Synthesis and Biological Activity of Mono-
and Diamides of 2,3-Secotriterpene Acids

I. A. Tolmacheva^a, E. V. Igosheva^a, Yu. B. Vikharev^a, V. V. Grishko^{a, 1},
O. V. Savinova^b, E. I. Boreko^b, and V. F. Eremin^b

^a Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, ul. Akad. Koroleva 3, Perm 614013, Russia

^b RSPC of Epidemiology and Microbiology, Ministry of Healthcare of the Republic of Belarus, Minsk 220114, Belarus

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

Abstract—Amides of four types were synthesized derived from 2,3-seco-18H-oleanane and 2,3-secolupane
mono- and dicarboxylic acids. The spectrum of diamide derivatives was expanded with C3–C3' and C28–C28'
biscondensed amides with two A-secotriterpene backbones obtained by the interaction of monocarboxylic A-
seco acids with lysine. Among the synthesized mono- and diamide derivatives, potential inhibitors of herpes
simplex virus type 1 replication were found, namely, some compounds with an ethyl -alaninate fragment
(EC₅₀ 8.7 and 4.1 M). The ethyl -alaninate diamide was shown to combine antiherpetic and anti-HIV activity
(EC₅₀ 5.1 M). For the active compounds, the ratios of maximum tolerable concentrations to EC₅₀ ranged from
9.7 to 40.8. The synthesized amides did not show any marked cytotoxic effects against human rabdomiosar-
coma RD TE32, A549 lung carcinoma, and melanoma MS cell lines.

Keywords: allobetulone, amides, antiviral activity, A-secotriterpenoids, betulin, betulonic acid, cytotoxic activ-
ity, herpes simplex virus, HIV-1, triterpenoid bisderivatives

DOI: 10.1134/S1068162013020143

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