THE SYNTHESIS AND INVESTIGATION OF NEW ELECTRONEUTRAL BERBERINE DERIVATIVES

Authors

  • Александр Д. Загребаев Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Олег Н. Буров Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Михаил Е. Клецкий Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Антон В. Лисовин Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Сергей В. Курбатов Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia
  • Олег Д. Демёхин Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don 344090, Russia

DOI:

https://doi.org/10.1007/6472

Keywords:

berberine, dihydroberberine, DFT calculations, C-nucleophiles, nucleophilic substitution.

Abstract

The possibility of obtaining electroneutral 8-substituted berberines was demonstrated experimentally as well as by DFT/B3LYP and ab initio MP2/HF quantum-chemical calculations with the 6-311+G(d,p) basis set. In alkaline media, it is possible to substitute the C-8 position of berberine with such C-nucleophiles as methyl ketones, acetic acid esters, nitriles, geminal di- and trihaloalkanes. This process proceeds stepwise. First, berberine is attacked by a hydroxide anion to form a covalently bonded 8-hydroxyberberine, then 8-hydroxyberberine reacts with a nucleophile in the nonionized (molecular) form.

Author Biographies

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

Младший научный сотрудник кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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

Доцент кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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

Доцент кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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

Младший научный сотрудник кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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

Заведующий кафедрой химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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

Младший научный сотрудник кафедры химии природных и высокомолекулярных соединений химического факульткта ЮФУ

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Published

2022-01-27

Issue

Vol. 58 No. 1 (2022)

Section

Original Papers