(2S)-N-[(2S)-1-amino-3-(4-fluorophenyl)-1-oxopropan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-N'-[6-oxo-6-(N-[1-(2-phenylethyl)piperidin-4-yl]anilino)hexyl]pentanediamide | 1435264-53-1

• 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: (2S)-N-[(2S)-1-amino-3-(4-fluorophenyl)-1-oxopropan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-N'-[6-oxo-6-(N-[1-(2-phenylethyl)piperidin-4-yl]anilino)hexyl]pentanediamide
• CAS: 1435264-53-1
• 化学式: C₇₃H₈₅ClFN₁₁O₉
• 分子量: 1315.0
• InChiKey: UBIDQBXUAQEXHG-QXDQPINWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  95
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  295
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  Fmoc-Glu(Boc)-OH 、 6-amino-N-(1-phenethylpiperidin-4-yl)-N-phenylhexanamide 、 、 Fmoc-L-酪氨酸 、 Fmoc-L-脯氨酸 、 Fmoc-L-色氨酸 、 N-芴甲氧羰基-L-4-氯苯丙氨酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以75%的产率得到(2S)-N-[(2S)-1-amino-3-(4-fluorophenyl)-1-oxopropan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-N'-[6-oxo-6-(N-[1-(2-phenylethyl)piperidin-4-yl]anilino)hexyl]pentanediamide
  参考文献：
  名称：

  Effect of anchoring 4-anilidopiperidines to opioid peptides

  摘要：

  We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.065

文献信息

• Effect of anchoring 4-anilidopiperidines to opioid peptides
  作者：Ravil R. Petrov、Yeon Sun Lee、Ruben S. Vardanyan、Lu Liu、Shou-wu Ma、Peg Davis、Josephine Lai、Frank Porreca、Todd W. Vanderah、Victor J. Hruby

  DOI：10.1016/j.bmcl.2013.03.065

  日期：2013.6

  We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides. (C) 2013 Elsevier Ltd. All rights reserved.