(S)-2-amino-N-(pbf)-5-guanidino-N-phenethylpentanamide | 1448586-47-7

• 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)-2-amino-N-(pbf)-5-guanidino-N-phenethylpentanamide
• 英文别名: H-Arg(Pbf)-NHEtPh；(2S)-2-amino-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-N-(2-phenylethyl)pentanamide
• CAS: 1448586-47-7
• 化学式: C₂₇H₃₉N₅O₄S
• 分子量: 529.704
• InChiKey: YOHOUBMLCWUFJU-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-(pbf)-5-guanidino-N-phenethylpentanamide 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Development of a Peptidomimetic Antagonist of Neuropeptide FF Receptors for the Prevention of Opioid-Induced Hyperalgesia

  摘要：

  Through the development of a new class of unnatural ornithine derivatives as bioisosteres of arginine, we have designed an orally active peptidomimetic antagonist of neuropeptide FF receptors (NPFFR). Systemic low-dose administration of this compound to rats blocked opioid-induced hyperalgesia, without any apparent side-effects. Interestingly, we also observed that this compound potentiated opioid-induced analgesia. This unnatural ornithine derivative provides a novel therapeutic approach for both improving analgesia and reducing hyperalgesia induced by opioids in patients being treated for chronic pain.

  DOI：

  10.1021/cn500219h
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以1.22 g的产率得到(S)-2-amino-N-(pbf)-5-guanidino-N-phenethylpentanamide
  参考文献：
  名称：

  N-Heteroarylation of Chiral α-Aminoesters by Means of Palladium-Catalyzed Buchwald–Hartwig Reaction

  摘要：

  N-Heteroaryl-alpha-amino acid derivatives are valuable pharmacological agents as peptidomimetics. Classical SNAr methods using acid catalysis and elevated temperatures could not be extended to various alpha-amino acids and fairly electrophilic heterocyclic partners. Here, we report a mild and versatile method of N-heteroarylation of chiral alpha-aminoesters without racemization, involving Buchwald-Hartwig conditions. It could be extended to various a-amino acids and azines. This efficient N-heteroarylation leads to (i) a chemical library of putative peptidomimetics combining diverse azaheterocycles with the chiral alpha-aminoesters and their corresponding derivatives (amides, alcohols, etc.) and (ii) arginine derivatives designed as NPFF receptor ligancls.

  DOI：

  10.1021/jo4011427

文献信息

• <i>N</i>-Heteroarylation of Chiral α-Aminoesters by Means of Palladium-Catalyzed Buchwald–Hartwig Reaction
  作者：Hassan Hammoud、Martine Schmitt、Emilie Blaise、Frédéric Bihel、Jean-Jacques Bourguignon

  DOI：10.1021/jo4011427

  日期：2013.8.16

  N-Heteroaryl-alpha-amino acid derivatives are valuable pharmacological agents as peptidomimetics. Classical SNAr methods using acid catalysis and elevated temperatures could not be extended to various alpha-amino acids and fairly electrophilic heterocyclic partners. Here, we report a mild and versatile method of N-heteroarylation of chiral alpha-aminoesters without racemization, involving Buchwald-Hartwig conditions. It could be extended to various a-amino acids and azines. This efficient N-heteroarylation leads to (i) a chemical library of putative peptidomimetics combining diverse azaheterocycles with the chiral alpha-aminoesters and their corresponding derivatives (amides, alcohols, etc.) and (ii) arginine derivatives designed as NPFF receptor ligancls.
• Development of a Peptidomimetic Antagonist of Neuropeptide FF Receptors for the Prevention of Opioid-Induced Hyperalgesia
  作者：Frédéric Bihel、Jean-Paul Humbert、Séverine Schneider、Isabelle Bertin、Patrick Wagner、Martine Schmitt、Emilie Laboureyras、Benoît Petit-Demoulière、Elodie Schneider、Catherine Mollereau、Guy Simonnet、Frédéric Simonin、Jean-Jacques Bourguignon

  DOI：10.1021/cn500219h

  日期：2015.3.18

  Through the development of a new class of unnatural ornithine derivatives as bioisosteres of arginine, we have designed an orally active peptidomimetic antagonist of neuropeptide FF receptors (NPFFR). Systemic low-dose administration of this compound to rats blocked opioid-induced hyperalgesia, without any apparent side-effects. Interestingly, we also observed that this compound potentiated opioid-induced analgesia. This unnatural ornithine derivative provides a novel therapeutic approach for both improving analgesia and reducing hyperalgesia induced by opioids in patients being treated for chronic pain.