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Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022

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Synthesis, Structure-Activity Relationship and Antibacterial Activity of Some Simple (E)-Chalcones

https://doi.org/10.14233/ajchem.2022.23930
Hari Bagale Thapa
Department of Chemistry, Tri-Chandra Multiple Campus, Tribhuvan University, Ghantaghar, Kathmandu, Nepal
Najma Bajracharya
Laboratory of Catalysis and Frontier Molecules, Faculty of Science, Nepal Academy of Science and Technology (NAST), Khumaltar, Lalitpur, Nepal
Sapana Thapa
Laboratory of Catalysis and Frontier Molecules, Faculty of Science, Nepal Academy of Science and Technology (NAST), Khumaltar, Lalitpur, Nepal
Gan B. Bajracharya
Laboratory of Catalysis and Frontier Molecules, Faculty of Science, Nepal Academy of Science and Technology (NAST), Khumaltar, Lalitpur, Nepal

Corresponding Author(s) : Gan B. Bajracharya

ganbajracharya@yahoo.com; gan.bajracharya@nast.gov.np

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.

Keywords

(E)-Chalcones Antimicrobial Claisen-Schmidt condensation Flavonoid Organic synthesis
Bagale Thapa, H., Bajracharya, N., Thapa, S., & B. Bajracharya, G. (2022). Synthesis, Structure-Activity Relationship and Antibacterial Activity of Some Simple (E)-Chalcones. Asian Journal of Chemistry, 34(11), 2935–2941. https://doi.org/10.14233/ajchem.2022.23930
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