N'-(1-(4-hydroxyphenyl)ethylidene)benzohydrazide | 120344-08-3

• 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'-(1-(4-hydroxyphenyl)ethylidene)benzohydrazide
• 英文别名: p-hydroxy acetophenone benzoylhydrazone；4-hydroxyacetophenone benzoylhydrazone；N-[1-(4-hydroxyphenyl)ethylideneamino]benzamide
• CAS: 120344-08-3
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: NFOBNNQARCVNTL-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C(Solv: ethanol (64-17-5))
• 密度：
  1.15±0.1 g/cm3(Predicted)

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

反应信息

• 作为反应物：
  描述：

  N'-(1-(4-hydroxyphenyl)ethylidene)benzohydrazide 、 zinc(II) chloride 以 乙醇 、 水 为溶剂， 以72%的产率得到Zn(4-hydroxyacetophenone benzoylhydrazone)Cl2(H2O)2
  参考文献：
  名称：

  Synthesis and Spectral Studies of Zinc Chloride Complexes with Some Acetophenone and 4-Hydroxy-Acetophenone Acylhydrazones

  摘要：

  DOI：

  10.1080/00945710009351827
• 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 N'-(1-(4-hydroxyphenyl)ethylidene)benzohydrazide
  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

• 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
• Synthesis, spectral studies of cobalt(II) tetrathiocyanoto dicuperate(I) complexes with some acylhydrazones and their antimicrobial activity
  作者：V. P. Singh、A. Singh

  DOI：10.1134/s1070328408050102

  日期：2008.5

  Cobalt(II) complexes of the type Co[Cu(NCS)(2)](2) center dot L, where L is acetophenonebenzoylhydrazone (Abh), acetophenoneisonicotinoylhydrazone (Ainh), acetophenonesalicyloylhydrazone (Ash), acetophenoneanthraniloylhydrazone (Aah), p-hydroxyacetophenonebenzoylhydrazone (Phabh), p-hydroxyacetophenoneisonicotinoylhydrazone (Phainh), p-hydroxyacetophenonesalicyloylhydrazone (Phash), and p-hydroxyacetophenoneanthraniloylhydrazone (Phaah) were synthesized and characterized by elemental analyses, molar conductance, magnetic moments, electronic and IR spectra, and X-ray diffraction studies. The complexes are insoluble in common organic solvents and are non-electrolytes. These complexes are coordinated through the >C=O and >C=N groups of the hydrazone ligands. The magnetic moments and electronic spectra suggest a spin-free octahedral geometry around Co(II). The X-ray diffraction parameters (a, b, c) for Co[Cu(SCN)(2)](2) Ainh and Co[Cu(SCN)(2)](2) . Phabh correspond to orthorhombic and tetragonal crystal lattices, respectively. The complexes show a fair antifungal and antibacterial activity against a number of fungi and bacteria. The activity increases with increasing concentration of the compounds.
• STUDIES ON COMPLEXES OF Co(II), Ni(II), Cu(Il), AND Cd(II) WITH ACETOPHENONE AND 4-HYDROXYACETOPHENONE BENZOYLHYDRAZONES
  作者：B. Singh、K. K. Narang、Rachana Srivastava

  DOI：10.1081/sim-100107204

  日期：2001.9.30

  Metal(II) complexes of the types [M(L)(2)Cl-2] . H2O and [Cu(4-HOABH)SO4(H2O)(2)] [M = Co(II), Ni(II), Cu(II) and Cd(II), L=acetophenone benzoylhydrazone (ABH), C6H5CONH-N=C(CH3)C6H5 and 4-hydroxyacetophenone benzoylhydrazone (4-HOABH), C6H5CONHN=C(CH3)C6H4OH], were prepared and characterized by elemental and thermal analyses, molar conductance, infrared, ESR and electronic spectral studies. Some of the complexes were screened against E. coli and Aspergillus niger for biological activity.
• Acetophenone benzoylhydrazones as antioxidant agents: Synthesis, in vitro evaluation and structure-activity relationship studies
  作者：Saeed Emami、Zahra Esmaili、Gholamreza Dehghan、Maryam Bahmani、Seyedeh Mahdieh Hashemi、Hassan Mirzaei、Mohammad Shokrzadeh、Seyed Ershad Moradi

  DOI：10.1016/j.foodchem.2018.06.083

  日期：2018.12

  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.
• Synthesis and Spectral Studies of Zinc Chloride Complexes with Some Acetophenone and 4-Hydroxy-Acetophenone Acylhydrazones
  作者：B. Singh、Rachana Srivastava、K. K. Narang

  DOI：10.1080/00945710009351827

  日期：2000.8.1