An azo coupling of berberine derivatives: an experimental and quantum-chemical study

An azo coupling of berberine derivatives: an experimental and quantum-chemical study

The possibility of synthesizing 12-(aryldiazo)berberrubines was demonstrated experimentally and by quantum-chemical calculations based on the Density Functional Theory in the B3LYP/6-31G(d,p) basis set. In weakly alkaline media, berberrubine can be substituted at position 12 by azo coupling reaction...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 59; no. 8; pp. 604 - 609
Main Authors: Popov, Andrey A., Dryapak, Angelina N., Burov, Oleg N., Kletskii, Mikhail E., Zagrebaev, Alexander D., Tkachuk, Anna V., Kurbatov, Sergey V., Aleshukina, Anna V., Goloshova, Elena V., Markova, Kristina G., Berezinskaya, Iraida S., Tverdokhlebova, Tatiana I.
Format: Journal Article
Language:English
Published: New York Springer US 01-08-2023
Springer
Springer Nature B.V
Subjects:
Chemical properties
Chemical reactions
Chemical synthesis
Chemistry
Chemistry and Materials Science
Coupling
Density functional theory
Density functionals
Nucleophiles
Organic Chemistry
Pharmacy
Quantum chemistry
Specific gravity
Substitution reactions
Surface active agents
diazonium salts
berberrubine
DFT calculations
electrophilic substitution
berberine
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Summary:The possibility of synthesizing 12-(aryldiazo)berberrubines was demonstrated experimentally and by quantum-chemical calculations based on the Density Functional Theory in the B3LYP/6-31G(d,p) basis set. In weakly alkaline media, berberrubine can be substituted at position 12 by azo coupling reactions with aryldiazonium salts. This process proceeds in steps: first, berberrubine transforms into the zwitterionic form of 9-oxoberberine, which then enters as a nucleophile into an azo coupling reaction with aryldiazonium salts to form a single product with the trans configuration of the fragments relative to the N=N double bond. The resulting 12-(aryldiazo)berberrubines may find use as antibiotic agents, as shown on the multidrug-resistant culture Acinetobacter lwoffii .
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03239-2