(E)-N'-(4-ethylbenzylidene)isonicotinohydrazide

• 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: (E)-N'-(4-ethylbenzylidene)isonicotinohydrazide
• 英文别名: N'-[(E)-(4-ethylphenyl)methylidene]pyridine-4-carbohydrazide；N-[(E)-(4-ethylphenyl)methylideneamino]pyridine-4-carboxamide
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: PLNPNWMJYXIHEZ-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异烟肼 、 4-乙基苯甲醛 以 乙醇 为溶剂， 反应 16.0h， 以96%的产率得到(E)-N'-(4-ethylbenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  Structure-based optimization of oxadiazole-based GSK-3 inhibitors

  摘要：

  Inhibition of glycogen synthase kinase-3 (GSK-3) induces neuroprotective effects, e.g. decreases beta-amyloid production and reduces tau hyperphosphorylation, which are both associated with Alzheimer's disease (AD). The two isoforms of GSK-3 in mammalians are GSK-3 alpha and beta, which share 98% homology in their catalytic domains. We investigated GSK-3 inhibitors based on 2 different scaffolds in order to elucidate the demands of the ATP-binding pocket [1]. Particularly, the oxadiazole scaffold provided potent and selective GSK-3 inhibitors. For example, the most potent inhibitor of the present series, the acetamide 26d, is characterized by an IC50 of 2 nM for GSK-3 alpha and 17 nM for GSK-3 beta. In addition, the benzodioxane 8g showed up to 27-fold selectivity for GSK-3 alpha over GSK-3 beta, with an IC50 of 35 nM for GSK-3 alpha. Two GSK-3 inhibitors were further profiled for efficacy and toxicity in the wild-type (wt) zebrafish embryo assay to evaluate simultaneously permeability and safety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.006

文献信息

• Anti-infective compounds
  申请人：Brodin Priscille

  公开号：US20110178077A1

  公开（公告）日：2011-07-21

  The present invention relates to small molecule compounds and their use in the treatment of bacterial infections, in particular Tuberculosis.

  本发明涉及小分子化合物及其在治疗细菌感染，特别是结核病方面的用途。
• (Hetero-)(arylidene)arylhydrazides as Multitarget-Directed Monoamine Oxidase Inhibitors
  作者：Ashique Palakkathondi、Jong Min Oh、Sanal Dev、T. M. Rangarajan、Swafvan Kaipakasseri、Fathima Sahla Kavully、Nicola Gambacorta、Orazio Nicolotti、Hoon Kim、Bijo Mathew

  DOI：10.1021/acscombsci.0c00136

  日期：2020.11.9

  Fourteen (hetero-)(arylidene)arylhydrazide derivatives (ABH1-ABH14) were synthesized, and their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE) were evaluated. Compound ABHS most potently inhibited MAO-B with an IC50 value of 0.025 +/- 0.0019 mu M; ABH2 and ABH3 exhibited high IC so values as well. Most of the compounds weakly inhibited MAO-A, except ABHS (IC50 = 3.31 +/- 0.41 mu M). Among the active compounds, ABH2 showed the highest selectivity index (SI) of 174 for MAO-B, followed by ABHS (SI = 132). ABH3 and ABHS effectively inhibited AChE with IC so values of 15.7 +/- 6.52 and 16.5 +/- 7.29 mu M, respectively, whereas the other compounds were weak inhibitors of AChE. ABHS was shown to be a reversible competitive inhibitor for MAO-A and MAO-B with K-i values of 0.96 +/- 0.19 and 0.024 +/- 0.0077 mu M, respectively, suggesting that this molecule can be considered as an interesting candidate for further development as a multitarget inhibitor relating to neurodegenerative disorders.
• US8785452B2
  申请人：——

  公开号：US8785452B2

  公开（公告）日：2014-07-22