(Z)-N’-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (Z)-N’-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide
• 英文别名: (Z)-N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide；N-[(Z)-anthracen-9-ylmethylideneamino]thiophene-2-carboxamide
• 化学式: C₂₀H₁₄N₂OS
• 分子量: 330.41
• InChiKey: VLKUKTAAZJYUAT-BKUYFWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 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：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N’-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide 以 乙腈 为溶剂， 反应 0.5h， 生成 (E)-N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide
  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：

  (E)-N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide 以 乙腈 为溶剂， 反应 0.33h， 生成 (Z)-N’-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide
  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

• In vitro evaluations of biomolecular interactions, antioxidant and anticancer activities of Nickel(II) and Copper(II) complexes with 1:2 coordination of anthracenyl hydrazone ligands
  作者：K.S. Neethu、S. Sivaselvam、M. Theetharappan、J. Ranjitha、N.S.P. Bhuvanesh、N. Ponpandian、M.A. Neelakantan、M.V. Kaveri

  DOI：10.1016/j.ica.2021.120419

  日期：2021.9

  A set of nickel(II) and copper(II) complexes incorporated anthracenyl hydrazone ligands were synthesized and characterized with the help of various spectroscopic techniques. Single-crystal XRD studies revealed that all four complexes have square planar geometry in which the hydrazones are coordinated through NO atoms with 1:2 metal to ligand stoichiometry. Bio-molecular interactions of these complexes

  合成了一组结合蒽基enyl配体的镍（II）和铜（II）配合物，并借助各种光谱技术对其进行了表征。单晶XRD研究表明，所有四个络合物均具有正方形平面几何形状，其中hydr通过1个原子比2的金属与配体化学计量的NO原子配位。使用紫外线和发射光谱研究分析了这些复合物的生物分子相互作用，结果表明化合物通过插层与小牛胸腺DNA（CT-DNA）相互作用，并与BSA牢固结合。理论研究进一步证实了这一点。借助于MTT测定法评估化合物对结肠癌细胞（HCT-15）和正常皮肤细胞（L929）的抗癌性质。证实了该复合物对癌细胞显示出极好的细胞毒性，而对正常细胞的毒性可忽略不计。通过DPPH自由基清除测定法检查了抗氧化活性，发现该复合物能够还原可用自由基。该复合物通过活性氧的产生引发细胞死亡，这是通过ROS测定来确定的。借助于扫描电子显微镜（SEM）已经观察到在用不同浓度的复合物处理的细胞系中观察到的形态学转化。流