1-<4-<1,1-(ethylenedioxy)ethyl>phenyl>-3-n-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one | 115892-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-<4-<1,1-(ethylenedioxy)ethyl>phenyl>-3-n-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one
• 英文别名: 1-{4-[1,1-(ethylenedioxy)ethyl]phenyl}-3-n-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one
• CAS: 115892-35-8
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: GYLMEBCIQMFEIW-UHFFFAOYSA-N

物化性质

• 熔点：
  281-283 °C
• 沸点：
  567.6±50.0 °C(predicted)
• 密度：
  1.259±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.58
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-<4-<1,1-(ethylenedioxy)ethyl>phenyl>-3-n-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 25.5h， 生成 1-<4-(hydroxyethyl)phenyl>-3-n-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Antiallergy agents. 1. Substituted 1,8-naphthyridin-2(1H)-ones as inhibitors of SRS-A release

  摘要：

  A novel class of antiallergy agents, the substituted 1,8-naphthyridin-2(1H)-ones, is described. The present compounds are orally active, potent inhibitors of allergic and nonallergic bronchospasm in animal models. Structure-activity studies of the lead compound in this series, 1-phenyl-3-n-butyl-4-hydroxynaphthyridin-2(1H)-one (11), identified three compounds of interest, 1-phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (12), 1-(3'-chlorophenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H )-one (87), and 1-(3'-methoxyphenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1 H)-one (89). The mechanism of antiallergy activity may involve inhibition of the release of the sulfidopeptide leukotrienes. 1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one, Sch 33303 (12), was selected for preclinical development as an antiallergy agent.

  DOI：

  10.1021/jm00119a010
• 作为产物：
  描述：

  2-(4-Acetyl-phenylamino)-nicotinic acid cyanomethyl ester 在 potassium tert-butylate 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 15.25h， 生成 1-<4-<1,1-(ethylenedioxy)ethyl>phenyl>-3-n-butyl-4-hydroxy-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Antiallergy agents. 1. Substituted 1,8-naphthyridin-2(1H)-ones as inhibitors of SRS-A release

  摘要：

  A novel class of antiallergy agents, the substituted 1,8-naphthyridin-2(1H)-ones, is described. The present compounds are orally active, potent inhibitors of allergic and nonallergic bronchospasm in animal models. Structure-activity studies of the lead compound in this series, 1-phenyl-3-n-butyl-4-hydroxynaphthyridin-2(1H)-one (11), identified three compounds of interest, 1-phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one (12), 1-(3'-chlorophenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H )-one (87), and 1-(3'-methoxyphenyl)-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1 H)-one (89). The mechanism of antiallergy activity may involve inhibition of the release of the sulfidopeptide leukotrienes. 1-Phenyl-3-(2-propenyl)-4-acetoxy-1,8-naphthyridin-2(1H)-one, Sch 33303 (12), was selected for preclinical development as an antiallergy agent.

  DOI：

  10.1021/jm00119a010