5-methoxy-2-((2-(3-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol | 1421930-28-0

• 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-(3-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol
• CAS: 1421930-28-0
• 化学式: C₁₅H₁₃F₃N₂O₂
• 分子量: 310.276
• InChiKey: GNLPLPIDGUPQEE-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 、 3-三氟甲基苯肼 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 5-methoxy-2-((2-(3-(trifluoromethyl)phenyl)hydrazineylidene)methyl)phenol
  参考文献：
  名称：

  具有 CK2 抑制和抗氧化特性的多功能抗阿尔茨海默病药物有机氟腙衍生物

  摘要：

  合成了一组新型腙衍生物并分析了它们的生物活性。测试了这些化合物对蛋白激酶 CK2 磷酸化活性的抑制作用，并在三种常用测定中测定了它们的抗氧化活性。评价腙对 DPPH、ABTS 和过氧自由基的自由基清除作用。几种化合物已被确定为良好的抗氧化剂以及有效的蛋白激酶 CK2 抑制剂。大多数含有 4-N(CH 3 ) 2残基或全氟苯环的腙在自由基清除测定中显示出高活性，并且在激酶测定中具有纳摩尔 IC 50值。

  DOI：

  10.1002/cmdc.202100047

文献信息

• Diaryl Hydrazones as Multifunctional Inhibitors of Amyloid Self-Assembly
  作者：Béla Török、Abha Sood、Seema Bag、Rekha Tulsan、Sanjukta Ghosh、Dmitry Borkin、Arleen R. Kennedy、Michelle Melanson、Richard Madden、Weihong Zhou、Harry LeVine、Marianna Török

  DOI：10.1021/bi3012059

  日期：2013.2.19

  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.