(4bS,8aR,9R)-11-(cyclopropylmethyl)-2,3,4,7,8,8a,9,10-octahydro-1H-9,4b-(epiminoethano)phenanthren-6(5H)-one | 1393735-87-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4bS,8aR,9R)-11-(cyclopropylmethyl)-2,3,4,7,8,8a,9,10-octahydro-1H-9,4b-(epiminoethano)phenanthren-6(5H)-one
• CAS: 1393735-87-9
• 化学式: C₂₀H₂₉NO
• 分子量: 299.456
• InChiKey: SLLOVXDJNIJVKL-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4bS,8aR,9R)-11-(cyclopropylmethyl)-2,3,4,7,8,8a,9,10-octahydro-1H-9,4b-(epiminoethano)phenanthren-6(5H)-one 在 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (E)-N-[(1S,9R,10R,13R)-17-(cyclopropylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadec-2(7)-en-13-yl]-3-(furan-3-yl)-N-methylprop-2-enamide
  参考文献：
  名称：

  Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: Synthesis of decahydro(iminoethano)phenanthrene derivatives and their pharmacologies

  摘要：

  To clarify the essential structures of an opioid kappa receptor selective agonist, nalfurafine, for binding to the kappa receptor, we designed and synthesized some nalfurafine derivatives and the decahydro(iminoethano)phenanthrene derivatives with a cyclohexene moiety as a surrogate for the phenol ring. In addition to the 6-amide side chain and the 17-nitrogen substituted by a cyclopropylmethyl group, the 4,5-epoxy ring, phenolic hydroxy group, and angular hydroxy group played important roles in eliciting the binding properties of nalfurafine but these three moieties were not indispensable for binding to the kappa receptor. Moreover, the phenol ring was also not essential for the binding to the kappa receptor, and the cyclohexene moiety would play an important role in fixing the conformation of decahydro(iminoethano) phenanthrene derivatives to effectively raise the amide side chain, rendering a conformation that resembled the active one of nalfurafine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.122
• 作为产物：
  描述：

  (1'S,9'R,10'R)-17'-(cyclopropylmethyl)spiro[1,3-dioxolane-2,13'-17-azatetracyclo[7.5.3.01,10.02,7]heptadec-2(7)-ene] 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以82%的产率得到(4bS,8aR,9R)-11-(cyclopropylmethyl)-2,3,4,7,8,8a,9,10-octahydro-1H-9,4b-(epiminoethano)phenanthren-6(5H)-one
  参考文献：
  名称：

  Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: Synthesis of decahydro(iminoethano)phenanthrene derivatives and their pharmacologies

  摘要：

  To clarify the essential structures of an opioid kappa receptor selective agonist, nalfurafine, for binding to the kappa receptor, we designed and synthesized some nalfurafine derivatives and the decahydro(iminoethano)phenanthrene derivatives with a cyclohexene moiety as a surrogate for the phenol ring. In addition to the 6-amide side chain and the 17-nitrogen substituted by a cyclopropylmethyl group, the 4,5-epoxy ring, phenolic hydroxy group, and angular hydroxy group played important roles in eliciting the binding properties of nalfurafine but these three moieties were not indispensable for binding to the kappa receptor. Moreover, the phenol ring was also not essential for the binding to the kappa receptor, and the cyclohexene moiety would play an important role in fixing the conformation of decahydro(iminoethano) phenanthrene derivatives to effectively raise the amide side chain, rendering a conformation that resembled the active one of nalfurafine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.122