H-Arg(Pbf)-NHBn | 1408237-86-4

• 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: H-Arg(Pbf)-NHBn
• CAS: 1408237-86-4
• 化学式: C₂₆H₃₇N₅O₄S
• 分子量: 515.677
• InChiKey: RRLIVMMQNQEHBN-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  146.4
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  H-Arg(Pbf)-NHBn 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：

  Fmoc-Arg(Pbf)-NHBn 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， 生成 H-Arg(Pbf)-NHBn
  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

文献信息

• Exploring the Phe-Gly Dipeptide-Derived Piperazinone Scaffold in the Search for Antagonists of the Thrombin Receptor PAR1
  作者：Ángel Valdivielso、M. García-López、Marta Gutiérrez-Rodríguez、Rosario Herranz

  DOI：10.3390/molecules19044814

  日期：——

  A series of Phe-Gly dipeptide-derived piperazinones containing an aromatic urea moiety and a basic amino acid has been synthesized and evaluated as inhibitors of human platelet aggregation induced by the PAR1 agonist SFLLRN and as cytotoxic agents in human cancer cells. The synthetic strategy involves coupling of a protected basic amino acid benzyl amide to 1,2- and 1,2,4-substituted-piperazinone derivatives, through a carbonylmethyl group at the N1-position, followed by formation of an aromatic urea at the exocyclic moiety linked at the C2 position of the piperazine ring and removal of protecting groups. None of the compounds showed activity in the biological evaluation.

  我们合成了一系列由 Phe-Gly 二肽衍生的哌嗪酮类化合物，其中含有一个芳香族脲基和一个碱性氨基酸，并将其作为 PAR1 激动剂 SFLLRN 诱导的人体血小板聚集的抑制剂和人体癌细胞的细胞毒剂进行了评估。合成策略包括将受保护的碱性氨基酸苄基酰胺通过 N1 位的羰基甲基与 1,2- 和 1,2,4- 取代的哌嗪酮衍生物偶联，然后在哌嗪环 C2 位连接的外环分子上形成芳香族脲，并去除保护基团。这些化合物都没有在生物评估中显示出活性。
• A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles
  作者：Pilar Ventosa-Andrés、M. Teresa García-López、Rosario Herranz

  DOI：10.1016/j.tetasy.2012.07.009

  日期：2012.8

  Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.