7-Spiroindanylnaltrexone | 153567-07-8

• 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: 7-Spiroindanylnaltrexone
• 英文别名: 17-(cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one-7-spiro-2'-indan；17-Cyclopropylmethyl-4,5-epoxy-3,14-dihydroxymorphinan-6-one-7-spiro-2'-indan；(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxyspiro[1,2,4,5,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-6,2'-1,3-dihydroindene]-7-one
• CAS: 153567-07-8
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: WLGQGKOZUDOESI-NZHOUOPXSA-N

物化性质

• 沸点：
  667.2±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-O-benzyl-17-(cyclopropylmethyl)-4,5α-epoxy-14-hydroxymorphinan-6-one-7-spiro-2'-indan 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 48.0h， 生成 7-Spiroindanylnaltrexone
  参考文献：
  名称：

  Synthesis of naltrexone-derived .delta.-opioid antagonists. Role of conformation of the .delta. address moiety

  摘要：

  Naltrindole (1) (NTI) is a highly potent and selective delta-opioid receptor antagonist. In an effort to understand the origin of the high potency, affinity, and selectivity of NTI, we have examined the conformational role of its indolic benzene moiety through the synthesis of related naltrexone derivatives 3-8, which contain the benzene moiety in different orientations and at different attachments in the molecule. One of these naltrexone derivatives, 5, whose 7-indanyl benzene moiety is orthogonal to ring C of the morphinan system, is a potent F-opioid receptor antagonist in vitro and in vivo. Computer-assisted molecular overlay studies of the minimized structures (2-8) revealed the importance of the position of the benzene moiety for effective interaction with delta-opioid receptors. In compounds 2, 4, and 5, the aromatic ring falls in the same region of space as that of the indolic benzene moiety of NTI, and all of these ligands possessed significant activity at delta-opioid receptors. Analogues (3 and 6-8) which were shown to have relatively weak delta-opioid receptor antagonist potency have their aromatic groups located in a space that is different from that of the more potent analogues.

  DOI：

  10.1021/jm00031a006