(S)-2-butyramido-3-(5-(3-(piperidin-4-yl)propoxy)-1H-indol-3-yl)propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-butyramido-3-(5-(3-(piperidin-4-yl)propoxy)-1H-indol-3-yl)propanoic acid
• 英文别名: (2S)-2-(butanoylamino)-3-[5-(3-piperidin-4-ylpropoxy)-1H-indol-3-yl]propanoic acid
• 化学式: C₂₃H₃₃N₃O₄
• 分子量: 415.533
• InChiKey: QSPIUWQKOVVACX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-羟基-L-色氨酸 在 盐酸 、 氯化亚砜 、 lithium hydroxide monohydrate 、 N,N-二乙基乙二胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 31.0h， 生成 (S)-2-butyramido-3-(5-(3-(piperidin-4-yl)propoxy)-1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  Design, synthesis of novel tryptophan derivatives for antiplatelet aggregation activity based on tripeptide pENW (pGlu-Asn-Trp)

  摘要：

  pENW, a three mer peptide derived from Agkistrodon acutus Guenther venom, has been found to be an antagonist of the GPIlb/IIIa receptor and shows antiplatelet aggregation activity. Based on pENW and a GPIIb/IIIa inhibitor Tirofiban, a series of tryptophan derivatives were designed, synthesized and evaluated for their antiplatelet aggregation activity induced by ADP. The most potent compound 87 was also tested for the bleeding time and antithrombotic activity in vivo in comparison with Tirofiban. The results indicated that 87 shows similar antiplatelet aggregation activity as Tirofiban to the aggregation of platelet induced by all of the four agonists, but has lower bleeding risk than Tirofiban, representing a promising lead compound for further study. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.016

文献信息

• Design, synthesis of novel tryptophan derivatives for antiplatelet aggregation activity based on tripeptide pENW (pGlu-Asn-Trp)
  作者：Zhouling Xie、Sen Feng、Ying Wang、Chen Cao、Jing Huang、Yahui Chen、Yi Kong、Zhiyu Li

  DOI：10.1016/j.ejmech.2015.07.016

  日期：2015.9

  pENW, a three mer peptide derived from Agkistrodon acutus Guenther venom, has been found to be an antagonist of the GPIlb/IIIa receptor and shows antiplatelet aggregation activity. Based on pENW and a GPIIb/IIIa inhibitor Tirofiban, a series of tryptophan derivatives were designed, synthesized and evaluated for their antiplatelet aggregation activity induced by ADP. The most potent compound 87 was also tested for the bleeding time and antithrombotic activity in vivo in comparison with Tirofiban. The results indicated that 87 shows similar antiplatelet aggregation activity as Tirofiban to the aggregation of platelet induced by all of the four agonists, but has lower bleeding risk than Tirofiban, representing a promising lead compound for further study. (C) 2015 Elsevier Masson SAS. All rights reserved.