4-[(3-oxo-4H-1,4-benzothiazin-7-yl)oxy]butanoic acid | 105763-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 4-[(3-oxo-4H-1,4-benzothiazin-7-yl)oxy]butanoic acid
• CAS: 105763-62-0
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: FUABNLYQWOCKRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(3-oxo-4H-1,4-benzothiazin-7-yl)oxy]butanoic acid 在 草酰氯 、 sodium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.0h， 生成 N-cyclohexyl-N-methyl-4-[(2,3-dihydro-3-oxo-2H-1,4-benzothiazin-7-yl)oxy]butyramide
  参考文献：
  名称：

  Inhibitors of cyclic AMP phosphodiesterase. 1. Analogs of cilostamide and anagrelide

  摘要：

  Evaluation of a series of lactam heterocyclic analogues of cilostamide (2) as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide (3) afforded the hybrid structure RS-82856 (1), shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.

  DOI：

  10.1021/jm00385a011
• 作为产物：
  描述：

  7-羟基-4H-苯并[1,4]噻嗪-3-酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-[(3-oxo-4H-1,4-benzothiazin-7-yl)oxy]butanoic acid
  参考文献：
  名称：

  Inhibitors of cyclic AMP phosphodiesterase. 1. Analogs of cilostamide and anagrelide

  摘要：

  Evaluation of a series of lactam heterocyclic analogues of cilostamide (2) as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide (3) afforded the hybrid structure RS-82856 (1), shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.

  DOI：

  10.1021/jm00385a011

文献信息

• JONES G. H.; VENUTI M. C.; ALVAREZ R.; BRUNO J. J.; BERKS A. H.; PRINCE A+, J. MED. CHEM., 30,(1987) N 2, 295-303
  作者：JONES G. H.、 VENUTI M. C.、 ALVAREZ R.、 BRUNO J. J.、 BERKS A. H.、 PRINCE A+

  DOI：——

  日期：——
• Inhibitors of cyclic AMP phosphodiesterase. 1. Analogs of cilostamide and anagrelide
  作者：Gordon H. Jones、Michael C. Venuti、Robert Alvarez、John J. Bruno、Andrew H. Berks、Anthony Prince

  DOI：10.1021/jm00385a011

  日期：1987.2

  Evaluation of a series of lactam heterocyclic analogues of cilostamide (2) as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide (3) afforded the hybrid structure RS-82856 (1), shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.