N'-(5-chloro-2-hydroxybenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide | 19161-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(5-chloro-2-hydroxybenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide
• 英文别名: N-(5-chloro-2-hydroxybenzylidene)-4-methoxybenzohydrazide；N-(4-Methoxy-benzoyl)-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin；4-Methoxy-benzoic acid (5-chloro-2-hydroxy-benzylidene)-hydrazide；N-[(5-chloro-2-hydroxyphenyl)methylideneamino]-4-methoxybenzamide
• CAS: 19161-64-9
• 化学式: C₁₅H₁₃ClN₂O₃
• mdl: MFCD00187044
• 分子量: 304.733
• InChiKey: MHRJHEHPEYZJAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(5-chloro-2-hydroxybenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide 在 lead(IV) tetraacetate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到
  参考文献：
  名称：

  FeCl₃ mediated synthesis of substituted indenones by a formal [2+2] cycloaddition/ring opening cascade of o-keto-cinnamates

  摘要：

  一种新颖的FeCl₃介导的形式[2+2]环加成/环开环串联反应被开发用于合成茚酮。该反应能容忍广泛的官能团，包括溴化物、氯化物、酰胺、酸和酯基团。

  DOI：

  10.1039/c5cc03040d
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 、 5-氯代水杨醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以97%的产率得到N'-(5-chloro-2-hydroxybenzylidene)-2-(4-methoxyphenyl)acetyl hydrazide
  参考文献：
  名称：

  组合烷基化剂作为 2-羟基苯甲醛酰腙的高选择性 N-烷基化的分辨率

  摘要：

  虽然 2-羟基苯甲醛酰腙，如水杨醛酰腙，是有趣的生物活性分子，但很少有人知道它们的 N-烷基化衍生物，而且以前只报道过甲基类似物。我们通过使用烷基化剂（例如，烷基溴和二烷基硫酸盐）的组合，实现了 2-羟基苯甲醛酰基腙作为其 Fe(III) 络合物的选择性 N-烷基化。检查了 15 种底物，并以中等至良好的产率合成了 45 种新的 2-羟基苯甲醛酰基（烷基）腙。在所有情况下，目标产物都得到了唯一的结果，没有产生 O-烷基化副产物。该方法为制备2-羟基苯甲醛酰基(烷基)腙提供了一种有效的途径。

  DOI：

  10.1055/s-0037-1611823

文献信息

• A New Dinuclear Copper(II)-Hydrazone Complex: Synthesis, Crystal Structure and Antibacterial Activity
  作者：Sevda ER、Hakan Ünver、Gökhan Dikmen

  DOI：10.2174/1570178620666221202090558

  日期：2023.4

  results were observed. Information about local and global chemical activity, the electrophilic and nucleophilic nature of copper(II) complex were theoretically obtained. The ligand and its copper(II) complex were investigated for their antibacterial effects against Gram (+) and Gram (-) bacteria. The results show that copper(II) complex was more effective in reducing cell viability of Enterococcus faecalis

  ：增加微生物耐药性已成为对人类的威胁。因此，需要合成新的活性抗菌化合物。铜络合物是这些类型的生物活性化合物之一，表现为具有广泛生物学用途的化合物。许多科学研究表明，铜络合物具有抗菌、抗疟疾、抗炎和抗癌活性。在这项研究中，设计、合成了一种基于腙配体（配体 A）的新型双铜 (II) 络合物，并对其作为抗菌剂进行了评估。铜 (II) 配合物的表征主要通过单晶 X 射线衍射和其他光谱技术（FT-IR 和元素分析）完成。为了确定化学结构和振动特性，进行了理论计算。采用DFT/B3LYP方法，LanL2DZ基组研究了铜(II)络合物的振动波数和HOMO-LUMO能隙。观察到实验结果和理论结果之间的一致性。从理论上获得了铜 (II) 配合物的局部和全局化学活性、亲电和亲核性质的信息。研究了配体及其铜 (II) 络合物对革兰氏 (+) 和革兰氏 (-) 细菌的抗菌作用。结果表明，与游离腙配体相比，铜 (II)
• 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.