2-carboxybenzaldehyde-isonicotinichydrazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-carboxybenzaldehyde-isonicotinichydrazone
• 英文别名: 2-carboxybenzaldehydeisonicotinoylhydrazone；2-[(2-isonicotinoylhydrazono)methyl]benzoic acid；2-[(pyridine-4-carbonylhydrazinylidene)methyl]benzoic acid
• 化学式: C₁₄H₁₁N₃O₃
• 分子量: 269.26
• InChiKey: RMLOMEXOUPLRRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-carboxybenzaldehyde-isonicotinichydrazone 、 乙酸酐 以72 %的产率得到2-(isonicotinamido)-3-oxoisoindolin-1-yl acetate
  参考文献：
  名称：

  邻甲酰基苯甲酸与异烟酸和羟基苯甲酸酰肼的反应

  摘要：

  摘要 烟酸酰肼和异烟酸酰肼与邻甲酰基苯甲酸在乙醇中反应导致形成相应的腙。发现邻甲酰基苯甲酸以醛形式与酰肼反应形成腙。当在乙酸酐中加热时，后者顺利环化成3-乙酰氧基异吲哚啉-1-酮。合成化合物的结构通过1 H 和13 C NMR 谱数据得到证实。研究了合成的腙和 3-乙酰氧基异吲哚啉-1-酮的抗自由基和抗病毒活性。鉴定出一种对 A 病毒株具有广谱病毒抑制作用的化合物。

  DOI：

  10.1134/s1070363223090025
• 作为产物：
  描述：

  异烟肼 、 邻羧基苯甲醛 以 乙醇 为溶剂， 以92 %的产率得到2-carboxybenzaldehyde-isonicotinichydrazone
  参考文献：
  名称：

  邻甲酰基苯甲酸与异烟酸和羟基苯甲酸酰肼的反应

  摘要：

  摘要 烟酸酰肼和异烟酸酰肼与邻甲酰基苯甲酸在乙醇中反应导致形成相应的腙。发现邻甲酰基苯甲酸以醛形式与酰肼反应形成腙。当在乙酸酐中加热时，后者顺利环化成3-乙酰氧基异吲哚啉-1-酮。合成化合物的结构通过1 H 和13 C NMR 谱数据得到证实。研究了合成的腙和 3-乙酰氧基异吲哚啉-1-酮的抗自由基和抗病毒活性。鉴定出一种对 A 病毒株具有广谱病毒抑制作用的化合物。

  DOI：

  10.1134/s1070363223090025

文献信息

• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.
• Crystal structure, antitumor activities and DNA-binding properties of the La(III) complex with Phthalazin-1(2H)-one prepared by a novel route
  作者：Yan Wang、Zheng-Yin Yang、Qin Wang、Qi-Kuan Cai、Kai-Bei Yu

  DOI：10.1016/j.jorganchem.2005.07.046

  日期：2005.11

  Phthalazin-1(2H)-one was prepared by a novel route. The La(III)-complex of phthalazin-1(2H)-one, [La(NO3)(3)center dot 4H(2)O center dot C8H7-N2O]center dot H2O, was synthesized and characterized on the basis of elemental analysis, thermal analyses (TG/DTA) and X-ray crystallography. In the complex, the coordination number of the La(III) ion is eleven. The interaction of the ligand and its complex with calf thymus DNA was investigated by spectrophotometric methods and viscosity measurements, respectively. Experimental results indicated that phthalazin-1 (2H)-one and the complex can bind to DNA by intercalation modes, but the binding affinity of La(III)complex is higher than that of the ligand. Comparative antitumor activities of La(III)-complex was investigated by HL-60 and A-549. IC50 = 2.6 x 10(-8), 3.3 x 10(-5) mg/mL are given. (c) 2005 Elsevier B.V. All rights reserved.
• Synthesis, characterization and DNA-binding studies of 2-carboxybenzaldehydeisonicotinoylhydrazone and its La(III), Sm(III) and Eu(III) complexes
  作者：Yuan Wang、Yan Wang、Zheng-Yin Yang

  DOI：10.1016/j.saa.2006.02.062

  日期：2007.2

  2-Carboxybenzaldehydeisonicotinoylhydrazone (HL), and its three lanthanide complexes, LnL(3)(.)4H(2)O [Ln = La(1), Sm(2), Eu(3)], have been synthesized and characterized on the basis of elemental analyses, molar conductivities, IR spectra and thermal analyses. In addition, the DNA-binding properties of the ligand and its complexes have been investigated by absorption, fluorescence and viscosity measurements. The experimental results indicated that the complexes (2) and (3) can bind to DNA, but the ligand and the complex (1) cannot; the binding affinity of the complex (3) is higher than that of the complex (2) and the intrinsic binding constant K-b of the complex (3) is 7.86 x 10(4) M-1. (c) 2006 Elsevier B.V. All rights reserved.