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

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-09-19 DOI:10.1007/s11172-024-4363-y

A. V. Petrova, V. S. Pokrovsky, E. F. Khusnutdinova, G. Babayeva, A. A. Kondurakiy, A. A. Chernysheva, A. E. Barmashov, O. B. Kazakova

引用次数: 0

Abstract

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.

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C(2) 位和 C(28) 位含有吡啶取代基的齐墩果酸新衍生物的合成及其细胞毒性

我们合成了在 C(2)和 C(28)位含有吡啶分子的新齐墩果酸衍生物。通过醛醇缩合在齐墩果酸的 C(2)位和 C(28)位引入杂环分子，通过 N-酰化在 C(28)位引入杂环分子。评估了合成化合物对 12 种肿瘤细胞系的细胞毒性。研究发现，带有 3-和 4-亚甲基吡啶基的氨基吡啶衍生齐墩果酸酰胺对人类前列腺癌细胞系 PC3 具有活性，其半数最大抑制浓度 (IC50) 值分别为 1.20 和 2.06 µmol L-1。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.