(E)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethyliden]isonicotinoyl-hydrazide | 1262304-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethyliden]isonicotinoyl-hydrazide
• 英文别名: N-[(E)-1-(2-hydroxy-4-methoxyphenyl)ethylideneamino]pyridine-4-carboxamide
• CAS: 1262304-90-4
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: HEKPAZXFGXJNOU-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  以 二甲基亚砜 为溶剂， 生成 (E)-N'-[1-(2-hydroxy-4-methoxyphenyl)ethyliden]isonicotinoyl-hydrazide
  参考文献：
  名称：

  金属结合光电开关，用于可见光反应性和可变弛豫动力学

  摘要：

  光开关部分的应用范围是多种多样的，因此设计具有可变的光化学和物理性质的开关的能力因此对于实现其潜力很重要。以前我们报道了（E）-N '-（1-（2-羟苯基）亚乙基）异烟酰肼（HAPI）的光致变色现象，这是一种首先开发为过渡金属螯合剂的芳酰yl化合物。本文中我们报告了结构相关的芳酰hydr螯合剂的合成，并探讨了这些修饰对其UVA，UVC和蓝光光反应性，光平稳态组成，光异构体热稳定性和相对铁的影响（III）绑定亲和力。这些发现将为用于金属门控光开关应用的下一代芳酰photo光开关提供信息。

  DOI：

  10.1039/c7pp00173h

文献信息

• Synthesis and Initial <i>in Vitro</i> Evaluations of Novel Antioxidant Aroylhydrazone Iron Chelators with Increased Stability against Plasma Hydrolysis
  作者：Katerina Hruskova、Petra Kovarikova、Petra Bendova、Pavlina Haskova、Eliska Mackova、Jan Stariat、Anna Vavrova、Katerina Vavrova、Tomas Simunek

  DOI：10.1021/tx100359t

  日期：2011.3.21

  Oxidative stress is known to contribute to a number of cardiovascular patholgies. Free intracellular iron ions participate in the Fenton reactior and therefore substantially contribute to the formation of highly toxic hydroxyl radicals and cellular injury. Earlier work on the intracellular iron chelator salicylaldehyde isonicotinoyl hydrazone (SIH) his demonstrated its Considerable promise as an agent to protect the heart against oxidative injury both in Vitro and in vivo. However, the major limitation of SIH is represented by its labile hydrazone bond that makes it prone to plasma hydrolysis. Hence, in order to improve the hydrazone bond stability, nine compounds were prepared by a substitution of salicylaldehyde by the respective methyl and ethylketone various electron donors or acceptors in the phenyl ring. All the synthesized aroylhydrazones displayed significant iron-chelating activities and eight chelators showed significantly higher stability in rabbit plasma than SIH. Furthermore, some of these chelators were observed to possess higher cytoprotective activities against oxidative injury and/or lower toxicity as compared to SIR. The results of the present study therefore indicate the possible applicability of several of these novel agents in the prevention and/or treatment of cardiovascular disorders with a known (or presumed) role of oxidative stress. In particular, the methylketone HAPI and nitro group-containing NHAPI merit further in vivo investigations.