N’-(2-hydroxy-5-bromobenzylidene)isonicotinohydrazide | 732-91-2

• 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’-(2-hydroxy-5-bromobenzylidene)isonicotinohydrazide
• 英文别名: isonicotinic acid (5-bromo-2-hydroxybenzylidene)hydrazide；N'-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide；isonicotinoyl(5-bromo-2-hydroxybenzylidene)hydrazide；5-bromosalicylaldehyde isonicotinoylhydrazone；N'-(5-bromo-2-hydroxybenzylidene)isoniazide；5-bromosalicylideneisonicotinoylhydrazine；5-Bromo salicylaldehyde isonicotinoyl hydrazone；N-[(5-bromo-2-hydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 732-91-2
• 化学式: C₁₃H₁₀BrN₃O₂
• mdl: MFCD00425531
• 分子量: 320.145
• InChiKey: UFNBDHGHPMABQB-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：

  五氯化钼 、 N’-(2-hydroxy-5-bromobenzylidene)isonicotinohydrazide 在 Na(CH₃COO) 、 CH₃COOH 作用下， 以 甲醇 为溶剂， 生成 [oxomolybdenum(V)(isonicotinoyl(5-bromo-2-hydroxybenzylidene)hydrazide(-H))Cl2]
  参考文献：
  名称：

  含席夫碱异烟酰基（5-溴-2-羟基苄叉）酰肼的氧钼（V）和二氧钼（VI）配合物的合成，物理化学，抗微生物和3D分子建模研究

  摘要：

  报道了一些新的含席夫碱的异氧烟碱（5-溴-2-羟基苄叉）酰肼（L）与5-溴水杨基醛和异烟碱酰肼的合成新的氧钼（V）和二氧钼（VI）配合物的合成。通过元素分析，摩尔电导，磁化率数据，IR，UV-Vis，EPR，1 H NMR和FAB质谱研究对复合物进行了表征。物理化学研究和光谱数据表明，L充当单价三齿螯合剂。FAB质谱和X波段EPR谱表明，络合物中的五价Mo本质上是单体的。复合物[MoO（L）Cl 2 ]（I）的X射线衍射研究与单位晶格尺寸为a的正交晶格对应= 16.11，b = 12.20，c = 7.5。通过循环伏安法研究了配合物的电化学行为。发现所有配合物均具有扭曲的八面体几何形状。通过热重技术研究了配合物I的热性质。筛选配体L以及配合物I和[MoO 2（L）Cl]（II）的体外抗菌活性。配合物显示出比L高的活性。还对配合物I进行了键长和键角的3D分子建模和分析。

  DOI：

  10.1134/s1070328410040044
• 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-bromobenzylidene)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

• 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。
• 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。
• Gallium (III) Complexes with 5-Bromosalicylaldehyde Benzoylhydrazones: In Silico Studies and In Vitro Cytotoxic Activity
  作者：Boryana Nikolova-Mladenova、Silvia Angelova、Georgi Momekov

  DOI：10.3390/molecules27175493

  日期：——

  Gallium (III) complexes with the ligands 5-bromosalicylaldehyde-4-hydroxybenzoylhydrazone and 5-bromosalicylaldehyde isonicotinoylhydrazone were synthesized to receive compounds with improved antiproliferative action. Compounds were characterized by elemental analysis, IR, and NMR spectroscopy. Density functional theory calculations with Becke’s 3-parameter hybrid functional and 6-31+G(d,p) basis set

  镓 (III) 与配体 5-溴水杨醛-4-羟基苯甲酰腙和 5-溴水杨醛异烟酰腙的配合物被合成以接收具有改进的抗增殖作用的化合物。通过元素分析、IR 和 NMR 光谱对化合物进行表征。使用 Becke 的 3 参数混合泛函和 6-31+G(d,p) 基组进行密度泛函理论计算，以研究配体和 Ga(III) 配合物的结构特征。使用顺铂和美法仑作为参考细胞毒剂，通过 MTT 染料还原试验进行细胞毒筛选。通式[Ga(HL) 2 ]NO 3建议获得的配合物。配合物是单核的，Ga(III) 离子被两个配体包围。配体充当单阴离子三齿 (ONO) 供体分子。分析揭示了通过去质子化的酚氧、偶氮甲碱-氮和酰胺-氧原子的配位结合。生物测定表明，所有化合物在低微摩尔浓度下对急性髓细胞白血病 HL-60 和 T 细胞白血病 SKW-3 细胞系均表现出浓度依赖性抗增殖活性。5-溴衍生物配体和镓(III)配合物的IC 5
• 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.
• Statistical molecular design of a focused salicylidene acylhydrazide library and multivariate QSAR of inhibition of type III secretion in the Gram-negative bacterium Yersinia
  作者：Markus K. Dahlgren、Caroline E. Zetterström、Åsa Gylfe、Anna Linusson、Mikael Elofsson

  DOI：10.1016/j.bmc.2010.02.022

  日期：2010.4

  A combined application of statistical molecular design (SMD), quantitative structure-activity relationship (QSAR) modeling and prediction of new active compounds was effectively used to develop salicylidene acylhydrazides as inhibitors of type III secretion (T3S) in the Gram-negative pathogen Yersinia pseudotuberculosis. SMD and subsequent synthesis furnished 50 salicylidene acylhydrazides in high purity. Based on data from biological evaluation in T3S linked assays 18 compounds were classified as active and 25 compounds showed a dose-dependent inhibition. The 25 compounds were used to compute two multivariate QSAR models and two multivariate discriminant analysis models were computed from both active and inactive compounds. Three of the models were used to predict 4416 virtual compounds in consensus and eight new compounds were selected as an external test set. Synthesis and biological evaluation of the test set in Y. pseudotuberculosis and the intracellular pathogen Chlamydia trachomatis validated the models. Y. pseudotuberculosis and C. trachomatis cell-based infection models showed that compounds identified in this study are selective and non-toxic inhibitors of T3S dependent virulence. (C) 2010 Elsevier Ltd. All rights reserved.