quinoline-2-carboxyaldehyde N⁴-phenylthiosemicarbazone | 107152-84-1

• 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: quinoline-2-carboxyaldehyde N⁴-phenylthiosemicarbazone
• 英文别名: quinoline-2-formaldehyde-4-phenylthiosemicarbazide；N-phenyl-2-(quinolin-2-ylmethylen)hydrazin-1-carbothioamide；2-quinolinecarboxyaldehyde-N4-phenylthiosemicarbazone；quinoline-2-carboxaldehyde-4-phenylthiosemicarbazone；N-phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide；quinoline-2-carbaldehyde-(4-phenyl thiosemicarbazone)；Chinolin-2-carbaldehyd-(4-phenyl-thiosemicarbazon)；1-phenyl-3-(quinolin-2-ylmethylideneamino)thiourea
• CAS: 107152-84-1
• 化学式: C₁₇H₁₄N₄S
• 分子量: 306.391
• InChiKey: MOMINPNNTHYBBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.31
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  quinoline-2-carboxyaldehyde N⁴-phenylthiosemicarbazone 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Role of the auxiliary ligand in determining the genotoxicity and mode of cell death of thiosemicarbazone Pd(ii) complexes

  摘要：

  We report how the cytotoxicity, mode of death and genotoxic effect of a series of square planar Pd(ii) complexes are determined by the auxiliary ligand coupled to the Pd(ii) ion, which is chelated by the tridentate thiosemicarbazone ligand.

  DOI：

  10.1039/d4dt00032c
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 5.5h， 生成 quinoline-2-carboxyaldehyde N⁴-phenylthiosemicarbazone
  参考文献：
  名称：

  Pd(II)和Pt(II)氨基硫脲复合物对不同人胶质母细胞瘤细胞系的构效关系

  摘要：

  十个氨基硫脲配体通过吡啶-2-甲醛、喹啉-2-甲醛、2-乙酰基吡啶、2-乙酰基喹啉或相应的2-吡啶基酮与氨基硫脲RNHC(S)NHNH 2和R=CH 3 , C 6 H缩合获得5个均以良好的收率制备。如1 _ _ _ _ _ _ H, 13 C 和，如适用，195Pt NMR 光谱结合 CHNS 分析。在四种人胶质母细胞瘤细胞系（GaMG、U87、U138 和 U343）上研究了标题化合物的细胞毒性。最活跃的化合物，具有 Pd(II) 金属中心、2-喹啉基环和近端 C 和远端 N 原子上的甲基基团，在 GaMG 细胞系上的 EC 50值为 2.1 μM，因此略高于比顺铂 (EC 50 3.4 μM) 更有效，并且比替莫唑胺 (EC 50 67.1 μM) 更有效。令人惊讶的是，EC 50值与“摇瓶法”测定的亲脂性呈负相关，并随着烷基取代基的长度而降低（C 1 >C 8 >C 10）。与不同

  DOI：

  10.1002/zaac.202200073

文献信息

• Quinoline-2-carboxaldehyde thiosemicarbazones and their Cu(II) and Ni(II) complexes as topoisomerase IIa inhibitors
  作者：Franco Bisceglie、Anastasia Musiari、Silvana Pinelli、Rossella Alinovi、Ilaria Menozzi、Eugenia Polverini、Pieralberto Tarasconi、Matteo Tavone、Giorgio Pelosi

  DOI：10.1016/j.jinorgbio.2015.08.008

  日期：2015.11

  thiosemicarbazones and their copper(II) and nickel(II) complexes were synthesized and characterized. In all complexes the ligands are in the E configuration with respect to the imino bond and behave as terdentate. The copper(II) complexes form square planar derivatives with one molecule of terdentate ligand and chloride ion. A further non-coordinated chloride ion compensates the overall charge. Nickel(II) ions form

  合成并表征了一系列喹啉-2-羧甲醛硫代半氨基甲酮及其铜（II）和镍（II）配合物。在所有配合物中，配体都在E中关于亚氨基键的构型并表现为齿状。铜（II）配合物与一分子的齿状配体和氯离子形成方形平面衍生物。另一个非配位的氯离子补偿了总电荷。镍（II）离子可与每个金属离子形成两个配体的八面体络合物，而与合成中使用的化学计量的金属：配体比率无关。测试了配体和复合物在组织细胞性淋巴瘤细胞系U937中的抗增殖特性。铜（II）衍生物在系统上比配体和镍络合物更具活性。所有铜衍生物都会在体外抑制拓扑异构酶IIa。使用计算方法提出了一个模型来解释这些化合物所表现出的不同程度的抑制作用。
• Developing a Novel Indium(III) Agent Based on Human Serum Albumin Nanoparticles: Integrating Bioimaging and Therapy
  作者：Zhenlei Zhang、Tongfu Yang、Juzheng Zhang、Wenjuan Li、Shanhe Li、Hongbin Sun、Hong Liang、Feng Yang

  DOI：10.1021/acs.jmedchem.1c01790

  日期：2022.4.14

  To effectively integrate diagnosis and therapy for tumors, we proposed to develop an indium (In) agent based on the unique property of human serum albumin (HSA) nanoparticles (NPs). A novel In(III) quinoline-2-formaldehyde thiosemicarbazone compound (C5) was optimized with remarkable cytotoxicity and fluorescence to cancer cells in vitro. An HSA–C5 complex NP delivery system was then successfully constructed

  为了有效整合肿瘤的诊断和治疗，我们建议开发一种基于人血清白蛋白 (HSA) 纳米粒子 (NPs) 独特性质的铟 (In) 剂。一种新型 In(III) 喹啉-2-甲醛缩氨基硫脲化合物 (C5) 进行了优化，在体外对癌细胞具有显着的细胞毒性和荧光性。随后成功构建了 HSA-C5 复合 NP 递送系统。重要的是，HSA-C5 复合物 NP在体内比单独的 C5 具有更强的生物成像和治疗效率。此外，基因芯片分析结果表明，C5/HSA-C5复合NPs通过多种机制作用于癌细胞：诱导自噬、细胞凋亡和抑制PI3K-Akt信号通路。
• A Series of α-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIα Catalytic Activity
  作者：He Huang、Qin Chen、Xin Ku、Linghua Meng、Liping Lin、Xiang Wang、Caihua Zhu、Yi Wang、Zhi Chen、Ming Li、Hualiang Jiang、Kaixian Chen、Jian Ding、Hong Liu

  DOI：10.1021/jm9014394

  日期：2010.4.22

  A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase II alpha catalytic inhibitor. Its inhibition on topoisomerase II alpha was due to direct interaction with the ATPase domain of topoisomerase I la which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase II alpha.
• α−N−heterocyclic thiosemicarbazone Fe(III) complex: Characterization of its antitumor activity and identification of anticancer mechanism
  作者：Yi Gou、Jun Wang、Shifang Chen、Zhan Zhang、Yao Zhang、Wei Zhang、Feng Yang

  DOI：10.1016/j.ejmech.2016.07.041

  日期：2016.11

  We synthesized an alpha-N-heterocyclic thiosemicarbazone ligand (L) and its Fe complex (C1) and assessed their chemical and biological properties in order to understand their marked activity. Electrochemical studies and ascorbate oxidation studies demonstrated that C1 shows considerable redox activity, and Fe-III/II redox potentials was within the range accessible to cellular oxidants and reductants. Absorption spectral, emission spectral and viscosity analysis reveal that L and C1 interacted with DNA through intercalation and C1 exhibited a higher DNA binding ability: Agarose gel electrophoresis experiments indicated that C1 exhibited the highest pBR322 DNA cleaving ability. In vitro, C1 showed significantly more anticancer activity than the ligand alone. Moreover, C1 induces production of reactive oxygen species (ROS) and DNA damage, resulting in activation of the p53 pathway, cell cycle arrest at the S phase, and mitochondria-mediated apoptosis by regulating the expression of Bcl-2 family proteins. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Bismuth complex of quinoline thiosemicarbazone restores carbapenem sensitivity in NDM-1-positive Klebsiella pneumoniae
  作者：Mirco Scaccaglia、Martina Rega、Cristina Bacci、Dario Giovanardi、Silvana Pinelli、Giorgio Pelosi、Franco Bisceglie

  DOI：10.1016/j.jinorgbio.2022.111887

  日期：2022.9