{5-[3-(Cyclohexyl-methyl-carbamoyl)-propoxy]-2-nitro-benzylamino}-acetic acid ethyl ester | 105763-67-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {5-[3-(Cyclohexyl-methyl-carbamoyl)-propoxy]-2-nitro-benzylamino}-acetic acid ethyl ester
• 英文别名: ethyl 2-[[5-[4-[cyclohexyl(methyl)amino]-4-oxobutoxy]-2-nitrophenyl]methylamino]acetate
• CAS: 105763-67-5
• 化学式: C₂₂H₃₃N₃O₆
• 分子量: 435.521
• InChiKey: HOYJBVOEVILSHM-UHFFFAOYSA-N

物化性质

• 沸点：
  601.5±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  111.01
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {5-[3-(Cyclohexyl-methyl-carbamoyl)-propoxy]-2-nitro-benzylamino}-acetic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 {2-Amino-5-[3-(cyclohexyl-methyl-carbamoyl)-propoxy]-benzylamino}-acetic acid ethyl ester
  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)-丁酸 在 草酰氯 、 sodium cyanoborohydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.0h， 生成 {5-[3-(Cyclohexyl-methyl-carbamoyl)-propoxy]-2-nitro-benzylamino}-acetic acid ethyl ester
  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