(S)-3-(2-methylpiperazin-1-yl)phenol | 1238951-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-3-(2-methylpiperazin-1-yl)phenol
• 英文别名: 3-[(2S)-2-Methyl-1-piperazinyl]phenol；3-[(2S)-2-methylpiperazin-1-yl]phenol
• CAS: 1238951-44-4
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: UXPDMYIUDIUZIW-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(2-methylpiperazin-1-yl)phenol 在 盐酸 、 硼烷四氢呋喃络合物 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 N-(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl-4-(4-methoxyphenoxy)benzamide
  参考文献：
  名称：

  Discovery of N-{4-[(3-Hydroxyphenyl)-3-methylpiperazin-1-yl]methyl-2-methylpropyl}-4-phenoxybenzamide Analogues as Selective Kappa Opioid Receptor Antagonists

  摘要：

  There is continuing interest in the discovery and development of new kappa opioid receptor antagonists. We recently reported that N-substituted 3-methyl-4-(3-hydroxyphenyl)piperazines were a new class of opioid receptor antagonists. In this study, we report the syntheses of two piperazine JDTic-like analogues. Evaluation of the two compounds in an in vitro [S-35]GTP gamma S binding assay showed that neither compound showed the high potency and kappa opioid receptor selectivity of JDTic. A library of compounds using the core scaffold 21 was synthesized and tested for their ability to inhibit [S-35]GTP gamma S binding stimulated by the selective kappa opioid agonist U69,593. These studies led to N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyll-2-methylpropyl]-4-phenoxybenzamide (11a), a compound that showed good kappa opioid receptor antagonist properties. An SAR study based on 11a provided 28 novel analogues. Evaluation of these 28 compounds in the [S-35]GTP gamma S binding assay showed that several of the analogues were potent and selective kappa opioid receptor antagonists.

  DOI：

  10.1021/jm400275h
• 作为产物：
  描述：

  (S)-tert-butyl-4-(3-methoxyphenyl)-3-methylpiperazine-1-carboxylate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-3-(2-methylpiperazin-1-yl)phenol
  参考文献：
  名称：

  1-Substituted 4-(3-Hydroxyphenyl)piperazines Are Pure Opioid Receptor Antagonists

  摘要：

  This report describes the discovery that 1-substituted 4-(3-hydroxy-phenyl)piperazines are pure opioid receptor antagonists. Compounds in this new series include N-phenylpropyl (3S)-3-methyl-4-(3-hydroxyphenyl)piperazine and (3R)-3-methyl-4-(3-hydroxyphenyl)piperazine both of which display low nanomolar potencies at mu, delta and kappa receptors and pure antagonist properties in a[(35)S]GTP gamma S assay.

  DOI：

  10.1021/ml100126b

文献信息

• ARYLPIPERAZINE OPIOID RECEPTOR ANTAGONISTS
  申请人：Carroll Frank I.

  公开号：US20120295919A1

  公开（公告）日：2012-11-22

  Provided are opioid receptor antagonists represented by the formula (I) where R, Y 3 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein.

  提供的阿片受体拮抗剂由式（I）表示，其中R、Y3、R1、R2、R3、R4和R5如本文所定义。
• 1-SUBSTITUTED 4-ARYLPIPERAZINE AS KAPPA OPIOID RECEPTOR ANTAGONISTS
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：US20150005315A1

  公开（公告）日：2015-01-01

  Provided are compounds represented by the formula: where R, Y 3 , R 1 , R 2 , R 3 , R 4 , R 6 , G, R 7 , E 1 , E 2 , A, B, W, X, Y and Z are as defined herein.

  提供的化合物由以下公式表示：其中R，Y3，R1，R2，R3，R4，R6，G，R7，E1，E2，A，B，W，X，Y和Z的定义如下。
• ARYLPIPERAZONE OPIOID RECEPTOR ANTAGONISTS
  申请人：Research Triangle Institute

  公开号：EP2539706A1

  公开（公告）日：2013-01-02
• US9273027B2
  申请人：——

  公开号：US9273027B2

  公开（公告）日：2016-03-01
• US9512105B2
  申请人：——

  公开号：US9512105B2

  公开（公告）日：2016-12-06