2-oxo-1,2-dihydroquinoline-3-carbaldehyde 4N-ethylthiosemicarbazone | 477734-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-oxo-1,2-dihydroquinoline-3-carbaldehyde 4N-ethylthiosemicarbazone
• 英文别名: 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-ethylthiosemicarbazone；H2-OQtsc-Et；1-ethyl-3-[(2-oxo-1H-quinolin-3-yl)methylideneamino]thiourea
• CAS: 477734-17-1
• 化学式: C₁₃H₁₄N₄OS
• 分子量: 274.346
• InChiKey: FFECZUUITROYDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-1,2-dihydroquinoline-3-carbaldehyde 4N-ethylthiosemicarbazone 、 bis-triphenylphosphine-palladium(II) chloride 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以74%的产率得到
  参考文献：
  名称：

  Role of Substitution at Terminal Nitrogen of 2-Oxo-1,2-dihydroquinoline-3-Carbaldehyde Thiosemicarbazones on the Coordination Behavior and Structure and Biological Properties of Their Palladium(II) Complexes

  摘要：

  A series of four new palladium(II) complexes of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazones with triphenylphosphine as coligand have been synthesized and characterized by the aid of various spectral techniques. The single-crystal X-ray diffraction studies revealed that the unsubstituted thiosemicarbazone ligand acted as monobasic tridentate (ONS-) in the cationic [Pd(H-Qtsc-H)(PPh3)]Cl complex, whereas the monosubstituted thiosemicarbazone ligands acted as monobasic bidentate (NS-) in their respective complexes, [PdCl(H-Qtsc-R)(PPh3)] (R = Me (2), Et (3), Ph (4)). To ascertain the potentials of the above Pd(II) complexes toward biomolecular interactions, additional experiments involving interaction with calf thymus DNA and bovine serum albumin were carried out. Moreover, all the palladium(II) complexes have been screened for their radical scavenging activity toward DPPH, O-2(-), OH, and NO radicals. The efficiency of the complexes in arresting the growth of human cervical cancer cells (He La), human laryngeal epithelial carcinoma cells (HEp-2), human liver carcinoma cells (Hep G2), and human skin cancer cells (A431) has also been studied along with the cell viability test against the noncancerous NIH 3T3 mouse embryonic fibroblasts cell lines under in vitro conditions. All the in vitro pharmacological evaluation results clearly revealed the relationship between the structure and the activity of the new Pd(II) complexes.

  DOI：

  10.1021/ic302258k
• 作为产物：
  描述：

  4-乙基-3-硫代氨基脲 、 1,2-二氢-2-氧代喹啉-3-甲醛 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到2-oxo-1,2-dihydroquinoline-3-carbaldehyde 4N-ethylthiosemicarbazone
  参考文献：
  名称：

  2-氧代-1,2-二氢喹啉-3-甲醛硫代半氨基唑酮中末端N取代对铜（ii）配合物的配位，结构，与蛋白质的相互作用，自由基清除和细胞毒活性的影响†

  摘要：

  四个 2-氧-1,2-二氢喹啉-3-甲醛N取代的硫代半碳素配体（H 2 -OQtsc-R，其中R = H，Me，Et或Ph）及其相应的新铜（II）配合物[CuCl 2（H 2 -OQtsc-H）]·2H 2 O（1），[CuCl 2（H 2 -OQtsc-Me）]·2H 2 O（2），[CuCl 2（H 2 -OQtsc-Et）（CH 3 OH）] Cl（3）和[CuCl（H- OQtsc-Ph）]·CH 3 OH（4为了合成末端N-取代对配位行为，结构和生物活性的影响，已经合成了Aβ-Aβ。单晶X射线衍射研究显示，该复合物1，2和3具有围绕中心金属离子的四方锥几何形状。在配合物1和2中，铜离子被具有ONS供体原子的配体配位，一个氯离子位于顶端位置，另一个氯离子位于基面上。配合物3由[CuCl 2（H 2 -OQtsc-Et）（CH 3 OH）] +组成阳离子和氯化物作为抗衡离子。铜离子由

  DOI：

  10.1039/c0dt01657h

文献信息

• Synthesis, characterization and in vitro pharmacological evaluation of new water soluble Ni(II) complexes of 4N-substituted thiosemicarbazones of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde
  作者：Eswaran Ramachandran、Duraisamy Senthil Raja、Nattamai S.P. Bhuvanesh、Karuppannan Natarajan

  DOI：10.1016/j.ejmech.2013.03.059

  日期：2013.6

  Four new Ni(II) complexes of general formula [Ni(H-2-Qtsc-R)(2)](NO3)(2) (H-2-Qtsc-R = 4N-substituted thiosemicarbazones of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde, where R = H (1), Me (2), Et (3), or Ph (4)) have been synthesized and characterized. The geometry of the complexes was confirmed by single crystal X-ray crystallography for one of the complexes (3). The binding affinity of the complexes with DNA and protein have been studied which indicate that they could interact with calf thymus DNA and bovine serum albumin protein. Investigations of antioxidative properties showed that all the complexes have strong radical scavenging properties. Cytotoxic studies showed that the complexes exhibited effective cytotoxic activity against a panel of human cancer cells without affecting the normal cells much. (C) 2013 Elsevier Masson SAS. All rights reserved.