(Z)-5-methoxy-N-methyl-2,3-dihydro-1H-inden-1-imine oxide | 176720-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (Z)-5-methoxy-N-methyl-2,3-dihydro-1H-inden-1-imine oxide
• 英文别名: 5-methoxy-N-methyl-2,3-dihydroinden-1-imine oxide
• CAS: 176720-14-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: FLNVQILBBGYQNG-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-methoxy-N-methyl-2,3-dihydro-1H-inden-1-imine oxide 在 potassium permanganate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 30.0h， 生成 6-methoxy-1-methylindenol[1,2-b]pyrrol-4(1H)-one
  参考文献：
  名称：

  Murphy, Fiona M.; Meegan, Mary Jane, Journal of Chemical Research, Miniprint, 1996, # 1, p. 301 - 315

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 、 N-甲基羟胺盐酸盐 在 sodium acetate 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 95.0 ℃ 、2.03 MPa 条件下， 反应 7.0h， 以52%的产率得到(Z)-5-methoxy-N-methyl-2,3-dihydro-1H-inden-1-imine oxide
  参考文献：
  名称：

  Synthesis, neuroprotective and antioxidant capacity of PBN-related indanonitrones

  摘要：

  In this work six PBN-related indanonitrones 1-6 have been designed, synthesized, and their neuroprotection capacity tested in vitro, under OGD conditions, in SH-SY5Y human neuroblastoma cell cultures. As a result, we have identified indanonitrones 1, 3 and 4 (EC50= 6.64 +/- 0.28 mu M) as the most neuroprotective agents, and in particular, among them, indanonitrone 4 was also the most potent and balanced nitrone, showing antioxidant activity in three experiments [LOX (100 mu M), APPH (51%), DPPH (36.5%)], being clearly more potent antioxidant agent than nitrone PBN. Consequently, we have identified (Z)-5-hydroxy-N-methyl-2,3-dihydro-1H-inden- 1-imine oxide (4) as a hit-molecule for further investigation.

  DOI：

  10.1016/j.bioorg.2019.01.071

文献信息

• Murphy, Fiona M.; Meegan, Mary Jane, Journal of Chemical Research, Miniprint, 1996, # 1, p. 301 - 315
  作者：Murphy, Fiona M.、Meegan, Mary Jane

  DOI：——

  日期：——
• Synthesis, neuroprotective and antioxidant capacity of PBN-related indanonitrones
  作者：Alicia Jiménez-Almarza、Daniel Diez-Iriepa、Mourad Chioua、Beatriz Chamorro、Isabel Iriepa、Ricardo Martínez-Murillo、Dimitra Hadjipavlou-Litina、María Jesús Oset-Gasque、José Marco-Contelles

  DOI：10.1016/j.bioorg.2019.01.071

  日期：2019.5

  In this work six PBN-related indanonitrones 1-6 have been designed, synthesized, and their neuroprotection capacity tested in vitro, under OGD conditions, in SH-SY5Y human neuroblastoma cell cultures. As a result, we have identified indanonitrones 1, 3 and 4 (EC50= 6.64 +/- 0.28 mu M) as the most neuroprotective agents, and in particular, among them, indanonitrone 4 was also the most potent and balanced nitrone, showing antioxidant activity in three experiments [LOX (100 mu M), APPH (51%), DPPH (36.5%)], being clearly more potent antioxidant agent than nitrone PBN. Consequently, we have identified (Z)-5-hydroxy-N-methyl-2,3-dihydro-1H-inden- 1-imine oxide (4) as a hit-molecule for further investigation.