Transformations of A-seco-18αH-oleanane hydroxynitriles
- 作者: Konysheva A.V.1, Krainova G.F.1, Eroshenko D.V.1, Dmitriev M.V.2, Grishko V.V.1
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隶属关系:
- Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences
- Perm State National Research University
- 期: 卷 68, 编号 12 (2019)
- 页面: 2252-2261
- 栏目: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/243556
- DOI: https://doi.org/10.1007/s11172-019-2695-9
- ID: 243556
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详细
2,3-Secooleanane hydroxynitriles undergo dehydration and anionotropic 1,2-migration of the methyl group C(24)H3 under the action of the SOCl2-CH2Cl2 system to form a mixture of isomeric Δ4-alkenes. A similar E1-elimination process in the presence of the H2SO4—AcOH system is accompanied by hydrolysis of the CN group giving A-ring unsaturated C(2)-ketones and diastereomeric ε-lactones. Epimeric 4,23-epoxides and isopropyl ketone were synthesized by oxidative transformations of 4,23-alkene, which was selectively formed from 2,3-secooleanane hydroxynitrile under the action of the POCl3-Py system. The in vitro cytotoxic evaluation by the MTT assay showed that the synthesized compounds are not toxic (IC50 > 100 μmol L−1) against the human cancer cell lines HEp-2, HCT116, MS, RD TE32, MCF-7, A549, and PC-3.
作者简介
A. Konysheva
Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences
Email: grishvic@gmail.com
俄罗斯联邦, 3 ul. Akademika Koroleva, Perm, 614013
G. Krainova
Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences
Email: grishvic@gmail.com
俄罗斯联邦, 3 ul. Akademika Koroleva, Perm, 614013
D. Eroshenko
Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences
Email: grishvic@gmail.com
俄罗斯联邦, 3 ul. Akademika Koroleva, Perm, 614013
M. Dmitriev
Perm State National Research University
Email: grishvic@gmail.com
俄罗斯联邦, 15 ul. Bukireva, Perm, 614990
V. Grishko
Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences
编辑信件的主要联系方式.
Email: grishvic@gmail.com
俄罗斯联邦, 3 ul. Akademika Koroleva, Perm, 614013
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