Preparation of leukotriene B4 inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells

Mari Kuramoto; Yoko Sakata; Kumi Terai; Ikuo Kawasaki; Jun-ichi Kunitomo; Takahiro Ohishi; Takehiko Yokomizo; Seiichi Takeda; Shuichi Tanaka; Yoshitaka Ohishi

doi:10.1039/B803313G

Preparation of leukotriene B₄ inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells†

Mari Kuramoto,^a Yoko Sakata,^a Kumi Terai,^a Ikuo Kawasaki,^a Jun-ichi Kunitomo,^a Takahiro Ohishi,^b Takehiko Yokomizo,^c Seiichi Takeda,^d Shuichi Tanaka^d and Yoshitaka Ohishi*^a

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* Corresponding authors

^a School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68, Koshien Kyuban-cho, Nishinomiya, Japan
E-mail: ikuo_k@mukogawa-u.ac.jp
Fax: +81 798 45 9953
Tel: +81 798 45 9953

^b Science of Environment and Mathematical Modeling, Graduate School of Engineering, Doshisha University, Kyotanabe, Kyoto, Japan

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

^d Fuso Pharmaceutical Industries, Ltd., 2-3-30, Morinomiya, Joto-ku, Osaka, Japan

Abstract

A series of 2-(2-aminothiazol-4-yl)benzo[b]furan and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives were prepared, and their leukotriene B₄ inhibitory activity and growth inhibitory activity in cancer cell lines were evaluated. Several compounds showed strong inhibition of calcium mobilization in CHO cells overexpressing human BLT₁ and BLT₂ receptors and growth inhibition to human pancreatic cancer cells MIA PaCa-2. 3-(4-Chlorophenyl)-2-[5-formyl-2-[(dimethylamino)methyleneamino]thiazol-4-yl]-5-methoxybenzo[b]furan 8b showed the most potent and selective inhibition for the human BLT₂receptor, and its IC₅₀ value was smaller than that of the selected positive control compound, ZK-158252. 3-(4-Chlorophenyl)-2-[2-[(dimethylamino)methyleneamino]-5-(2-hydroxyethyliminomethyl)thiazol-4-yl]-5-methoxybenzo[b]furan 9a displayed growth inhibitory activity towards MIA PaCa-2.

Organic & Biomolecular Chemistry

Preparation of leukotriene B₄ inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells†

Abstract

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Preparation of leukotriene B₄ inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells

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Organic & Biomolecular Chemistry