Effect of nitrogen-containing derivatives of the plant triterpenes betulin and glycyrrhetic acid on the growth of MT-4, MOLT-4, CEM, and Hep G2 tumor cells

Novel semisynthetic derivatives of betulin and betulinic acid with cytotoxic activity

“…The method followed that described for compound 14 but using compound 3 (242 mg, 0.5 mmol) and CDI (162 mg, 1 mmol) in anhydrous THF (10 ml) at reflux for 7 h. The resulting white solid was purified by FCC using petroleum ether 40 s, 3H, OCOCH 3 ), 1.69 (s, 3H, H-30), 1.05 (s, 3H), 0.99 (s, 3H), 0.95 (s, 6H), 0.89 (s, 3H); 13 4.1.1.14. 3b-Acetoxy-lup-20(29)-en-28-yl-1H-imidazole-1-carboxylate (20). The method followed that described for compound 14 but using compound 4 (242 mg, 0.5 mmol) and CDI (162 mg, 1 mmol) in anhydrous THF (10 ml) at reflux for 5 h. The resulting white solid was purified by FCC using petroleum ether 40 (23).…”

“…18,19 However, some derivatives were found to be active. 19,20 The structures of 1 and 2 consist of a 30-carbon skeleton which has three available sites for simple chemical modifications at C-3, C-20 and C-28. Modifications of the parent structure of these compounds at these positions can produce potentially important derivatives, found to be more effective than the starting ones, thus making them appealing for further development as antitumour drugs.…”

“…Modifications of the parent structure of these compounds at these positions can produce potentially important derivatives, found to be more effective than the starting ones, thus making them appealing for further development as antitumour drugs. 18,[20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] Nitrogen-containing derivatives of 1 and 2, such as Betulin 1: R = CH 2 OH Betulinic acid 2: R = COOH amine derivatives, 21,23,35 oxime derivatives, 21,23,30 amino acid conjugates, 22 amide derivatives, 20,32 hydrazine 29 and hydrazone derivatives, [28][29][30]35 imidazolide derivatives, 37 and other N-heterocyclic derivatives 24,31,34,36 have been reported to possess antiproliferative effect against tumour cell lines.…”

Synthesis and properties of 2-cyanoethoxy derivatives of dammarane triterpenoids

“…It was shown that the introduction of substituents of various electronic nature resulted in formation of new metabolically stable candidate substances. For instance, the succinate of 18β-glycyrrhetic acid [3], as well as dimethyl succinate and dimethyl glutarate (at С 3 and С 28 ) of betulin proved to be promising compounds with a high anti-HIV action. Betulinic acid dimethyl succinate became the basic compound of antiviral pharmaceutical bevirimat used in the treatment of AIDS and enteroviruses [2,3].…”

“…For instance, the succinate of 18β-glycyrrhetic acid [3], as well as dimethyl succinate and dimethyl glutarate (at С 3 and С 28 ) of betulin proved to be promising compounds with a high anti-HIV action. Betulinic acid dimethyl succinate became the basic compound of antiviral pharmaceutical bevirimat used in the treatment of AIDS and enteroviruses [2,3]. It is also known that amides, hydrazones, hydrazides, oxazoles, cyanalkyl and other nitrogen-containing betulin and oleanane acids derivatives are capable to suppress the reproduction of viruses of influenza, papilloma, enterovirus ECHO6, and herpes [4][5][6][7][8][9][10][11][12][13].…”