RESUMEN
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.
RESUMEN
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.
Asunto(s)
Abietanos/síntesis química , Antiinflamatorios no Esteroideos/síntesis química , Abietanos/química , Abietanos/farmacología , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Antivirales/síntesis química , Antivirales/química , Antivirales/farmacología , Carragenina , Edema/inducido químicamente , Edema/tratamiento farmacológico , Virus de la Influenza A/efectos de los fármacos , Ratones , Estereoisomerismo , Relación Estructura-Actividad , Pruebas de Toxicidad AgudaRESUMEN
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.
Asunto(s)
Acetatos/química , Formaldehído/química , Triterpenos/química , Ésteres , Espectroscopía de Resonancia Magnética , Espectrofotometría InfrarrojaRESUMEN
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.
Asunto(s)
Alphainfluenzavirus/efectos de los fármacos , Antivirales/química , Antivirales/farmacología , Simplexvirus/efectos de los fármacos , Triterpenos/química , Triterpenos/farmacología , Antivirales/síntesis química , Catálisis , Humanos , Compuestos de Rutenio/química , Saponinas/química , Triterpenos/síntesis químicaRESUMEN
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.
Asunto(s)
Alcaloides/aislamiento & purificación , Delphinium/química , Diterpenos/aislamiento & purificación , Cromatografía Liquida , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Componentes Aéreos de las Plantas/química , Extractos Vegetales/químicaRESUMEN
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.
Asunto(s)
Fosfatidilcolinas/química , Piridinas/química , Espectroscopía de Resonancia Magnética , Conformación Molecular , Estructura Molecular , Teoría CuánticaRESUMEN
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.
Asunto(s)
Adyuvantes Inmunológicos/síntesis química , Fármacos Anti-VIH/síntesis química , Antiinflamatorios no Esteroideos/síntesis química , Triterpenos/síntesis química , Adyuvantes Inmunológicos/uso terapéutico , Adyuvantes Inmunológicos/toxicidad , Animales , Fármacos Anti-VIH/uso terapéutico , Fármacos Anti-VIH/toxicidad , Antiinflamatorios no Esteroideos/uso terapéutico , Antiinflamatorios no Esteroideos/toxicidad , Formación de Anticuerpos/efectos de los fármacos , Artritis/tratamiento farmacológico , Betula/química , Quemaduras/tratamiento farmacológico , Línea Celular , Supervivencia Celular/efectos de los fármacos , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Proteína p24 del Núcleo del VIH/análisis , VIH-1/efectos de los fármacos , Humanos , Dosificación Letal Mediana , Ratones , Corteza de la Planta/química , Ratas , Úlcera Gástrica/tratamiento farmacológico , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/uso terapéutico , Triterpenos/toxicidadRESUMEN
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.