N'-[(4-oxo-4H-chromen-3-yl)methylidene]nicotinohydrazide | 164594-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N'-[(4-oxo-4H-chromen-3-yl)methylidene]nicotinohydrazide
• 英文别名: N-((4-oxo-4H-cromen-3yl)methylene)isonicotinohydrazide；4-Pyridinecarboxylic acid, 2-[(4-oxo-4H-1-benzopyran-3-yl)methylene]hydrazide；N-[(4-oxochromen-3-yl)methylideneamino]pyridine-4-carboxamide
• CAS: 164594-16-5
• 化学式: C₁₆H₁₁N₃O₃
• 分子量: 293.282
• InChiKey: YFNDGAPTSYRUMC-UHFFFAOYSA-N

物化性质

• 熔点：
  278 °C(Solvent: Ethanol)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氰化四丁基铵 、 N'-[(4-oxo-4H-chromen-3-yl)methylidene]nicotinohydrazide 以 水 为溶剂， 生成
  参考文献：
  名称：

  Selective and sensitive colorimetric sensor for CN⁻ in the absence and presence of metal ions (Cu²⁺/Ni²⁺): mimicking logic gate behaviour

  摘要：

  Enone基阴离子传感器由于在去质子化时发生色度反应和共轭基团中的可变出现而具有重要意义。

  DOI：

  10.1039/c6ra14237k
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 N'-[(4-oxo-4H-chromen-3-yl)methylidene]nicotinohydrazide
  参考文献：
  名称：

  Selective and sensitive colorimetric sensor for CN⁻ in the absence and presence of metal ions (Cu²⁺/Ni²⁺): mimicking logic gate behaviour

  摘要：

  Enone基阴离子传感器由于在去质子化时发生色度反应和共轭基团中的可变出现而具有重要意义。

  DOI：

  10.1039/c6ra14237k

文献信息

• 3-Formylchromones: Potential antiinflammatory agents
  作者：Khalid M. Khan、Nida Ambreen、Uzma Rasool Mughal、Saima Jalil、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.ejmech.2010.05.065

  日期：2010.9

  3-formylchromone (1) and its derivatives 2–24 and evaluation of their potential antiinflammatory activities is reported here. These compounds were characterized by 1H NMR, EI MS, IR, and UV spectroscopic techniques and elemental analysis. The synthesized compounds were evaluated by using various in vitro and in vivo assay models for antiinflammatory activity and their effects were compared with known standard

  -3-甲酰（的合成和表征1）及其衍生物2 - 24其潜在的抗炎活性的和评价此处报告。这些化合物通过1 H NMR，EI MS，IR和UV光谱技术和元素分析进行​​表征。通过使用各种体外和体内测定模型评估合成的化合物的抗炎活性，并将其作用与已知的标准药物（如阿司匹林和消炎痛）进行比较。在所有测试的化合物，1，2，5，6，9，14，16 - 19，21 - 23，显示出有前途的抗炎活性。 结果和比吸收率已在本报告中进行了讨论。
• DNA-binding properties and antioxidant activity of lanthanide complexes with the Schiff base derived from 3-carbaldehyde chromone and isonicotinyl hydrazine
  作者：Yong Li、Zhengyin Yang

  DOI：10.1080/00958972.2010.496127

  日期：2010.6.10

  of 105 (mol L−1)−1, and the lanthanide complexes bind stronger than the free ligand alone. Antioxidant activities of the ligand and lanthanide complexes were determined by superoxide and hydroxyl radical scavenging methods in vitro. The ligand and complexes possess strong scavenging effects, and the lanthanide complexes show stronger antioxidant activities than the ligand and some standard antioxidants

  结构分析表明配体和镧系元素离子形成单核 10 配位 ([Ln L2 · (NO3)2] · NO3 [Ln(III) = La、Sm、Nd 和 Yb；L 是色酮-3-甲醛-(异烟酰基）腙）配合物，其金属与配体的化学计量比为 1:2。DNA 结合研究表明，配体及其镧系元素复合物可以通过嵌入模式与小牛胸腺 DNA 结合，结合常数为 105 (mol L-1)-1，并且镧系元素复合物的结合力强于单独的游离配体。配体和镧系元素配合物的抗氧化活性通过体外超氧化物和羟基自由基清除方法测定。配体和配合物具有很强的清除作用，镧系元素配合物显示出比配体和一些标准抗氧化剂（如维生素 C）更强的抗氧化活性。
• Activity of some 3-formylchromone derivatives on the induction of chloroplast-free mutants in Euglena gracilis
  作者：Pavlı́na Foltı́nová、Margita Lácová、Dušan Loos

  DOI：10.1016/s0014-827x(99)00114-7

  日期：2000.1

  The hereditary bleaching test on Euglena gracilis was used for detecting extranuclear mutations. The highest bleaching activity (induction of the chloroplast-free mutants) was shown by the 6-R-3-formylchromones. On the other hand, bleaching-inactive 6-R-3-formylchromone acylhydrazones (derived from gallic and salicylic acids), added at sufficient concentrations in the case of chloroplast mutagenesis in E. gracilis, act as a potent antimutagen. This effect appeared to be a unique feature of chromone derivatives, but was dependent on the type of mutagen. These substances were very effective against the bleaching activity of acridine orange, and were less effective against N-methyl-N'-nitro-N-nitrosoguanidine. The genotoxic effects of these mutagens was reduced, especially during the first stages of induction of this specific cytoplasmic mutation. The experimental study of mutagenicity and antimutagenicty of 3-formylchromone hydrazones was reinforced by data obtained by the semi-empirical AM1 method and lipophilicity values. (C) 2000 Elsevier Science S.A. All rights reserved.
• Synthesis, antimicrobial activity and bleaching effect of some reaction products of 4-oxo-4H-benzopyran-3-carboxaldehydes with aminobenzothiazoles and hydrazides
  作者：Hafez M. El-Shaaer、Pavlína Foltínová、Margita Lácová、Jarmila Chovancová、Henrieta Stankovičová

  DOI：10.1016/s0014-827x(98)00015-9

  日期：1998.3

  The synthesis of the biologically active novel systems derived from reaction of 3-formylchromones with three types of amino derivatives, 6-R-2-2-aminobenzothiazoles, 6-amino-2-R-3-thiobenzothiazoles and hydrazide derivatives (derived from cyanoacetic, isonicotine, salicylic and gallic acids) was carried out. The structures of the prepared compounds have been proved by elemental analysis, H-1 NMR and IR spectra. Antimicrobial activity was studied against the following microorganisms-bacteria G(+) (Staphylococcus aureus 29/58, Bacillus subtilis 18/66), G(-) (Escherichia coli 326/71, Pseudomonas aeruginosa); yeasts: Candida albicans, Saccharomyces cerevisiae; moulds: Microsporum gypseum, Aspergillus niger, Scopulariopsis brevicaulis; and against typical and atypical mycobacteria: Mycobacterium tuberculosis (H37Rv), Mycobacterium kansasii (PFG8), Mycobacterium avium (My 80/72), Mycobacterium fortuitum (1021). The hereditary bleaching effect on the plastid system of Euglena gracilis, a unique phenomenon of the biological activity of chromone derivatives, is reported. The bleaching test on E. gracilis is used for detecting extranuclear mutations. (C) 1998 Elsevier Science S.A. All rights reserved.
• Acylhydrazones as isoniazid derivatives with multi-target profiles for the treatment of Alzheimer’s disease: Radical scavenging, myeloperoxidase/acetylcholinesterase inhibition and biometal chelation
  作者：Daniela Corrêa Santos、Ruan Roberto Henriques、Marcos Antonio de Abreu Lopes Junior、André Borges Farias、Thayssa Lisboa do Couto Nogueira、João Victor Fernandes Quimas、Nelilma Correia Romeiro、Leandro Louback da Silva、Andréa Luzia Ferreira de Souza

  DOI：10.1016/j.bmc.2020.115470

  日期：2020.5

  Acylhydrazones la-o, derived from isoniazid, were synthesized and evaluated for Myeloperoxidase (MPO) and Acetylcholinesterase (AChE) inhibition, as well as their antioxidant and metal chelating activities, with the purpose of investigating potential multi-target profiles for the treatment of Alzheimer's disease. Synthesized compounds were tested using the 2,2-diphenyl-2-picrylhydrazyl (DPPH) method and 1i, 1j and 1 m showed radical scavenging ability. Compounds 1b, 1 h, 1i , 1 m and 1o inhibited MPO activity (10 mu M) at 96.1 +/- 5.5%, 90 +/- 2.1%, 100.3 +/- 1.7%, 80.1 +/- 9.4% and 82.2 +/- 10.6%, respectively, and only compound 1 m was able to inhibit 54.2 +/- 1.7% of AChE activity (100 mu M). Docking studies of the most potent compound 1 m were carried out, and the computational results provided the theoretical basis of enzyme inhibition. Furthermore, compound 1 m was able to form complexes with Fe2+ and Zn2+ ions in a 2:1 ligand:metal ratio according to the Job Plot method.