4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-3-carboxy-propyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester | 142374-08-1

• 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: 4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-3-carboxy-propyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: (3S)-3-(butylsulfonylamino)-4-[4-[4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]butoxy]phenyl]butanoic acid
• CAS: 142374-08-1
• 化学式: C₂₈H₄₆N₂O₇S
• 分子量: 554.748
• InChiKey: HMGAPXZKUPFOSM-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-3-carboxy-propyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester 、 三氟乙酸 在 苯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-3-(Butane-1-sulfonylamino)-4-[4-(4-piperidin-4-yl-butoxy)-phenyl]-butyric acid; compound with trifluoro-acetic 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
• 作为产物：
  描述：

  4-{4-[4-((S)-2-Benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-3-carboxy-propyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester
  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

文献信息

• Non-Peptide Fibrinogen Receptor Antagonists. 2. Optimization of a Tyrosine Template as a Mimic for Arg-Gly-Asp
  作者：Melissa S. Egbertson、Charles T.-C. Chang、Mark E. Duggan、Robert J. Gould、Wasyl Halczenko、George D. Hartman、William L. Laswell、Joseph J. Lynch、Robert J. Lynch

  DOI：10.1021/jm00042a007

  日期：1994.8

  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.