Preparation of 2- and 4-(2-alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[b]furans having potent antagonistic activity against human leukotriene B4 BLT1 and/or BLT2 receptors.
(E)-2-Acetyl-4-(2-diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy)benzo[b]furan (4b) with a characteristic conformation and (E)-2-(2-morpholinocarbo-1-methylvinyl)-7-ethoxycarbopropoxybenzo[b]furan ((E)-3b) were prepared and evaluated for their leukotriene B4(LTB4) antagonistic activity. Compound 4b showed potent antagonistic activity against human BLT1 and BLT2 receptors. Compound (E)-3b displayed selective BLT2 receptor antagonistic activity. Both compounds were inactive to cysteinyl LT receptors.
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
Kunitomo
Jun-ichi
J
Yamashita
Masayuki
M
Ohta
Shunsaku
S
Nabe
Takeshi
T
Kohno
Shigekatsu
S
Yokomizo
Takehiko
T
Shimizu
Takao
T
Ohishi
Yoshitaka
Y
D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016466:CHO Cells; D002118:Calcium / Q000378:metabolism; D020013:Calcium Signaling / Q000187:drug effects; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006224:Cricetinae; D018360:Crystallography, X-Ray; D015870:Gene Expression; D006801:Humans; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D058919:Purinergic P2 Receptor Antagonists; D018102:Receptors, Leukotriene B4 / Q000037:antagonists & inhibitors* / Q000235:genetics / Q000378:metabolism; D018048:Receptors, Purinergic P2 / Q000235:genetics / Q000378:metabolism
C495855:2-(2-morpholinocarbo-1-methylvinyl)-7-ethoxycarbopropoxybenzo(b)furan; C495854:2-acetyl-4-(2-diethylcarbamoyl-1-methylvinyl)-7-(1-phenylethoxy)benzo(b)furan; D001572:Benzofurans; D002219:Carbamates; C513240:LTB4R protein, human; C485878:LTB4R2 protein, human; D009025:Morpholines; D058919:Purinergic P2 Receptor Antagonists; D018102:Receptors, Leukotriene B4; D018048:Receptors, Purinergic P2; D002118:Calcium