Synthesis of 2-, 4- and 5-(2-Alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[<i>b</i>]furans and their Leukotriene B<sub>4</sub> Receptor Antagonistic Activity

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  • ANDO Kumiko
    Faculty of Pharmaceutical Sciences, Mukogawa Women's University

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  • 選択的LTB<sub>4</sub>受容体阻害活性を有する2-Alkylcarbamoyl-1-methylvinylbenzo[<i>b</i>]furan 誘導体の合成とそのコンフォメーション
  • 選択的LTB4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
  • センタクテキ LTB4 ジュヨウタイ ソガイ カッセイ オ ユウスル 2 Alkylcarbamoyl 1 methylvinylbenzo b furan ユウドウタイ ノ ゴウセイ ト ソノ コンフォメーション

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Abstract

  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 B4 (LTB4) receptor antagonists. (E)-2-(2-Diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy)benzo[b]furan (4v) showed selective inhibition of the human BLT2 receptor (hBLT2). On the other hand, (E)-2-acetyl-4-(2-diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy)benzo[b]furan (7c) inhibited both human BLT1 receptor (hBLT1) and hBLT2. 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.<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 125 (11), 863-874, 2005-11-01

    The Pharmaceutical Society of Japan

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