Preparation of 2- and 4-(2-alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[b]furans having potent antagonistic activity against human leukotriene B4 BLT1 and/or BLT2 receptors

Kumiko Ando; Eriko Tsuji; Yuko Ando; Jun-ichi Kunitomo; Masayuki Yamashita; Shunsaku Ohta; Takeshi Nabe; Shigekatsu Kohno; Takehiko Yokomizo; Takao Shimizu; Yoshitaka Ohishi

doi:10.1039/B411286E

Preparation of 2- and 4-(2-alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[b]furans having potent antagonistic activity against human leukotriene B₄ BLT₁ and/or BLT₂ receptors†

Kumiko Ando,^a Eriko Tsuji,^a Yuko Ando,^a Jun-ichi Kunitomo,^a Masayuki Yamashita,^b Shunsaku Ohta,^b Takeshi Nabe,^b Shigekatsu Kohno,^b Takehiko Yokomizo,^cde Takao Shimizu^ce and Yoshitaka Ohishi*^a

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^a School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya, Japan
E-mail: yohishi@mwu.mukogawa-u.ac.jp
Fax: +798 41 2792
Tel: +798 45 9953

^b Kyoto Pharmaceutical University, Misasagi, Yamashinaku, Kyoto, Japan

^c Department of Biochemistry and Molecular Biology, Faculty of Medicine, University of Tokyo, 7-3-1 Hongo Bunkyo-ku, Tokyo, Japan

^d PRESTO, 7-3-1 Hongo Bunkyo-ku, Tokyo, Japan

^e CREST of JST, 7-3-1 Hongo Bunkyo-ku, Tokyo, Japan

Abstract

(E)-2-Acetyl-4-(2-diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy)benzo[b]furan (4b) with a characteristic conformation and (E)-2-(2-morpholinocarbo-1-methylvinyl)-7-ethoxycarbopropoxybenzo[b]furan ((E)-3b) were prepared and evaluated for their leukotriene B₄ (LTB₄) antagonistic activity. Compound 4b showed potent antagonistic activity against human BLT₁ and BLT₂ receptors. Compound (E)-3b displayed selective BLT₂ receptor antagonistic activity. Both compounds were inactive to cysteinyl LT receptors.

Organic & Biomolecular Chemistry

Preparation of 2- and 4-(2-alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[b]furans having potent antagonistic activity against human leukotriene B₄ BLT₁ and/or BLT₂ receptors†

Abstract

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Preparation of 2- and 4-(2-alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[b]furans having potent antagonistic activity against human leukotriene B₄ BLT₁ and/or BLT₂ receptors

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Organic & Biomolecular Chemistry