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Synthesis of 1,2-azole derivatives on the basis of α,β-unsaturated triterpene aldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

α,β-Unsaturated lupane and 19β,28-epoxy-18α-oleanane aldehydes were used in the synthesis of triterpenoids bearing substituted 1,2-azole moieties (1-acetyl-3-methyl-4,5-dihydro-1H-pyrazole and 3-methyl-4,5-dihydroisoxazole) at the rings А and Е. The route of synthesis for these 1,2-azole derivatives of triterpenes included an aldol condensation of α,β-unsaturated aldehydes with acetone, the products of which (α,β-unsaturated methyl ketone and β-hydroxy ketone) underwent a further cycloaddition reaction with acetylhydrazide and hydroxylamine. Cytotoxic activity studies of the synthesized compounds against seven cancer cell lines (Hep-2, HCT116, MS, RD TE32, A549, MCF-7, and PC-3) showed that the highest cytotoxicity (IC50 0.66–11.97 μM) against all tested cell lines was exihbited by 19β,28-epoxy-18α-oleanane aldehyde and the products of its condensation reactions with acetone and acetylhydrazide.

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This work was performed with financial support from the Russian Foundation for Basic Research (grant 18-03-00050).

The authors would like to express their gratitude to the Collective Use Center of Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences “Investigation of Materials and Compounds” for the spectral, analytic, and biological studies.

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 3 Akademika Koroleva St., Perm, 614013, Russia

    Mikhail A. Nazarov, Irina A. Tolmacheva, Daria V. Eroshenko, Olga A. Maiorova & Victoria V. Grishko

  2. Perm State National Research University, 15 Bukireva St., Perm, 614990, Russia

    Maksim V. Dmitriev

Authors
  1. Mikhail A. Nazarov
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  2. Irina A. Tolmacheva
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  3. Daria V. Eroshenko
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  4. Olga A. Maiorova
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  6. Victoria V. Grishko
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Correspondence to Irina A. Tolmacheva.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1321–1328

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Nazarov, M.A., Tolmacheva, I.A., Eroshenko, D.V. et al. Synthesis of 1,2-azole derivatives on the basis of α,β-unsaturated triterpene aldehydes. Chem Heterocycl Comp 56, 1321–1328 (2020). https://doi.org/10.1007/s10593-020-02817-y

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  • DOI: https://doi.org/10.1007/s10593-020-02817-y

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