N'-(2-hydroxy-5-nitrobenzylidene)salicylhydrazide | 41377-55-3

• 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-nitrobenzylidene)salicylhydrazide
• 英文别名: 2-Hydroxy-benzoesaeure-5-nitrosalicyliden-hydrazon；5-nitrosalicylaldehyde o-hydroxybenzoylhydrazone；2-hydroxy-N'-(2-hydroxy-5-nitrobenzylidene)benzohydrazide；2-hydroxy-N-[(2-hydroxy-5-nitrophenyl)methylideneamino]benzamide
• CAS: 41377-55-3
• 化学式: C₁₄H₁₁N₃O₅
• 分子量: 301.258
• InChiKey: MQOPAZCGNSWGJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 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：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-(2-hydroxy-5-nitrobenzylidene)salicylhydrazide 、 manganese(ll) chloride 以 乙醇 为溶剂， 生成 {Mn(II)(5-nitrosalicylaldehyde o-hydroxybenzoylhydrazone(1-))2}
  参考文献：
  名称：

  3-和5-取代的水杨醛邻羟基苯甲酰hydr的某些金属配合物的合成，表征和抗肿瘤活性

  摘要：

  与3-和5-取代的水杨醛的Mn（II），铁（III），铁（II），钴（II），镍（II），铜（II），锌（II）和Pt（II）配合物Ô制备了羟基苯甲酰肼（XSBH，X = H，3-NO 2，3 -CH 3 O，5-Cl，5-Br，5-CH 3或5-NO 2），并通过元素分析，电导测量，磁化率（从室温到液氮温度）和光谱研究。这些研究表明以下结构：Mn（XSBH）2的单体，高自旋，扭曲的八面体；Fe（XSBH）SO 4 ·H 2的单体高旋转五坐标O; Fe（XSBH）Cl的二聚物，高自旋酚盐桥接的五坐标；Co（XSBH）Cl·2H 2 O的二聚体，高旋转五坐标；Ni（XSBH）Cl·2H 2 O的二聚体低旋转五坐标；Zn（XSBH）的二聚体，四坐标；M（XSBH）Cl·H 2 O（M = Cu（II）或Pt（II））的正方形平面结构。

  DOI：

  10.1016/s0020-1693(00)90726-6
• 作为产物：
  描述：

  水杨酰肼 、 5-硝基水杨醛 以 乙醇 为溶剂， 反应 0.25h， 生成 N'-(2-hydroxy-5-nitrobenzylidene)salicylhydrazide
  参考文献：
  名称：

  水杨腙席夫碱钒(IV)和(V)配合物的表征和抗糖尿病活性

  摘要：

  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。

  DOI：

  10.1007/s11243-020-00437-1

文献信息

• [EN] VANADIUM COMPLEXES WITH HYDRAZIDE-HYDRAZONES, PROCESS FOR THEIR PREPARATION, PHARMACEUTICAL FORMULATIONS AND THE USE OF THEREOF.<br/>[FR] COMPLEXES DU VANADIUM AVEC DES HYDRAZIDE-HYDRAZONES, LEUR PROCÉDÉ DE PRÉPARATION, FORMULATIONS PHARMACEUTIQUES ET LEUR UTILISATION
  申请人：UNIV JAGIELLONSKI

  公开号：WO2014073992A1

  公开（公告）日：2014-05-15

  Vanadium complexes of the general formula M[VX(ONO)y(L)n]-mS, wherein X is oxygen or is absent, L is L1or L2, wherein Li represents a halogen anion or a neutral molecule or deprotonated solvent selected from the group comprising C1-C12 alcohols and/or water, and L2 is a neutral or anionic NN, NO or OO-donor ligand selected from the group consisting of: polypyridine, 1,10-phenanthroline, pyrones, quinoline or pyridine carboxylic acids, S is a neutral solvent molecule selected from the group consisting of C 1-C4 alcohols, water or sulfuric acid, M may be absent, and when present it is monocharged alkali metal cation, ammonium cation, alkylammonium cation, and the letters O and N represent atom, by which the ligand is bound to vanadium. The invention also includes a method for making vanadium complexes, pharmaceutical preparations containing these complexes and the use of the complexes.

  通用公式为M[VX(ONO)y(L)n]-mS的钒配合物，其中X为氧或不存在，L为L1或L2，其中Li代表卤素阴离子或中性分子或脱质子溶剂，该溶剂选自包括C1-C12醇类和/或水的组，L2为中性或带负电荷的NN、NO或OO-给体配体，选自以下组：多吡啶、1,10-邻菲啰啉、吡喁酮、喹啉或吡啶羧酸，S为选自C1-C4醇类、水或硫酸的中性溶剂分子，M可能不存在，若存在，则为带单电荷的碱金属阳离子、铵阳离子、烷基铵阳离子，字母O和N代表配体与钒结合的原子。该发明还包括制备钒配合物的方法、含有这些配合物的药物制剂以及这些配合物的用途。
• 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.
• Nickel and zinc complexes with a monodentate heterocycle and tridentate Schiff base ligands: self-assembly to one- and two-dimensional supramolecular networks<i>via</i>hydrogen bonding
  作者：Xiao-Hua Chen、Qiong-Jie Wu、Zhi-Yu Liang、Chun-Rong Zhan、Jian-Bin Liu

  DOI：10.1107/s0108270109011263

  日期：2009.5.15

  In the complex (morpholine)[2-hydroxy-N'-(5-nitro-2-oxido-benzylidene)benzohydrazidato]nickel(II), [Ni(C(14)H(9)N(3)O(5))-(C(4)H(9)NO)], (I), the Ni(II) center is in a square- planar N(2)O(2) coordination geometry. The complex bis[mu-2-hydroxy-N'-(2-oxidobenzylidene)benzohydrazidato]bis[(morpholine)-zinc(II)], [Zn(2)(C(14)H(10)N(2)O(3))(2)(C(4)H(9)NO)(2)], (II), consists of a neutral centrosymmetric dimer with a coplanar Zn(2)(mu(2)-O)(2) core. The two Zn(II) centers are bridged by phenolate O atoms. Each Zn(II) center exhibits a distorted square-pyramidal stereochemistry, in which the four in- plane donors come from the O,N,O'-tridentate 2-hydroxy-N'-(2-oxidobenzylidene)-benzohydrazidate(2-) ligand and a symmetry-related phenolate O atom, and the axial position is coordinated to the N atom from the morpholine molecule. There are intramolecular phenol-hydrazide O-H center dot center dot center dot N hydrogen bonds present in both (I) and (II). In (I), square-planar nickel complexes are linked by intermolecular morpholine-morpholine N-H center dot center dot center dot O hydrogen bonds, leading to a one-dimensional chain, while in (II) an infinite two-dimensional network is formed via intermolecular hydrogen bonds between the coordinated morpholine NH groups and the uncoordinated phenolate O atoms.