Journal of Siberian Federal University. Chemistry / Synthesis of Biologically Active Betulin-based Triterpene Compounds

Full text (.pdf)
Issue
Journal of Siberian Federal University. Chemistry. 2011 4 (4)
Authors
Kuznetsov, Boris N.; Levdansky, Vladimir A.; Kuznetsova, Svetlana A.; Kogay, Tamara I.
Contact information
Kuznetsov, Boris N. : Siberian Federal University Institute of Chemistry and Chemical Technology SB RAS , 79 Svobodny, Krasnoyarsk, 660041 Russia 42 st. K. Marx, Krasnoyarsk, 660049 Russia , e-mail: ; Levdansky, Vladimir A. : Siberian Federal University Institute of Chemistry and Chemical Technology SB RAS , 79 Svobodny, Krasnoyarsk, 660041 Russia 42 st. K. Marx, Krasnoyarsk, 660049 Russia; Kuznetsova, Svetlana A. : Siberian Federal University Institute of Chemistry and Chemical Technology SB RAS , 79 Svobodny, Krasnoyarsk, 660041 Russia 42 st. K. Marx, Krasnoyarsk, 660049 Russia; Kogay, Tamara I. : Siberian Federal University , 79 Svobodny, Krasnoyarsk, 660041 Russia
Keywords
betulin. outer birch bark; synthesis; betulinic acid; amide and aminoderivatives of betulinic acid; betulin diacetate; allobetulin
Abstract

Paper describes the developed by authors the novel methods of triterpene compounds synthesis from biologically active betulin, which have prospects for the design the new drugs. The improved method of betulinic acid synthesis by sodium betulonate reduction by BH4 in water medium is developed. The method of betulonic acid reduction to betulinic acid at conditions of phase-transfer catalysis was suggested which makes it possible to increase the betulinic acid yield up to 99 %. With the use of carbodiimide methods the next derivatives of betulinic acid were synthesized: cyclohexyl amide (yield 89 %), propyl amide (yield 84 %), tretbuthyl ether of valine (yield 83 %), tretbythyl ether of tyrosine (yield 84 %). The new one-step methods of synthesis of betulin diacetate by acetilation of outer bark and allobetuline synthesis by boiling in toluene or p-xylene of outer birch bark impregnated by sulphonic or ortophosphoric acids were developed.

Pages
408-423
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/2659