(3'aRS,6'aSR)-1-cyclodecyl-5'-methyl-2'-phenylhexahydrospiro[piperidine-4,1'(2'H)-pyrrolo[3,4-c]pyrrole]

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3'aRS,6'aSR)-1-cyclodecyl-5'-methyl-2'-phenylhexahydrospiro[piperidine-4,1'(2'H)-pyrrolo[3,4-c]pyrrole]
• 英文别名: (3aS,6aR)-1'-cyclodecyl-2-methyl-5-phenylspiro[3,3a,6,6a-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-4,4'-piperidine]
• 化学式: C₂₇H₄₃N₃
• 分子量: 409.659
• InChiKey: BKZJNLHLIQDJQK-ZEQKJWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-benzyl-4-(phenylimino)piperidine 在 palladium on activated charcoal titanium(IV) isopropylate 、 lithium aluminium tetrahydride 、 氢气 、 溶剂黄146 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 为溶剂， 反应 79.5h， 生成 (3'aRS,6'aSR)-1-cyclodecyl-5'-methyl-2'-phenylhexahydrospiro[piperidine-4,1'(2'H)-pyrrolo[3,4-c]pyrrole]
  参考文献：
  名称：

  Novel Hexahydrospiro[piperidine-4,1‘-pyrrolo[3,4-c]pyrroles]:  Highly Selective Small-Molecule Nociceptin/Orphanin FQ Receptor Agonists

  摘要：

  Novel hexahydrospiro[piperidine-4,1'-pyrrolo[3,4-c]pyrroles that act as potent and selective orphanin FQ/nociceptin (N/OFQ) receptor (NOP) agonists were identified. The best compound, (+)-5a, potently inhibited H-3-N/OFQ binding to the NOP receptor (K-i = 0.49 nM) but was > 1000-fold less potent in binding to MOP, KOP, and DOP opiate receptors. Further, (+)-5a potently stimulated GTPgammaS binding to NOP membranes (EC50 = 65 nM) and inhibited forskolin-mediated cAMP accumulation in NOP-expressing cells (EC50 = 9.1 nM) with a potency comparable to that of the natural peptide agonist N/OFQ. These results indicate that (+)-5a is a highly selective and potent small-molecule full agonist of the NOP receptor.

  DOI：

  10.1021/jm0209174