(E)-N'-(1-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethylidene)isonicotinohydrazide | 1262304-93-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (E)-N'-(1-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethylidene)isonicotinohydrazide
• 英文别名: (E)-N'-(1-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethylidene)isonicotinoylhydrazide
• CAS: 1262304-93-7
• 化学式: C₁₇H₁₃N₃O₄
• 分子量: 323.308
• InChiKey: PSTMXXMCVGCRGC-VXLYETTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  104.79
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  异烟肼 、 8-乙酰基-7-羟基香豆素 以 乙醇 为溶剂， 反应 0.33h， 以61%的产率得到(E)-N'-(1-(7-hydroxy-2-oxo-2H-chromen-8-yl)ethylidene)isonicotinohydrazide
  参考文献：
  名称：

  Synthesis and Initial in Vitro Evaluations of Novel Antioxidant Aroylhydrazone Iron Chelators with Increased Stability against Plasma Hydrolysis

  摘要：

  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.

  DOI：

  10.1021/tx100359t