(E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazinecarbothioamide | 1313215-51-8

• 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: (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazinecarbothioamide
• 英文别名: (E)-N,N-dimethyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide；N,N-dimethyl-2-(2-quinolinylmethylene)hydrazinecarbothioamide；N,N-dimethyl-2-(quinolin-2-yl-methylene)hydrazinecarbothioamide；N,N-Dimethyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide；1,1-dimethyl-3-[(E)-quinolin-2-ylmethylideneamino]thiourea
• CAS: 1313215-51-8
• 化学式: C₁₃H₁₄N₄S
• 分子量: 258.347
• InChiKey: KQMMLQQHWDVXNI-NTEUORMPSA-N

物化性质

• 沸点：
  407.0±37.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  gallium(III) trichloride 、 (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazinecarbothioamide 以 甲醇 为溶剂， 反应 0.5h， 以77%的产率得到
  参考文献：
  名称：

  具有有效和选择性抗癌活性的2‑喹啉羧甲醛硫半碳镓镓（III）配合物的构效关系。

  摘要：

  合成并表征了六种镓（III）与2-喹啉甲醛甲醛硫代半碳酸盐类似物的配合物（Ga1-Ga6）。这些镓（III）配合物表现出有效的抗癌活性，超过了相应的无金属配体的抗癌活性。重要的是，这些镓（III）配合物对肿瘤细胞具有很强的选择性。通过研究细胞机制，我们发现配体的亲脂性与镓（III）配合物的抗肿瘤活性密切相关。此外，我们选择了具有最佳抗肿瘤活性的Ga6来研究细胞凋亡的机制。Caspase-3和9激活以及膜联蛋白V-FITC /碘化丙啶（PI）双重染色研究表明，Ga6促进A549细胞株的凋亡。Ga6诱导细胞内活性氧（ROS）并破坏线粒体膜电位。

  DOI：

  10.1016/j.jinorgbio.2018.11.017
• 作为产物：
  描述：

  喹啉-2-甲醛 、 4,4-二甲基-3-氨基硫脲单水合物 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以77%的产率得到(E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazinecarbothioamide
  参考文献：
  名称：

  具有有效和选择性抗癌活性的2‑喹啉羧甲醛硫半碳镓镓（III）配合物的构效关系。

  摘要：

  合成并表征了六种镓（III）与2-喹啉甲醛甲醛硫代半碳酸盐类似物的配合物（Ga1-Ga6）。这些镓（III）配合物表现出有效的抗癌活性，超过了相应的无金属配体的抗癌活性。重要的是，这些镓（III）配合物对肿瘤细胞具有很强的选择性。通过研究细胞机制，我们发现配体的亲脂性与镓（III）配合物的抗肿瘤活性密切相关。此外，我们选择了具有最佳抗肿瘤活性的Ga6来研究细胞凋亡的机制。Caspase-3和9激活以及膜联蛋白V-FITC /碘化丙啶（PI）双重染色研究表明，Ga6促进A549细胞株的凋亡。Ga6诱导细胞内活性氧（ROS）并破坏线粒体膜电位。

  DOI：

  10.1016/j.jinorgbio.2018.11.017

文献信息

• Investigation of the Biological Properties of (Hetero)Aromatic Thiosemicarbazones
  作者：Maciej Serda、Anna Mrozek-Wilczkiewicz、Josef Jampilek、Matus Pesko、Katarina Kralova、Marcela Vejsova、Robert Musiol、Alicja Ratuszna、Jaroslaw Polanski

  DOI：10.3390/molecules171113483

  日期：——

  Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds) were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116). Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The structure-activity relationships are discussed for all of the compounds.

  采用微波辅助法设计并合成了两系列基于硫代 semicarbazone 的铁螯合剂（共 27 个化合物）。根据相似性搜索，以喹啉和卤代苯为母体骨架。通过 HPLC 测量并计算所合成化合物的亲脂性。对所合成的化合物进行了针对八种病原真菌的初级体外筛选。仅有少数化合物显示出中等的抗真菌活性，其中(E)-2-(喹啉-2-基乙烯基)-N,N-二甲基胼硫代卡巴脒对大部分测试的真菌株的抗真菌活性均优于氟康唑。采用人结肠癌细胞系(HCT-116) 测量其抗增殖活性。部分测试化合物显示出亚微摩尔级的抗增殖活性。此外，还测试了它们抑制菠菜（Spinacia oleracea L.）叶绿体中光合电子传递（PET）的能力。对于所有化合物，讨论了其结构-活性关系。
• Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy
  作者：Maciej Serda、Danuta S. Kalinowski、Anna Mrozek-Wilczkiewicz、Robert Musiol、Agnieszka Szurko、Alicja Ratuszna、Namfon Pantarat、Zaklina Kovacevic、Angelica M. Merlot、Des R. Richardson、Jaroslaw Polanski

  DOI：10.1016/j.bmcl.2012.07.030

  日期：2012.9

  Iron chelators have emerged as a potential anti-cancer treatment strategy. In this study, a series of novel thiosemicarbazone iron chelators containing a quinoline scaffold were synthesized and characterized. A number of analogs show markedly greater anti-cancer activity than the 'gold-standard' iron chelator, desferrioxamine. The anti-proliferative activity and iron chelation efficacy of several of these ligands (especially compound 1b), indicates that further investigation of this class of thiosemicarbazones is worthwhile. (C) 2012 Elsevier Ltd. All rights reserved.
• Evaluation of DNA binding and DNA cleavage of nickel(II) complexes with tridentate α-N-heterocyclic thiosemicarbazones ligands
  作者：JunGang Deng、Gaoxing Su、Peng Chen、Yunpeng Du、Yi Gou、Yani Liu

  DOI：10.1016/j.ica.2017.11.013

  日期：2018.2

  Two mononuclear thiosemicarbazones nickel(II) complexes of the type [Ni(L1)(2)] (1) and [Ni(HL2)(L2)] (2), where HL1 = (E)-N-methyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide and HL2 = (E)-N, N-dimethyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamidehave been synthesized and characterized by X-ray crystallography, infrared spectroscopy, elemental analysis and DFT calculations. Single-crystal diffraction analysis revealed that the HL1 ligands in 1 are predominantly in the thiolato resonance forms, while the HL2 ligands in 2 coordinate in thiolato and thione forms simultaneously. The interactions of both nickel(II) complexes with calf thymus DNA (CT-DNA) and supercoiled pBR322 plasmid DNA were investigated by fluorescence and UV-visible spectra, viscosity measurement, as well as agarose gel electrophoresis. The results of binding experiments displayed that both nickel(II) complexes were able to interact with CT-DNA via intercalative mode with a moderate binding affinity in the order 2 > 1. Gel electrophoresis assay revealed that the complexes could cleave the pBR322 plasmid DNA in a dose-dependent manner. (C) 2017 Elsevier B.V. All rights reserved.
• Structure−activity relationships of 2‑quinolinecarboxaldehyde thiosemicarbazone gallium(III) complexes with potent and selective anticancer activity
  作者：Wanbao Cao、Jinxu Qi、Kun Qian、Liang Tian、Zhen Cheng、Yihong Wang

  DOI：10.1016/j.jinorgbio.2018.11.017

  日期：2019.2

  Six gallium(III) complexes (Ga1-Ga6) with 2‑quinolinecarboxaldehyde thiosemicarbazone analogues were synthesized and characterized. These gallium(III) complexes exhibited potent anticancer activity and exceeded that of the corresponding metal free ligands. Importantly, these gallium(III) complexes have a strong selectivity for tumor cells. Through the study of cellular mechanisms, we have found that

  合成并表征了六种镓（III）与2-喹啉甲醛甲醛硫代半碳酸盐类似物的配合物（Ga1-Ga6）。这些镓（III）配合物表现出有效的抗癌活性，超过了相应的无金属配体的抗癌活性。重要的是，这些镓（III）配合物对肿瘤细胞具有很强的选择性。通过研究细胞机制，我们发现配体的亲脂性与镓（III）配合物的抗肿瘤活性密切相关。此外，我们选择了具有最佳抗肿瘤活性的Ga6来研究细胞凋亡的机制。Caspase-3和9激活以及膜联蛋白V-FITC /碘化丙啶（PI）双重染色研究表明，Ga6促进A549细胞株的凋亡。Ga6诱导细胞内活性氧（ROS）并破坏线粒体膜电位。