(E)-N-phenyl-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide | 6839-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-N-phenyl-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide
• 英文别名: (2E)-N-phenyl-2-(pyridin-2-ylmethylidene)hydrazinecarbothioamide；(E)-4-phenyl-1-(pyridin-2-ylmethylene)thiosemicarbazide；(E)-N-phenyl-2-(pyridin-2-ylmethylene)hydrazinecarbothioamide；(4E)-pyridine-2-carbaldehyde 4-phenylthiosemicarbazone；pyridine-2-carbaldehyde-(4-phenyl thiosemicarbazone)；Pyridin-2-carbaldehyd-(4-phenyl-thiosemicarbazon)；N(4)-phenyl-2-formylpyridine thiosemicarbazone；1-phenyl-3-[(E)-pyridin-2-ylmethylideneamino]thiourea
• CAS: 6839-89-0
• 化学式: C₁₃H₁₂N₄S
• 分子量: 256.331
• InChiKey: JHWPKWSWTSDZLG-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  (E)-N-phenyl-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide 、 溴乙酸 在 sodium acetate 作用下， 以 乙醇 为溶剂， 以62 %的产率得到(E)-3-phenyl-2-((E)-(pyridin-2-ylmethylene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Structural design, synthesis, and anti-Trypanosomatidae profile of new Pyridyl-thiazolidinones

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115310
• 作为产物：
  描述：

  苯胺 在 hydrazine hydrate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (E)-N-phenyl-2-(pyridin-2-ylmethylene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  含有吲哚片段作为有效和选择性抗癌剂的新型硫半脲类衍生物。

  摘要：

  高效，安全的抗癌药物的研发仍在促进人类健康。在本报告中，设计并合成了一系列新型的含吲哚片段的硫半碳环素衍生物。大多数化合物对PC3，MGC803和EC109细胞系均表现出优异的抗增殖活性，且IC50（0.14-12μM）低。特别地，化合物5j可以选择性地抑制三个测试的肿瘤细胞中的PC3细胞，IC50值为0.14μM，这可能归因于将吲哚片段引入TSC结构后的协同作用。同时，与3-AP和DPC相比，化合物5j在PC3细胞中对两种正常的WPMY-1和GES-1细胞系表现出更高的选择性。我们还发现5j可以有效抑制PC3细胞增殖，定植并诱导细胞凋亡。更重要的是，5j可能通过阻止EMT过程来显着抑制迁移和侵袭，但对细胞周期没有影响。总体而言，我们的研究结果表明，具有吲哚硫半脲的结构的5j可以用作进一步优化和开发的有用的抗癌药物。

  DOI：

  10.1016/j.ejmech.2019.111764

文献信息

• Pyridyl-1,3,4-thiadiazole; eine neue Variante der Thiadiazol-Synthese
  作者：P. Hemmerich、B. Prijs、H. Erlenmeyer

  DOI：10.1002/hlca.19580410714

  日期：——

  Thiosemicarbazones of aromatic aldehydes react with acetic anhydride to give well-defined N4,S-diacetyl derivatives, which readily undergo oxidative cyclisation to 2-aryl-4-acetamido-1,3,4-thiadiazoles. From these intermediates, aryl-thiadiazoles – especially 2-(2′-pyridyl)-1,3,4-thiadiazole, inaccessible by the common methods – can be obtained by acidic deacetylation, SANDMEYER substitution and catalytic

  芳族醛的硫代氨基甲唑酮与乙酸酐反应，得到定义明确的N 4，S-二乙酰基衍生物，该衍生物易于氧化环化成2-芳基-4-乙酰氨基-1,3,4-噻二唑。从这些中间体，可以通过酸性脱乙酰基化，SANDMEYER取代和催化脱卤来获得芳基-噻二唑，尤其是2-（2'-吡啶基）-1,3,4-噻二唑，这是常规方法难以达到的。
• Novel thiosemicarbazone derivatives containing indole fragment as potent and selective anticancer agent
  作者：Zhangxu He、Hui Qiao、Feifei Yang、Wenjuan Zhou、Yunpeng Gong、Xinhui Zhang、Haojie Wang、Bing Zhao、Liying Ma、Hong-min Liu、Wen Zhao

  DOI：10.1016/j.ejmech.2019.111764

  日期：2019.12

  are still on the way to human health. In this report, a series of novel thiosemicarbazone derivatives containing indole fragment were designed and synthesized. Most compounds exhibited excellent antiproliferative activity against PC3, MGC803 and EC109 cell lines with low micromolar IC50 (0.14-12μM). Especially, compound 5j can selectively inhibit PC3 cells in three tested tumor cells with IC50 value of

  高效，安全的抗癌药物的研发仍在促进人类健康。在本报告中，设计并合成了一系列新型的含吲哚片段的硫半碳环素衍生物。大多数化合物对PC3，MGC803和EC109细胞系均表现出优异的抗增殖活性，且IC50（0.14-12μM）低。特别地，化合物5j可以选择性地抑制三个测试的肿瘤细胞中的PC3细胞，IC50值为0.14μM，这可能归因于将吲哚片段引入TSC结构后的协同作用。同时，与3-AP和DPC相比，化合物5j在PC3细胞中对两种正常的WPMY-1和GES-1细胞系表现出更高的选择性。我们还发现5j可以有效抑制PC3细胞增殖，定植并诱导细胞凋亡。更重要的是，5j可能通过阻止EMT过程来显着抑制迁移和侵袭，但对细胞周期没有影响。总体而言，我们的研究结果表明，具有吲哚硫半脲的结构的5j可以用作进一步优化和开发的有用的抗癌药物。
• Coordination of Thiosemicarbazones and Bis(thiosemicarbazones) to Bismuth(III) as a Strategy for the Design of Metal‐Based Antibacterial Agents
  作者：Josane A. Lessa、Débora C. Reis、Jeferson G. Da Silva、Lúcia T. Paradizzi、Nayane F. da Silva、Mariany de Fátima A. Carvalho、Sarah A. Siqueira、Heloisa Beraldo

  DOI：10.1002/cbdv.201100447

  日期：2012.9

  glyoxaldehyde bis(thiosemicarbazone) (H2Gy4DH) and its 4‐Et (H2Gy4Et) and 4‐Ph (H2Gy4Ph) derivatives. The complexes exhibited antibacterial activities against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, and Pseudomonas aeruginosa. Coordination to BiIII proved to be an effective strategy to increase the antibacterial activity of the thiosemicarbazones and bis(thiosemicarbazones)

  配合物 [Bi(2Fo4Ph)Cl2] (1), [Bi(2Ac4Ph)Cl2] (2), [Bi(2Bz4Ph)Cl2] (3), [Bi(H2Gy3DH)Cl3] (4), [Bi(H2Gy4Et) (OH)2Cl] (5) 和 [Bi(H2Gy4Ph)Cl3] (6) 是用吡啶-2-甲醛 4-苯基缩氨基硫 (H2Fo4Ph)、1-(吡啶-2-基)乙酮 4-苯基缩氨基硫 (H2Ac4Ph) 制备的)、苯基(吡啶-2-基)甲酮4-苯基氨基硫脲(H2Bz4Ph)，以及乙醛双(氨基硫脲)(H2Gy4DH)及其4-Et(H2Gy4Et)和4-Ph(H2Gy4Ph)衍生物。该复合物对金黄色葡萄球菌、表皮葡萄球菌、粪肠球菌和铜绿假单胞菌具有抗菌活性。事实证明，与 BiIII 的配合是提高缩氨基硫脲和双（缩氨基硫脲）抗菌活性的有效策略。
• Profft et al., Journal fur praktische Chemie (Leipzig 1954), 1955, vol. <4>2, p. 147,159
  作者：Profft et al.

  DOI：——

  日期：——
• Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents
  作者：Xin-Hui Zhang、Bo-Wang、Yuan-Yuan Tao、Qin Ma、Hao-Jie Wang、Zhang-Xu He、Hui-Pan Wu、Yi-Han Li、Bing Zhao、Li-Ying Ma、Hong-Min Liu

  DOI：10.1016/j.ejmech.2020.112349

  日期：2020.8

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.