1-(2-hydroxyphenyl)ethanone benzoylhydrazone | 22233-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-(2-hydroxyphenyl)ethanone benzoylhydrazone
• 英文别名: N′-(1-(2-hydroxyphenyl) ethylidene) benzohydrazide；(2-hydroxy-α-methyl-benzylidene)-benzoylhydrazine；benzoic acid [1-(2-hydroxyphenyl)ethylidene]hydrazide；N'-(1-(2-hydroxyphenyl)ethylidene)benzohydrazide；o-hydroxy acetophenone benzoyl hydrazone；o-hydroxyacetophenone benzoyl hydrazone；N-[1-(2-hydroxyphenyl)ethylideneamino]benzamide
• CAS: 22233-86-9
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: QOTDSLFPCMBSIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)ethanone benzoylhydrazone 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到1-(2-苯甲酰基苯基)乙酮
  参考文献：
  名称：

  Synthesis of 1,2-Diacylbenzenes fromo-Hydroxyaryl Ketone Acylhydrazones Using [(Diacetoxy)iodo]benzene

  摘要：

  2′-羟基乙酰苯和2′-羟基丙酰苯肼酮3在室温下使用[(二乙酸氧基)-碘]苯在二氯甲烷中氧化为1,2-二酰基苯4，反应具有合成实用性和高产率。

  DOI：

  10.1055/s-1993-25857
• 作为产物：
  描述：

  苯甲酸甲酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-(2-hydroxyphenyl)ethanone benzoylhydrazone
  参考文献：
  名称：

  Acetophenone benzoylhydrazones as antioxidant agents: Synthesis, in vitro evaluation and structure-activity relationship studies

  摘要：

  Acetophenone and its analogues are naturally-occurring compounds found in many foods and plants. In this study, a series of acetophenone benzoylhydrazones 5a-o were designed and synthesized as new potential antioxidant agents. Designed molecules contain hydrazone and phenolic hydroxyl moieties which possibly contribute to antioxidant activity. The antioxidant properties of compounds 5a-o in terms of reducing ability and radical-scavenging activity were assessed by using FRAP and DPPH tests, respectively. While the unsubstituted compound 5a had the superior capacity in the FRAP assay, the 2,4-dihydroxyacetophenone analogue 5g was the most potent radical scavenger in the DPPH method. The antioxidant potential of representative compounds 5a and 5g was further confirmed by TEAC and ORAC assays. Cell viability assays revealed that while the promising compounds 5a and 5g had no significant toxicity against HepG2 and NIH3T3 cells, they potently protected HepG2 cells against H2O2 -induced oxidative damage at low concentrations. Furthermore, spectroscopic studies with different biometals demonstrated that 5g was able to interact with Cu2+ to form a 1:1 complex.

  DOI：

  10.1016/j.foodchem.2018.06.083

文献信息

• Diazaborines Are a Versatile Platform to Develop ROS‐Responsive Antibody Drug Conjugates**
  作者：João P. M. António、Joana Inês Carvalho、Ana S. André、Joana N. R. Dias、Sandra I. Aguiar、Hélio Faustino、Ricardo M. R. M. Lopes、Luis F. Veiros、Gonçalo J. L. Bernardes、Frederico A. Silva、Pedro M. P. Gois

  DOI：10.1002/anie.202109835

  日期：2021.12

  The oxidation of physiologically stable diazaborines in the presence of reactive oxygen species (ROS) is the key to the construction of ROS-responsive antibody–drug conjugates. These conjugates are a new class of therapeutics that combine the lethality of potent cytotoxic drugs with the targeting ability of antibodies to selectively deliver drugs to cancer cells.

  在活性氧 (ROS) 存在下，生理稳定的二氮杂硼化物的氧化是构建 ROS 响应性抗体-药物偶联物的关键。这些偶联物是一类新的治疗方法，它将强效细胞毒性药物的杀伤力与抗体的靶向能力相结合，选择性地将药物输送到癌细胞。
• Synthesis, structure and solution chemistry of a family of dinuclear hydrazonato-vanadium(V) complexes with [OV(μ-O)VO]4+ core
  作者：Bipul Mondal、Tarun Ghosh、Manas Sutradhar、Gurunath Mukherjee、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.poly.2008.03.018

  日期：2008.6

  [VOL}2μ-O] (1–4) complexes were synthesized from the reaction of [VIVO(acac)2] with an equimolar amount of H2L [H2L is the general abbreviation of hydrazone ligands (H2L1–4) derived from the condensation of benzoyl hydrazine with either 2-hydroxyacetophenone or its para substituted derivatives] in acetone or CH2Cl2 or acetonitrile. These V2O3L2 complexes were also obtained from the reaction of VOSO4 with

  双核trioxidic [VOL} 2 μ-O]（1 - 4）复合物从[V的反应合成IV O（ACAC）2 ]与H的等摩尔量的2 L [ħ 2 L是腙的通用缩写苯甲酰肼与2-羟基苯乙酮或其对位取代衍生物的缩合反应得到的配体（H 2 L 1-4）在丙酮或CH 2 Cl 2或乙腈中。这些V 2 O 3 L 2配合物也是从VOSO 4与H的反应中获得的。在甲醇水溶液（50％V / V）中存在两个当量乙酸钠的情况下，也来自[V IV O（L）（bipy / phen）]络合物在CH 2 Cl 2溶液中的分解，生成2 L乙酸。[V IV O（acac）2 ]分别与H 2 L 2和H 2 L 4反应，得到具有C 2 / c空间群的2和4的黑色单斜晶体。在丙酮中，其中各个配体经完全去质子化的烯醇形式经子午键合到钒上。V–O键的长度遵循以下顺序：V–O（氧代）
• Synthesis, structure and solution chemistry of dioxidovanadium(V) complexes with a family of hydrazone ligands. Evidence of formation of centrosymmetric dimers via H-bonds in the solid state
  作者：Bipul Mondal、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.ica.2010.03.053

  日期：2010.6

  formation of centrosymmetric dimers while the complex 12 (containing only one hydrogen atom in the cationic part) exhibits normal H-bonding. The nature of the H-bonds in each of the four centrosymmetric dimeric complexes is different. These complexes have potential catalytic activity in the aerial oxidation of l -ascorbic acid and are converted into the [VO(L)(hq)] complexes containing VO 3+ motif on reaction

  [V IV O（acac）2]与三齿ONO供体配体（H 2 L 1-4，通用缩写H 2 L；由苯甲酰肼与2-羟基苯乙酮及其5的缩合反应而得）的甲醇溶液反应取代的衍生物）在比吡啶强碱性的中性单齿烷基胺碱（例如乙胺，二乙胺，三乙胺和哌啶）的存在下（一般缩写B）产生BH + [VO 2 L]-（1-16）配合物。这16种络合物中的5种在结构上具有特征，表明钒在扭曲的方形锥体环境中存在于分子的阴离子部分[VO 2 L]-中。配合物5、6、15和16在其阳离子部分包含两个与胺N原子相连的H原子（例如，二乙基铵和哌啶鎓离子）与相邻分子发生H键合，导致形成中心对称的二聚体，而配合物12（在阳离子部分仅含一个氢原子）表现出正常的H键合。四个中心对称二聚体复合物中的每一个的H键性质不同。这些配合物在1-抗坏血酸的空中氧化中具有潜在的催化活性，并在与等摩尔量的8-羟基喹啉（Hhq）在甲醇中反应时转化为含有VO
• Syntheses and structural investigation of some alkali metal ion-mediated LVVO2− (L2− = tridentate ONO ligands) species: DNA binding, photo-induced DNA cleavage and cytotoxic activities
  作者：Subhashree P. Dash、Alok K. Panda、Sagarika Pasayat、Rupam Dinda、Ashis Biswas、Edward R. T. Tiekink、Yogesh P. Patil、M. Nethaji、Werner Kaminsky、Subhadip Mukhopadhyay、Sujit K. Bhutia

  DOI：10.1039/c4dt00883a

  日期：——

  104 M−1. Complexes 1–8 were also tested for DNA nuclease activity against pUC19 plasmid DNA which showed that 6 and 7 had the best DNA binding and photonuclease activity; these results support their good protein binding and cleavage activity with binding constants ranging from 104 to 105 M−1. Finally, the in vitro antiproliferative activity of all complexes was assayed against the HeLa cell line. Some

  八个碱金属离子介导的双氧钒（V），[V V O 2 L 1-6 } A（H 2 O）n ] ∝，A = Li +，Na +，K +和Cs +的配合物，含三齿描述了通过ONO供体原子配位的芳酰肼磺酸酯配体。通过元素分析，IR，UV-Vis和NMR光谱法成功地表征了所有合成的配体和金属配合物。的X射线晶体学调查3，5-7示出的存在扭曲NO 4对于LVO协调的几何形状2 -在每种情况下，与变化的μ-氧桥和/或μ-AQUA与该碱金属离子的大小相关有趣的变化桥接：与小栗+，没有桥接-O被发现而是四个离子聚集体被发现与Na +，链为K +，最后为Cs +层。两个（5）或三维（3，6和7）架构通过氢键固结。发现dioxidovanadium（V）配合物表现出DNA结合活性，这是由于它们通过凹槽结合模式与CT-DNA相互作用，结合常数范围为10。3至10 4 M -1。还测试了复合物1–8对pUC19质
• AlCl3·6H2O-catalyzed Schiff-base reaction between aryl ketones and aromatic acylhydrazines/hydrazines in water
  作者：Zhi Xiang Zhao、Ting Li、Li Ping Cheng、Meng Li、Zhi Jian Zhong、Wan Pang

  DOI：10.1007/s00706-019-02488-2

  日期：2019.10

  types of Schiff-bases. In this study, a green synthesis of aromatic hydrazones and acylhydrazones via Schiff-base reaction of aryl ketones and aromatic acylhydrazines/hydrazines had been reported. In the synthesis, water was used as solvent and AlCl3·6H2O was used as catalyst. The reaction is simple, highly efficient, and eco-friendly. Graphic abstract

  摘要希夫碱在分析，生物医学以及材料科学领域具有重要的应用。dra和酰基hydr是席夫碱的两种代表性类型。在该研究中，已经报道了通过芳基酮和芳族酰基肼/肼的席夫碱反应绿色合成芳族肼和酰基hydr。在合成中，水用作溶剂，AlCl 3 ·6H 2 O用作催化剂。该反应简单，高效且环保。 图形摘要