(4bS,8aS,9R)-3-(benzyloxy)-11-(cyclobutylmethyl)-8a-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene | 1310086-70-4

• 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: (4bS,8aS,9R)-3-(benzyloxy)-11-(cyclobutylmethyl)-8a-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
• CAS: 1310086-70-4
• 化学式: C₂₉H₃₇NO₂
• 分子量: 431.618
• InChiKey: CWNMOJVQSIESER-SSBOKUKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4bS,8aS,9R)-3-(benzyloxy)-11-(cyclobutylmethyl)-8a-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene 在 4-二甲氨基吡啶 、 palladium on carbon 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 MCL-693
  参考文献：
  名称：

  Synthesis and binding affinity of novel mono- and bivalent morphinan ligands for κ, μ, and δ opioid receptors

  摘要：

  A novel series of homo-and heterodimeric ligands containing kappa/mu agonist and mu agonist/antagonist pharmacophores joined by a 10-carbon ester linker chain were synthesized and evaluated for their in vitro binding affinity at kappa, mu, and delta opioid receptors, and their functional activities were determined at kappa and mu receptors in [S-35] GTP gamma S functional assays. Most of these compounds had high binding affinity at mu and kappa receptors (K-i values less than 1 nM). Compound 15b, which contains butorphan (1) at one end of linking chain and butorphanol (5) at the other end, was the most potent ligand in this series with binding affinity K-i values of 0.089 nM at the mu receptor and 0.073 nM at the kappa receptor. All of the morphinan-derived ligands were found to be partial kappa and mu agonists; ATPM-derived ligands 12 and 11 were found to be full kappa agonists and partial mu agonists. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.052
• 作为产物：
  描述：

  溴甲苯 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.25h， 生成 (4bS,8aS,9R)-3-(benzyloxy)-11-(cyclobutylmethyl)-8a-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
  参考文献：
  名称：

  Synthesis and binding affinity of novel mono- and bivalent morphinan ligands for κ, μ, and δ opioid receptors

  摘要：

  A novel series of homo-and heterodimeric ligands containing kappa/mu agonist and mu agonist/antagonist pharmacophores joined by a 10-carbon ester linker chain were synthesized and evaluated for their in vitro binding affinity at kappa, mu, and delta opioid receptors, and their functional activities were determined at kappa and mu receptors in [S-35] GTP gamma S functional assays. Most of these compounds had high binding affinity at mu and kappa receptors (K-i values less than 1 nM). Compound 15b, which contains butorphan (1) at one end of linking chain and butorphanol (5) at the other end, was the most potent ligand in this series with binding affinity K-i values of 0.089 nM at the mu receptor and 0.073 nM at the kappa receptor. All of the morphinan-derived ligands were found to be partial kappa and mu agonists; ATPM-derived ligands 12 and 11 were found to be full kappa agonists and partial mu agonists. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.052