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Issue 4, 2004
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Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity

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Abstract

Novel 3-acetoacetylaminobenzo[b]furan derivatives having a modified triene system at the 3-position were synthesized starting with 3-aminobenzo[b]furans. The enol isomers, 3-[(3-hydroxybut-2-enonyl)amino]benzo[b]furans (1), of the 3-acetoacetylaminobenzo[b]furans were obtained as stable isomers owing to formation of a hydrogen bonding between the enol hydroxyl group and the amidocarbonyl group. The planarity of the C-2 substituent through the C-3 side chain suggested the existence of a modified conjugational triene system in the enol compound. Cysteinyl leukotriene 1 and 2 receptor antagonistic activities for these compounds were evaluated. 2-(4-Cyanobenzoyl or ethoxycarbonyl)-3-[(2-cyano-3-hydroxybut-2-enonyl)amino]benzo[b]furans (15g, 15o, 15u) were moderately active.

Graphical abstract: Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity

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Supplementary files

Article information


Submitted
13 Oct 2003
Accepted
17 Dec 2003
First published
28 Jan 2004

Org. Biomol. Chem., 2004,2, 625-635
Article type
Paper

Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity

K. Ando, E. Tsuji, Y. Ando, N. Kuwata, J. Kunitomo, M. Yamashita, S. Ohta, S. Kohno and Y. Ohishi, Org. Biomol. Chem., 2004, 2, 625
DOI: 10.1039/B312682J

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