(4bR,8R,8aS,9aS,11aS,11bR)-7-(cyclopropylmethyl)-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 | 1391951-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4bR,8R,8aS,9aS,11aS,11bR)-7-(cyclopropylmethyl)-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
• CAS: 1391951-51-1
• 化学式: C₂₄H₂₈N₂O₅
• 分子量: 424.497
• InChiKey: INPVMGLTYCGQPK-JEJCCYHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.26
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4bR,8R,8aS,9aS,11aS,11bR)-7-(cyclopropylmethyl)-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 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.67h， 生成 (4bR,8R,8aS,9aS,11aS,11bR)-7-(cyclopropylmethyl)-1-hydroxy-11-(2-phenethyl)-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：

  (5R,6S,6'R,9R,13S,14S)-17-(cyclopropylmethyl)-4,5-epoxy-6,6'-epoxy-14-hydroxy-3-methoxy-6-methylmorphinan-6'-carboxyamide 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 12.0h， 生成 (4bR,8R,8aS,9aS,11aS,11bR)-7-(cyclopropylmethyl)-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