Synthesis and antibacterial activity of egonol derivatives

Abstract

Synthesis of egonol derivatives, 5-(3″-chloropropyl)-7-methoxy-2-(3′,4′-methylenedioxyphenyl)benzofuran 1, 5-(3″-bromopropyl)-7-methoxy-2-(3′,4′-methylenedioxyphenyl)benzofuran 2, 3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propanal 3, 5-(3″-iodopropyl)-7-methoxy-2-(3′,4′-methylenedioxyphenyl)benzofuran 4, 5-[3-(3″-bromopropyloxy) propyl]-7-methoxy-2-(3′,4′-methylenedioxyphenyl)benzofuran 5, 3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propylmethanoate 6, 3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propyloleate 7, 5-[3″-hydroxypropyl]-6-bromo-7-methoxy-2-(3′,4′-methylenedioxyphenyl)benzofuran 8, 4-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]butanenitrile 9, 3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propylbenzoate 10, 5-[3″-hydroxypropyl]-7-methoxy-3-nitro-2-(3′,4′-methylenedioxyphenyl)benzofuran 11 and their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Candida albicans and Escherichia coli are reported. The starting material egonol 5-[3″-(hydroxy)propyl]-7-methoxy-2-(3′, 4′methylenedioxyphenyl)benzofuran was isolated from seeds of Styrax officinalis L. The structural elucidication of these compounds (1-11) was established using 1D (1H, 13C), 2D NMR (HMBC, HMQC, COSY) and LCMS spectroscopic data. While egonol and some synthesised new compounds show similar antibacterial activity and MIC values against S. aureus, B. subtilis, C. albicans and E. coli, other new derivatives show different activity against S. aureus, B. subtilis, C. albicans and E. coli. © 2008 Elsevier Ltd. All rights reserved.