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Transformations of A-seco-18αH-oleanane hydroxynitriles

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Abstract

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.

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Authors and Affiliations

  1. Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch of the Russian Academy of Sciences, 3 ul. Akademika Koroleva, 614013, Perm, Russian Federation

    A. V. Konysheva, G. F. Krainova, D. V. Eroshenko & V. V. Grishko

  2. Perm State National Research University, 15 ul. Bukireva, 614990, Perm, Russian Federation

    M. V. Dmitriev

Authors
  1. A. V. Konysheva
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  2. G. F. Krainova
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  3. D. V. Eroshenko
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  4. M. V. Dmitriev
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  5. V. V. Grishko
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Correspondence to V. V. Grishko.

Additional information

The study was performed within the framework of the State assignment of the Ministry of Science and Higher Education of the Russian Federation (No. AAAA-A18-118030790037-7).

The synthesized compounds were analyzed using the equipment of the Center for Collective Use “Research of Materials and Substances” of the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2252–2261, December, 2019.

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Konysheva, A.V., Krainova, G.F., Eroshenko, D.V. et al. Transformations of A-seco-18αH-oleanane hydroxynitriles. Russ Chem Bull 68, 2252–2261 (2019). https://doi.org/10.1007/s11172-019-2695-9

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  • DOI: https://doi.org/10.1007/s11172-019-2695-9

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