approach to a skeletal modification of triterpenoid cycle E. An activity of the synthesized compounds was found toward the viruses of type A influenza and herpes simplex.
Assuntos
Alphainfluenzavirus/efeitos dos fármacos , Antivirais/química , Antivirais/farmacologia , Simplexvirus/efeitos dos fármacos , Triterpenos/química , Triterpenos/farmacologia , Antivirais/síntese química , Catálise , Humanos , Compostos de Rutênio/química , Saponinas/química , Triterpenos/síntese químicaRESUMO
Uraline, a new norditerpenoid alkaloid, was isolated from aerial parts of Delphinium uralense. The structure of 1alpha,7,8-trihydroxy-6beta,14alpha,16beta-trimethoxy-18-N-(2-methyl)succinylanthranoyloxyaconane was ascribed to the new compound on the basis of 1H and 13C NMR, IR, and mass spectra. The known alkaloids methyllycaconitine and delcorine were also isolated from the plant.
Assuntos
Alcaloides/isolamento & purificação , Delphinium/química , Diterpenos/isolamento & purificação , Cromatografia Líquida , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Componentes Aéreos da Planta/química , Extratos Vegetais/químicaRESUMO
The effect of pyridine on the electronic structure and conformational state of cell phosphatidylcholine was studied by the methods of quantum chemistry and 13C NMR spectroscopy. It was shown that the interaction of the pi-system of pyridine electrons with the choline group of phosphatidylcholine leads to the formation of a complex. Changes in the conformational states due to the formation of this complex were revealed.
Assuntos
Fosfatidilcolinas/química , Piridinas/química , Espectroscopia de Ressonância Magnética , Conformação Molecular , Estrutura Molecular , Teoria QuânticaRESUMO
The assignment of NMR resonances of lupane triterpenoids was refined by the example of 3,28-dinicotinoylbetulin, obtained by acylation of betulin. Hepatoprotective, untiulcer, antiinflammatory, reparative, and anti-HIV activities were found for the compound. In addition, it was demonstrated to have immunomodulatory activity, for the first time detected among lupane triterpenoids. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2002, vol. 28, no. 6; see also http://www.maik.ru.
Assuntos
Adjuvantes Imunológicos/síntese química , Fármacos Anti-HIV/síntese química , Anti-Inflamatórios não Esteroides/síntese química , Triterpenos/síntese química , Adjuvantes Imunológicos/uso terapêutico , Adjuvantes Imunológicos/toxicidade , Animais , Fármacos Anti-HIV/uso terapêutico , Fármacos Anti-HIV/toxicidade , Anti-Inflamatórios não Esteroides/uso terapêutico , Anti-Inflamatórios não Esteroides/toxicidade , Formação de Anticorpos/efeitos dos fármacos , Artrite/tratamento farmacológico , Betula/química , Queimaduras/tratamento farmacológico , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Proteína do Núcleo p24 do HIV/análise , HIV-1/efeitos dos fármacos , Humanos , Dose Letal Mediana , Camundongos , Casca de Planta/química , Ratos , Úlcera Gástrica/tratamento farmacológico , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/uso terapêutico , Triterpenos/toxicidadeRESUMO
Hemisuccinates, hemiphthalates, acetylsalicylates, cinnamates, and p-methoxycinnamates of lupeol, betulin, and 3-O-acetylbetulin were synthesized via interaction with corresponding acid anhydrides or acid chlorides. A number of betulin esters in position 3 and 28 were shown to exhibit a pronounced hepatoprotective effect similar to that of betulin and silibor. These experimental data were in a good agreement with the computer prediction of their biological activity. Betulin 3,28-bis-hemiphthalate was more effective than carsil in models of experimental hepatitis caused by carbon tetrachloride, tetracycline, and ethanol.
