N′-(5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide

• 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′-(5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide
• 英文别名: 5-chloro-2-hydroxybenzaldehyde nicotinoylhydrazone；N-[(5-chloro-2-hydroxyphenyl)methylideneamino]pyridine-3-carboxamide
• 化学式: C₁₃H₁₀ClN₃O₂
• mdl: MFCD00433552
• 分子量: 275.694
• InChiKey: WZSCOZWXTCWXQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 N′-(5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide 反应 0.33h， 以0.839 g的产率得到
  参考文献：
  名称：

  钒 (III-V) 配合物中的三齿 ONO 配体 - 合成、表征和生物活性

  摘要：

  摘要 介绍了基于 5-氯-和 5-羟基-水杨醛和选定酰肼的 16 种新型钒配合物的合成、性质，包括单晶结构和生物活性，三齿 ONO Schiff 碱配体 L。在钒的不同氧化态下合成了几种类型的配合物：[VO(L)(phen)]（其中 phen 表示 1,10-菲咯啉）与 V(IV)、[VO(L)(solv)]（其中 solv用 V(IV 或 V) 表示溶剂分子 H2O 或 EtO-)，用 V(V) 表示 [VO2L] 和 [VOL(H2O)2]，用 V(III) 表示 [VL2]。所有配合物均通过元素分析、IR、UV-Vis、EPR 光谱、循环伏安法和热重测量表征。通过单晶 X 射线衍射证实了两种 V(V) 配合物的分子结构。

  DOI：

  10.1016/j.molstruc.2020.129205
• 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′-(5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide
  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。
• Synthesis, Spectral Characterization and Crystal Structures of Dioxidomolybdenum(VI) Complexes Derived from Nicotinoylhydrazones
  作者：T. M. Asha、M. R. P. Kurup

  DOI：10.1007/s10870-018-0756-9

  日期：2019.12

  Cis-dioxidomolybdenum(VI) complexes [MoO2L1(DMSO)] (1), [MoO2L2(H2O)]·DMF (2) and [MoO2L3(DMF)] (3) were synthesized by solution based reactions of aroylhydrazones (H2L1 = 5-chloro-2-hydroxybenzaldehyde nicotinoylhydrazone, H2L2 = 2-hydroxy-5-iodobenzaldehyde nicotinoylhydrazone and H2L3 = 3,5-dichloro-2-hydroxybenzaldehyde nicotinoylhydrazone) with bis(acetylacetonato)dioxidomolybdenum(VI) complex, [MoO2(acac)2] in

  顺式二氧化钼 (VI) 配合物 [MoO2L1(DMSO)] (1)、[MoO2L2(H2O)]·DMF (2) 和 [MoO2L3(DMF)] (3) 通过基于溶液的芳酰腙 (H2L1 = 5) 反应合成-氯-2-羟基苯甲醛烟酰腙，H2L2 = 2-羟基-5-碘苯甲醛烟酰腙和 H2L3 = 3,5-二氯-2-羟基苯甲醛烟酰腙）与双（乙酰丙酮）二氧化钼（VI）络合物，[Mo]ac）在 DMSO 或 DMF 存在下。合成的芳酰腙及其钼配合物通过元素分析、光谱技术（FT-IR、UV-Vis、1H NMR）和电导率测量进行表征。最后通过单晶X射线衍射研究证实了配合物的三维结构。1的晶体结构，2 和 3 分别通过直接方法求解，并分别使用 SHELXS97 和 SHELXL2014 软件程序通过全矩阵最小二乘法计算进行细化。配合物 1 在单斜空间群 P21/c 中结晶，Z = 4，而配合物 2 和 3
• 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.
• Tridentate ONO ligands in vanadium(III-V) complexes - synthesis, characterization and biological activity
  作者：Janusz Szklarzewicz、Anna Jurowska、Maciej Hodorowicz、Grzegorz Kazek、Monika Głuch-Lutwin、Jacek Sapa、Monika Papież

  DOI：10.1016/j.molstruc.2020.129205

  日期：2021.1

  denote solvent molecule H2O or EtO−) with V(IV or V), [VO2L] and [VOL(H2O)2] with V(V) and [VL2] with V(III). All complexes were characterized by elemental analysis, IR, UV-Vis, EPR spectroscopy, cyclic voltammetry and thermogravimetric measurements. The molecular structures of two V(V) complexes were confirmed by single-crystal X-ray diffraction. The stability of complexes in solution as well as the

  摘要 介绍了基于 5-氯-和 5-羟基-水杨醛和选定酰肼的 16 种新型钒配合物的合成、性质，包括单晶结构和生物活性，三齿 ONO Schiff 碱配体 L。在钒的不同氧化态下合成了几种类型的配合物：[VO(L)(phen)]（其中 phen 表示 1,10-菲咯啉）与 V(IV)、[VO(L)(solv)]（其中 solv用 V(IV 或 V) 表示溶剂分子 H2O 或 EtO-)，用 V(V) 表示 [VO2L] 和 [VOL(H2O)2]，用 V(III) 表示 [VL2]。所有配合物均通过元素分析、IR、UV-Vis、EPR 光谱、循环伏安法和热重测量表征。通过单晶 X 射线衍射证实了两种 V(V) 配合物的分子结构。