2-((4-((E)-2-(3,5-dimethoxystyryl))phenylamino)methyl)-4-(dimethylamino)phenol | 1446410-54-3

• 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: 2-((4-((E)-2-(3,5-dimethoxystyryl))phenylamino)methyl)-4-(dimethylamino)phenol
• 英文别名: 2-[[4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]anilino]methyl]-4-(dimethylamino)phenol
• CAS: 1446410-54-3
• 化学式: C₂₅H₂₈N₂O₃
• 分子量: 404.509
• InChiKey: ARWNSSJFJLNQOG-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-((E)-2-(3,5-dimethoxystyryl))phenylamino)methyl)-4-(dimethylamino)phenol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以60%的产率得到5-((E)-2-(4-(5-(dimethylamino)-2-hydroxybenzylamino)phenyl)ethenyl)benzene-1,3-diol
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Multitarget-Directed Resveratrol Derivatives for the Treatment of Alzheimer’s Disease

  摘要：

  A series of multitarget-directed resveratrol derivatives was designed and synthesized for the treatment of Alzheimer's disease (AD). In vitro studies indicated that most of the target compounds exhibit significant inhibition of self-induced beta-amyloid (A beta) aggregation and Cu(II)-induced A beta(1-42) aggregation and acted as potential antioxidants and biometal chelators. In particular, compounds 5d and 10d are potential lead compounds for AD therapy (5d, IC50 = 7.56 mu M and 10d, IC50 = 6.51 mu M for self-induced A beta aggregation; the oxygen radical absorbance capacity assay using fluorescein (ORAC-FL) values are 4.72 and 4.70, respectively). Moreover, these compounds are capable of disassembling the highly structured A beta fibrils generated by self- and Cu(II)-induced A beta aggregation. Furthermore, 5d crossed the blood-brain barrier (BBB) in vitro and did not exhibit any acute toxicity in mice at doses of up to 2000 mg/kg. Taken together, the data indicate that 5d is a very promising lead compound for AD.

  DOI：

  10.1021/jm400567s
• 作为产物：
  描述：

  (E)-1,3-二甲氧基-5-(4-硝基苯乙烯基)苯 在 sodium tetrahydroborate 、 乙醇 、 对甲苯磺酸 、 tin(ll) chloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 2-((4-((E)-2-(3,5-dimethoxystyryl))phenylamino)methyl)-4-(dimethylamino)phenol
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Multitarget-Directed Resveratrol Derivatives for the Treatment of Alzheimer’s Disease

  摘要：

  A series of multitarget-directed resveratrol derivatives was designed and synthesized for the treatment of Alzheimer's disease (AD). In vitro studies indicated that most of the target compounds exhibit significant inhibition of self-induced beta-amyloid (A beta) aggregation and Cu(II)-induced A beta(1-42) aggregation and acted as potential antioxidants and biometal chelators. In particular, compounds 5d and 10d are potential lead compounds for AD therapy (5d, IC50 = 7.56 mu M and 10d, IC50 = 6.51 mu M for self-induced A beta aggregation; the oxygen radical absorbance capacity assay using fluorescein (ORAC-FL) values are 4.72 and 4.70, respectively). Moreover, these compounds are capable of disassembling the highly structured A beta fibrils generated by self- and Cu(II)-induced A beta aggregation. Furthermore, 5d crossed the blood-brain barrier (BBB) in vitro and did not exhibit any acute toxicity in mice at doses of up to 2000 mg/kg. Taken together, the data indicate that 5d is a very promising lead compound for AD.

  DOI：

  10.1021/jm400567s