(E)-2-(3,4-dichlorobenzylidene)-N-phenylhydrazinecarbothioamide | 1422955-09-6

• 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-(3,4-dichlorobenzylidene)-N-phenylhydrazinecarbothioamide
• 英文别名: 3,4-Dichlorobenzaldehyde 4-phenyl-3-thiosemicarbazone；1-[(E)-(3,4-dichlorophenyl)methylideneamino]-3-phenylthiourea
• CAS: 1422955-09-6
• 化学式: C₁₄H₁₁Cl₂N₃S
• 分子量: 324.233
• InChiKey: BRAXXKQWALMLSB-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 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：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  马来酸酐 、 (E)-2-(3,4-dichlorobenzylidene)-N-phenylhydrazinecarbothioamide 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 以45.5%的产率得到2-[[(3,4-Dichlorophenyl)methylene]hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acid
  参考文献：
  名称：

  Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids

  摘要：

  In the present communication, a new series of 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids (2a-p) have been synthesized. Benzaldehyde 4-phenyl-3-thiosemicarbazones substituted (la-p) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were characterized by IR, H-1 and (13) C NMR. The in vitro anti-Toxoplasma gondii activity of la-p and 2a-p was evaluated. The 4-thiazolidinones (2a-p) were screened for their ill vitro antimicrobial activity. For anti-Toxoplasma gondii activity, in general, all compounds promoted decreases in the percentage of infected cells leading to parasite elimination. These effects on intracellular parasites also caused a decrease in the mean number of tachyzoites. In addition, most of the 4-thiazolidinones showed more effective toxicity against intracellular parasites, with IC50 values ranging from 0.05 to 1 mM. According to results of antimicrobial activity, compounds 2f, 21, and 2p showed best activity against Mycobacterium luteus, 2c was more active against Mycobacterium tuberculosis, and 2g, 21, and 2n showed same activity as nistatin (standard drug) against Candida sp. (4249). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.025
• 作为产物：
  描述：

  4-苯基-3-硫代氨基脲 、 3,4-二氯苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.2h， 以86%的产率得到(E)-2-(3,4-dichlorobenzylidene)-N-phenylhydrazinecarbothioamide
  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

• MARTVON A.; STANKOVSKY S.; UHER M., CHEM. 2VESTI, 1980, 34, NO 1, 118-124
  作者：MARTVON A.、 STANKOVSKY S.、 UHER M.

  DOI：——

  日期：——
• 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, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids
  作者：Thiago M. de Aquino、André P. Liesen、Rosa E.A. da Silva、Vânia T. Lima、Cristiane S. Carvalho、Antônio R. de Faria、Janete M. de Araújo、José G. de Lima、Antonio J. Alves、Edésio J.T. de Melo、Alexandre J.S. Góes

  DOI：10.1016/j.bmc.2007.09.025

  日期：2008.1

  In the present communication, a new series of 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids (2a-p) have been synthesized. Benzaldehyde 4-phenyl-3-thiosemicarbazones substituted (la-p) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were characterized by IR, H-1 and (13) C NMR. The in vitro anti-Toxoplasma gondii activity of la-p and 2a-p was evaluated. The 4-thiazolidinones (2a-p) were screened for their ill vitro antimicrobial activity. For anti-Toxoplasma gondii activity, in general, all compounds promoted decreases in the percentage of infected cells leading to parasite elimination. These effects on intracellular parasites also caused a decrease in the mean number of tachyzoites. In addition, most of the 4-thiazolidinones showed more effective toxicity against intracellular parasites, with IC50 values ranging from 0.05 to 1 mM. According to results of antimicrobial activity, compounds 2f, 21, and 2p showed best activity against Mycobacterium luteus, 2c was more active against Mycobacterium tuberculosis, and 2g, 21, and 2n showed same activity as nistatin (standard drug) against Candida sp. (4249). (c) 2007 Elsevier Ltd. All rights reserved.