(2R)-2-amino-3-{[((3R)-1-{3-[1-(tert-butoxycarbonyl)-4-piperidinyl]propanoyl}-3-piperidinyl)carbonyl]amino}propanoic acid | 355388-25-9

• 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: (2R)-2-amino-3-{[((3R)-1-{3-[1-(tert-butoxycarbonyl)-4-piperidinyl]propanoyl}-3-piperidinyl)carbonyl]amino}propanoic acid
• 英文别名: (2R)-2-amino-3-[[(3R)-1-[3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]propanoyl]piperidine-3-carbonyl]amino]propanoic acid
• CAS: 355388-25-9
• 化学式: C₂₂H₃₈N₄O₆
• 分子量: 454.567
• InChiKey: BXCPPLVAWYGCME-IAGOWNOFSA-N

物化性质

• 沸点：
  696.7±55.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-3-{[((3R)-1-{3-[1-(tert-butoxycarbonyl)-4-piperidinyl]propanoyl}-3-piperidinyl)carbonyl]amino}propanoic acid 、 对甲氧基苯甲酰氯 在 N-三甲基硅基乙酰胺 、 盐酸 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 反应 2.5h， 以98%的产率得到(2R)-2-[(4-methoxybenzoyl)amino]-3-[[(3R)-1-(3-piperidin-4-ylpropanoyl)piperidine-3-carbonyl]amino]propanoic acid
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of potent GPIIb/IIIa antagonists: discovery of FK419

  摘要：

  The discovery of the non-peptide antiplatelet injectable agent FK419 is reported. Based on the P-turn structure of RGD peptide sequences in the a chain of fibrinogen, which binds the glycoprotein IIb/IIIa (GPIIb/IIIa) on the surface of platelets to induce platelet aggregation, the prototype 2 was designed. After further substituent effects were investigated at the a-position of the carboxylic acid in 2, we enhanced platelet aggregation inhibition, and discovered the useful feature of reduced prolongation of bleeding time. Finally, the potent platelet aggregation inhibitor FK419 (3) could be discovered. FK419 shows a safe feature of reduced prolongation of bleeding time, as well as potent inhibition of platelet aggregation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.056
• 作为产物：
  描述：

  1-N-BOC-4-哌啶丙酸 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2R)-2-amino-3-{[((3R)-1-{3-[1-(tert-butoxycarbonyl)-4-piperidinyl]propanoyl}-3-piperidinyl)carbonyl]amino}propanoic acid
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of potent GPIIb/IIIa antagonists: discovery of FK419

  摘要：

  The discovery of the non-peptide antiplatelet injectable agent FK419 is reported. Based on the P-turn structure of RGD peptide sequences in the a chain of fibrinogen, which binds the glycoprotein IIb/IIIa (GPIIb/IIIa) on the surface of platelets to induce platelet aggregation, the prototype 2 was designed. After further substituent effects were investigated at the a-position of the carboxylic acid in 2, we enhanced platelet aggregation inhibition, and discovered the useful feature of reduced prolongation of bleeding time. Finally, the potent platelet aggregation inhibitor FK419 (3) could be discovered. FK419 shows a safe feature of reduced prolongation of bleeding time, as well as potent inhibition of platelet aggregation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.056