11’-syn-spiro[[1,3]dioxolane-2,8'-[4.3.3]propellan]-11'-ol | 96089-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11’-syn-spiro[[1,3]dioxolane-2,8'-[4.3.3]propellan]-11'-ol
• CAS: 96089-24-6；96149-85-8
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: LGIIINWFBDXJBQ-CLLJXQQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  11’-syn-spiro[[1,3]dioxolane-2,8'-[4.3.3]propellan]-11'-ol 在 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以97%的产率得到8-keto<4.3.3>propellan-11-syn-ol
  参考文献：
  名称：

  Stereoselective synthesis and pharmacological evaluation of [4.3.3]propellan-8-amines as analogs of adamantanamines

  摘要：

  Amantadine (1) exerts its anti-Parkinson effects by inhibition of the NMDA associated cation channel and its antiviral activity by inhibition of the M2 protein channel of influenza A viruses. Herein the synthesis, NMDA receptor affinity and anti-influenza activity of analogous propellanamines 3 are reported. The key steps in the synthesis of the diastereomeric propellanamines syn-3 and anti-3 are diastereoselective reduction of the ketone 7 with L-Selectride to give anti-11, Mitsunobu inversion of the alcohol anti-13 into syn-13, and S(N)2 substitution of diastereomeric mesylates syn-14 and anti-14 with NaN3. The affinity of the propellanamines syn-3 and anti-3 to the PCP binding site of the NMDA receptor is similar to that of amantadine (K-i = 11 mu M). However, both propellanamines syn-3 and anti-3 do not exhibit activity against influenza A viruses. Compared to amantadine (1), the structurally related propellanamines syn-3 and anti-3 retain the NMDA antagonistic activity but loose the antiviral activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.030
• 作为产物：
  描述：

  1,2-环己二酮 在 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 甲苯 为溶剂， 反应 102.5h， 生成 11’-syn-spiro[[1,3]dioxolane-2,8'-[4.3.3]propellan]-11'-ol
  参考文献：
  名称：

  Stereoselective synthesis and pharmacological evaluation of [4.3.3]propellan-8-amines as analogs of adamantanamines

  摘要：

  Amantadine (1) exerts its anti-Parkinson effects by inhibition of the NMDA associated cation channel and its antiviral activity by inhibition of the M2 protein channel of influenza A viruses. Herein the synthesis, NMDA receptor affinity and anti-influenza activity of analogous propellanamines 3 are reported. The key steps in the synthesis of the diastereomeric propellanamines syn-3 and anti-3 are diastereoselective reduction of the ketone 7 with L-Selectride to give anti-11, Mitsunobu inversion of the alcohol anti-13 into syn-13, and S(N)2 substitution of diastereomeric mesylates syn-14 and anti-14 with NaN3. The affinity of the propellanamines syn-3 and anti-3 to the PCP binding site of the NMDA receptor is similar to that of amantadine (K-i = 11 mu M). However, both propellanamines syn-3 and anti-3 do not exhibit activity against influenza A viruses. Compared to amantadine (1), the structurally related propellanamines syn-3 and anti-3 retain the NMDA antagonistic activity but loose the antiviral activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.030

文献信息

• Propellanes-LXXVI
  作者：Lusi Senegör、Pnina Ashkenazi、David Ginsburg

  DOI：10.1016/s0040-4020(01)91283-9

  日期：1984.1
• SENEGOER, L.;ASHKENAZI, P.;GINSBURG, D., TETRAHEDRON, 1984, 40, N 24, 5271-5272
  作者：SENEGOER, L.、ASHKENAZI, P.、GINSBURG, D.

  DOI：——

  日期：——