methyl (2S)-3-[4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexoxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate | 142356-08-9

• 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: methyl (2S)-3-[4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexoxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 142356-08-9
• 化学式: C₂₉H₄₀N₂O₇
• 分子量: 528.646
• InChiKey: SSBARQALJXJDMU-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-[4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexoxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 30.0h， 生成 methyl (2S)-2-acetamido-3-[4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexoxy]phenyl]propanoate
  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：

  N-(6-羟基己基)氨基甲酸叔丁酯 在 四溴化碳 、 sodium hydride 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 67.0h， 生成 methyl (2S)-3-[4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexoxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
  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