N'-(2,5-dihydroxybenzylidene)isonicotinohydrazide | 863014-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N'-(2,5-dihydroxybenzylidene)isonicotinohydrazide
• CAS: 863014-04-4
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: NFRQYAFDZJLKFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.81
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  异烟肼 、 2,5-二羟基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以80%的产率得到N'-(2,5-dihydroxybenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  Acylhydrazones as isoniazid derivatives with multi-target profiles for the treatment of Alzheimer’s disease: Radical scavenging, myeloperoxidase/acetylcholinesterase inhibition and biometal chelation

  摘要：

  Acylhydrazones la-o, derived from isoniazid, were synthesized and evaluated for Myeloperoxidase (MPO) and Acetylcholinesterase (AChE) inhibition, as well as their antioxidant and metal chelating activities, with the purpose of investigating potential multi-target profiles for the treatment of Alzheimer's disease. Synthesized compounds were tested using the 2,2-diphenyl-2-picrylhydrazyl (DPPH) method and 1i, 1j and 1 m showed radical scavenging ability. Compounds 1b, 1 h, 1i , 1 m and 1o inhibited MPO activity (10 mu M) at 96.1 +/- 5.5%, 90 +/- 2.1%, 100.3 +/- 1.7%, 80.1 +/- 9.4% and 82.2 +/- 10.6%, respectively, and only compound 1 m was able to inhibit 54.2 +/- 1.7% of AChE activity (100 mu M). Docking studies of the most potent compound 1 m were carried out, and the computational results provided the theoretical basis of enzyme inhibition. Furthermore, compound 1 m was able to form complexes with Fe2+ and Zn2+ ions in a 2:1 ligand:metal ratio according to the Job Plot method.

  DOI：

  10.1016/j.bmc.2020.115470

文献信息

• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.