N-benzoyl-N′-(2-hydroxy-4-nitrophenyl)thiourea | 5197-09-1

• 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: N-benzoyl-N′-(2-hydroxy-4-nitrophenyl)thiourea
• 英文别名: N-(2-hydroxy-4-nitrophenyl)-N'-benzoylthiourea；N-[[(2-hydroxy-4-nitrophenyl) amino]thioxomethyl]benzamide；N-((2-hydroxy-4-nitrophenyl)carbamothioyl)benzamide；N-[(2-hydroxy-4-nitrophenyl)carbamothioyl]benzamide
• CAS: 5197-09-1
• 化学式: C₁₄H₁₁N₃O₄S
• 分子量: 317.325
• InChiKey: KTHKNTXDSYSCOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoyl-N′-(2-hydroxy-4-nitrophenyl)thiourea 生成 甲烷
  参考文献：
  名称：

  Structure–property relationship studies of copper(I) complexes of nanosized hypodentate ligands and evaluation of their antitumor and antimicrobial activities

  摘要：

  We report the preparation of four nanosized isomers of N-benzoyl-N-(hydroxyphenyl) thioureas by nanoprecipitation. Direct reactions with CuCl(2)2H(2)O gave the corresponding complexes in good yields. The structures of the ligands and their copper complexes were characterized using different analytical and spectroscopic measurements. In all complexes, the data revealed non-electrolytic mononuclear three-coordinate copper(I) complexes, where the ligand is hypodentate to copper ion via thioamide sulfur. Thermal studies revealed high thermal stability of the complexes compared to their parent ligands and the mechanism of decomposition and the thermodynamic parameters were evaluated. The ligands and their complexes were screened against different pathogenic microorganisms, and subjected to in vitro antioxidant and cytotoxic activities against three human cell lines. Compared to other isomers, N-benzoyl-N-(o-hydroxyphenyl) thiourea exhibited significant antimicrobial activity and had higher activity than the standard fungicides and bacteriocides. All copper complexes showed inhibitory potencies, however [Cu(H2L2)(2)Cl] exhibited remarkable inhibitory activities against the examined cancer cell lines as evident by the range of IC50 values (4.0-7.4g/mL) and the percentage of cell viability. The results obtained can find medical applications as new therapeutic nanoparticle agents.

  DOI：

  10.1080/00958972.2014.982551
• 作为产物：
  描述：

  苯甲酰氯 以 丙酮 为溶剂， 生成 N-benzoyl-N′-(2-hydroxy-4-nitrophenyl)thiourea
  参考文献：
  名称：

  硫脲衍生物作为新型支架醛缩酶抑制剂的设计，合成和杀藻活性。

  摘要：

  通过使用新的基于片段的虚拟筛选策略，从果蓝藻（CyFBA）的果糖-1、6-二磷酸醛缩酶的活性位点重新发现了两个系列的新型FBA-II抑制剂（硫脲衍生物）。相比之下，与N-（苯基氨基甲硫酰基）苯甲酰胺衍生物（L1-L13）相比，大多数N-（2-苯甲酰基肼-1-碳硫基）苯甲酰胺衍生物（L14〜L22）显示出更高的CyFBA-II抑制活性。尤其是，化合物L14不仅显示出较高的CyFBA-II活性（Ki = 0.65μM），而且还显示出最有效的针对拟球藻sp。的体内活性。PCC 6803（EC50 = 0.09 ppm），比以前的抑制剂（EC50 = 0.6 ppm）高（7倍）。通过联合使用DOX计算方案，MM-PBSA和定点诱变分析进一步阐明了化合物L14和CyFBA-II的结合模式。积极的结果表明，这项研究中采用的策略有望迅速发现具有新型支架的有效抑制剂。令人满意的除藻剂活性表明，硫脲衍生物很

  DOI：

  10.1016/j.bmc.2019.01.023

文献信息

• Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
  作者：Oleksandr Grytsai、Oksana Valiashko、Manon Penco-Campillo、Maeva Dufies、Anais Hagege、Luc Demange、Sonia Martial、Gilles Pagès、Cyril Ronco、Rachid Benhida

  DOI：10.1016/j.bioorg.2020.104271

  日期：2020.11

  Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect

  合成了携带3-氨基-1,2,4-三唑支架的两个系列的化合物，并使用XTT分析评估了它们对一组癌细胞系的抗癌活性。重新讨论了第一批吡啶基衍生物的1,2,4-三唑合成。生物学结果表明，对于这两个系列，不能替代的3-氨基-1,2,4-三唑核的有效性以及在三唑的3位的3-溴苯基氨基部分具有明显的有益作用（化合物2.6和4.6）在多个测试的细胞系上。此外，我们的结果指出了这些化合物的抗血管生成活性。总体而言，5-芳基-3-苯基氨基-1,2,4-三唑结构具有有前途的双重抗癌活性。
• Structure–property relationship studies of copper(I) complexes of nanosized hypodentate ligands and evaluation of their antitumor and antimicrobial activities
  作者：Amel F. ElHusseiny、Ali Eldissouky、Ahmed M. Al-Hamza、Hammed H.A.M. Hassan

  DOI：10.1080/00958972.2014.982551

  日期：2015.1.17

  We report the preparation of four nanosized isomers of N-benzoyl-N-(hydroxyphenyl) thioureas by nanoprecipitation. Direct reactions with CuCl(2)2H(2)O gave the corresponding complexes in good yields. The structures of the ligands and their copper complexes were characterized using different analytical and spectroscopic measurements. In all complexes, the data revealed non-electrolytic mononuclear three-coordinate copper(I) complexes, where the ligand is hypodentate to copper ion via thioamide sulfur. Thermal studies revealed high thermal stability of the complexes compared to their parent ligands and the mechanism of decomposition and the thermodynamic parameters were evaluated. The ligands and their complexes were screened against different pathogenic microorganisms, and subjected to in vitro antioxidant and cytotoxic activities against three human cell lines. Compared to other isomers, N-benzoyl-N-(o-hydroxyphenyl) thiourea exhibited significant antimicrobial activity and had higher activity than the standard fungicides and bacteriocides. All copper complexes showed inhibitory potencies, however [Cu(H2L2)(2)Cl] exhibited remarkable inhibitory activities against the examined cancer cell lines as evident by the range of IC50 values (4.0-7.4g/mL) and the percentage of cell viability. The results obtained can find medical applications as new therapeutic nanoparticle agents.
• Design, synthesis and algicides activities of thiourea derivatives as the novel scaffold aldolase inhibitors
  作者：Shan Xiao、Lin Wei、Zongqin Hong、Li Rao、Yanliang Ren、Jian Wan、Lingling Feng

  DOI：10.1016/j.bmc.2019.01.023

  日期：2019.3

  further elucidated by jointly using DOX computational protocol, MM-PBSA and site-directed mutagenesis assays. The positive results suggest that strategy adopted in this study was promising to rapidly discovery the potent inhibitors with novel scaffolds. The satisfactory algicide activities suggest that the thiourea derivatives is very likely to be a promising lead for the development of novel specific

  通过使用新的基于片段的虚拟筛选策略，从果蓝藻（CyFBA）的果糖-1、6-二磷酸醛缩酶的活性位点重新发现了两个系列的新型FBA-II抑制剂（硫脲衍生物）。相比之下，与N-（苯基氨基甲硫酰基）苯甲酰胺衍生物（L1-L13）相比，大多数N-（2-苯甲酰基肼-1-碳硫基）苯甲酰胺衍生物（L14〜L22）显示出更高的CyFBA-II抑制活性。尤其是，化合物L14不仅显示出较高的CyFBA-II活性（Ki = 0.65μM），而且还显示出最有效的针对拟球藻sp。的体内活性。PCC 6803（EC50 = 0.09 ppm），比以前的抑制剂（EC50 = 0.6 ppm）高（7倍）。通过联合使用DOX计算方案，MM-PBSA和定点诱变分析进一步阐明了化合物L14和CyFBA-II的结合模式。积极的结果表明，这项研究中采用的策略有望迅速发现具有新型支架的有效抑制剂。令人满意的除藻剂活性表明，硫脲衍生物很