N-3-(4-piperidinepropionyl)-(R)-(-)-nipecotyl[(S)-3-amino-3-(3,4-methylenedioxyphenyl)]propionic acid

• 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: N-3-(4-piperidinepropionyl)-(R)-(-)-nipecotyl[(S)-3-amino-3-(3,4-methylenedioxyphenyl)]propionic acid
• 英文别名: (S)-3-Benzo[1,3]dioxol-5-yl-3-{[(R)-1-(3-piperidin-4-yl-propionyl)-piperidine-3-carbonyl]-amino}-propionic acid；(3S)-3-(1,3-benzodioxol-5-yl)-3-[[(3R)-1-(3-piperidin-4-ylpropanoyl)piperidine-3-carbonyl]amino]propanoic acid
• 化学式: C₂₄H₃₃N₃O₆
• 分子量: 459.543
• InChiKey: XVIKFFNGSSURCJ-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-(-)-ethyl 3-amino-3-[5-(benzo-1,3-dioxole)]propanoate 在 N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 生成 N-3-(4-piperidinepropionyl)-(R)-(-)-nipecotyl[(S)-3-amino-3-(3,4-methylenedioxyphenyl)]propionic acid
  参考文献：
  名称：

  Solid-phase parallel synthesis applied to lead optimization: Discovery of potent analogues of the GPIIb/IIIa antagonist RWJ-50042

  摘要：

  A study of beta-turn peptide mimetics, related to the C-terminal gamma-chain of fibrinogen and containing a nipecotic acid scaffold, led to RWJ-50042 (1), an interesting fibrinogen receptor (GPIIb/IIIa) antagonist. To enhance potency, we employed solid-phase parallel synthesis for the preparation of over 200 analogues in a protocol of optimization cycles. This strategy produced several promising nipecotamide analogues, such as 25, which is 35 times more potent than 1 in vitro. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00438-6

文献信息

• Solid-phase parallel synthesis applied to lead optimization: Discovery of potent analogues of the GPIIb/IIIa antagonist RWJ-50042
  作者：William J. Hoekstra、Bruce E. Maryanoff、Patricia Andrade-Gordon、Judith H. Cohen、Michael J. Costanzo、Bruce P. Damiano、Barbara J. Haertlein、Bruce D. Harris、Jack A. Kauffman、Patricia M. Keane、David F. McComsey、Frank J. Villani、Stephen C. Yabut

  DOI：10.1016/0960-894x(96)00438-6

  日期：1996.10

  A study of beta-turn peptide mimetics, related to the C-terminal gamma-chain of fibrinogen and containing a nipecotic acid scaffold, led to RWJ-50042 (1), an interesting fibrinogen receptor (GPIIb/IIIa) antagonist. To enhance potency, we employed solid-phase parallel synthesis for the preparation of over 200 analogues in a protocol of optimization cycles. This strategy produced several promising nipecotamide analogues, such as 25, which is 35 times more potent than 1 in vitro. Copyright (C) 1996 Elsevier Science Ltd.