5-chloro-1H-indole-3-carboxaldehyde isonicotinoyl hydrazone | 1264746-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-chloro-1H-indole-3-carboxaldehyde isonicotinoyl hydrazone
• CAS: 1264746-60-2
• 化学式: C₁₅H₁₁ClN₄O
• 分子量: 298.732
• InChiKey: KBIYILIHAZEDEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.14
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  异烟肼 、 5-氯吲哚-3-甲醛 以 乙醇 为溶剂， 反应 2.5h， 以78.9%的产率得到5-chloro-1H-indole-3-carboxaldehyde isonicotinoyl hydrazone
  参考文献：
  名称：

  Electrochemical Behavior of Indole-3-Carboxaldehyde Izonicotinoyl Hydrazones: Discussion on Possible Biological Behavior

  摘要：

  电化学技术为药物分子及其在体内的机制（如新陈代谢）提供了宝贵的信息，而新陈代谢是药物发现的重要作用之一。由于许多生理过程都依赖于氧化还原反应，因此不难发现电化学反应与生物反应在电子转移方面的联系。为了研究这一提议，我们合成了两种化合物，即 1-甲基吲哚-3-甲醛偶氮烟酰基腙和 5-氯-1H-吲哚-3-甲醛偶氮烟酰基腙，并利用不同的伏安技术对其进行了表征和电化学检测，以评估其可能的生物行为。讨论了相应电极反应的特征。在不同的介质中，合成的化合物获得了线性响应，检测限较低。

  DOI：

  10.2174/1386207311004070619

文献信息

• Synthesis and antioxidant activity evaluations of melatonin-based analogue indole-hydrazide/hydrazone derivatives
  作者：Ayse Didem Yılmaz、Tulay Coban、Sibel Suzen

  DOI：10.3109/14756366.2011.594048

  日期：2012.6.1

  Melatonin (MLT) is a hormone synthesized from the pineal gland. It is a direct scavenger of free radicals, which is related to its capability to defend cells from oxidative stress. Recently MLT-related compounds are under investigation to establish which exhibit the maximum activity with the lowest side effects. In this study 5-chloroindole hydrazide/hydrazone derivatives were synthesized from 5-chloroindole-3-carboxaldehyde and phenyl hydrazine derivatives. All the compounds characterized and in vitro antioxidant activity was investigated against MLT and BHT. Most of the compounds showed strong inhibitory effect on the superoxide radical scavenging assay at 1 mM concentration (79 to 95%). Almost all the tested compounds possessed strong scavenging activity against the DPPH radical scavenging activity with IC50 values (2 to 60 mu M). Lastly, compound 1j revealed stronger inhibitory activity against MLT in the LP inhibitory assay at 0.1mM concentration (51%) while the rest of the compounds showed moderate inhibition.