N'-(anthracen-9-ylmethylene)isonicotinohydrazide | 71727-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N'-(anthracen-9-ylmethylene)isonicotinohydrazide
• 英文别名: N-Isonicotinoyl-N'--hydrazin；N-Isonicotinoyl-N'-(anthracen-9-yl-methylen)-hydrazin；9-Anthraldehyde isonicotinoyl hydrazone；N-(anthracen-9-ylmethylideneamino)pyridine-4-carboxamide
• CAS: 71727-59-8
• 化学式: C₂₁H₁₅N₃O
• mdl: MFCD00185847
• 分子量: 325.37
• InChiKey: SFZNDNWHTDVIPK-UHFFFAOYSA-N

物化性质

• 熔点：
  273-275 °C
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苦味酸 、 N'-(anthracen-9-ylmethylene)isonicotinohydrazide 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以62%的产率得到(E)-N'-(anthracen-9-ylmethylene)isonicotinohydrazide compound with picric acid (1:1)
  参考文献：
  名称：

  A colorimetric and fluorescent chemosensor for the detection of an explosive—2,4,6-trinitrophenol (TNP)

  摘要：

  描述了一种用于特异性识别 TNP 的荧光和比色受体 (L)。这种显着亲和力的起源由相应的主客体复合物L·TNP的晶体结构揭示。

  DOI：

  10.1039/c1cc10400d
• 作为产物：
  描述：

  异烟肼 、 9-蒽甲醛 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 N'-(anthracen-9-ylmethylene)isonicotinohydrazide
  参考文献：
  名称：

  PhoP/PhoQ 抑制剂的效果导向合成以调节沙门氏菌毒力

  摘要：

  沙门氏菌属 是导致食源性感染的主要原因之一。PhoP/PhoQ 双组分调节系统是沙门氏菌的主要毒力调节剂。尽管 PhoP/PhoQ 是解除沙门氏菌毒力的理想目标，但迄今为止报道的抑制剂很少。我们描述了一种新的平台，通过该平台直接从含有氨基硫脲和单腙、二腙和三腙的反应介质中直接从大约 185 种化合物中选择一种抑制剂。为此，应用了串联文库制备、薄层色谱 (TLC) 生物自显影和效果导向反卷积。我们说明了这种以效果为导向的合成方法在识别食品领域新的有用生物活性化合物方面的潜力。

  DOI：

  10.1021/acs.jafc.2c01087

文献信息

• Mechano-Luminescent Behavior of a Pyridine-Containing Anthracene Derivative: Role of Aromatic Stacking Interactions
  作者：G. Gogoi、D. Kashyap、R. J. Sarma

  DOI：10.1021/acs.cgd.8b00271

  日期：2018.9.5

  Isonicotinic acid anthracen-9-ylmethylene-hydrazide (AI), prepared from anthracene-9-carboxaldehyde and isoniazid, exhibited mechano-responsive luminescent emissions; for instance, gentle pressing of the weakly emissive crystals of AI (λem 527 nm) produced a yellow-green emissive material (λem 540 nm). Also, the mechano-luminescent emissions of AI could be easily switched “off” upon exposure to N,N-dimethylformamide. Contrastingly, under the same conditions, benzoic acid anthracen-9-ylmethylene-hydrazide (AB) did not exhibit mechano-responsive luminescent emissions. On the basis of UV–vis, fluorescence, Fourier transform infrared spectroscopy, and powder X-ray diffraction (XRD) studies, we suggest that mechano-luminescent emissions of AI were triggered by mechanically induced deformations in the lattice, which affected the intermolecular interactions and aromatic stacking behavior. Again, the mechano-luminescent emissions of AI were switched off when mixed with oxalic acid, although accompanied by a concomitant change in color, from yellow-green to red. Single crystal XRD studies provided vital insights into the interactions of AI with oxalic acid, highlighting the role of hydrogen bonding and anion-mediated aromatic-π interactions.

  由蒽-9-甲醛和异烟肼制备的异烟酸蒽-9-基亚甲基肼（AI）显示出机械响应发光发射；例如，轻轻按压 AI 的弱发光晶体（λem 527 纳米）会产生黄绿色发光物质（λem 540 纳米）。此外，AI 的机械发光在暴露于 N,N-二甲基甲酰胺时很容易被 "关闭"。相反，在相同的条件下，苯甲酸蒽-9-基亚甲基肼（AB）没有表现出机械响应发光。根据紫外-可见光、荧光、傅立叶变换红外光谱和粉末 X 射线衍射（XRD）研究，我们认为 AI 的机械发光是由机械引起的晶格变形引发的，这种变形影响了分子间的相互作用和芳香堆积行为。同样，在与草酸混合时，AI 的机械发光也会被关闭，但同时颜色会从黄绿色变为红色。单晶 XRD 研究为了解 AI 与草酸的相互作用提供了重要线索，突出了氢键和阴离子介导的芳香-π 相互作用的作用。
• Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens
  作者：Ján Imrich、Zdenka Bedlovičová、Pavol Kristian、Ivan Danihel、Stanislav Böhm、Danica Sabolová、Mária Kožurková、Helena Paulíková、Karel D. Klika

  DOI：10.3987/com-09-s(s)83

  日期：——

  Three series of carbohydrazides or hydrazones bearing either acridine or anthracene pharmacophores were synthesized as potential noncovalent DNA-binding antitumor agents. Carbohydrazides with an acridine or anthracene moiety were prepared from appropriate acridine or anthracene carbaldehydes via cyclocondensation with selected hydrazides whilst hydrazones with a 10H-acridin-9-ylidene moiety were obtained by condensation of (acridin-9-yl)hydrazine with various aldehydes or ketones. The spectroscopic properties of the first two series revealed efficient fluorescence implying that the compounds could be amenable for use as biomarkers. The structures of the compounds were characterized by spectral methods (UV-vis, fluorescence, IR, and (1)H, (13)C, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO, and AM I). The first carbohydrazide series was also tested against human leukemia cell line HL-60 wherein the phenyl-substituted derivative was found to possess the highest activity.
• A colorimetric and fluorescent chemosensor for the detection of an explosive—2,4,6-trinitrophenol (TNP)
  作者：Yu Peng、Ai-Jiang Zhang、Ming Dong、Ya-Wen Wang

  DOI：10.1039/c1cc10400d

  日期：——

  A fluorescent and colorimetric receptor (L) for specific recognition of TNP was described. The origins of this remarkable affinity was disclosed by the crystal structure of corresponding host–guest complex L·TNP.

  描述了一种用于特异性识别 TNP 的荧光和比色受体 (L)。这种显着亲和力的起源由相应的主客体复合物L·TNP的晶体结构揭示。
• Effect-Directed Synthesis of PhoP/PhoQ Inhibitors to Regulate <i>Salmonella</i> Virulence
  作者：Ignacio Cabezudo、Carlos A. Lobertti、Eleonora García Véscovi、Ricardo L. E. Furlan

  DOI：10.1021/acs.jafc.2c01087

  日期：2022.6.8

  so far. We describe a novel platform by which an inhibitor was selected out of around 185 compounds directly from reaction media containing thiosemicarbazones and mono-, di-, and trihydrazones. To achieve this, tandem library preparation, thin-layer chromatography (TLC) bioautography, and effect-directed deconvolution were applied. We illustrate the potential of this effect-directed synthesis for the

  沙门氏菌属 是导致食源性感染的主要原因之一。PhoP/PhoQ 双组分调节系统是沙门氏菌的主要毒力调节剂。尽管 PhoP/PhoQ 是解除沙门氏菌毒力的理想目标，但迄今为止报道的抑制剂很少。我们描述了一种新的平台，通过该平台直接从含有氨基硫脲和单腙、二腙和三腙的反应介质中直接从大约 185 种化合物中选择一种抑制剂。为此，应用了串联文库制备、薄层色谱 (TLC) 生物自显影和效果导向反卷积。我们说明了这种以效果为导向的合成方法在识别食品领域新的有用生物活性化合物方面的潜力。