Synthesis and antibacterial activity of egonol derivatives
Makaleler > Tam Makale · 2008
Yazarlar: Safiye EMİRDAĞ, Yurdanur AKGÜL, Huseyin Anıl
BIOORGANIC & MEDICINAL CHEMISTRY, SCI Expanded İndekslerine Giren Dergi, Uluslararası, 2008, cilt 16, ss 4431-4437
DOI: 10.1016/j.bmc.2008.02.057
Özet
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-5yl] 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 (H-1, C-13), 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. (C) 2008 Elsevier Ltd. All rights reserved.