Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT1 and/or BLT2 inhibitory activities

Kumiko Ando; Yoko Kawamura; Yukiko Akai; Jun-ichi Kunitomo; Takehiko Yokomizo; Masayuki Yamashita; Shunsaku Ohta; Takahiro Ohishi; Yoshitaka Ohishi

doi:10.1039/B710935K

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Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT₁ and/or BLT₂ inhibitory activities†‡

Kumiko Ando,^a Yoko Kawamura,^a Yukiko Akai,^a Jun-ichi Kunitomo,^a Takehiko Yokomizo,^b Masayuki Yamashita,^c Shunsaku Ohta,^c Takahiro Ohishi^d and Yoshitaka Ohishi*^a

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences, Mukogawa Women's University, 11–68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan
E-mail: yohishi@mukogawa-u.ac.jp
Fax: +798 45 9953
Tel: +798 45 9953

^b Department of Medical Biochemistry, Graduate School of Medical Sciences, Kyushu University, Maidashi 3-1-1, Higashi-ku, Fukuoka, Japan

^c Kyoto Pharmaceutical University, Misasagi, Yamashinaku, Kyoto 607-8412, Japan

^d Science of Environment and Mathematical Modeling, Graduate School of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan

Abstract

Several 2-alkylcarbamoyl-1-alkylvinylbenzo[b]furans were designed to find a selective leukotriene B₄ (LTB₄) receptor antagonist. 2-(2-Alkylcarbamoyl-1-alkylvinyl)benzo[b]furans having a substituent group at the 3-position, 4-(2-alkylcarbamoyl-1-methylvinyl)benzo[b]furans having a substituent group at the 3-position, and 7-(2-alkylcarbamoyl-1-methylvinyl)benzo[b]furans and 3-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans were prepared and evaluated for LTB₄receptor (BLT₁ and BLT₂) inhibitory activities. (E)-3-Amino-4-[2-[2-(3,4-dimethoxyphenyl)ethylcarbamoyl]-1-methylvinyl]benzo[b]furan ((E)-17c) showed potent and selective inhibitory activity for BLT₂. On the other hand, (E)-7-(2-diethylcarbamoyl-1-methylvinyl)benzo[b]furan ((E)-27a) showed potent inhibitory activity for both BLT₁ and BLT₂.

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Article information

DOI: https://doi.org/10.1039/B710935K
Article type: Paper
Submitted: 17 Jul 2007
Accepted: 26 Oct 2007
First published: 29 Nov 2007

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Org. Biomol. Chem., 2008,6, 296-307

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Preparation of 2-, 3-, 4- and 7-(2-alkylcarbamoyl-1-alkylvinyl)benzo[b]furans and their BLT₁ and/or BLT₂ inhibitory activities

K. Ando, Y. Kawamura, Y. Akai, J. Kunitomo, T. Yokomizo, M. Yamashita, S. Ohta, T. Ohishi and Y. Ohishi, Org. Biomol. Chem., 2008, 6, 296 DOI: 10.1039/B710935K

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Organic & Biomolecular Chemistry