Synthetic Transformations of Higher Triterpenoids. XXX.¹
Synthesis
and Cytotoxic Activity of Betulonic Acid Amides
with Fragments of Nitroxyl Radicals

A. N. Antimonova^a, N. I. Petrenko^a, E. E. Shults^{a, 2}, Yu. F. Polienko^a, M. M. Shakirov^a, I. G.
Irtegova^a, M. A. Pokrovskii^b, K. M. Sherman^b, I. A. Grigor’ev^a, A. G. Pokrovskii^b, and G. A.
Tolstikov^a

^a Vorozhtsov Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences,
pr. Lavrentieva 9, Novosibirsk, 630090 Russia

^b Novosibirsk State University, Novosibirsk

Received August 16, 2012; in final form, September 27, 2012

Abstract—Interaction of betulonic acid chloride with 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl, 3amino-
2,2,5,5-tetramethylpyrrolidine-1-oxyl, and 3-aminomethyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl yielded the
corresponding triterpene amides. The synthesized derivatives of betulonic acid were shown to exhibit a cyto-
toxic activity on models of the CEM-13, U-937, and MT-4 tumor cells. The concentration of the most active N-
[3-oxo-28-norlup-20(29)-en-17-carbamoyl-(2,2,6,6-tetramethylpiperidine-4-yl)-1-oxyl that inhibited survival
of the tumor cells by 50% (CCID₅₀) proved to be 5.7–33.1 M.

Keywords: betulin, betulonic acid, amides, nitroxyl radicals, tumor cells

DOI: 10.1134/S1068162013020027

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