(S)-N-(1-(2-amino-3-phenylpropanoyl)piperidin-4-yl)-N-phenylpropionamide | 937738-85-7

• 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-phenylpropanoyl)piperidin-4-yl)-N-phenylpropionamide
• 英文别名: N-[1-[(2S)-2-amino-3-phenylpropanoyl]piperidin-4-yl]-N-phenylpropanamide
• CAS: 937738-85-7
• 化学式: C₂₃H₂₉N₃O₂
• 分子量: 379.502
• InChiKey: GQARBTXKMGQGGN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(2-amino-3-phenylpropanoyl)piperidin-4-yl)-N-phenylpropionamide 在 N-甲基吗啉 、 (benzotriazo-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 0.66h， 生成
  参考文献：
  名称：

  Chiral Effect of a Phe Residue in Position 3 of the Dmt¹-l(or d)-Tic² Analogues on Opioid Functional Activities

  摘要：

  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.

  DOI：

  10.1021/ml400115n
• 作为产物：
  描述：

  4-苯胺-1-苯甲基哌啶 在 palladium on activated charcoal N-甲基吗啉 、 TEA 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 84.33h， 生成 (S)-N-(1-(2-amino-3-phenylpropanoyl)piperidin-4-yl)-N-phenylpropionamide
  参考文献：
  名称：

  Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at μ and δ opioid receptors

  摘要：

  New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on mu and delta opioid receptor interactions. These analogues showed broad (47 nM-76 mu M) but selective (up to 17-fold) binding affinities at the V opioid receptor over the 6 opioid receptor, as predicted from the message-address concept. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.114

文献信息

• Development of Novel Enkephalin Analogues that Have Enhanced Opioid Activities at Both μ and δ Opioid Receptors
  作者：Yeon Sun Lee、Ravil Petrov、Chad K. Park、Shou-wu Ma、Peg Davis、Josephine Lai、Frank Porreca、Ruben Vardanyan、Victor J. Hruby

  DOI：10.1021/jm061465o

  日期：2007.11.1

  Enkephalin analogues with a 4-anilidopiperidine scaffold have been designed and synthesized to achieve therapeutic benefit for the treatment of pain due to mixed mu and delta opioid agonist activities. Ligand 16, in which a Dmt-substituted enkephalin-like structure was linked to the N-phenyl-N-piperidin-4-yl propionamide moiety, showed very high binding affinities (0.4 nM) at mu and delta receptors with an increased hydrophobicity (aLogP = 2.96). This novel lead compound was found to have very potent agonist activities in MVD (1.8 nM) and GPI (8.5 nM) assays.
• Development of Potent μ and δ Opioid Agonists with High Lipophilicity
  作者：Yeon Sun Lee、Vinod Kulkarani、Scott M. Cowell、Shou-wu Ma、Peg Davis、Katherine E. Hanlon、Todd W. Vanderah、Josephine Lai、Frank Porreca、Ruben Vardanyan、Victor J. Hruby

  DOI：10.1021/jm100982d

  日期：2011.1.13

  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
• 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.
• Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at μ and δ opioid receptors
  作者：Yeon Sun Lee、Joel Nyberg、Sharif Moye、Richard S. Agnes、Peg Davis、Shou-wu Ma、Josephine Lai、Frank Porreca、Ruben Vardanyan、Victor J. Hruby

  DOI：10.1016/j.bmcl.2007.01.114

  日期：2007.4

  New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on mu and delta opioid receptor interactions. These analogues showed broad (47 nM-76 mu M) but selective (up to 17-fold) binding affinities at the V opioid receptor over the 6 opioid receptor, as predicted from the message-address concept. (c) 2007 Elsevier Ltd. All rights reserved.