The Synthesis and Investigation of New Electroneutral Berberine Derivatives
Publication type: Journal Article
Publication date: 2022-01-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
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.
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Zagrebaev A. D. et al. The Synthesis and Investigation of New Electroneutral Berberine Derivatives // Chemistry of Heterocyclic Compounds. 2022. Vol. 58. No. 1. pp. 45-57.
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Zagrebaev A. D., Burov O. N., Kletskii M. Е., Lisovin A. V., Kurbatov S. V., Demekhin O. D. The Synthesis and Investigation of New Electroneutral Berberine Derivatives // Chemistry of Heterocyclic Compounds. 2022. Vol. 58. No. 1. pp. 45-57.
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TY - JOUR
DO - 10.1007/s10593-022-03055-0
UR - https://doi.org/10.1007/s10593-022-03055-0
TI - The Synthesis and Investigation of New Electroneutral Berberine Derivatives
T2 - Chemistry of Heterocyclic Compounds
AU - Zagrebaev, Alexander D
AU - Burov, Oleg N
AU - Kletskii, Mikhail Е
AU - Lisovin, Anton V
AU - Kurbatov, Sergey V.
AU - Demekhin, Oleg D
PY - 2022
DA - 2022/01/01
PB - Springer Nature
SP - 45-57
IS - 1
VL - 58
SN - 0009-3122
SN - 1573-8353
ER -
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BibTex (up to 50 authors)
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@article{2022_Zagrebaev,
author = {Alexander D Zagrebaev and Oleg N Burov and Mikhail Е Kletskii and Anton V Lisovin and Sergey V. Kurbatov and Oleg D Demekhin},
title = {The Synthesis and Investigation of New Electroneutral Berberine Derivatives},
journal = {Chemistry of Heterocyclic Compounds},
year = {2022},
volume = {58},
publisher = {Springer Nature},
month = {jan},
url = {https://doi.org/10.1007/s10593-022-03055-0},
number = {1},
pages = {45--57},
doi = {10.1007/s10593-022-03055-0}
}
Cite this
MLA
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Zagrebaev, Alexander D., et al. “The Synthesis and Investigation of New Electroneutral Berberine Derivatives.” Chemistry of Heterocyclic Compounds, vol. 58, no. 1, Jan. 2022, pp. 45-57. https://doi.org/10.1007/s10593-022-03055-0.