(E)-N-phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide | 1313215-50-7

• 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: (E)-N-phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide
• 英文别名: 2-formylquinoline N(4)-phenylthiosemicarbazone；N-phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide；1-phenyl-3-[(E)-quinolin-2-ylmethylideneamino]thiourea
• CAS: 1313215-50-7
• 化学式: C₁₇H₁₄N₄S
• 分子量: 306.391
• InChiKey: MOMINPNNTHYBBO-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 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：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cobalt(II) chloride hexahydrate 、 (E)-N-phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide 以 乙醇 为溶剂， 反应 1.0h， 以78%的产率得到[Co(PQTS)₂]Cl·H₂O
  参考文献：
  名称：

  基于 α-N-杂环缩氨基硫脲配体的 Co(III) 复合物：DNA 结合、DNA 切割和拓扑异构酶 I/II 抑制活性研究

  摘要：

  摘要 在本研究中，三种 α-N-杂环缩氨基硫脲钴 (III) 配合物 [Co(QTS)2]NO3·(C2H5OH)0.5·H2O、[Co(MQTS)2]NO3·H2O 和 [Co(PQTS) )2]Cl·H2O，其中 HQTS = (E)-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide，HMQTS = (E)-N-methyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide，HPQTS = ( E)-N-苯基-2-(喹啉-2-基亚甲基)肼碳硫酰胺，已通过X射线晶体学、元素分析和光谱方法合成和表征，其结构已通过密度泛函理论(DFT)计算预测. 这些钴 (III) 复合物与 DNA 的相互作用通过光谱滴定、粘度测量以及琼脂糖凝胶电泳进行了研究。所有复合物都表现出与 DNA 结合的嵌入模式。尤其，所有钴

  DOI：

  10.1016/j.molstruc.2018.04.074
• 作为产物：
  描述：

  喹啉-2-甲醛 、 4-苯基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.2h， 生成 (E)-N-phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide
  参考文献：
  名称：

  Investigation of the Biological Properties of (Hetero)Aromatic Thiosemicarbazones

  摘要：

  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。

  DOI：

  10.3390/molecules171113483

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, Cytotoxic and Antimalarial Activities of Benzoyl Thiosemicarbazone Analogs of Isoquinoline and Related Compounds
  作者：Ratchanok Pingaew、Supaluk Prachayasittikul、Somsak Ruchirawat

  DOI：10.3390/molecules15020988

  日期：——

  Thiosemicarbazone analogs of papaveraldine and related compounds 1-6 were synthesized and evaluated for cytotoxic and antimalarial activities. The cytotoxic activity was tested against HuCCA-1, HepG2, A549 and MOLT-3 human cancer cell lines. Thiosemicarbazones 1-5 displayed cytotoxicity toward all the tested cell lines, while compounds 2-5 selectively showed potent activity against the MOLT-3 cell

  合成了罂粟碱和相关化合物 1-6 的 Thiosemiccarbazone 类似物，并评估了其细胞毒性和抗疟活性。针对 HuCCA-1、HepG2、A549 和 MOLT-3 人类癌细胞系测试了细胞毒活性。Thiosemiccarbazones 1-5 对所有测试的细胞系都显示出细胞毒性，而化合物 2-5 则选择性地对 MOLT-3 细胞系显示出有效的活性。值得注意的是，N(4)-phenyl-2-benzoylpyridine thiosemicarbazone 4 对 HuCCA-1、HepG2、A549 和 MOLT-3 细胞系表现出最有效的活性，IC50 值分别为 0.03、4.75、0.04 和 0.004 microg/mL。此外，2-苯甲酰基吡啶硫代氨基脲 3 和 4 对恶性疟原虫具有抗疟活性，IC50 为 10-7 至 < 10-6 M。
• 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.
• Co(III) complexes based on α-N-heterocyclic thiosemicarbazone ligands: DNA binding, DNA cleavage, and topoisomerase I/II inhibitory activity studies
  作者：JunGang Deng、Tao Li、Gaoxing Su、Qi-Pin Qin、Yani Liu、Yi Gou

  DOI：10.1016/j.molstruc.2018.04.074

  日期：2018.9

  The interactions of these cobalt(III) complexes with DNA were investigated by spectroscopic titration, viscosity measurement, as well as agarose gel electrophoresis. All complexes exhibited an intercalative mode of binding with DNA. Notably, all cobalt(III) complexes exhibited significant inhibitory effects on topoisomerase I (Topo I) and topoisomerase II (Topo II) activity at a low concentration (25 μM)

  摘要 在本研究中，三种 α-N-杂环缩氨基硫脲钴 (III) 配合物 [Co(QTS)2]NO3·(C2H5OH)0.5·H2O、[Co(MQTS)2]NO3·H2O 和 [Co(PQTS) )2]Cl·H2O，其中 HQTS = (E)-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide，HMQTS = (E)-N-methyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide，HPQTS = ( E)-N-苯基-2-(喹啉-2-基亚甲基)肼碳硫酰胺，已通过X射线晶体学、元素分析和光谱方法合成和表征，其结构已通过密度泛函理论(DFT)计算预测. 这些钴 (III) 复合物与 DNA 的相互作用通过光谱滴定、粘度测量以及琼脂糖凝胶电泳进行了研究。所有复合物都表现出与 DNA 结合的嵌入模式。尤其，所有钴