859709-74-3Relevant academic research and scientific papers
Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity
Ando, Kumiko,Tsuji, Eriko,Ando, Yuko,Kuwata, Noriko,Kunitomo, Jun-Ichi,Yamashita, Masayuki,Ohta, Shunsaku,Kohno, Shigekatsu,Ohishi, Yoshitaka
, p. 625 - 635 (2004)
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-hydroxybul-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[e]furans (15g, 15o, 15u) were moderately active.
Synthesis of 2-, 4- And 5-(2-alkylcarbamoyl-l-methylvinyl)-7- alkyloxybenzo[b]furans and their leukotriene 64 receptor antagonistic activity
Ando, Kumiko,Tsuji, Eriko,Ando, Yuko,Kunitomo, Jun-Ichi,Kobayashi, Reina,Yokomizo, Takehiko,Shimizu, Takao,Yamashita, Masayuki,Ohta, Shunsaku,Nabe, Takeshi,Kohno, Shigekatsu,Ohishi, Yoshitaka
, p. 2129 - 2139 (2007/10/03)
Variable benzo[6]furan derivatives having (E)- and (Z)-2-alkylcarbamoyl-l- methylvinyl groups at the 2-, 4- and 5-positions and a carboxylpropoxy or (1-phenyl)ethoxy group at the 7-position were prepared to find novel and selective leukotriene B4 (LTB4) receptor antagonists. (E)-2-(2-Diethylcarbamoyl- l-methylvinyl)-7-(1-phenylethoxy)benzo[b]furan (4v) showed selective inhibition to the human BLT2 receptor (hBLT2). On the other hand, (E)-2-acetyl-4-(2-diethylcarbamoyl-l-methylvinyl)-7-(l-phenylethoxy)benzo[b] furan (7v) inhibited both human BLTi receptor (hBLT1) and hBLT 2. The (E)-2-(2-diethylcarbamoyl-l-methylvinyl) group lay on approximately the same plane as the benzo[e]furan ring, whereas the (E)-4-(2-diethylcarbamoyl-l-methylvinyl) group had the torsion angle (45.7°) from the benzo[e]furan ring plane. However, the (Z)-(2-alkylcarbamoyl-l- methylvinyl)benzo[b]furans were inactive. The inhibitory activity depended on the conformation of the 2-diethylcarbamoyl-l-methylvinyl group. The Royal Society of Chemistry 2005.
