(4b'R,8a'S,9'R)-11'-benzyl-3'-methoxy-7',8',9',10'-tetrahydro-5'H,8a'H-spiro[[1,3]dioxolane-2,6'-[9,4b](epiminoethano)phenanthren]-8a'-ol | 1256921-76-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (4b'R,8a'S,9'R)-11'-benzyl-3'-methoxy-7',8',9',10'-tetrahydro-5'H,8a'H-spiro[[1,3]dioxolane-2,6'-[9,4b](epiminoethano)phenanthren]-8a'-ol
• CAS: 1256921-76-2
• 化学式: C₂₆H₃₁NO₄
• 分子量: 421.536
• InChiKey: GFZQYAFAJZPNQT-DGWZTRNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4b'R,8a'S,9'R)-11'-benzyl-3'-methoxy-7',8',9',10'-tetrahydro-5'H,8a'H-spiro[[1,3]dioxolane-2,6'-[9,4b](epiminoethano)phenanthren]-8a'-ol 在 盐酸 、 水 作用下， 以92%的产率得到(1R,9R,10S)-17-benzyl-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
  参考文献：
  名称：

  Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration

  摘要：

  We have reported previously the novel delta-opioid agonist, SN-28, which was more potent in in vitro assays than the prototype delta-agonists, TAN-67 and SNC-80. However, when administered by subcutaneous injection, this compound showed no analgesic effect at dosages greater than 30 mg/kg in the acetic acid writhing test. We speculated that SN-28 was not effective in the test because the presence of the charged ammonium groups prevented its penetration through the blood-brain barrier. On the basis of our proposal, we designed the novel delta-agonist, KNT-127, which was effective with systemic administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.083
• 作为产物：
  描述：

  14-Hydroxy-3-methoxy-6-oxo-morphinan 6-Ethylene Ketal 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到(4b'R,8a'S,9'R)-11'-benzyl-3'-methoxy-7',8',9',10'-tetrahydro-5'H,8a'H-spiro[[1,3]dioxolane-2,6'-[9,4b](epiminoethano)phenanthren]-8a'-ol
  参考文献：
  名称：

  Design and synthesis of KNT-127, a δ-opioid receptor agonist effective by systemic administration

  摘要：

  We have reported previously the novel delta-opioid agonist, SN-28, which was more potent in in vitro assays than the prototype delta-agonists, TAN-67 and SNC-80. However, when administered by subcutaneous injection, this compound showed no analgesic effect at dosages greater than 30 mg/kg in the acetic acid writhing test. We speculated that SN-28 was not effective in the test because the presence of the charged ammonium groups prevented its penetration through the blood-brain barrier. On the basis of our proposal, we designed the novel delta-agonist, KNT-127, which was effective with systemic administration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.083