(E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide | 91397-02-3

• 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: (E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide
• 英文别名: (E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinohydrazide；1-thiophen-2-yl-ethanone isonicotinoylhydrazone；isonicotinic acid-(1-[2]thienyl-ethylidenehydrazide)；Isonicotinsaeure-(1-[2]thienyl-aethylidenhydrazid)；N'-(1-(2-Thienyl)ethylidene)isonicotinohydrazide；N-[(E)-1-thiophen-2-ylethylideneamino]pyridine-4-carboxamide
• CAS: 91397-02-3
• 化学式: C₁₂H₁₁N₃OS
• 分子量: 245.305
• InChiKey: ZVBINISUCJCXIC-NTEUORMPSA-N

物化性质

• 熔点：
  260 °C
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 溶解度：
  >36.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.13h， 生成 (Z)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide
  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)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 1.5h， 生成 (E)-N'-(1-(thiophen-2-yl)ethylidene)isonicotinic hydrazide
  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

• Spectroscopic studies, DFT calculations, cytotoxicity activity, and docking stimulation of novel metal complexes of Schiff base ligand of isonicotinohydrazide derivative
  作者：Nelly H. Mahmoud、Ghada H. Elsayed、Asmaa Aboelnaga、Asmaa M. Fahim

  DOI：10.1002/aoc.6697

  日期：2022.7

  thermal stability and the kinetic parameter for all complexes were elucidated via TGA analysis and Coats-Redfern method. XRD study suggested that the complexes have a partially amorphous structure which was further confirmed by calculating the crystallinity index. Moreover, the synthesized metal complexes exhibited excellent cytotoxicity activity contra lung cancer cells (A549) and liver cancer cells

  在该说明中，异烟酰肼衍生物 ( 3 )( L ) 的反应性与 Cr( III )、Fe( III )、Co( II )、Ni( II )、Cu( II ) 和 Zn( II ) 得到相应的稳定的金属配位化合物。合成的金属配位化合物通过元素分析、紫外-可见光、FT-IR、TGA、质量、1 H NMR、XRD、磁性和摩尔电导分析等物理化学和分析分析进行确认。除 Zn( II) 具有扭曲的四面体排列的复合体。通过 TGA 分析和 Coats-Redfern 方法阐明了所有配合物的热稳定性和动力学参数。XRD研究表明配合物具有部分无定形结构，通过计算结晶度指数进一步证实了这一点。此外，使用中性红摄取试验，合成的金属配合物对肺癌细胞（A549）和肝癌细胞（HepG2 ）表现出优异的细胞毒活性。Fe( III )、Ni( II )和Zn( II )的配合物对A549和HepG2表现出比阿霉素更高的细胞毒作用细胞孵育
• Carrara et al., Gazzetta Chimica Italiana, 1953, vol. 83, p. 459,470
  作者：Carrara et al.

  DOI：——

  日期：——
• Fast Synthesis of <i>N</i>-Acylhydrazones Employing a Microwave Assisted Neat Protocol
  作者：Marta M. Andrade、Maria Teresa Barros

  DOI：10.1021/cc9001444

  日期：2010.3.8

  A variety of N-acylhydrazones were synthesized Under microwave irradiation within 2.5-10 min, starting from benzo, salicyloyl, and isonicotinic hydrazides. The protocol developed employs microwave irradiation in the absence of solvents and catalysts, leading to high yields. The results are reproducible in a 500 mg to 5 g scale.
• Acylhydrazones as Widely Tunable Photoswitches
  作者：Derk Jan van Dijken、Petr Kovaříček、Svante P. Ihrig、Stefan Hecht

  DOI：10.1021/jacs.5b09519

  日期：2015.12.2

  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.