N-Boc-Pro-Phe-(N-Me)Phe-OMe | 94779-19-8

• 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: N-Boc-Pro-Phe-(N-Me)Phe-OMe
• 英文别名: BocPro-Phe-MePheOMe；tert-butyl (2S)-2-[[(2S)-1-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]-methylamino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 94779-19-8
• 化学式: C₃₀H₃₉N₃O₆
• 分子量: 537.656
• InChiKey: COCLHKXVDJKDNK-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Boc-Pro-Phe-(N-Me)Phe-OMe 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.17h， 生成 N-Boc-Tyr-Pro-Phe-(N-Me)Phe-NH(CH₂)₂OH
  参考文献：
  名称：

  Hybrid peptides endomorphin-2/DAMGO: Design, synthesis and biological evaluation

  摘要：

  Endomorphin-2 [Tyr-Pro-Phe-Phe-NH2] and DAMGO [Tyr-D-Ala-Gly-(N-Me)Phe-Gly-ol] are natural (EM2) and synthetic (DAMGO) opioid peptides both selective for mu opioid receptor with high analgesic activity. In this work we report synthesis, in vitro and in vivo biological evaluation of five new hybrid EM2/DAMGO analogues, with the aim to obtain compounds with high affinity at mu-opioid receptor, high activity in animal nociception tests (hot plate and tail flick) and improved enzymatic stability. Double N-methylation on both Phe residues and C-terminal ethanolamide led to analogue 6e, which possesses a good in vitro mu affinity (K-i(mu) = 34 nM), combined with a remarkable in vivo antinociceptive activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.044
• 作为产物：
  描述：

  N-Boc-Phe-(N-Me)Phe-OMe 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-Boc-Pro-Phe-(N-Me)Phe-OMe
  参考文献：
  名称：

  Hybrid peptides endomorphin-2/DAMGO: Design, synthesis and biological evaluation

  摘要：

  Endomorphin-2 [Tyr-Pro-Phe-Phe-NH2] and DAMGO [Tyr-D-Ala-Gly-(N-Me)Phe-Gly-ol] are natural (EM2) and synthetic (DAMGO) opioid peptides both selective for mu opioid receptor with high analgesic activity. In this work we report synthesis, in vitro and in vivo biological evaluation of five new hybrid EM2/DAMGO analogues, with the aim to obtain compounds with high affinity at mu-opioid receptor, high activity in animal nociception tests (hot plate and tail flick) and improved enzymatic stability. Double N-methylation on both Phe residues and C-terminal ethanolamide led to analogue 6e, which possesses a good in vitro mu affinity (K-i(mu) = 34 nM), combined with a remarkable in vivo antinociceptive activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.044

文献信息

• Hexapeptide amides
  申请人：Sterling Drug Inc.

  公开号：US04472305A1

  公开（公告）日：1984-09-18

  N-Terminal L-prolyl or D-prolyl hexapeptide amides useful as Substance P agonists and/or antagonists and as analgesics and/or antihypertensives and a process for preparing them are disclosed.

  本发明公开了N-端L-脯氨酰或D-脯氨酰六肽酰胺，其可用作物质P激动剂和/或拮抗剂，以及作为镇痛剂和/或降压剂，还公开了一种制备它们的方法。