1-(pyridin-2-yl)ethanone (Z)-thiosemicarbazone

• 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: 1-(pyridin-2-yl)ethanone (Z)-thiosemicarbazone
• 英文别名: 2-(1-(pyridine-2-yl)ethylidene)hydrazine-1-carbothioamide；[(Z)-1-pyridin-2-ylethylideneamino]thiourea
• 化学式: C₈H₁₀N₄S
• 分子量: 194.26
• InChiKey: RIFVPOHZBSIFRL-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  alpha-溴-4-甲氧基苯乙酮 、 1-(pyridin-2-yl)ethanone (Z)-thiosemicarbazone 在 高氯酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以71.75%的产率得到(4-(4-methoxy phenyl)-2-(2-(1-pyridine-2-yl)ethylidene)hydrazinyl)thiazole
  参考文献：
  名称：

  激发新型吡啶-噻唑基 Co(III)、Mn(II) 和 Ni(II) 配合物的体外抗癌活性：合成、结构、DFT、对接和 MD 模拟研究

  摘要：

  (4-(4-甲氧基苯基)-2-(2-(1-吡啶-2-基)亚乙基)肼基)噻唑( PytH·ClO 4 )的高氯酸盐及其金属高氯酸盐衍生物，即[Co( Pyt ) 2 ]ClO 4 ( 1 )、[Mn( PytH ) 2 ](ClO 4 ) 2 ( 2 ) 和 [Ni( PytH ) 2 ](ClO 4 ) 2 ( 3 )，通过单X射线晶体学和光谱方法。配体在空间群P 2 1 /中结晶n在一个近乎平面的结构中。复合盐的整体几何形状被描述为具有 MN 6发色团的扭曲八面体。配体 ( PytH·ClO 4 )对“软”Mn(II) 和 Ni(II) 中心表现为中性N , N , N-三齿供体，而去质子化的配体稳定“硬” Co(III) 中心. PytH·ClO 4、1、2和3的 DNA 结合常数 ( K b ) 值采用紫外可见分光光度法测定，K b值为 9.29 × 10 5, 7.11 × 10 5

  DOI：

  10.1021/acs.jcim.1c01280
• 作为产物：
  描述：

  (1-吡啶-2-基乙亚基氨基)硫脲 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 1-(pyridin-2-yl)ethanone (Z)-thiosemicarbazone
  参考文献：
  名称：

  Pelagatti, Paolo; Venturini, Andrea; Leporati, Andrea, Journal of the Chemical Society, Dalton Transactions, 1998, # 16, p. 2715 - 2721

  摘要：

  DOI：

文献信息

• Significant photocytotoxic effect of an iron(<scp>iii</scp>) complex of a Schiff base ligand derived from vitamin B₆and thiosemicarbazide in visible light
  作者：Tukki Sarkar、Samya Banerjee、Akhtar Hussain

  DOI：10.1039/c5ra04207k

  日期：——

  An iron(iii)–Schiff base complex derived from vitamin B₆and thiosemicarbazide is significantly photocytotoxic to HeLa cancer cells in visible light (400 nm–700 nm) but non-toxic in the absence of light.

  从维生素B6和硫脲衍生的铁（III）-席夫碱配合物在可见光（400 nm-700 nm）下对HeLa癌细胞具有显著的光细胞毒性，但在没有光的情况下无毒。
• Synthesis and Structure−Activity Relationships of Parasiticidal Thiosemicarbazone Cysteine Protease Inhibitors against <i>Plasmodium falciparum</i>, <i>Trypanosoma brucei</i>, and <i>Trypanosoma cruzi</i>
  作者：Doron C. Greenbaum、Zachary Mackey、Elizabeth Hansell、Patricia Doyle、Jiri Gut、Conor R. Caffrey、Julia Lehrman、Philip J. Rosenthal、James H. McKerrow、Kelly Chibale

  DOI：10.1021/jm030549j

  日期：2004.6.1

  We have synthesized a library of thiosemicarbazones and screened them against three parasitic cysteine proteases, cruzain, falcipain-2, and rhodesain, and against the respective parasite sources of these three proteases, Trypanosoma cruzi, Plasmodium falciparum, and Trypanosoma brucei. The screens identified compounds that were effective against the enzymes and the parasites but also some compounds that were parasiticidal despite a lack of activity against the proteases. Several compounds were effective in killing all tested parasites. These promising lead compounds were tested for general toxicity in mice, and only one produced observable toxicity after 62 h. Our results suggest that thiosemicarbazones represent validated drug leads that kill several species of protozoan parasites through the inhibition of cysteine proteases as well as other novel targets.
• Saxena, Chitra; Singh, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1996, vol. 35, # 8, p. 707 - 709
  作者：Saxena, Chitra、Singh

  DOI：——

  日期：——
• Fahmi, Nighat; Singh, Journal of the Indian Chemical Society, 1996, vol. 73, # 6, p. 257 - 259
  作者：Fahmi, Nighat、Singh

  DOI：——

  日期：——
• US5281597A
  申请人：——

  公开号：US5281597A

  公开（公告）日：1994-01-25