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Molecules 2017, 22(5), 687; doi:10.3390/molecules22050687

Synthesis and Bioactivity Evaluation of Novel 2-Salicyloylbenzofurans as Antibacterial Agents

1
Department of Medicinal Chemistry, Faculty of Pharmacy, Ton Duc Thang University, Ho Chi Minh City 700000, Vietnam
2
Department of Pharmaceutics, Faculty of Pharmacy, Da Nang University of Medical Technology and Pharmacy, Da Nang 550000, Vietnam
3
Department of Organic Chemistry, Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh City, Ho Chi Minh City 700000, Vietnam
4
Department of Microbiology and Parasitology, Faculty of Pharmacy, University of Medicine and Pharmacy at Ho Chi Minh City, Ho Chi Minh City 700000, Vietnam
*
Authors to whom correspondence should be addressed.
Academic Editors: Diego Muñoz-Torrero and Kelly Chibale
Received: 21 March 2017 / Revised: 16 April 2017 / Accepted: 21 April 2017 / Published: 25 April 2017
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [879 KB, uploaded 25 April 2017]   |  

Abstract

In order to discover new antibacterial agents, series of 2-salicyloylbenzofuran derivatives were designed, synthesized and evaluated for their antibacterial activities against three Gram-(+) strains (methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and Streptococcus faecalis (S. faecalis) ATCC 29212) and one Gram-(−) strain (Escherichia coli (E. coli) ATCC 25922). The 2-salicyloylbenzofuran heterocycles were generated by Rap–Stoermer condensation of salicylaldehydes with phenacyl bromides and then converted to diverse O-ether derivatives by Williamson synthesis. The targeted products were screened for in vitro qualitative (zone of inhibition) and quantitative (MIC) antibacterial activities by agar well diffusion assay and agar dilution method. Amongst the compounds, those bearing carboxylic acid functional group were found to exhibit reasonable activity against Gram-(+) bacterial strains including S. faecalis, MSSA and MRSA with the most potent antibacterial agent 8h (MICs = 0.06–0.12 mM). Besides, the 2-salicyloylbenzofurans partly displayed inhibitory activity against MRSA with the best MICs = 0.14 mM (8f) and 0.12 mM (8h). Finally, the antibacterial results preliminarily suggested that the substituent bearing carboxylic acid group at salicyloyl-C2 and the bromine atoms on the benzofuran moiety seem to be the functionality necessary for antibacterial activities. View Full-Text
Keywords: 2-salicyloylbenzofuran; benzofuran; antibacterial activity; MRSA; Rap–Stoermer condensation; Williamson synthesis 2-salicyloylbenzofuran; benzofuran; antibacterial activity; MRSA; Rap–Stoermer condensation; Williamson synthesis
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MDPI and ACS Style

Phan, P.-T.T.; Nguyen, T.-T.T.; Nguyen, H.-N.T.; Le, B.-K.N.; Vu, T.T.; Tran, D.C.; Pham, T.-A.N. Synthesis and Bioactivity Evaluation of Novel 2-Salicyloylbenzofurans as Antibacterial Agents. Molecules 2017, 22, 687.

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