(E)-2-(2,3-dichlorobenzylidene)-N-ethylhydrazinecarbothioamide | 1422955-03-0

• 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)-N-ethylhydrazinecarbothioamide
• 英文别名: 2,3-Dichlorobenzaldehyde N-ethylthiosemicarbazone；1-[(E)-(2,3-dichlorophenyl)methylideneamino]-3-ethylthiourea
• CAS: 1422955-03-0
• 化学式: C₁₀H₁₁Cl₂N₃S
• mdl: MFCD04488060
• 分子量: 276.189
• InChiKey: BHMVTTJPRHWWBG-MKMNVTDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.5
• 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)-N-ethylhydrazinecarbothioamide 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到RuCl(CO)((E)-2-(2,3-dichlorobenzylidene)-N-ethylhydrazinecarbothioamide)(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：

  4-乙基-3-硫代氨基脲 、 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67%的产率得到(E)-2-(2,3-dichlorobenzylidene)-N-ethylhydrazinecarbothioamide
  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。
• 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。