2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-phenylthiosemicarbazone | 881659-96-7

• 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 N-phenylthiosemicarbazone
• 英文别名: 1-[(2-oxo-1H-quinolin-3-yl)methylideneamino]-3-phenylthiourea
• CAS: 881659-96-7
• 化学式: C₁₇H₁₄N₄OS
• 分子量: 322.39
• InChiKey: UVGZPNBLXCJGKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  nickel(II) nitrate hexahydrate 、 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-phenylthiosemicarbazone 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.03.059
• 作为产物：
  描述：

  N-乙酰苯胺 在 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-phenylthiosemicarbazone
  参考文献：
  名称：

  取代喹诺酮缩氨基硫脲的合成、抗菌活性及对接研究

  摘要：

  摘要 在室温下合成了15种2-喹诺酮缩氨基硫脲衍生物，其中11种是新的。关键中间体是喹诺酮甲醛，通过缩氨基硫脲与醛部分的反应从中形成缩氨基硫脲。合成化合物的结构通过一维和二维核磁共振谱和质谱进行了阐明。合成的化合物显示出对金黄色葡萄球菌、金黄色葡萄球菌罗森巴赫 (MRSA)、铜绿假单胞菌、肺炎克雷伯菌、大肠杆菌和鼠伤寒沙门氏菌的抗菌活性范围为 0.80 至 36.49 mM。当更大的卤素如氯和溴在喹诺酮支架上的 C-6 处被取代时以及当缩氨基硫脲部分上存在平面苯基时，可以看到最佳活性。当较小的氟原子存在于 C-6 或当甲基连接到缩氨基硫脲时，活性会降低。这组化合物显示出高负结合亲和力，这表明有希望的抗微生物活性。氨基硫脲上带有苯基的6-氯衍生物具有最大的负结合亲和力。图形概要

  DOI：

  10.1080/10426507.2019.1618298

文献信息

• Effect of terminal N-substitution in 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazones on the mode of coordination, structure, interaction with protein, radical scavenging and cytotoxic activity of copper(ii) complexes
  作者：Duraisamy Senthil Raja、Ganesan Paramaguru、Nattamai S. P. Bhuvanesh、Joseph H. Reibenspies、Rajalingam Renganathan、Karuppannan Natarajan

  DOI：10.1039/c0dt01657h

  日期：——

  geometry around the central metal ion. In the complexes 1 and 2, the copper ion is coordinated by the ligand with ONS donor atoms, one chloride ion in apical position and the other chloride in the basal plane. Complex 3 consists of [CuCl2(H2-OQtsc-Et)(CH3OH)]+ cation and a chloride as counter ion. The copper ion is coordinated by the ligand with ONS donor atoms and by one chloride ion in the basal plane

  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
• Ruthenium(II) complexes encompassing 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazone hybrid ligand: A new versatile potential catalyst for dehydrogenative amide synthesis
  作者：Sellappan Selvamurugan、Rangasamy Ramachandran、Govindan Prakash、Muthukumaran Nirmala、Periasamy Viswanathamurthi、Shoji Fujiwara、Akira Endo

  DOI：10.1016/j.ica.2015.12.024

  日期：2017.1

  Ruthenium(II) complexes (1-6) supported by a series of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde substituted thiosemicarbazone ligands [2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazone (L-1), 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-methyl thiosemicarbazone (L-2), 2-oxo-1,2-dihydroquinoline-3-carbaldehyde N-phenylthiosemicarbazone (L-3)] have been synthesized and structurally characterized by analytical, spectroscopic methods and X-ray crystallographic technique. The studies revealed that the ligands act as mononegative tridentate in ruthenium(II) complexes and a distorted octahedral geometry has been proposed for the complexes. In addition, the complexes have been found to catalyze the amidation of alcohols with amines in the presence of KtBuO-toluene system. The catalyst 3 displayed higher activity in substrates, including phenyl-, pyridine-, furan-, and thiophene-substituted alcohols with primary and secondary amines. The protocol is highly attractive because of easily available starting materials, high atom efficiency and environmental friendliness. (C) 2015 Elsevier B.V. All rights reserved.
• 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
  作者：Eswaran Ramachandran、Duraisamy Senthil Raja、Nigam. P. Rath、Karuppannan Natarajan

  DOI：10.1021/ic302258k

  日期：2013.2.4

  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.
• Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones
  作者：Hogantharanni Govender、Chunderika Mocktar、Hezekiel M. Kumalo、Neil A. Koorbanally

  DOI：10.1080/10426507.2019.1618298

  日期：2019.11.2

  spectrometry. The synthesized compounds showed antibacterial activity with MBCs in the range 0.80 to 36.49 mM against Staphylococcus aureus, Staphylococcus aureus Rosenbach (MRSA), Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Salmonella typhimurium. The best activity was seen when a larger halogen such as chlorine and bromine were substituted at C-6 on the quinolone scaffold and when

  摘要 在室温下合成了15种2-喹诺酮缩氨基硫脲衍生物，其中11种是新的。关键中间体是喹诺酮甲醛，通过缩氨基硫脲与醛部分的反应从中形成缩氨基硫脲。合成化合物的结构通过一维和二维核磁共振谱和质谱进行了阐明。合成的化合物显示出对金黄色葡萄球菌、金黄色葡萄球菌罗森巴赫 (MRSA)、铜绿假单胞菌、肺炎克雷伯菌、大肠杆菌和鼠伤寒沙门氏菌的抗菌活性范围为 0.80 至 36.49 mM。当更大的卤素如氯和溴在喹诺酮支架上的 C-6 处被取代时以及当缩氨基硫脲部分上存在平面苯基时，可以看到最佳活性。当较小的氟原子存在于 C-6 或当甲基连接到缩氨基硫脲时，活性会降低。这组化合物显示出高负结合亲和力，这表明有希望的抗微生物活性。氨基硫脲上带有苯基的6-氯衍生物具有最大的负结合亲和力。图形概要
• 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.