| 1609379-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1609379-27-2
• 化学式: C₃₁H₄₅NO₄
• 分子量: 495.703
• InChiKey: OWCVWDAGFSFFMV-CKFBAWMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 六甲基磷酰三胺 、 丙烷-1-硫醇 、 sodium hydride 、 盐酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (3′S,5α,6R,7R,14α)-3′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethanomorphinan-7-yl)-3′-(4’,4’-dimethyl)pentan-3′-ol hydrochloride
  参考文献：
  名称：

  Selectively Promiscuous Opioid Ligands: Discovery of High Affinity/Low Efficacy Opioid Ligands with Substantial Nociceptin Opioid Peptide Receptor Affinity

  摘要：

  Emerging clinical and preclinical evidence suggests that a compound displaying high affinity for mu, K, and delta opioid (MOP, KOP, and DOP) receptors and antagonist activity at each, coupled with moderate affinity and efficacy at nociceptin opioid peptide (NOP) receptors will have utility as a relapse prevention agent for multiple types of drug abuse. Members of the orvinol family of opioid ligands have the desired affinity profile but have typically displayed substantial efficacy at MOP and or KOP receptors. In this study it is shown that a phenyl ring analogue (1d) of buprenorphine displays the desired profile in vitro with high, nonselective affinity for the MOP, KOP, and DOP receptors coupled with moderate affinity for NOP receptors. In vivo, Id lacked any opioid agonist activity and was an antagonist of both the MOP receptor agonist morphine and the KOP receptor agonist ethylketocydazocine, confirming the desired opioid receptor profile in vivo.

  DOI：

  10.1021/jm401964y
• 作为产物：
  描述：

  magnesium,2-methylpropane,bromide 、 N-cyclopropylmethyl-6,14-dihydro-20-methylnorthevinone 在 lanthanium (III) chloride bis(lithium chloride) complex 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Selectively Promiscuous Opioid Ligands: Discovery of High Affinity/Low Efficacy Opioid Ligands with Substantial Nociceptin Opioid Peptide Receptor Affinity

  摘要：

  Emerging clinical and preclinical evidence suggests that a compound displaying high affinity for mu, K, and delta opioid (MOP, KOP, and DOP) receptors and antagonist activity at each, coupled with moderate affinity and efficacy at nociceptin opioid peptide (NOP) receptors will have utility as a relapse prevention agent for multiple types of drug abuse. Members of the orvinol family of opioid ligands have the desired affinity profile but have typically displayed substantial efficacy at MOP and or KOP receptors. In this study it is shown that a phenyl ring analogue (1d) of buprenorphine displays the desired profile in vitro with high, nonselective affinity for the MOP, KOP, and DOP receptors coupled with moderate affinity for NOP receptors. In vivo, Id lacked any opioid agonist activity and was an antagonist of both the MOP receptor agonist morphine and the KOP receptor agonist ethylketocydazocine, confirming the desired opioid receptor profile in vivo.

  DOI：

  10.1021/jm401964y