ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and cytotoxic activity of triterpenoids with N,O-heterocyclic fragments based on 2-formyl-1(2)-ene derivative of methyldihydrobetulonate

Mikhail A. Nazarov, Irina A. Tolmacheva, Olga N. Gagarskih, and Victoria V. Grishko

Institute of Technical Chemistry of Ural Branch of the RAS, Perm, Russia

E-mail: tolmair@gmail.com

Received: 20 October 2022  Accepted: 5 December 2022

Abstract:

In this research, there were for the first time synthesized some new triterpenoids with moieties of substituted pyrazole, isoxazole, and pyran-4-one on A cycle based on 2-formyl-3-oxolup-1(2)-en-28-oic acid methyl ester. The structures of the synthesized compounds were elucidated by standard spectroscopic techniques (FT-IR, 1D and 2D NMR). The key stage of the triterpene heterocycles production involved aldol condensation of lupane aldehyde with acetone. The cytotoxic activity of the synthesized compounds against cancer cell lines was evinced as being that expressed mostly (IC₅₀ 4.31–15.61 µM) for oxo-substituted derivatives 2, 3, and 9. Pyrazole 6 has selective cytotoxicity (IC₅₀ 8.33 µM) against MCF-7 cells.

Graphical abstract

Keywords: Triterpenoids; Aldol condensation; 1,2-Azole; Pyran-4-one; Cytotoxic activity

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02624-z

Chemical Papers 77 (4) 2219–2227 (2023)