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New 13-vinyl derivatives of berberine: synthesis and characterization

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Chemistry of Heterocyclic Compounds Aims and scope

The possibility of obtaining electroneutral substituted 13-vinylberberines was demonstrated experimentally and via quantum-chemical DFT/B3LYP calculations in the 6-31++G(d,p) basis set. The introduction of pharmacophoric fragments conjugated through vinyl moiety opened new possibilities for structural modification of berberine, enabling pronounced changes in tropicity toward supramolecular biological structures. The newly synthesized 13-vinylberberines were stable in their reduced form due to significant intramolecular electron density transfer from berberine ring system to the vinyl moiety bearing electron-withdrawing groups. It was demonstrated that berberine derivatives may exist not only in ion pair form consisting of organic cation and inorganic anion, but also as zwitterionic structures featuring significant intramolecular charge transfer. The obtained 13-vinylberberines exhibited biological activity against the highly pathogenic Vibrio cholerae.

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The reported study was funded by the Russian Foundation for Basic Research (RFBR) project number 20-33-90263.

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Authors and Affiliations

  1. Department of Chemistry, Southern Federal University, 7 Zorge St, Rostov-on-Don, 344090, Russia

    Oleg D. Demekhin, Oleg N. Burov, Mikhail E. Kletskii, Anton V. Lisovin & Sergey V. Kurbatov

  2. Rostov-on-Don Plague Control Research Institute, 117/40 M. Gorky St, Rostov-on-Don, 344002, Russia

    Elena A. Bereznyak & Alena V. Trishina

Authors
  1. Oleg D. Demekhin
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  2. Oleg N. Burov
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  3. Mikhail E. Kletskii
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  4. Anton V. Lisovin
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  5. Sergey V. Kurbatov
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  6. Elena A. Bereznyak
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  7. Alena V. Trishina
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Correspondence to Mikhail E. Kletskii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(2/3), 144–152

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Demekhin, O.D., Burov, O.N., Kletskii, M.E. et al. New 13-vinyl derivatives of berberine: synthesis and characterization. Chem Heterocycl Comp 58, 144–152 (2022). https://doi.org/10.1007/s10593-022-03067-w

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  • DOI: https://doi.org/10.1007/s10593-022-03067-w

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