(E)-4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzhydrazide | 1373329-40-8

• 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: (E)-4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzhydrazide
• 英文别名: (E)-2-acetylpyridine p-nitro-benzoylhydrazone；H2AcpNO2Ph；4-nitro-N-[(E)-1-pyridin-2-ylethylideneamino]benzamide
• CAS: 1373329-40-8
• 化学式: C₁₄H₁₂N₄O₃
• 分子量: 284.274
• InChiKey: MPQLUIRDVHIZEX-MHWRWJLKSA-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：

  (E)-4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzhydrazide 以 乙腈 为溶剂， 反应 0.67h， 生成 (Z)-4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzhydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  (Z)-4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzhydrazide 以 乙腈 为溶剂， 反应 2.08h， 生成 (E)-4-nitro-N'-(1-(pyridin-2-yl)ethylidene)benzhydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519

文献信息

• Tricarbonylrhenium(<scp>i</scp>) complexes with 2-acetylpyridine-derived hydrazones are cytotoxic to NCI-H460 human large cell lung cancer
  作者：Camila Vargas Garcia、Gabrieli Lessa Parrilha、Bernardo Lages Rodrigues、Sarah Fernandes Teixeira、Ricardo Alexandre de Azevedo、Adilson Kleber Ferreira、Heloisa Beraldo

  DOI：10.1039/c6nj00050a

  日期：——

  cancer. Complexes (2) and (3) induced apoptosis on NCI-H460 cells. Complex (2) induced mitochondrial damage while treatment with 3 showed a later response, suggesting that probably the same effect would be observed at higher concentrations or longer treatments. Both complexes (2) and (3) showed a high antioxidant activity, 2 being more potent in reducing intracellular reactive oxygen species (ROS) production

  络合物[ReCl（CO）3（H2AcPh）]（1），[ReCl（CO）3（H2Ac p ClPh）]·0.5C 7 H 8（2）和[ReCl（CO）3（H2Ac p NO 2 Ph）用2-乙酰基吡啶-苯基hydr（H2AcPh）及其对-氯苯基hydr （H2Ac p ClPh）和对-硝基苯基hydr（H2Ac p NO 2 Ph）类似物获得]·0.5C 7 H 8（3）。协调tricarbonylrhenium（我）对NCI-H460人大细胞肺癌具有更高的抗增殖活性。复合物（2）和（3）诱导NCI-H460细胞凋亡。复合物（2）诱导线粒体损伤，而用3处理则显示出较晚的响应，这表明在更高浓度或更长的治疗时间可能会观察到相同的效果。配合物（2）和（3）均显示出高的抗氧化活性，2在减少细胞内活性氧（ROS）产生方面更有效。
• Silver(<scp>i</scp>) complexes with 2-acetylpyridinebenzoylhydrazones exhibit antimicrobial effects against yeast and filamentous fungi
  作者：Ane F. Santos、Isabella P. Ferreira、Jacqueline A. Takahashi、Gabriel L. S. Rodrigues、Carlos B. Pinheiro、Letícia R. Teixeira、Willian R. Rocha、Heloisa Beraldo

  DOI：10.1039/c7nj04280a

  日期：——

  2-Acetylpyridinebenzoylhydrazones and their silver(i) complexes show antimicrobial effects and deserve to be investigated as antifungal drug candidates.

  2-乙酰基吡啶苯甲酰肼及其银（i）配合物表现出抗微生物作用，值得作为抗真菌药物候选进行研究。
• Organotin(IV) complexes with 2-acetylpyridine benzoyl hydrazones: antimicrobial activity
  作者：Angel A. R. Despaigne、Lorena F. Vieira、Isolda C. Mendes、Fernanda B. da Costa、Nivaldo L. Speziali、Heloisa Beraldo

  DOI：10.1590/s0103-50532010000700012

  日期：——

  Reaction of n-butyltin trichloride, [(BuSnCl3)-Sn-n], and phenyltin trichloride, [PhSnCl3], with 2-acetylpyridine benzoyl hydrazone (H2AcPh), 2-acetylpyridine para-chloro-benzoyl hydrazone (H2AcpClPh) and 2-acetylpyridine para-nitro-benzoyl hydrazone (H2AcpNO(2) Ph) gave [(BuSn)-Sn-n(2AcPh)Cl-2] (1), [(BuSn)-Sn-n(2AcpClPh)Cl-2] (2), [(BuSn)-Sn-n(2AcpNO(2)Ph)Cl-2] (3), [PhSn(2AcPh)Cl-2] (4), [PhSn(2AcpClPh)Cl-2] (5) and [PhSn(2AcpNO(2)Ph)Cl-2] (6) as products. Among the hydrazones H2AcpClPh proved to be the most active against Staphylococcus aureus and Candida albicans. Upon coordination the antibacterial activity of both tin and the hydrazones significantly increases. Complexes 2 and 5 revealed to be the most active as antimicrobial agents.