New 13-vinyl derivatives of berberine: synthesis and characterization
Oleg D Demekhin
1
,
Oleg N Burov
1
,
Mikhail E Kletskii
1
,
Anton V Lisovin
1
,
Sergey V. Kurbatov
1
,
Elena A Bereznyak
2
,
Alena V Trishina
2
2
Rostov-on-Don Plague Control Research Institute, Rostov-on-Don, Russia
|
Publication type: Journal Article
Publication date: 2022-02-01
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 substituted 13-vinylberberines was demonstrated experimentally and via quantum-chemical DFT/B3LYP calculations in the 6-31++G(d,p) basis set. The introduction of pharmacophoric fragments conjugated through vinyl moiety opened new possibilities for structural modification of berberine, enabling pronounced changes in tropicity toward supramolecular biological structures. The newly synthesized 13-vinylberberines were stable in their reduced form due to significant intramolecular electron density transfer from berberine ring system to the vinyl moiety bearing electron-withdrawing groups. It was demonstrated that berberine derivatives may exist not only in ion pair form consisting of organic cation and inorganic anion, but also as zwitterionic structures featuring significant intramolecular charge transfer. The obtained 13-vinylberberines exhibited biological activity against the highly pathogenic Vibrio cholerae.
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Demekhin O. D. et al. New 13-vinyl derivatives of berberine: synthesis and characterization // Chemistry of Heterocyclic Compounds. 2022. Vol. 58. No. 2-3. pp. 144-152.
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Demekhin O. D., Burov O. N., Kletskii M. E., Lisovin A. V., Kurbatov S. V., Bereznyak E. A., Trishina A. V. New 13-vinyl derivatives of berberine: synthesis and characterization // Chemistry of Heterocyclic Compounds. 2022. Vol. 58. No. 2-3. pp. 144-152.
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TY - JOUR
DO - 10.1007/s10593-022-03067-w
UR - https://doi.org/10.1007/s10593-022-03067-w
TI - New 13-vinyl derivatives of berberine: synthesis and characterization
T2 - Chemistry of Heterocyclic Compounds
AU - Demekhin, Oleg D
AU - Burov, Oleg N
AU - Kletskii, Mikhail E
AU - Lisovin, Anton V
AU - Kurbatov, Sergey V.
AU - Bereznyak, Elena A
AU - Trishina, Alena V
PY - 2022
DA - 2022/02/01
PB - Springer Nature
SP - 144-152
IS - 2-3
VL - 58
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2022_Demekhin,
author = {Oleg D Demekhin and Oleg N Burov and Mikhail E Kletskii and Anton V Lisovin and Sergey V. Kurbatov and Elena A Bereznyak and Alena V Trishina},
title = {New 13-vinyl derivatives of berberine: synthesis and characterization},
journal = {Chemistry of Heterocyclic Compounds},
year = {2022},
volume = {58},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007/s10593-022-03067-w},
number = {2-3},
pages = {144--152},
doi = {10.1007/s10593-022-03067-w}
}
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MLA
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Demekhin, Oleg D., et al. “New 13-vinyl derivatives of berberine: synthesis and characterization.” Chemistry of Heterocyclic Compounds, vol. 58, no. 2-3, Feb. 2022, pp. 144-152. https://doi.org/10.1007/s10593-022-03067-w.