選択的LTB_4受容体阻害活性を有する2-Alkylcarbamoyl-1-methylvinylbenzo[b]furan誘導体の合成とそのコンフォメーション

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Variable 7-carboxylpropoxy or (1-phenyl) ethoxybenzo [b] furan derivatives with (E)-and (Z)-2-alkylcarbamoyl-1-methylvinyl groups at the 2-, 4-, and 5-positions were prepared to find novel and selective leukotriene B_4 (LTB_4) receptor antagonists. (E)-2-(2-Diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy) benzo [b] furan (4v) showed selective inhibition of the human BLT_2 receptor (hBLT_2). On the other hand, (E)-2-acetyl-4-(2-diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy) benzo [b] furan (7c) inhibited both human BLT_1 receptor (hBLT_1) and hBLT_2. The (E)-2-(2-diethylcarbamoyl-1-methylvinyl) group lay on approximately the same plane as the benzo [b] furan ring, whereas the (E)-4-(2-diethylcarbamoyl-1-methylvinyl) group had a torsion angle (45.7°) from the benzo [b] furan ring plane. However, the (Z)-(2-alkylcarbamoyl-1-methylvinyl) benzo [b] furans were inactive. The inhibitory activity depended on the conformation of the 2-alkylcarbamoyl-1-methylvinyl groups.
公益社団法人日本薬学会の論文
2005-11-01