School of Pharmaceutical Sciences, Mukogawa-Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan.
Org Biomol Chem. 2004 Feb 21;2(4):625-35. doi: 10.1039/b312682j. Epub 2004 Jan 28.
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.
新型 3-乙酰乙酰氨基苯并[b]呋喃衍生物在 3 位具有修饰的三烯系统，该化合物是由 3-氨基苯并[b]呋喃起始合成得到的。3-乙酰乙酰氨基苯并[b]呋喃的烯醇异构体（）为稳定异构体，这是由于烯醇羟基和酰胺羰基之间形成氢键所致。通过 C-3 侧链上的 C-2 取代基的平面性表明，在烯醇化合物中存在修饰的共轭三烯系统。对这些化合物的半胱氨酰白三烯 1 和 2 受体拮抗活性进行了评估。2-(4-氰基苯甲酰基或乙氧羰基)-3-[(2-氰基-3-羟基丁-2-烯基)氨基]苯并[b]呋喃（、）具有中等活性。
