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Regioselective Transformation of the Cyano Group of Triterpene α,β-Alkenenitriles

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Chemistry of Natural Compounds Aims and scope

Unsaturated acids, including difficultly accessible ceanothane-type ones, were prepared via alkaline hydrolysis of semi-synthetic triterpenoids with 1-cyano- or 3-methyl-1-cyanoalkene fragments in five-membered ring A. Regioselective reduction of 1-cyano-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene by DIBAL-H synthesized 2-aminomethyl-19β,28-epoxy-2-nor-18αH-olean-1(3)-ene. The synthesized triterpene derivatives possessed virucidal activity against herpes simplex virus type 1 (HSV-1) according to screening for inhibitory and virucidal activity. Methyl ceanotha-1(3),20(30)-dien-2,28-dioic acid 5 (ET50 28.3 min) and its 3-methyl derivative 7 (ET50 17.7 min) were the most active compounds.

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Acknowledgment

The work was supported financially by the Perm Territory Administration under Scientific Project No. C-26/056 and grants of the RFBR No. 16-53-00029Bel-_a and of the BRFBR No. M16P-012.

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, 614013, Russia

    A. V. Konysheva, I. A. Tolmacheva & V. V. Grishko

  2. RNPC of Epidemiology and Microbiology, Ministry of Health of the Republic of Belarus, 220114, Minsk, Belarus

    O. V. Savinova & E. I. Boreko

Authors
  1. A. V. Konysheva
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  2. I. A. Tolmacheva
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  3. O. V. Savinova
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  4. E. I. Boreko
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  5. V. V. Grishko
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Correspondence to V. V. Grishko.

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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2017, pp. 585–588.

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Konysheva, A.V., Tolmacheva, I.A., Savinova, O.V. et al. Regioselective Transformation of the Cyano Group of Triterpene α,β-Alkenenitriles. Chem Nat Compd 53, 687–690 (2017). https://doi.org/10.1007/s10600-017-2091-3

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  • DOI: https://doi.org/10.1007/s10600-017-2091-3

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