{1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester | 623950-07-2

• 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: {1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxo-1-[(2S)-2-(5-phenyl-1H-imidazol-2-yl)piperidin-1-yl]propan-2-yl]carbamate
• CAS: 623950-07-2
• 化学式: C₃₀H₃₈N₄O₄
• 分子量: 518.656
• InChiKey: FXVJLJYQTMAIJQ-AHWVRZQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 生成 (S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-1-[(S)-2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-propan-1-one
  参考文献：
  名称：

  Identification of potent phenyl imidazoles as opioid receptor agonists

  摘要：

  Using previously reported opioid receptor (OR) agonist analogs 4a-c as starting points, the structure-activity relationship (SAR) for their related series has been further refined. This SAR Study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist within the series. in addition, it was discovered that 4-(aminocarbonyl)-2,6-dimethyl-Phe is a reasonable bioisostere surrogate for the DMT moiety, as supported by the OR activities Of Compounds 4x and 4y. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.082
• 作为产物：
  描述：

  2-(4-phenyl-1H-imidazol-2-yl)-piperidine 、 N-Boc-2,6-二甲基-L-酪氨酸 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 作用下， 以 DMF (N,N-dimethyl-formamide) 、 水 为溶剂， 以82%的产率得到{1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Novel compounds as opioid receptor modulators

  摘要：

  这项发明针对的是作为阿片受体调节剂、拮抗剂和激动剂的新型化合物，它们可用于治疗由阿片类药物调节的疾病，如疼痛和胃肠疾病。

  公开号：

  US20040010014A1

文献信息

• Novel compounds as opioid receptor modulators
  申请人：——

  公开号：US20040010014A1

  公开（公告）日：2004-01-15

  This invention is directed towards novel compounds as opioid receptor modulators, antagonists, and agonists useful for the treatment of opioid modulated disorders such as pain and gastrointestinal disorders.

  这项发明针对的是作为阿片受体调节剂、拮抗剂和激动剂的新型化合物，它们可用于治疗由阿片类药物调节的疾病，如疼痛和胃肠疾病。
• Heterocyclic derivatives as opioid receptor modulators
  申请人：Janssen Pharmaceutica NV

  公开号：EP2275105B1

  公开（公告）日：2016-10-05
• Identification of potent phenyl imidazoles as opioid receptor agonists
  作者：Henry J. Breslin、Chaozhong Cai、Tamara A. Miskowski、Santosh V. Coutinho、Sui-Po Zhang、Pamela Hornby、Wei He

  DOI：10.1016/j.bmcl.2006.01.082

  日期：2006.5

  Using previously reported opioid receptor (OR) agonist analogs 4a-c as starting points, the structure-activity relationship (SAR) for their related series has been further refined. This SAR Study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist within the series. in addition, it was discovered that 4-(aminocarbonyl)-2,6-dimethyl-Phe is a reasonable bioisostere surrogate for the DMT moiety, as supported by the OR activities Of Compounds 4x and 4y. (C) 2006 Elsevier Ltd. All rights reserved.