4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide | 397286-92-9

• 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: 4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide
• 英文别名: 2-acetylpyridine-para-nitro-phenylhydrazone；2-acetylpyridine-para-nitrophenylhydrazone；4-nitro-N-(1-pyridin-2-ylethylideneamino)benzamide
• CAS: 397286-92-9
• 化学式: C₁₄H₁₂N₄O₃
• 分子量: 284.274
• InChiKey: MPQLUIRDVHIZEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide 、 三氯化锑 以 甲醇 为溶剂， 反应 4.0h， 以67%的产率得到[2-acetylpyridine-para-nitrophenylhydrazonato(dichloro)antimony(III)]
  参考文献：
  名称：

  Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones

  摘要：

  Antimony(III) [Sb(L)Cl-2] complexes were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph) and 2-acetylpyridine-para-hydroxy-phenylhydrazone (H2AcpOHPh) along with the 2-benzoylpyridine-phenylhydrazone analogs H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh (HL). [Sb(2BzpClPh)Cl-2], complex (6), (IC50 = 4.91 +/- 1.20 mu mol L-1) was as active as nystatin (IC50= 4.44 +/- 0.76 mu mol L-1) and twofold more active than H2BzpClPh (IC50= 10.05 +/- 0.67 mu mol L-1) against Candida dubliniensis. While H2BzpClPh proved to be inactive against Candida glabrata, 6 (IC50 = 10.11 +/- 0.64 mu mol L-1) was more active than miconazole nitrate (IC50= 19.50 +/- 4.53 mu mol L-1). Similarly, H2BzpNO(2)Ph revealed to be inactive against Candida lusitaniae whereas complex [Sb(2BzpNO(2)Ph)Cl-2] (7) (IC50 = 8.54 +/- 2.21 mu mol L-1) proved to be as active as nystatin (IC50 = 5.31 +/- 0.84 mu mol L-1). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.05.004
• 作为产物：
  描述：

  对硝基苯甲酸乙酯 在 盐酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 8.17h， 生成 4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide
  参考文献：
  名称：

  两种新型芳酰腙的合成、分子结构、光谱分析和细胞毒活性

  摘要：

  摘要 两种新的芳酰腙，即 4-硝基-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide, NPHY (4) 和 4-nitro-N'-(1-(thiophen-2-yl)ethylidene)苯甲酰肼，NPHT (5) 已制备并通过 1H NMR、13C NMR、FT-IR、紫外-可见光谱和质谱进行表征。所有量子计算都是在 DFT 理论水平上进行的，使用 B3LYP 泛函和 6-31G (d,p) 作为基组。发现 TD-DFT 计算的电子跃迁与实验结果非常一致。正常振动模式的分配是通过使用 Gar2ped 计算势能分布 (PED) 完成的。进行了 HOMO-LUMO 分析并计算了反应性描述符。6.12–6.26 eV 的全局亲电指数 (ω) 表明这些芳酰基腙是强亲电试剂。通过“分子中的原子”(AIM) 方法分析分子内相互作用。此外，计算出的这些腙的第一静态超极化率

  DOI：

  10.1016/j.molstruc.2017.01.059

文献信息

• Bismuth(III) complexes with 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones: Antimicrobial and cytotoxic activities and effects on the clonogenic survival of human solid tumor cells
  作者：Isabella P. Ferreira、Elisa D.L. Piló、Angel A. Recio-Despaigne、Jeferson G. Da Silva、Jonas P. Ramos、Lucas B. Marques、Pedro H.D.M. Prazeres、Jacqueline A. Takahashi、Elaine M. Souza-Fagundes、Willian Rocha、Heloisa Beraldo

  DOI：10.1016/j.bmc.2016.05.007

  日期：2016.7

  Complexes [Bi(2AcPh)Cl-2]center dot 0.5H(2)O (1), [Bi(2AcpClPh)Cl-2] (2), [Bi(2AcpNO(2)Ph)Cl-2] (3), [Bi(2AcpOHPh)Cl-2]center dot 2H(2)O (4), [Bi(H2BzPh)Cl-3]center dot 2H(2)O (5), [Bi(H2BzpClPh)Cl-3] (6), [Bi(2BzpNO(2)Ph)Cl-2]center dot 2H(2)O (7) and [Bi(H2BzpOHPh)Cl-3]center dot 2H(2)O (8) were obtained with 2-acetylpyridine phenylhydrazone (H2AcPh), its -para-chloro-phenyl-(H2AcpClPh), -para-nitro-phenyl (H2AcpNO(2)Ph) and -para-hydroxy-phenyl (H2AcpOHPh) derivatives, as well as with the 2-benzoylpyridine phenylhydrazone analogues (H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh).Upon coordination to bismuth(III) antibacterial activity against Gram-positive and Gram-negative bacterial strains significantly improved except for complex (4).The cytotoxic effects of the compounds under study were evaluated on HL-60, Jurkat and THP-1 leukemia, and on MCF-7 and HCT-116 solid tumor cells, as well as on non-malignant Vero cells. In general, 2-acetylpyridine-derived hydrazones proved to be more potent and more selective as cytotoxic agents than the corresponding 2-benzoylpyridine-derived counterparts.Exposure of HCT-116 cells to H2AcpClPh, H2AcpNO(2)Ph and complex (3) led to 99% decrease of the clonogenic survival. The IC50 values of these compounds were three-fold smaller when cells were cultured in soft-agar (3D) than when cells were cultured in monolayer (2D), suggesting that they constitute interesting scaffolds, which should be considered in further studies aiming to develop new drug candidates for the treatment of colon cancer. (C) 2016 Elsevier Ltd. All rights reserved.
• Complexation of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones to copper(II) as an effective strategy for antimicrobial activity improvement
  作者：Angel A. Recio Despaigne、Fernanda B. Da Costa、Oscar E. Piro、Eduardo E. Castellano、Sonia R.W. Louro、Heloisa Beraldo

  DOI：10.1016/j.poly.2012.03.017

  日期：2012.5

  Complexes [Cu(2AcPh)Cl]center dot 2H(2)O (1), [Cu(2AcpClPh)Cl]center dot 2H(2)O (2), [Cu(2AcpNO(2)Ph)Cl] (3), [Cu(2BzPh)Cl] (4). [Cu(2BzpClPh)Cl] (5) and [Cu(2BzpNO(2)Ph)Cl] (6) were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph), 2-benzoylpyridine-phenylhydrazone (H2BzPh), 2-benzoylpyridine-para-chloro-phenylhydrazone (H2BzpClPh) and 2-benzoylpyridine-para-nitro-phenylhydrazone (H2BzpNO(2)Ph). The hydrazones showed poor antibacterial effect against Staphylococcus aureus, Enterococcus faecalis and Pseudomonas aeruginosa but demonstrated significant antifungal activity against Candida albicans. Upon coordination to copper(II) the antibacterial and antifungal activities appreciably increased. H2AcpClPh, H2BzpClPh and their copper(II) complexes (2) and (5), respectively, were as active as fluconazole against C. albicans. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis, molecular structure, spectral analysis and cytotoxic activity of two new aroylhydrazones
  作者：Ravindra Kumar Singh、Ashok Kumar Singh、Sahabjada Siddiqui、Mohammad Arshad、Asif Jafri

  DOI：10.1016/j.molstruc.2017.01.059

  日期：2017.5

  dose dependent manner. Cytotoxic potencies (IC50) of these hydrazones against MCF7 and DU145 cell lines were found in range of 54.67–85.67 μM. The result of ROS activity provides supportive data for molecular mechanism of these hydrazones, which is related to apoptotic cellular death. Nuclear condensation assay performed by DAPI staining shows fragmented and condensed nuclei in MCF7 cells, suggesting cell

  摘要 两种新的芳酰腙，即 4-硝基-N'-(1-(pyridin-2-yl)ethylidene)benzohydrazide, NPHY (4) 和 4-nitro-N'-(1-(thiophen-2-yl)ethylidene)苯甲酰肼，NPHT (5) 已制备并通过 1H NMR、13C NMR、FT-IR、紫外-可见光谱和质谱进行表征。所有量子计算都是在 DFT 理论水平上进行的，使用 B3LYP 泛函和 6-31G (d,p) 作为基组。发现 TD-DFT 计算的电子跃迁与实验结果非常一致。正常振动模式的分配是通过使用 Gar2ped 计算势能分布 (PED) 完成的。进行了 HOMO-LUMO 分析并计算了反应性描述符。6.12–6.26 eV 的全局亲电指数 (ω) 表明这些芳酰基腙是强亲电试剂。通过“分子中的原子”(AIM) 方法分析分子内相互作用。此外，计算出的这些腙的第一静态超极化率
• Effect of coordination to antimony(III) on the antifungal activity of 2-acetylpyridine- and 2-benzoylpyridine-derived hydrazones
  作者：Elisa D.L. Piló、Angel A. Recio-Despaigne、Jeferson G. Da Silva、Isabella P. Ferreira、Jaqueline A. Takahashi、Heloisa Beraldo

  DOI：10.1016/j.poly.2015.05.004

  日期：2015.9

  Antimony(III) [Sb(L)Cl-2] complexes were obtained with 2-acetylpyridine-phenylhydrazone (H2AcPh), 2-acetylpyridine-para-chloro-phenylhydrazone (H2AcpClPh), 2-acetylpyridine-para-nitro-phenylhydrazone (H2AcpNO(2)Ph) and 2-acetylpyridine-para-hydroxy-phenylhydrazone (H2AcpOHPh) along with the 2-benzoylpyridine-phenylhydrazone analogs H2BzPh, H2BzpClPh, H2BzpNO(2)Ph, H2BzpOHPh (HL). [Sb(2BzpClPh)Cl-2], complex (6), (IC50 = 4.91 +/- 1.20 mu mol L-1) was as active as nystatin (IC50= 4.44 +/- 0.76 mu mol L-1) and twofold more active than H2BzpClPh (IC50= 10.05 +/- 0.67 mu mol L-1) against Candida dubliniensis. While H2BzpClPh proved to be inactive against Candida glabrata, 6 (IC50 = 10.11 +/- 0.64 mu mol L-1) was more active than miconazole nitrate (IC50= 19.50 +/- 4.53 mu mol L-1). Similarly, H2BzpNO(2)Ph revealed to be inactive against Candida lusitaniae whereas complex [Sb(2BzpNO(2)Ph)Cl-2] (7) (IC50 = 8.54 +/- 2.21 mu mol L-1) proved to be as active as nystatin (IC50 = 5.31 +/- 0.84 mu mol L-1). (C) 2015 Elsevier Ltd. All rights reserved.