3-[(3R,4R)-1-(3-呋喃-2-基丙基)-3,4-二甲基哌啶-4-基]苯酚 | 149710-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 3-[(3R,4R)-1-(3-呋喃-2-基丙基)-3,4-二甲基哌啶-4-基]苯酚
• 英文名称: (+/-)-1-<3-(2-furanyl)propyl>-3(R^*),4(R^*)-dimethyl-4-(3-hydroxyphenyl)piperidine
• 英文别名: Phenol, 3-(1-(3-(2-furanyl)propyl)-3,4-dimethyl-4-piperidinyl)-, cis-；3-[(3R,4R)-1-[3-(furan-2-yl)propyl]-3,4-dimethylpiperidin-4-yl]phenol
• CAS: 149710-89-4
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: MDNFUQZTHRJSGF-OXJNMPFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4,5,6-Tetrahydro-4-(3-methoxyphenyl)-N,N,1,4-tetramethyl-3-pyridinemethanamine 在 platinum on activated charcoal 盐酸 、 Proton Sponge 、 氯甲酸乙烯酯 、 氢溴酸 、 氢气 、 溶剂黄146 、 三乙胺 、 红铝 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 3-[(3R,4R)-1-(3-呋喃-2-基丙基)-3,4-二甲基哌啶-4-基]苯酚
  参考文献：
  名称：

  Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for .mu.- and .kappa.-opioid receptors

  摘要：

  A series of racemic N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines were evaluated for opioid agonist and antagonist activity at mu and kappa receptors. Several highly potent mu and kappa antagonists were discovered; however, no compounds with high selectivity for either the mu or kappa receptor were identified. Importantly, no derivative was found to have significant opioid agonist activity. Two derivatives were resolved, and the activities of the enantiomers were investigated. Only a limited stereochemical effect on opioid receptor selectivities was observed. The structure-activity relationships described establish the existence of an important lipophilic binding site distal to the nitrogen for both mu and kappa receptors and confirm the pure opioid antagonist pharmacophore nature of the trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine structure.

  DOI：

  10.1021/jm00072a001

文献信息

• Structure-activity relationships of trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for .mu.- and .kappa.-opioid receptors
  作者：Dennis M. Zimmerman、J. David Leander、Buddy E. Cantrell、Jon K. Reel、John Snoddy、Laurane G. Mendelsohn、Bryan G. Johnson、Charles H. Mitch

  DOI：10.1021/jm00072a001

  日期：1993.10

  A series of racemic N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines were evaluated for opioid agonist and antagonist activity at mu and kappa receptors. Several highly potent mu and kappa antagonists were discovered; however, no compounds with high selectivity for either the mu or kappa receptor were identified. Importantly, no derivative was found to have significant opioid agonist activity. Two derivatives were resolved, and the activities of the enantiomers were investigated. Only a limited stereochemical effect on opioid receptor selectivities was observed. The structure-activity relationships described establish the existence of an important lipophilic binding site distal to the nitrogen for both mu and kappa receptors and confirm the pure opioid antagonist pharmacophore nature of the trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine structure.