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Synthesis of Chalcone‐Derived Heteroaromatics with Antibacterial Activities
Author(s) -
Jin Hui,
Jiang Xia,
Yoo Hyebin,
Wang Tingshu,
Sung Chul Gi,
Choi Umji,
Lee ChangRo,
Yu Haiyang,
Koo Sangho
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003397
Subject(s) - chalcone , chemistry , pyrrole , acinetobacter baumannii , antibacterial activity , combinatorial chemistry , acetylation , ethyl acetoacetate , staphylococcus aureus , organic chemistry , stereochemistry , catalysis , biochemistry , bacteria , biology , gene , pseudomonas aeruginosa , genetics
An efficient synthetic method of medicinally important chalcone‐derived heteroaromatics was proposed, which comprised of conjugate addition of ethyl acetoacetate to chalcones, followed by Mn III /Co II ‐catalyzed oxidative deacetylation. Paal‐Knorr reactions of the resulting 1,4‐dicarbonyl compounds containing various phenyl substituents produced the corresponding 2‐carboethoxy‐3,5‐diphenyl furans, pyrroles, and thiophenes. The scope, mechanism, and electronic requirements for the phenyl substituents of chalcones in the key radical‐medicated deacetylation reaction were fully elucidated. Antibacterial activities of the 21 chalcone‐derived heteroaromatics were screened for Escherichia coli , Staphylococcus aureus , and Acinetobacter baumannii . The parent pyrrole 5 a showed most effective inhibition for E. coli and one third of the heteroaromatics exhibited significant inhibition for S. aureus at the concentration of 64 μg/mL.