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

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...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-11, Vol.55 (11), p.1128-1130
Main Authors: Demekhin, Oleg D., Zagrebaev, Aleksander D., Burov, Oleg N., Kletskii, Mikhail E., Pavlovich, Natal’ya V., Bereznyak, Elena A., Tsimbalistova, Marina V., Kurbatov, Sergey V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-019-02589-0