N-环己基-N-甲基-4-[(3,4-二氢-2-氧代-1H-喹唑啉-6-基)氧基]丁酰胺 | 105763-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: N-环己基-N-甲基-4-[(3,4-二氢-2-氧代-1H-喹唑啉-6-基)氧基]丁酰胺
• 中文别名: 丁酰胺,N-环己基-N-甲基-4-[(1,2,3,4-四氢-2-羰基-6-喹唑啉基)氧代]-
• 英文名称: N-cyclohexyl-N-methyl-4-[(3,4-dihydro-2-oxo-1H-quinazolin-6-yl)oxy]butyramide
• 英文别名: N-cyclohexyl-N-methyl-4-[(2-oxo-3,4-dihydro-1H-quinazolin-6-yl)oxy]butanamide
• CAS: 105763-56-2
• 化学式: C₁₉H₂₇N₃O₃
• 分子量: 345.442
• InChiKey: PXDHBHMHUWUNSC-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  541.8±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基环己胺 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 sodium carbonate 、 溴甲烯基二甲基溴化铵 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~110.0 ℃ 、344.73 kPa 条件下， 反应 4.0h， 生成 N-环己基-N-甲基-4-[(3,4-二氢-2-氧代-1H-喹唑啉-6-基)氧基]丁酰胺
  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.