3-[1-(3-cyclohex-3-enyl-3(R,S)-hydroxypropyl)-3(R),4(R)-dimethylpiperidin-4-yl]phenol | 661467-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-[1-(3-cyclohex-3-enyl-3(R,S)-hydroxypropyl)-3(R),4(R)-dimethylpiperidin-4-yl]phenol
• CAS: 661467-31-8
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: IGWUDKPQTCVALC-UKLGZHLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.7
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[1-(3-cyclohex-3-enyl-3(R,S)-hydroxypropyl)-3(R),4(R)-dimethylpiperidin-4-yl]phenol 在 palladium on activated charcoal 超重氢 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-[1-((3-cyclohexyl-[3,4-(3)H2])-3(R,S)-hydroxypropyl)-(3R,4R)-dimethylpiperidin-4-yl]phenol
  参考文献：
  名称：

  Na+-dependent high affinity binding of [3H]LY515300, a 3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid receptor inverse agonist

  摘要：

  Analogues of 3,4-dimethyl-4-(3-hydroxyphenyl)piperidines are high affinity inverse agonists for mu-, delta- and kappa-opioid receptors. To characterize inverse agonist binding, we synthesized a high specific activity radioligand from this series, [H-3]LY515300 (3-[1-((3-cyclohexyl-[3,4-(3) H-2])-3 (R,S)-hydroxypropyl)-3 (R),4(R)-dimethylpiperidin-4-yl]phenol). In membranes expressing cloned human opioid receptors, [H-3]LY515300 binding was saturable and exhibited low nonspecific binding. [H-3]LY515300 bound with high affinity to the mu(K-d = 0.07 nM), delta- (K-d = 0.92 nM) and kappa-(K-d = 0.45 nM) opioid receptors. High affinity [H-3]LY515300 binding to all opioid receptors was Na+-dependent, a characteristic of inverse agonists. Displacement by standard opioid compounds yielded K-i values consistent with their known opioid receptor affinities. Autoradiographic localization of specific [H-3]LY515300 binding in rat and guinea pig brain was high in areas known to express high levels of opioid (particularly mu-opioid receptor) binding sites including the caudate, nucleus accumbens, and nucleus tractus solitarius. Thus, [H-3]LY515300 is the first radiolabeled opioid receptor inverse agonist useful for the study of opioid receptors in cell lines and native tissues. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2003.09.043
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 sodium carbonate 作用下， 生成 3-[1-(3-cyclohex-3-enyl-3(R,S)-hydroxypropyl)-3(R),4(R)-dimethylpiperidin-4-yl]phenol
  参考文献：
  名称：

  Na+-dependent high affinity binding of [3H]LY515300, a 3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid receptor inverse agonist

  摘要：

  Analogues of 3,4-dimethyl-4-(3-hydroxyphenyl)piperidines are high affinity inverse agonists for mu-, delta- and kappa-opioid receptors. To characterize inverse agonist binding, we synthesized a high specific activity radioligand from this series, [H-3]LY515300 (3-[1-((3-cyclohexyl-[3,4-(3) H-2])-3 (R,S)-hydroxypropyl)-3 (R),4(R)-dimethylpiperidin-4-yl]phenol). In membranes expressing cloned human opioid receptors, [H-3]LY515300 binding was saturable and exhibited low nonspecific binding. [H-3]LY515300 bound with high affinity to the mu(K-d = 0.07 nM), delta- (K-d = 0.92 nM) and kappa-(K-d = 0.45 nM) opioid receptors. High affinity [H-3]LY515300 binding to all opioid receptors was Na+-dependent, a characteristic of inverse agonists. Displacement by standard opioid compounds yielded K-i values consistent with their known opioid receptor affinities. Autoradiographic localization of specific [H-3]LY515300 binding in rat and guinea pig brain was high in areas known to express high levels of opioid (particularly mu-opioid receptor) binding sites including the caudate, nucleus accumbens, and nucleus tractus solitarius. Thus, [H-3]LY515300 is the first radiolabeled opioid receptor inverse agonist useful for the study of opioid receptors in cell lines and native tissues. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2003.09.043