N'-(5-bromo-2-hydroxybenzylidene)nicotinohydrazide | 41377-52-0

• 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-bromo-2-hydroxybenzylidene)nicotinohydrazide
• 英文别名: N-[(5-bromo-2-hydroxyphenyl)methylideneamino]pyridine-3-carboxamide
• CAS: 41377-52-0
• 化学式: C₁₃H₁₀BrN₃O₂
• mdl: MFCD00431145
• 分子量: 320.145
• InChiKey: DBMMBUWTQUXOCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-bromo-2-hydroxybenzylidene)nicotinohydrazide 以 甲醇 为溶剂， 反应 1.17h， 以87%的产率得到C₁₃H₈BrN₃O₄V
  参考文献：
  名称：

  含配体的新型二氧化钒（V）配合物：合成，晶体结构及其在CH键功能化中的催化应用

  摘要：

  从配体衍生的新的二氧化钒（V）络合物已经以高收率合成。通过元素分析，IR，UV-Visible和1 H NMR光谱对复合物进行表征。两种配合物的结构通过单晶X射线晶体学确定。配合物1在单斜P2 1 / n空间群中结晶，单元参数a = 8.3725（5）Å，b = 15.0475（17）Å，c = 32.227（3）Å，α= 90°，β= 91.846（5）o，γ＝ 90°。配合物2在三斜P-1空间群中结晶，a = 8.1871（7）Å，b = 11.2605（17）Å，c = 11.4031（18）Å，α= 105.961（14）°，β= 110.528（12）o且γ= 96.387（10）o。两种络合物都是可以催化碳原子的有效催化剂H键官能化反应。

  DOI：

  10.1016/j.jorganchem.2018.08.025
• 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-bromo-2-hydroxybenzylidene)nicotinohydrazide
  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

• Antimicrobial Activities of Synthetic Arylidine Nicotinic and Isonicotinic Hydrazones
  作者：Muhammad Hayat、Khalid Mohammed Khan、Sumayya Saeed、Uzma Salar、Momin Khan、Taimoor Baig、Aqeel Ahmad、Shahnaz Parveen、Muhammad Taha

  DOI：10.2174/1570180814666170914120337

  日期：2018.8.27

  showed significant to moderate antimicrobial activities against Gram positive and Gram negative bacterial cultures. Few compounds also showed antifungal activity against fungal cultures. Minimum Inhibitory Concentration (MIC) was calculated for the most active compounds 1, 7, 11, 19, 34, 46, 50, 51, and 55 against gram positive and gram negative cultures. Conclusion: Newly identified compounds may serve

  背景：尽管可以使用多种抗菌剂，但病原菌的再次出现仍然是严重的医学问题。鉴定新的，安全的和选择性的抗菌剂是药物化学研究的主要兴趣。 方法：研究了合成的亚芳基烟碱和异烟碱（1-63）库的抗菌活性。 结果：许多衍生物显示出对革兰氏阳性和革兰氏阴性细菌培养物具有显着至中等的抗菌活性。很少有化合物也显示出对真菌培养物的抗真菌活性。计算了对革兰氏阳性和革兰氏阴性培养物活性最高的化合物1、7、11、19、34、46、50、51和55的最低抑菌浓度（MIC）。 结论：新鉴定的化合物可作为未来研究的先导，以获得更强大的抗菌剂。
• Modification of magnetic nanoparticles surface by oxovanadium(V) complex as a highly efficient heterogeneous nanocatalyst for the green sulfoxidation of sulfides
  作者：Mehdi Fallah-Mehrjardi、Hadi Kargar

  DOI：10.1016/j.inoche.2021.109016

  日期：2021.12

  The present study describes the synthesis of a new nanomagnetic-supported oxovanadium(V) complex with the tridentate Schiff base ligand derived from the condensation reaction between 5-bromosalicylaldehyde and nicotinic acid hydrazide. The supported complex was fully characterized using various physicochemical techniques such as FT-IR, SEM, EDS, TEM, XRD and VSM. Moreover, the obtained heterogeneous

  本研究描述了一种新的纳米磁性负载氧钒 (V) 配合物与三齿席夫碱配体的合成，该配体源自 5-溴水杨醛和烟酸酰肼之间的缩合反应。使用各种物理化学技术，如 FT-IR、SEM、EDS、TEM、XRD 和 VSM，对负载的复合物进行了全面表征。此外，在回流条件下，通过在乙醇中使用 H 2 O 2将获得的多相纳米催化剂用于不同烷基和芳基硫化物的亚砜化。磁性纳米催化剂可以磁性回收，可以重复使用多次而不会显着损失活性。
• Conformation- and Coordination Mode-Dependent Stimuli-Responsive Salicylaldehyde Hydrazone Zn(II) Complexes
  作者：Han-Wen Zheng、Dong-Dong Yang、Yong-Sheng Shi、Tong Xiao、Hong-Wei Tan、Xiang-Jun Zheng

  DOI：10.1021/acs.inorgchem.3c00035

  日期：2023.4.24

  their potential applications. Schiff base with O,N,O-hydrazone shows excellent luminescence properties with multi-coordination sites for different coordination modes. In this work, three salicylaldehyde hydrazone Zn(II) complexes (1, 2a, 2b) were synthesized and their stimuli-responsive behaviors in different states were explored. Only complex 1 exhibits reversible and self-recoverable photochromic

  响应外部刺激的发光 Zn(II) 配合物由于其潜在的应用而受到广泛关注。具有 O,N,O-腙的席夫碱显示出优异的发光特性，具有针对不同配位模式的多配位点。在这项工作中，合成了三种水杨醛腙 Zn(II) 配合物 ( 1 , 2a , 2b )，并探索了它们在不同状态下的刺激响应行为。只有复合物1在溶液中表现出可逆和自恢复的光致变色和光致发光特性。这可能是由于构型翻转和激发态分子内质子转移 (ESIPT) 过程。在固态下，2a具有明显的力致变色发光特性，这是由于分子间相互作用的破坏，由晶态向非晶态转变所致。由于结构中有效的卤素键相互作用，2a和2b具有延迟荧光特性。2a可以通过力/蒸汽刺激进行晶相转变为其多晶型2b。有趣的是，2b显示光致变色特性，这可归因于紫外线照射引起的电子转移和自由基的产生。由于不同的构象和配位模式，三种 Zn(II) 配合物表现出不同的刺激响应特性。该工作展示了水杨醛腙
• 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.
• New dioxido-vanadium(V) complexes containing hydrazone ligands: Syntheses, crystal structure and their catalytic application toward C H bond functionalization
  作者：Sunshine D. Kurbah、M. Asthana、I. Syiemlieh、Alzelia A. Lywait、M. Longchar、R.A. Lal

  DOI：10.1016/j.jorganchem.2018.08.025

  日期：2018.12

  New dioxido-vanadium(V) complexes derived from hydrazone ligands have been synthesized in good yield. The complexes were characterized by elemental analysis, IR, UV–Visible and 1H NMR spectroscopies. The structure of both the complexes was established by Single Crystal X-ray crystallography. Complex 1 crystallized in monoclinic P21/n space group, with cell parameters a = 8.3725(5) Å, b = 15.0475(17)

  从配体衍生的新的二氧化钒（V）络合物已经以高收率合成。通过元素分析，IR，UV-Visible和1 H NMR光谱对复合物进行表征。两种配合物的结构通过单晶X射线晶体学确定。配合物1在单斜P2 1 / n空间群中结晶，单元参数a = 8.3725（5）Å，b = 15.0475（17）Å，c = 32.227（3）Å，α= 90°，β= 91.846（5）o，γ＝ 90°。配合物2在三斜P-1空间群中结晶，a = 8.1871（7）Å，b = 11.2605（17）Å，c = 11.4031（18）Å，α= 105.961（14）°，β= 110.528（12）o且γ= 96.387（10）o。两种络合物都是可以催化碳原子的有效催化剂H键官能化反应。