(Z)-N-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methanamine oxide | 176720-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (Z)-N-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methanamine oxide
• 英文别名: (Z)-5-fluoro-N-methyl-2,3-dihydro-1H-inden-1-imine oxide；5-fluoro-N-methyl-2,3-dihydroinden-1-imine oxide
• CAS: 176720-13-1
• 化学式: C₁₀H₁₀FNO
• 分子量: 179.194
• InChiKey: NPUISNYQBWLJQF-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯基乙烯基亚砜 、 (Z)-N-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methanamine oxide 以 甲苯 为溶剂， 反应 6.0h， 以11.3%的产率得到6-Fluoro-1-methyl-1,4-dihydro-indeno[1,2-b]pyrrole
  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：

  3-(3-fluorophenyl)propanoyl chloride 在 三氯化铝 、 sodium acetate 、 sodium chloride 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 (Z)-N-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methanamine oxide
  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：

文献信息

• Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: solvent-free microwave-assisted stereoselective synthesis and theoretical calculations
  作者：Loredana Maiuolo、Pedro Merino、Vincenzo Algieri、Monica Nardi、Maria Luisa Di Gioia、Beatrice Russo、Ignacio Delso、Matteo Antonio Tallarida、Antonio De Nino

  DOI：10.1039/c7ra09995a

  日期：——

  because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding

  螺-羟吲哚由于其抗病毒特性而被广泛应用。然而，在文献中，很少报道合成其前体羟吲哚-硝酮的实例。在本文中，我们最初提出了一种快速，高效的合成方法，该方法通过Isatin或茚满酮衍生物与各种羟胺之间的无溶剂微波辅助反应来合成酮硝酮。合成协议简便，干净，快速，高产量且具有立体选择性。然后，我们探索了通过无溶剂的MW辅助1,3-偶极环加成合成含核苷的螺-异​​恶唑烷与靛红和茚满酮核的可能性，获得了良好的收率（74-85％），以及区域和非对映选择性。
• Antiproliferative activity of novel isatinyl/indanyl nitrones (INs) as potential spin trapping agents of free radical intermediates
  作者：Loredana Maiuolo、Giordana Feriotto、Vincenzo Algieri、Monica Nardi、Beatrice Russo、Maria Luisa Di Gioia、Emilia Furia、Matteo Antonio Tallarida、Carlo Mischiati、Antonio De Nino

  DOI：10.1039/c7md00537g

  日期：——

  A series of ketonitrones derived from isatin and indanone (INs) were synthesized and evaluated for their antiproliferative activities against several human cancer cell lines. Then, the antioxidant properties of these substrates were measured by the DPPH test to report their biological activity in terms of their spin trapping action. In particular, one substrate has showed very high biological and scavenging

  合成了一系列源自靛红和茚满酮 (IN) 的酮硝酮，并评估了它们对几种人类癌细胞系的抗增殖活性。然后，通过 DPPH 测试测量这些底物的抗氧化性能，以报告它们在自旋捕获作用方面的生物活性。特别是，一种底物显示出非常高的生物和清除活性，这可能是由于其自旋捕获活性和结构之间的强相关性。
• 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.