Synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran as a beta-amyloid aggregation inhibitor.
An efficient synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran (8), a potent beta-amyloid aggregation inhibitor, is described. 5-Chloro-2-(4-methoxyphenyl)benzofuran (3) was obtained by the one-pot synthesis of 4-chlorophenol with omega-(methylsulfinyl)-p-methoxyacetophenone (1) under Pummerer reaction conditions, and it was followed by the desulfurization of the resultant 5-chloro-3-methylthio-2-(4-methoxyphenyl)benzofuran (2e). Acylation of benzofuran 3 with 4-(3-bromopropoxy)benzoyl chloride (6) gave the ketone 7, which was converted into compound 8 by the treatment of diethylamine.
Choi
Hong-Dae
HD
Department of Chemistry, Dongeui University, Busan 614-714, Korea. hdchoi@dongeui.ac.kr
Seo
Pil-Ja
PJ
Son
Byeng-Wha
BW
Kang
Byoung-Won
BW
D016229:Amyloid beta-Peptides / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D001572:Benzofurans / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D016229:Amyloid beta-Peptides; D001572:Benzofurans; C105430:benzofuran