Synthesis and cytotoxicity of new oleanonic acid derivatives bearing pyridine substituent at positions C(2) and C(28)

New oleanonic acid derivatives bearing the pyridine moieties at the positions C(2) and C(28) were synthesized. Heterocyclic moieties were introduced in position C(2) of oleanonic acid by aldol condensation, and in position C(28) by N-acylation. Cytotoxicity of the synthesized compounds was evaluated against 12 tumor cell lines. Aminopyridine-derived oleanonic acid amides with 3- and 4-pyridinylmethylidene group were found to be active against a human prostate cancer cell line PC3 with half maximal inhibitory concentration (IC50) values equal to 1.20 and 2.06 µmol L−1, respectively. © Springer Science+Business Media LLC 2024.

Authors
Petrova A.V. , Pokrovsky V.S. , Khusnutdinova E.F. , Babayeva G. , Kondurakiy A.A. , Chernysheva A.A. , Barmashov A.E. , Kazakova O.B.
Journal
Russian Chemical Bulletin
Number of issue
8
Language
English
Pages
2400-2407
Status
Published
Link
External link
DOI
10.1007/S11172-024-4363-Y
Volume
73
Year
2024
Organizations
  • 1 Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, 71 prosp. Oktyabrya, Ufa, 450054, Russian Federation
  • 2 Research Institute of Experimental Diagnostics and Therapy of Tumors, National Medical Research Center of Oncology named after N. N. Blokhin, 23 Kashirskoe shosse, Moscow, 115478, Russian Federation
  • 3 Institute of Medicine, People’s Friendship University of Russia, 8 ul. Miklukho-Maklaya, Moscow, 117198, Russian Federation
  • 4 Dmitry Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., Moscow, 125047, Russian Federation
Keywords
Claisen—Schmidt condensation; cytotoxicity; furfural; oleanonic acid; pyridinecarboxaldehyde
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