N-cyclohexyl-N-methyl-4-<4-amino-3-(hydroxymethyl)phenoxy>butyramide | 105763-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-cyclohexyl-N-methyl-4-<4-amino-3-(hydroxymethyl)phenoxy>butyramide
• 英文别名: 4-[4-amino-3-(hydroxymethyl)phenoxy]-N-cyclohexyl-N-methylbutanamide
• CAS: 105763-57-3
• 化学式: C₁₈H₂₈N₂O₃
• 分子量: 320.432
• InChiKey: KUTCBKUZPPOYNI-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  552.7±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  75.79
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  光气 、 N-cyclohexyl-N-methyl-4-<4-amino-3-(hydroxymethyl)phenoxy>butyramide 以 四氢呋喃 为溶剂， 反应 1.0h， 以20%的产率得到N-cyclohexyl-N-methyl-4-[(2-oxo-4H-3,1-benzoxazin-6-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：

  N-甲基环己胺 在 sodium tetrahydroborate 、 sodium carbonate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 8.5h， 生成 N-cyclohexyl-N-methyl-4-<4-amino-3-(hydroxymethyl)phenoxy>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

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：——