Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Structure-Activity Relationship and Antibacterial Activity of Some Simple (E)-Chalcones
Corresponding Author(s) : Gan B. Bajracharya
Asian Journal of Chemistry,
Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022
Abstract
In present work, 14 simple (E)-chalcones (1-14), synthesized via the Claisen-Schmidt condensation between arylmethyl ketone and aromatic aldehyde in the presence of either in NaOH or H3BO3, were tested for in vitro antibacterial activity against two Gram-positive (Staphylococcus aureus and Bacillus subtilis) and three Gram-negative (Escherichia coli, Enterobacter cloacae and Klebsiella pneumoniae) bacterial strains. Among them, (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (8) was found most efficient, while (E)-3-(4-(dimethylamino)phenyl)-1-phenylprop-2-en-1-one (4) and (E)-1-(2,4-dihydroxyphenyl)-3-(4-(dimethylamino)-phenyl)prop-2-en-1-one (14) were completely ineffective. The rest of the (E)-chalcones have displayed moderate to good antibacterial activity, particularly against Gram-positive bacteria, while E. coli was found resistant. From the structure-activity relationship (SAR) analysis, it is revealed that the presence of a strong electron-withdrawing group (NO2) in ring A and the presence of electron-donating group in ring B of (E)-chalcones could enhance the antibacterial activity. The presence of hydroxyl and/or alkoxyl substituents in both 3 and 4 positions of ring B proved beneficial.
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