N′-(2-hydroxy-5-nitrophenyl-methylidene)-3-pyridincarbohydrazide | 41377-69-9

• 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-nitrophenyl-methylidene)-3-pyridincarbohydrazide
• 英文别名: nicotinoylhydrazone 5-nitrosalicylic aldehyde；Nicotinsaeure-5-nitrosalicyliden-hydrazon；2-hydroxy-5-nitro-benzaldehyde nicotinoylhydrazone；N-[(2-hydroxy-5-nitrophenyl)methylideneamino]pyridine-3-carboxamide
• CAS: 41377-69-9
• 化学式: C₁₃H₁₀N₄O₄
• 分子量: 286.247
• InChiKey: RMDCAYMHYAZECJ-UHFFFAOYSA-N

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：

  molybdenium(VI) dioxodichloride 、 N′-(2-hydroxy-5-nitrophenyl-methylidene)-3-pyridincarbohydrazide 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到
  参考文献：
  名称：

  二氧钼 (VI) 与酰基腙的配合物。烟酰腙 5-亚硝基水杨醛 (H2L) 和溶剂合物 МоО2(L)·Me2SO 的晶体结构

  摘要：

  摘要 合成了烟酰腙5-硝基水杨醛(H 2 L) 和溶剂合物МоО 2 (L)·Me 2 SO ( I )，并通过红外光谱和X射线衍射研究了它们的结构。根据 X 射线衍射数据，I中的钼原子具有由两个顺式-O 2 (oxo) 配体组成的八面体配位体，N(L),O(Solv) 原子在O(oxo) 的反位上和两个O(L) 原子在O(oxo)的顺式位置和彼此的反位置。Mo原子以三齿(2O，N)双螯合物方式配位配体L 2- 。平均键长I是：Mo-O(oxo) 1.690 Å，Mo-N(L) 2.249 Å，Mo-O(L) 1.965 Å，Mo-O(Me2SO) 2.260 Å，O(oxo)MoO(oxo) 键角为 105.1°。考虑了配体 L 2-从 H 2 L 通过时的几何参数变化和配合物I中 Mo 原子的配位。得到了加合物МоО 2 Сl 2 ⋅2H 2 L ( II )，并根据红外光谱数据对其结构进行了讨论。

  DOI：

  10.1134/s0036023622050151
• 作为产物：
  描述：

  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-nitrophenyl-methylidene)-3-pyridincarbohydrazide
  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

• Acid–Base Properties and Kinetics of Hydrolysis of Aroylhydrazones Derived from Nicotinic Acid Hydrazide
  作者：T. Benković、D. Kontrec、V. Tomišić、A. Budimir、N. Galić

  DOI：10.1007/s10953-016-0504-8

  日期：2016.8

  synthesized from nicotinic acid hydrazide and differently substituted benzaldehydes. The protonation constants of the 12 resulting hydrazones, as well as of the starting compounds, were determined in methanol/water 1/1 mixtures by spectrophotometric–potentiometric batch titrations. In order to determine the effect of substituents on the stability of the C=N bond, the kinetics of hydrolysis of hydrazones was

  摘要 以烟酸酰肼和不同取代的苯甲醛为原料合成了一系列芳酰腙。在甲醇/水 1/1 混合物中通过分光光度法-电位分批滴定法测定 12 个所得腙以及起始化合物的质子化常数。为了确定取代基对 C=N 键稳定性的影响，在酸性和碱性介质中用分光光度法研究腙的水解动力学。HPLC 方法用于研究所选化合物的水解，观察到水解和缩合反应之间的平衡。根据色谱和分光光度数据计算得出的观察到的速率常数非常一致。电喷雾质谱法用于测定反应产物。对于 2,3- 和 2,5- 二羟基取代的苯甲醛衍生物，在碱性介质中观察到氧化和醌的形成。另一方面，与 N'-salicylidene-3-pyridinecarbohydrazide 相比，2,4-二羟基衍生物表现出更高的稳定性。
• Copper(II) complexes of aroylhydrazones: Preparation and structural characterization
  作者：Adriana Kenđel、Snežana Miljanić、Darko Kontrec、Željka Soldin、Nives Galić

  DOI：10.1016/j.molstruc.2020.127783

  日期：2020.5

  nitrogen and oxygen of the phenolic hydroxyl group were proposed as the coordination sites for the copper(II) ion. In all applied synthesis conditions Cu(II) complexes were obtained in Cu(II)/hydrazone molar ratio of 1/1, except for a hydrazone with nitro group, which did not form a complex with Cu(II) regardless of the synthetic conditions. Vibrational spectra indicated that hydrazone having only ortho-hydroxyl

  摘要 利用红外(IR)和拉曼光谱分析了苯环上不同取代基的烟酸酰肼和水杨醛衍生物得到的芳酰腙固体铜配合物的结构。研究的芳香腙作为中性、单阴离子或双阴离子三齿配体，取决于络合过程中采用的互变异构体形式。水杨醛环上的各种附加取代基不参与金属配位，因此羰基/烯醇氧、偶氮甲碱氮和酚羟基的氧被提议作为铜（II）离子的配位位点。在所有应用的合成条件下，Cu(II)/腙摩尔比为 1/1 得到 Cu(II) 配合物，但带有硝基的腙除外，无论合成条件如何，它都不会与 Cu(II) 形成络合物。振动光谱表明，腙在双 CN 键上仅具有邻羟基基团，而腙在苯环的对位上具有额外的 OH 基团，形成了以水为配体的单体铜 (II) 配合物，而腙与间位取代基（Cl、OCH3）形成双核铜配合物，其中两个铜（II）离子通过酚氧原子桥接腙分子。通过热重分析研究了制备的铜 (II) 配合物的热性能。振动光谱表明，腙在双 CN 键上仅
• Characterization and antidiabetic activity of salicylhydrazone Schiff base vanadium(IV) and (V) complexes
  作者：Janusz Szklarzewicz、Anna Jurowska、Maciej Hodorowicz、Grzegorz Kazek、Barbara Mordyl、Elżbieta Menaszek、Jacek Sapa

  DOI：10.1007/s11243-020-00437-1

  日期：2021.3

  Twenty-four oxidovanadium(IV,V) complexes with tridentate Schiff base ligands based on 5-nitrosalicylaldehyde, 5-methoxysalicylaldehyde, or 5-sulfosalicylaldehyde and respective hydrazide were isolated, and characterized using physicochemical and spectroscopic methods. Three of them were structurally characterized by single-crystal X-ray structure determination. The biological activity studies included

  分离出基于 5-硝基水杨醛、5-甲氧基水杨醛或 5-磺基水杨醛和各自酰肼的三齿席夫碱配体的 24 种氧化钒 (IV, V) 配合物，并使用物理化学和光谱方法对其进行表征。其中三个通过单晶 X 射线结构测定进行结构表征。生物活性研究包括对人酪氨酸磷酸酶的抑制、对肌细胞 C2C12、脂肪细胞 3T3-L1 和人肝细胞 HepG2 细胞系的研究、肌细胞和脂肪细胞的葡萄糖摄取以及细胞毒性试验。在溶液中不稳定的复合物表现出其他 V(IV) 复合物的典型生物活性，而稳定的复合物则表现出更高的配体依赖性活性。
• 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.