(1S,3aS,5aS,6R,11bR,11cR)-14-allyl-3-benzyl-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-epoxynaphtho[1,2-e]indol-2-one | 1391951-31-7

• 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: (1S,3aS,5aS,6R,11bR,11cR)-14-allyl-3-benzyl-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-epoxynaphtho[1,2-e]indol-2-one
• CAS: 1391951-31-7
• 化学式: C₂₉H₃₂N₂O₅
• 分子量: 488.583
• InChiKey: YQAXNURQASHBOZ-HRPGWMCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.47
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,3aS,5aS,6R,11bR,11cR)-14-allyl-3-benzyl-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-epoxynaphtho[1,2-e]indol-2-one 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 (4bR,8R,8aS,9aS,11aS,11bR)-7-allyl-11-benzyl-1-hydroxy-5,6,7,8,9a,11b-hexahydro-8a,11a-ethano-4,8-methano-9,12,14-trioxa-7,11-diazabenzo[a]benzo[4,5]cycloocta[1,2,3-gh]pentalen-10(11H)-one
  参考文献：
  名称：

  Novel Delta Opioid Receptor Agonists with Oxazatricyclodecane Structure

  摘要：

  We synthesized compounds 4a,c-f,h,i containing the oxazatricyclodecane structure from a novel rearrangement reaction product 2a. All the prepared compounds 4a,c-f,h,i exhibited full agonistic activities for the delta opioid receptor (DOR). Among them, the N-methyl derivative 4c was highly selective, and the most effective DOR agonist in functional assays. Subcutaneous administration of 4c produced dose-dependent and NTI (selective DOR antagonist)-reversible antinociception lacking any convulsive behaviors in the mice acetic acid writhing tests. The N-methyl derivative 4c is expected to be a promising lead compound for selective DOR agonists with a novel chemotype.

  DOI：

  10.1021/ml400491k
• 作为产物：
  描述：

  (1S,3aS,5aS,6R,11bR,11cR)-3-benzyl-14-(cyclopropylmethyl)-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-epoxynaphtho[1,2-e]indol-2-one 在 碳酸氢钠 、 potassium carbonate 、 氯甲酸-2,2,2-三氯乙酯 作用下， 以 N,N-二甲基甲酰胺 、 1,1,2,2-四氯乙烷 为溶剂， 反应 23.0h， 生成 (1S,3aS,5aS,6R,11bR,11cR)-14-allyl-3-benzyl-3a,11-dihydroxy-10-methoxy-1,3,3a,4,5,6,7,11c-octahydro-2H-6,11b-(iminoethano)-1,5a-epoxynaphtho[1,2-e]indol-2-one
  参考文献：
  名称：

  Novel Delta Opioid Receptor Agonists with Oxazatricyclodecane Structure

  摘要：

  We synthesized compounds 4a,c-f,h,i containing the oxazatricyclodecane structure from a novel rearrangement reaction product 2a. All the prepared compounds 4a,c-f,h,i exhibited full agonistic activities for the delta opioid receptor (DOR). Among them, the N-methyl derivative 4c was highly selective, and the most effective DOR agonist in functional assays. Subcutaneous administration of 4c produced dose-dependent and NTI (selective DOR antagonist)-reversible antinociception lacking any convulsive behaviors in the mice acetic acid writhing tests. The N-methyl derivative 4c is expected to be a promising lead compound for selective DOR agonists with a novel chemotype.

  DOI：

  10.1021/ml400491k