3-(n-butyl)-4-hydroxy-1-(3-methylthiophenyl)-1,8-naphthyridin-2-(1H)-one | 89108-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(n-butyl)-4-hydroxy-1-(3-methylthiophenyl)-1,8-naphthyridin-2-(1H)-one
• 英文别名: 3-(n-butyl)-4-hydroxy-1-(3-methylthiophenyl)-1,8-naphthyridin-2(1H)-one；3-(n-Butyl)-4-hydroxy-1-(3-methylthiophenyl)-1,8-naphthyridin-2(1H)one；3-Butyl-4-hydroxy-1-[3-(methylsulfanyl)phenyl]-1,8-naphthyridin-2(1H)-one；3-butyl-4-hydroxy-1-(3-methylsulfanylphenyl)-1,8-naphthyridin-2-one
• CAS: 89108-93-0
• 化学式: C₁₉H₂₀N₂O₂S
• 分子量: 340.446
• InChiKey: UWJIHUGSQFGHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(n-butyl)-4-hydroxy-1-(3-methylthiophenyl)-1,8-naphthyridin-2-(1H)-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 33.0h， 生成 1-<3-(methylsulfonyl)phenyl>-3-n-butyl-4-acetoxy-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：

  3-氨基茴香硫醚 在 potassium tert-butylate 、 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 28.25h， 生成 3-(n-butyl)-4-hydroxy-1-(3-methylthiophenyl)-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

文献信息

• Composition containing 1-phenyl-1,8-naphthridin-2(1H)-ones and a
  申请人：Schering Corporation

  公开号：US04551463A1

  公开（公告）日：1985-11-05

  Certain substitute 1,8-naphthyridines and 1,5,8-azanaphthyridines are useful in treating and preventing ulcers in mammals. Methods for preparing the compounds and methods for their use are also described.

  某些替代的1,8-萘啶和1,5,8-氮杂萘啶可用于治疗和预防哺乳动物的溃疡。还描述了制备这些化合物的方法及其使用方法。
• 1-Phenyl-1,8-naphthridin-2(1H)-ones
  申请人：Schering Corporation

  公开号：US04492702A1

  公开（公告）日：1985-01-08

  Certain substituted 1,8-naphthyridines and 1,5,8-azanaphthyridines are useful for treating allergic reactions in mammals. Certain of the compounds may also be utilized to treat chronic obstructive lung diseases in mammals. Methods for preparing the compounds and methods for their use are also described.

  某些取代的1,8-萘啶和1,5,8-氮杂萘啶可用于治疗哺乳动物的过敏反应。其中一些化合物还可用于治疗哺乳动物的慢性阻塞性肺疾病。制备这些化合物的方法及其使用方法也有所描述。
• Method for treating allergic reactions and compositions therefore
  申请人：Schering Corporation

  公开号：US04628055A1

  公开（公告）日：1986-12-09

  Certain substituted 1,8-naphthyridines and 1,5,8-azanaphthyridines are useful for treating allergic reactions in mammals. Certain of the compounds may also be utilized to treat chronic obstructive lung diseases in mammals. Methods for preparing the compounds and methods for their use are also described.

  某些取代的1,8-萘啶和1,5,8-氮杂萘啶对于治疗哺乳动物的过敏反应是有用的。其中某些化合物也可以用于治疗哺乳动物的慢性阻塞性肺疾病。本文还描述了制备这些化合物的方法以及它们的使用方法。
• SHERLOCK, M. H.
  作者：SHERLOCK, M. H.

  DOI：——

  日期：——
• SHERLOCK, MARGARET H.;KAMINSKI, JAMES J.;TOM, WING C.;LEE, JOE F.;WONG, S+, J. MED. CHEM., 31,(1988) N 11, C. 2108-2121
  作者：SHERLOCK, MARGARET H.、KAMINSKI, JAMES J.、TOM, WING C.、LEE, JOE F.、WONG, S+

  DOI：——

  日期：——