5-methoxy-2-((2-(4-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol | 1421930-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-methoxy-2-((2-(4-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol
• CAS: 1421930-26-8
• 化学式: C₁₅H₁₃F₃N₂O₂
• 分子量: 310.276
• InChiKey: SCACBOYHOQKTKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.85
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 4-(三氟甲基)苯肼 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 5-methoxy-2-((2-(4-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol
  参考文献：
  名称：

  Diaryl Hydrazones as Multifunctional Inhibitors of Amyloid Self-Assembly

  摘要：

  The design and application of an effective, new class of multifunctional small molecule inhibitors of amyloid self-assembly are described. Several compounds based on the diaryl hydrazone scaffold were designed. Forty-four substituted derivatives of this core structure were synthesized using a variety of benzaldehydes and phenylhydrazines and characterized. The inhibitor candidates were evaluated in multiple assays, including the inhibition of amyloid beta (A beta) fibrillogenesis and oligomer formation and the reverse processes, the disassembly of preformed fibrils and oligomers. Because the structure of the hydrazone-based inhibitors mimics the redox features of the antioxidant resveratrol, the radical scavenging effect of the compounds was evaluated by colorimetric assays against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals. The hydrazone scaffold was active in all of the different assays. The structure-activity relationship revealed that the substituents on the aromatic rings had a considerable effect on the overall activity of the compounds. The inhibitors showed strong activity in fibrillogenesis inhibition and disassembly, and even greater potency in the inhibition of oligomer formation and oligomer disassembly. Supporting the quantitative fluorometric and colorimetric assays, size exclusion chromatographic studies indicated that the best compounds practically eliminated or substantially inhibited the formation of soluble, aggregated A beta species, as well. Atomic force microscopy was also applied to monitor the morphology of A beta deposits. The compounds also possessed the predicted antioxidant properties; approximately 30% of the synthesized compounds showed a radical scavenging effect equal to or better than that of resveratrol or ascorbic acid.

  DOI：

  10.1021/bi3012059