4,6-dimethoxy-3-(2-nitro-5-benzyloxybenzylidene)phthalide | 887645-00-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,6-dimethoxy-3-(2-nitro-5-benzyloxybenzylidene)phthalide
• 英文别名: 4,6-dimethoxy-3-[(2-nitro-5-phenylmethoxyphenyl)methylidene]-2-benzofuran-1-one
• CAS: 887645-00-3
• 化学式: C₂₄H₁₉NO₇
• 分子量: 433.417
• InChiKey: KDDONIFITHKGSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-3-(2-nitro-5-benzyloxybenzylidene)phthalide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到4,6-dimethoxy-2-(2-nitro-5-benzyloxyphenyl)indane-1,3-dione
  参考文献：
  名称：

  New ligands at the melatonin binding site MT3

  摘要：

  The third melatonin binding site, MT3 is a non-classical one since it is not a seven transmembrane domains receptor, but an enzyme, quinone reductase 2. A major concern for the study of the physiological role of this site is the lack of specific ligands, permitting to more accurately dissect the pathways linked to the activation of MT3. Indeed, in the course of finding new ligands, we identified a new series of compounds with affinity to the binding site in the nM range, particularly 2,3-dimethoxy 7-hydroxy 10-methyl 5H 10H indeno(1,2-b)indol-10-one (DMHMIO), with a Ki of 190 pM. Based on slightly different and novel synthons compared to most of the compounds used in melatonin pharmacology studies, these compounds offer new perspective for the description of the melatonin pathways, so much more by not having any affinity towards the MTI and MT2 'classical' melatonin receptors. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.12.002
• 作为产物：
  描述：

  3-bromo-4,6-dimethoxy-3H-2-benzofuran-1-one 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.5h， 生成 4,6-dimethoxy-3-(2-nitro-5-benzyloxybenzylidene)phthalide
  参考文献：
  名称：

  New ligands at the melatonin binding site MT3

  摘要：

  The third melatonin binding site, MT3 is a non-classical one since it is not a seven transmembrane domains receptor, but an enzyme, quinone reductase 2. A major concern for the study of the physiological role of this site is the lack of specific ligands, permitting to more accurately dissect the pathways linked to the activation of MT3. Indeed, in the course of finding new ligands, we identified a new series of compounds with affinity to the binding site in the nM range, particularly 2,3-dimethoxy 7-hydroxy 10-methyl 5H 10H indeno(1,2-b)indol-10-one (DMHMIO), with a Ki of 190 pM. Based on slightly different and novel synthons compared to most of the compounds used in melatonin pharmacology studies, these compounds offer new perspective for the description of the melatonin pathways, so much more by not having any affinity towards the MTI and MT2 'classical' melatonin receptors. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.12.002