N'-(2-hydroxy-5-nitrobenzylidene)isonicotinohydrazide | 41377-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-(2-hydroxy-5-nitrobenzylidene)isonicotinohydrazide
• 英文别名: N'-(2-hydroxy-5-nitrobenzylidene)isoniazide；Isonicotinsaeure-5-nitrosalicyliden-hydrazon；N-[(2-hydroxy-5-nitrophenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 41377-70-2
• 化学式: C₁₃H₁₀N₄O₄
• mdl: MFCD00643735
• 分子量: 286.247
• InChiKey: PIEWMLRJDLRRIA-UHFFFAOYSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-(2-hydroxy-5-nitrobenzylidene)isonicotinohydrazide 、 copper dichloride 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  设计水杨醛异烟酰酰azo作为具有可调螯合和释放铜的铜（II）离子载体，以击中癌细胞的氧化跟腱

  摘要：

  与正常细胞相比，在癌细胞中观察到更高水平的铜，还原型谷胱甘肽（GSH）和活性氧（ROS），赞成将铜离子载体开发为促氧化抗癌剂（PAA）来达到改变的氧化还原稳态的想法（氧化还原阿基里斯脚跟） ）的癌细胞。在这项工作中，我们使用水杨醛异烟酰yl（SIH-1）作为碱性支架，通过在对位引入吸电子硝基和给电子甲氧基来设计具有可调节的螯合和释放Cu（II）的Cu（II）离子载体。酚羟基位置，或通过使用甲基封闭酚羟基位点。这些分子被用来探测铜的螯合和释放如何影响它们的离子作用和靶向癌细胞氧化还原阿基里斯足跟的能力。在这些分子中，SIH-1被认为是比HUVEC细胞更能优先杀死HepG2细胞的最有力的Cu（II）离子载体，并且在相对较高的细胞毒性和更好的选择性方面，它还优于临床试验中评估的铜离子载体氯碘喹。尽管SIH-1形成的Cu（II）配合物比其他分子具有更高的稳定常数，但其较高的氧化电位是由GSH释放铜

  DOI：

  10.1016/j.freeradbiomed.2018.09.017
• 作为产物：
  描述：

  异烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N'-(2-hydroxy-5-nitrobenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

  摘要：

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.040

文献信息

• Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structure–microbicidal activity relationship
  作者：Lei Xia、Yu-Fen Xia、Li-Rong Huang、Xiao Xiao、Hua-Yong Lou、Tang-Jingjun Liu、Wei-Dong Pan、Heng Luo

  DOI：10.1016/j.ejmech.2015.04.042

  日期：2015.6

  There is an urgent need to develop new antibacterial agents because of multidrug resistance by bacteria and fungi. Schiff bases (aldehyde or ketone-like compounds) exhibit intense antibacterial characteristics, and are therefore, promising candidates as antibacterial agents. To investigate the mechanism of action of newly designed benzaldehyde Schiff bases, a series of high-yielding benzaldehyde Schiff bases were synthesized, and their structures were determined by NMR and MS spectra data. The structure microbicidal activity relationship of derivatives was investigated, and the antibacterial mechanisms were investigated by gene assays for the expression of functional genes in vitro using Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The active compounds were selective for certain active groups. The polar substitution of the R-2 group of the amino acids in the Schiff bases, affected the antibacterial activity against E. coli and S. aureus; specific active group at the R-3 or R-4 groups of the acylhydrazone Schiff bases could improve their inhibitory activity against these three tested organisms. The antibacterial mechanism of the active benzaldehyde Schiff bases appeared to regulate the expression of metabolism-associated genes in E. coli, hemolysis-associated genes in B. subtilis, and key virulence genes in S. aureus. Some benzaldehyde Schiff bases were bactericidal to all the three strains and appeared to regulate gene expression associated with metabolism, hemolysis, and virulence, in vitro. The newly designed benzaldehyde Schiff bases possessed unique antibacterial activity and might be potentially useful for prophylactic or therapeutic intervention of bacterial infections. (C) 2015 Published by Elsevier Masson SAS.
• 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.
• Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs
  作者：Gregory L. Backes、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmc.2015.04.040

  日期：2015.7

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.
• Designing salicylaldehyde isonicotinoyl hydrazones as Cu(II) ionophores with tunable chelation and release of copper for hitting redox Achilles heel of cancer cells
  作者：Yuan Ji、Fang Dai、Bo Zhou

  DOI：10.1016/j.freeradbiomed.2018.09.017

  日期：2018.12

  molecules, SIH-1 was identified as the most potent Cu(II) ionophore to kill preferentially HepG2 cells over HUVEC cells, and also superior to clioquinol, a copper ionophore evaluated in clinical trials, in terms of its relatively higher cytotoxicity and better selectivity. Higher oxidative potential, despite of lower stability constant, of the Cu(II) complex formed by SIH-1 than by the other molecules, is

  与正常细胞相比，在癌细胞中观察到更高水平的铜，还原型谷胱甘肽（GSH）和活性氧（ROS），赞成将铜离子载体开发为促氧化抗癌剂（PAA）来达到改变的氧化还原稳态的想法（氧化还原阿基里斯脚跟） ）的癌细胞。在这项工作中，我们使用水杨醛异烟酰yl（SIH-1）作为碱性支架，通过在对位引入吸电子硝基和给电子甲氧基来设计具有可调节的螯合和释放Cu（II）的Cu（II）离子载体。酚羟基位置，或通过使用甲基封闭酚羟基位点。这些分子被用来探测铜的螯合和释放如何影响它们的离子作用和靶向癌细胞氧化还原阿基里斯足跟的能力。在这些分子中，SIH-1被认为是比HUVEC细胞更能优先杀死HepG2细胞的最有力的Cu（II）离子载体，并且在相对较高的细胞毒性和更好的选择性方面，它还优于临床试验中评估的铜离子载体氯碘喹。尽管SIH-1形成的Cu（II）配合物比其他分子具有更高的稳定常数，但其较高的氧化电位是由GSH释放铜