(E)-2-(2,3-dichlorobenzylidene)hydrazinecarbothioamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(2,3-dichlorobenzylidene)hydrazinecarbothioamide
• 英文别名: 2,3-Dichlorobenzaldehyde thiosemicarbazone；[(E)-(2,3-dichlorophenyl)methylideneamino]thiourea
• 化学式: C₈H₇Cl₂N₃S
• 分子量: 248.136
• InChiKey: MUEBZTOJMDYECK-UUILKARUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [RuHCl(CO)(PPh₃)₃] 、 (E)-2-(2,3-dichlorobenzylidene)hydrazinecarbothioamide 以 甲醇 为溶剂， 反应 3.0h， 以72%的产率得到RuH(CO)((E)-2-(2,3-dichlorobenzylidene)hydrazinecarbothioamide)(PPh3)2
  参考文献：
  名称：

  钌（II）羰基配合物

  摘要：

  摘要本文提出了含有硫代半碳zone配体的Ru（II）羰基配合物的组合实验和计算研究。已经获得了五种新颖的[Ru（H / Cl）（L）（PPh 3）2]配合物，并通过IR，1 H，13 C，31 P NMR，UV-Vis光谱和X射线晶体学进行了表征。它们的电子结构已使用密度泛函理论（DFT）方法确定，并用于讨论其性能。配体的供体-受体性质与苯环上的取代基位置相关。还检查了配合物的发光性质。

  DOI：

  10.1016/j.poly.2013.03.045
• 作为产物：
  描述：

  氨基硫脲 、 2,3-二氯苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.2h， 以78%的产率得到(E)-2-(2,3-dichlorobenzylidene)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 and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain
  作者：Xiaohui Du、Chun Guo、Elizabeth Hansell、Patricia S. Doyle、Conor R. Caffrey、Tod P. Holler、James H. McKerrow、Fred E. Cohen

  DOI：10.1021/jm010459j

  日期：2002.6.1

  American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that X-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T cruzi. 3'-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.
• Microwave assisted synthesis, X-ray crystallography and DFT calculations of selected aromatic thiosemicarbazones
  作者：Maciej Serda、Jan G. Małecki、Anna Mrozek-Wilczkiewicz、Robert Musioł、Jarosław Polański

  DOI：10.1016/j.molstruc.2012.11.050

  日期：2013.4

  Series of four benzaldehyde thiosemicarbazones has been synthesized under microwave irradiation and characterized structurally by means of infrared and NMR spectroscopies and mass spectrometry. Their crystal structures were determined by single crystal X-ray analysis followed by DFT calculations. Partial charges on the molecular surface and dipole moments of the structures were calculated. Crystal structures are stabilized by intramolecular hydrogen bonding and stacking interactions. Studied compounds are interesting as antiproliferative and antifungal agents acting through interactions with iron. Thus presented results may be useful in design new more active or specific structures. (C) 2012 Elsevier B.V. All rights reserved.
• Ruthenium(II) carbonyl complexes with thiosemicarbazone ligands
  作者：J.G. Małecki、A. Maroń、M. Serda、J. Polański

  DOI：10.1016/j.poly.2013.03.045

  日期：2013.6

  Abstract This paper presents a combined experimental and computational study of Ru(II) carbonyl complexes containing thiosemicarbazone ligands. Five novel [Ru(H/Cl)(L)(PPh 3 ) 2 ] complexes have been obtained and characterized by IR, 1 H, 13 C, 31 P NMR, UV–Vis spectroscopy and X-ray crystallography. Their electronic structures have been determined using the density functional theory (DFT) method and

  摘要本文提出了含有硫代半碳zone配体的Ru（II）羰基配合物的组合实验和计算研究。已经获得了五种新颖的[Ru（H / Cl）（L）（PPh 3）2]配合物，并通过IR，1 H，13 C，31 P NMR，UV-Vis光谱和X射线晶体学进行了表征。它们的电子结构已使用密度泛函理论（DFT）方法确定，并用于讨论其性能。配体的供体-受体性质与苯环上的取代基位置相关。还检查了配合物的发光性质。