N-((1H-pyrrol-3-yl)methyl)-4-((E)-2-(3,5-dimethoxystyryl))aniline | 1446410-63-4

• 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: N-((1H-pyrrol-3-yl)methyl)-4-((E)-2-(3,5-dimethoxystyryl))aniline
• 英文别名: 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-N-(1H-pyrrol-3-ylmethyl)aniline
• CAS: 1446410-63-4
• 化学式: C₂₁H₂₂N₂O₂
• 分子量: 334.418
• InChiKey: GNJNEMFMQNZJAR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 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 N-((1H-pyrrol-3-yl)methyl)-4-((E)-2-(3,5-dimethoxystyryl))aniline
  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

文献信息

• Design, Synthesis, and Evaluation of Multitarget-Directed Resveratrol Derivatives for the Treatment of Alzheimer’s Disease
  作者：Chuanjun Lu、Yueyan Guo、Jun Yan、Zonghua Luo、Hai-Bin Luo、Ming Yan、Ling Huang、Xingshu Li

  DOI：10.1021/jm400567s

  日期：2013.7.25

  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.