Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity.
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 (), 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 (, ) were moderately active.
Ando
Kumiko
K
School of Pharmaceutical Sciences, Mukogawa-Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan.
Tsuji
Eriko
E
Ando
Yuko
Y
Kuwata
Noriko
N
Kunitomo
Jun-Ichi
J
Yamashita
Masayuki
M
Ohta
Shunsaku
S
Kohno
Shigekatsu
S
Ohishi
Yoshitaka
Y
D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D006224:Cricetinae; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D018077:Receptors, Leukotriene / Q000378:metabolism*; D013329:Structure-Activity Relationship
D001572:Benzofurans; D018077:Receptors, Leukotriene; C412375:cysteinyl leukotriene receptor 2