3-O-benzyl-7-(5',6'-benzo-2'-spiroindanyl)oxymorphone | 190315-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-O-benzyl-7-(5',6'-benzo-2'-spiroindanyl)oxymorphone
• 英文别名: (4R,4aS,7aR,12bS)-4a-hydroxy-3-methyl-9-phenylmethoxyspiro[1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-6,2'-1,3-dihydrocyclopenta[b]naphthalene]-7-one
• CAS: 190315-16-3
• 化学式: C₃₆H₃₃NO₄
• 分子量: 543.662
• InChiKey: PEENVVFALGXVBN-VHZJUZHNSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-7-(5',6'-benzo-2'-spiroindanyl)oxymorphone 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以75%的产率得到7-(5',6'-benzo-2'-spiroindanyl)oxymorphone
  参考文献：
  名称：

  7-Spiroindanyl Derivatives of Naltrexone and Oxymorphone as Selective Ligands for δ Opioid Receptors

  摘要：

  A series consisting of spiroindanyl (5-7), benzospiroindanyl (8-10), and spiroperinaphthyl (11) derivatives of naltrexone and oxymorphone were synthesized in order to investigate the role of an orthogonal-oriented ''address'' for delta opioid receptors. All of the ligands exhibited a preference for delta receptors in vitro. The 7-benzospiroindanyl derivative 8 (BSINTX) was the most selective delta opioid receptor antagonist in vitro. In mice BSINTX antagonized the delta(1)-selective agonist, [D-Pen(2),D-Pen(5)]enkephalin without significantly affecting the antinociceptive potency of delta(2), mu, and kappa agonists. The results of this study are consistent with an orthogonally-oriented address favoring delta(1) activity.

  DOI：

  10.1021/jm9700880
• 作为产物：
  描述：

  2,3-萘磺酸二甲基乙酸酯 在 lithium aluminium tetrahydride 、 12-冠醚-4 、 三溴化磷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 3-O-benzyl-7-(5',6'-benzo-2'-spiroindanyl)oxymorphone
  参考文献：
  名称：

  7-Spiroindanyl Derivatives of Naltrexone and Oxymorphone as Selective Ligands for δ Opioid Receptors

  摘要：

  A series consisting of spiroindanyl (5-7), benzospiroindanyl (8-10), and spiroperinaphthyl (11) derivatives of naltrexone and oxymorphone were synthesized in order to investigate the role of an orthogonal-oriented ''address'' for delta opioid receptors. All of the ligands exhibited a preference for delta receptors in vitro. The 7-benzospiroindanyl derivative 8 (BSINTX) was the most selective delta opioid receptor antagonist in vitro. In mice BSINTX antagonized the delta(1)-selective agonist, [D-Pen(2),D-Pen(5)]enkephalin without significantly affecting the antinociceptive potency of delta(2), mu, and kappa agonists. The results of this study are consistent with an orthogonally-oriented address favoring delta(1) activity.

  DOI：

  10.1021/jm9700880