Synthesis and Pharmacological Activity of Betulin Dinicotinate

The assignment of NMR resonances of lupane triterpenoids was refined by the example of 3O,28O-dinicotinoylbetulin, obtained by acylation of betulin. Hepatoprotective, antiulcer, 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 synthesis and hepatoprotective activity of esters of the lupane group triterpenoids

Hemisuccinates, hemiphthalates, acetylsalicylates, cinnamates, andp-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-bishemiphthalate was more effective than carsil in models of experimental hepatitis caused by carbon tetrachloride, tetracycline, and ethanol.     

Synthesis and pharmacological activity of betulin dinicotinate

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.     

Synthesis of the lupane group triterpenoids and there hepatoprotective activity

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.