phenyl N-[[2-amino-5-[4-[cyclohexyl(methyl)amino]-4-oxobutoxy]phenyl]methyl]carbamate | 105763-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: phenyl N-[[2-amino-5-[4-[cyclohexyl(methyl)amino]-4-oxobutoxy]phenyl]methyl]carbamate
• CAS: 105763-55-1
• 化学式: C₂₅H₃₃N₃O₄
• 分子量: 439.555
• InChiKey: PMYJGWCAXFMYSD-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  645.2±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenyl N-[[2-amino-5-[4-[cyclohexyl(methyl)amino]-4-oxobutoxy]phenyl]methyl]carbamate 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以90%的产率得到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
• 作为产物：
  描述：

  4-(3-甲酰基-4-硝基苯氧基)丁酰氯 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， 25.0~100.0 ℃ 、344.73 kPa 条件下， 反应 3.5h， 生成 phenyl N-[[2-amino-5-[4-[cyclohexyl(methyl)amino]-4-oxobutoxy]phenyl]methyl]carbamate
  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：——