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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 11, pp 1128–1130 | Cite as

The first 13-vinyl derivatives of berberine: synthesis and antimicrobial activity

  • Oleg D. Demekhin
  • Aleksander D. Zagrebaev
  • Oleg N. BurovEmail author
  • Mikhail E. Kletskii
  • Natal’ya V. Pavlovich
  • Elena A. Bereznyak
  • Marina V. Tsimbalistova
  • Sergey V. Kurbatov
Article
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A method for the synthesis of berberine 13-vinyl derivatives has been developed consisting of an initial reaction of triethyl orthoformate with CH acids in the presence of catalytic amounts of p-toluenesulfonic acid followed by the reaction of electrophilic ethoxyethylenes with dihydroberberine. 13-Vinyldihydroberberines are resistant to spontaneous oxidation or disproportionation and can be oxidized to the corresponding 13-substituted ionic forms with silver chloride. The synthesized vinyl berberines were demonstrated to inhibit the development of a number of especially dangerous microorganisms.

Keywords

activated ethylenes berberine dihydroberberine antimicrobial activity electrophilic substitution 

Notes

Acknowledgement

The study was funded by the Southern Federal University.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Oleg D. Demekhin
    • 1
  • Aleksander D. Zagrebaev
    • 1
  • Oleg N. Burov
    • 1
    Email author
  • Mikhail E. Kletskii
    • 1
  • Natal’ya V. Pavlovich
    • 2
  • Elena A. Bereznyak
    • 2
  • Marina V. Tsimbalistova
    • 2
  • Sergey V. Kurbatov
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussia
  2. 2.Federal Government Health Institution “Rostov-on-Don Plague Control Research Institute”, Federal Service for Surveillance in the Sphere of Consumers Rights Protection and Human WelfareRostov-on-DonRussia

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