methyl 3-(S)-amino>-4-<4-<<piperidin-4-yl>propyl>oxy>phenyl>butanoate | 142408-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(S)-amino>-4-<4-<<piperidin-4-yl>propyl>oxy>phenyl>butanoate
• 英文别名: tert-butyl 4-[3-[4-[(2S)-4-methoxy-4-oxo-2-(phenylmethoxycarbonylamino)butyl]phenoxy]propyl]piperidine-1-carboxylate
• CAS: 142408-92-2
• 化学式: C₃₂H₄₄N₂O₇
• 分子量: 568.711
• InChiKey: WOVPUVJGLNWRJL-MHZLTWQESA-N

物化性质

• 沸点：
  683.5±55.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-(S)-amino>-4-<4-<<piperidin-4-yl>propyl>oxy>phenyl>butanoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 tert-butyl 4-[3-[4-[(2S)-2-amino-4-methoxy-4-oxobutyl]phenoxy]propyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Non-Peptide Fibrinogen Receptor Antagonists. 2. Optimization of a Tyrosine Template as a Mimic for Arg-Gly-Asp

  摘要：

  Inhibitors of platelet-fibrinogen binding offer an opportunity to interrupt the final, common pathway for platelet aggregation. Small molecule inhibitors of the platelet fibrinogen receptor GPIIb/IIIa were prepared and evaluated for their ability to prevent platelet aggregation. Compound 23m (L-700,462/MK-383) inhibited in vitro platelet aggregation with an IC50 of 9 nM and demonstrated a selectivity of > 24 000-fold between platelet and human umbilical vein endothelial cell fibrinogen receptors. Dose-dependent inhibition of ex vivo platelet aggregation induced by ADP was achieved with iv infusions of 0.1-10 mu g/kg/min of 23m in anesthetized dogs, with 10 mu g/kg/min completely inhibiting platelet aggregation during the entire 6 h infusion protocol. Platelet aggregatability returned rapidly after the termination of the 23m infusions. These features suggest that 23m may be useful in the treatment of arterial occlusive disorders.

  DOI：

  10.1021/jm00042a007
• 作为产物：
  描述：

  4-吡啶丙醇 在 palladium on activated charcoal N-甲基吗啉 、 咪唑 、 sodium hydroxide 、 氢气 、 碘 、 silver benzoate 、 caesium carbonate 、 三乙胺 、 三苯基二氯化膦 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -15.0~25.0 ℃ 、344.73 kPa 条件下， 反应 104.83h， 生成 methyl 3-(S)-amino>-4-<4-<<piperidin-4-yl>propyl>oxy>phenyl>butanoate
  参考文献：
  名称：

  Non-Peptide Fibrinogen Receptor Antagonists. 2. Optimization of a Tyrosine Template as a Mimic for Arg-Gly-Asp

  摘要：

  Inhibitors of platelet-fibrinogen binding offer an opportunity to interrupt the final, common pathway for platelet aggregation. Small molecule inhibitors of the platelet fibrinogen receptor GPIIb/IIIa were prepared and evaluated for their ability to prevent platelet aggregation. Compound 23m (L-700,462/MK-383) inhibited in vitro platelet aggregation with an IC50 of 9 nM and demonstrated a selectivity of > 24 000-fold between platelet and human umbilical vein endothelial cell fibrinogen receptors. Dose-dependent inhibition of ex vivo platelet aggregation induced by ADP was achieved with iv infusions of 0.1-10 mu g/kg/min of 23m in anesthetized dogs, with 10 mu g/kg/min completely inhibiting platelet aggregation during the entire 6 h infusion protocol. Platelet aggregatability returned rapidly after the termination of the 23m infusions. These features suggest that 23m may be useful in the treatment of arterial occlusive disorders.

  DOI：

  10.1021/jm00042a007