Synthesis and Antibacterial Activity Study of C-3 α, β-Unsaturated Ketone Linked Benzofuran Derivatives

Wenlu Liu,Xizhen Jiang

doi:10.4172/2161-0401.1000164

Abstract

Based on a benzofuran skeleton bearing aryl substituent at its C-3 position through an α, β-unsaturated ketone linker, twenty-one new compounds were chemically synthesized and biologically evaluated for their antibacterial activities against four bacteria, Escherichia coli, Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus, and Bacillus subtilis. Nine of the synthesized benzofuran derivatives exhibited antibacterial activities. Among them, compound 7e showed excellent MIC80 values from 0.78 to 1.56 μg/mL and was comparable to the positive control drugs.

Highlights

Oligostilbenes have been widely investigated as bioactive functional molecules in recent years
It is presumed that the C-3 position of benzofuran ring was a potential functional site, and the single or double hydroxyl substituted phenyl and mathanone linker on C-3 position were essential for antibacterial activity of benzofuran families
The hydroxyl-bearing compounds 7c-7g, 8k-8n showed the marked antibacterial activities against all four bacteria, whereas methoxyl group or halogen (F, Cl) atoms bearing ones showed no inhibitory effect against bacterial lines tested

Summary

Introduction

Oligostilbenes have been widely investigated as bioactive functional molecules in recent years. Substitution of the double bond linker with furan moiety is an effective method of structural modification in designing new derivatives from natural oligostilbene [1,2,3,4]. Natural product corsifuran C, a furan-substituted oligostilbene analogue bearing 4-methoxyphenyl group at the C-2′ position (Figure 1) was reported as a neuron-protective and anti-tumor agent. Another natural product viniferin, which bearing a substituted phenyl at the C-3′ position of its benzofuran skeleton, presented antimicrobial, antiviral, antifungal, and antitumor activities (Figure 1). According to our previous SAR analysis [9], a key improvement of antibacterial activities was produced by introducing hydroxyl substituted phenyl and methanone linker into the C-3 position of the benzofuran skeleton. The benzoyl chloride could be replaced by acetyl chloride and reacted with

Methods

Results

Conclusion