(3S)-3-(butylsulfonylamino)-4-[4-[3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propoxy]phenyl]butanoic acid | 1025988-45-7

• 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: (3S)-3-(butylsulfonylamino)-4-[4-[3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propoxy]phenyl]butanoic acid
• CAS: 1025988-45-7
• 化学式: C₂₇H₄₄N₂O₇S
• 分子量: 540.722
• InChiKey: HWADDGPSXAMZDN-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S)-3-(butylsulfonylamino)-4-[4-[3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propoxy]phenyl]butanoic acid 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 3-(S)--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
• 作为产物：
  描述：

  4-吡啶丙醇 在 palladium on activated charcoal N-甲基吗啉 、 咪唑 、 lithium hydroxide 、 sodium hydroxide 、 氢气 、 碘 、 silver benzoate 、 碳酸氢钠 、 caesium carbonate 、 三乙胺 、 三苯基二氯化膦 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 溶剂黄146 、 乙酸乙酯 、 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 152.83h， 生成 (3S)-3-(butylsulfonylamino)-4-[4-[3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propoxy]phenyl]butanoic acid
  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