(1S,1'S,3aS,3'aS,5aS,5'aS,6R,6'R,11bR,11'bR,11cR,11'cR)-11,11'-(methylenbis(oxy))bis(3-benzyl-14-(cyclopropylmethyl)-3a-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) | 1550230-22-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (1S,1'S,3aS,3'aS,5aS,5'aS,6R,6'R,11bR,11'bR,11cR,11'cR)-11,11'-(methylenbis(oxy))bis(3-benzyl-14-(cyclopropylmethyl)-3a-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: 1550230-22-2
• 化学式: C₆₁H₆₈N₄O₁₀
• 分子量: 1017.23
• InChiKey: ZCNJRFRHURWMIW-HWWXVGNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  75.0
• 可旋转键数：
  14.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  142.94
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 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 、 二溴甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以66%的产率得到(4bR,8R,8aS,9aS,11aS,11bR)-11-benzyl-7-(cycloprpylmethyl)-1-methoxy-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