cyclo[Phe-D-Pro-Phe-D-Trp] | 1176206-18-0

• 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: cyclo[Phe-D-Pro-Phe-D-Trp]
• 英文别名: c[L-Phe-D-pro-L-Phe-D-trp]；(3S,6R,9S,12R)-3,9-dibenzyl-6-(1H-indol-3-ylmethyl)-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone
• CAS: 1176206-18-0
• 化学式: C₃₄H₃₅N₅O₄
• 分子量: 577.683
• InChiKey: GIZJWWQFOGQPRY-RRGQHJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  H-D-Trp-Phe-D-Pro-Phe-OH 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以32%的产率得到cyclo[Phe-D-Pro-Phe-D-Trp]
  参考文献：
  名称：

  Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist

  摘要：

  The tryptophan isomers of the cyclic tetrapeptide CJ-15,208, reported to be a kappa opioid receptor (KOR) antagonist [Saito, T.; Hirai, H.; Kim, Y. J.: Kojima, Y.; Matsunaga, Y.; Nishida, H.; Sakakibara, T.; Suga, O.; Sujaku, T.; Kojima, N. J. Antibiot. (Tokyo) 2002, 55, 847-854.], were synthesized to determine the tryptophan stereochemistry in the natural product. A strategy was developed to select linear precursor peptides that favor cyclization using molecular modeling, and optimized cyclization conditions are reported. The optical rotation of the L-Trp isomer is consistent with that of the natural product. Unexpectedly both isomers exhibit similar nanomolar affinity for KOR. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.086

文献信息

• Cyclic tetrapeptide stereoisomers
  申请人：University of Kansas

  公开号：US10259843B2

  公开（公告）日：2019-04-16

  Cyclic tetrapeptide stereochemical isomers of CJ-15,208, pharmaceutical compositions from such cyclic tetrapeptides, and methods of using such pharmaceutical compositions. The cyclic tetrapeptide compounds and pharmaceutical compositions disclosed herein are potent analgesics active in several pain models with generally minimal tolerance and reduced likelihood to induce addiction relative to other known opiates.

  CJ-15,208的环状四肽立体化学异构体、这种环状四肽的药物组合物以及使用这种药物组合物的方法。本文公开的环四肽化合物和药物组合物是在多种疼痛模型中有效的强效镇痛剂，与其他已知的阿片类药物相比，其耐受性通常很小，诱发成瘾的可能性也较低。
• Macrocyclic peptides and derivatives thereof with opioid activity
  申请人：University of Florida Research Foundation, Incorporated

  公开号：US11325944B2

  公开（公告）日：2022-05-10

  The invention relates to macrocyclic peptides and pharmaceutical compositions thereof. The invention further relates to pharmaceutical compositions for modulating opioid receptor activity.

  本发明涉及大环肽及其药物组合物。本发明还涉及调节阿片受体活性的药物组合物。
• CYCLIC TETRAPEPTIDES
  申请人：Aldrich Jane V.

  公开号：US20110190212A1

  公开（公告）日：2011-08-04

  Cyclic tetrapeptides that are kappa opioid receptor (KOR) antagonists can be used in therapeutic applications for treating, inhibiting, and/or preventing drug addiction, drug use, or drug seeking behavior in a subject. This can include subjects that have a history of drug addiction. The drug can be selected from cocaine, alcohol, amphetamines, methamphetamines, nicotine, opiate, or combinations thereof. These cyclic tetrapeptides can also be useful for treating, inhibiting, and/or preventing stress-induced drug seeking behavior.
• CYCLIC TETRAPEPTIDE STEREOISOMERS
  申请人：University of Kansas

  公开号：US20190241612A1

  公开（公告）日：2019-08-08

  Cyclic tetrapeptide stereochemical isomers of CJ-15,208, pharmaceutical compositions from such cyclic tetrapeptides, and methods of using such pharmaceutical compositions. The cyclic tetrapeptide compounds and pharmaceutical compositions disclosed herein are potent analgesics active in several pain models with generally minimal tolerance and reduced likelihood to induce addiction relative to other known opiates.
• CYCLIC TETRAPEPTIDE ANALOGS
  申请人：University of Kansas

  公开号：US20210024576A1

  公开（公告）日：2021-01-28

  The present technology provides compounds of Formula I (or pharmaceutically acceptable salts and/or solvates thereof) that are useful in treating a CNS-related disorder such as schizophrenia, schizoaffective disorder, migraine, depression, pain, drug addiction, drug use, and/or drug seeking behavior. Also provided are compositions, medicaments, and methods including such compounds.