THE FIRST 13-VINYL DERIVATIVES OF BERBERINE: SYNTHESIS AND ANTIMICROBIAL ACTIVITY

Authors

  • Олег Д. Демехин Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Александр Д. Загребаев Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Олег Н. Буров Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Михаил Е. Клецкий Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Наталья В. Павлович Federal Government Health Institution ''Rostov-on-Don Plague Control Research Institute'', Federal Service for Surveillance in the Sphere of Consumers Rights Protection and Human Welfare 117/40 M. Gor'kogo St., Rostov-on-Don 344002, Russia
  • Елена А. Березняк Federal Government Health Institution ''Rostov-on-Don Plague Control Research Institute'', Federal Service for Surveillance in the Sphere of Consumers Rights Protection and Human Welfare 117/40 M. Gor'kogo St., Rostov-on-Don 344002, Russia
  • Марина В. Цимбалистова Federal Government Health Institution ''Rostov-on-Don Plague Control Research Institute'', Federal Service for Surveillance in the Sphere of Consumers Rights Protection and Human Welfare 117/40 M. Gor'kogo St., Rostov-on-Don 344002, Russia
  • Сергей В. Курбатов Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

DOI:

https://doi.org/10.1007/5270

Keywords:

activated ethylenes, berberine, dihydroberberine, antimicrobial activity, electrophilic substitution.

Abstract

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.

Author Biographies

Олег Д. Демехин, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

аспирант кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Александр Д. Загребаев, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

аспирант кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Олег Н. Буров, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

доцент кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Михаил Е. Клецкий, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

доцент кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

Сергей В. Курбатов, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

заведующий кафедрой химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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Published

2019-11-13

Issue

Vol. 55 No. 11 (2019)

Section

Short Communications