(S)-N-(1-(2-amino-3-(4-chlorophenyl)propanoyl)piperidin-4-yl)-N-phenylpropionamide | 1033015-74-5

• 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: (S)-N-(1-(2-amino-3-(4-chlorophenyl)propanoyl)piperidin-4-yl)-N-phenylpropionamide
• CAS: 1033015-74-5
• 化学式: C₂₃H₂₈ClN₃O₂
• 分子量: 413.947
• InChiKey: DKPFEGYTYRQAOQ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66.64
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(2-amino-3-(4-chlorophenyl)propanoyl)piperidin-4-yl)-N-phenylpropionamide 在 N-甲基吗啉 、 (benzotriazole-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成
  参考文献：
  名称：

  Development of Potent μ and δ Opioid Agonists with High Lipophilicity

  摘要：

  An SAR study on the Dmt-substituted enkephalin-like tetrapeptide with a N-phenyl-N-piperidin-4-ylpropionamide moiety at the C-terminal was performed and has resulted in highly potent ligands at mu and delta opioid receptors In general, ligands with the substitution of D-Nle(2) and halogenation of the aromatic ring of Phe(4) showed highly increased opioid activities Ligand 6 with good biological activities in vitro demonstrated potent in vivo antihyperalgesic and antiallodynic effects in the tail-flick assay

  DOI：

  10.1021/jm100982d
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 0.33h， 生成 (S)-N-(1-(2-amino-3-(4-chlorophenyl)propanoyl)piperidin-4-yl)-N-phenylpropionamide
  参考文献：
  名称：

  Development of Potent μ and δ Opioid Agonists with High Lipophilicity

  摘要：

  An SAR study on the Dmt-substituted enkephalin-like tetrapeptide with a N-phenyl-N-piperidin-4-ylpropionamide moiety at the C-terminal was performed and has resulted in highly potent ligands at mu and delta opioid receptors In general, ligands with the substitution of D-Nle(2) and halogenation of the aromatic ring of Phe(4) showed highly increased opioid activities Ligand 6 with good biological activities in vitro demonstrated potent in vivo antihyperalgesic and antiallodynic effects in the tail-flick assay

  DOI：

  10.1021/jm100982d

文献信息

• Chiral Effect of a Phe Residue in Position 3 of the Dmt¹-<scp>l</scp>(or <scp>d</scp>)-Tic² Analogues on Opioid Functional Activities
  作者：Yeon Sun Lee、HongChang Qu、Peg Davis、Shou-Wu Ma、Ruben Vardanyan、Josephine Lai、Frank Porreca、Victor J. Hruby

  DOI：10.1021/ml400115n

  日期：2013.7.11

  In this letter, we describe a structure-activity relationships study, specifically related to the chirality of third amino acid residue in our H-Dmt-L(or D)-Tic analogues, of which C-terminus is attached to a piperidinyl moiety. Observed selectivities and functional activities of these analogues demonstrated that the chiralities of the second and third position residues are crucial for determining whether these ligands act as antagonists or agonists at the delta opioid receptor, but not at the mu opioid receptor.