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

• DOI: 10.1007/s10593-019-02589-0
• Publication Date: 2019-11-25T04:26:31Z
• Authors: Oleg D. Demekhin; Aleksander D. Zag...; Oleg N. Burov; Mikhail E. Kletskii; Natal’ya V. Pavlo...; Elena A. Bereznyak; Marina V. Tsimbal...; Sergey V. Kurbatov
• Keywords: 0301 basic medicine; 03 medical and health sciences; 3. Good health

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.