N-benzoyl-N’-(3,4-dichlorophenyl)thiourea | 19249-85-5

• 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’-(3,4-dichlorophenyl)thiourea
• 英文别名: N-((3,4-dichlorophenyl)carbamothioyl)benzamide；3-benzoyl-1-(3,4-dichlorophenyl)thiourea；N-(3.4-Dichlorphenyl)-N'-benzoylthioharnstoff；N-benzoyl-N'-(3,4-dichloro-phenyl)-thiourea；N-Benzoyl-N'-(3,4-dichlor-phenyl)-thioharnstoff；N-[(3,4-dichlorophenyl)carbamothioyl]benzamide
• CAS: 19249-85-5
• 化学式: C₁₄H₁₀Cl₂N₂OS
• 分子量: 325.218
• InChiKey: OUYWANSYAWDBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 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：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzoyl-N’-(3,4-dichlorophenyl)thiourea 在 sodium hydroxide 作用下， 反应 0.15h， 以90%的产率得到1-(3,4-二氯苯基)-2-硫脲
  参考文献：
  名称：

  Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

  摘要：

  制备芳基硫脲的改进方法包括将苯甲酰异硫氰酸酯与苯胺在丙酮中反应，然后用5%氢氧化钠水溶液对生成的N-芳基-N'-苯甲酰硫脲进行去苯甲酰化。双环烷基硫脲和N-(芳烷基)硫脲（例如9H-9-芴基硫脲）可直接由相应的异硫氰酸酯与氨反应制备。

  DOI：

  10.1055/s-1988-27605
• 作为产物：
  描述：

  苯甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 N-benzoyl-N’-(3,4-dichlorophenyl)thiourea
  参考文献：
  名称：

  Solution-phase microwave assisted parallel synthesis of N,N′-disubstituted thioureas derived from benzoic acid: Biological evaluation and molecular docking studies

  摘要：

  An efficient and facile microwave-assisted solution phase parallel synthesis for a 26-member library of N,N'-disubstituted thiourea analogs were accomplished successfully. The reaction time for synthesis of analogs was drastically reduced from a reported 8-12 h to only 10 min. Compounds were more than 95% pure, as characterized by modern analytical techniques, i.e. H-1 & C-13 NMR and FT-IR. The solid phase structural analysis has also been performed by single crystal XRD analysis. Synthesized compounds were preliminary screened for their in vitro urease inhibition and antifungal activity. Most of the compounds were found to be potent inhibitors of urease. However, the most significant activity was found for 11 with IC50 of 1.67 mu M. The docking scores correlate with the IC50 values of inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.012

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。
• Synthesis and antitumor evaluation of 5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)-N-arylthiazol-2-amines
  作者：Z. L. Wu、Y. L. Fang、Y. T. Tang、M. W. Xiao、J. Ye、G. X. Li、A. X. Hu

  DOI：10.1039/c6md00234j

  日期：——

  The strategy for designing target compounds as antitumor agents.

  设计靶向化合物作为抗肿瘤药物的策略。
• Coordination Chemistry of Organoruthenium Compounds with Benzoylthiourea Ligands and their Biological Properties
  作者：Shahida Parveen、Kelvin K. H. Tong、Muhammad Khawar Rauf、Mario Kubanik、Muhammad Ashraf Shaheen、Tilo Söhnel、Stephen M. F. Jamieson、Muhammad Hanif、Christian G. Hartinger

  DOI：10.1002/asia.201801798

  日期：2019.4.15

  involving the S donor atom and surprisingly in bidentate coordination mode a deprotonated thiourea nitrogen resulting in a 4‐membered ring structure around the metal center. DFT calculations were used to explain the differences in coordination behavior. These were complemented by stability studies and biological investigations of the compounds as anticancer agents. Several of the synthesized derivatives

  苯甲硫脲衍生物的特征是几个能够与金属中心配位的供体原子。我们在这里报告了一系列的Ru（η 6 - p-苯甲基）配合物，采用苯甲酰基硫脲衍生物作为配体。此类配体通常通过其S和O供体原子与金属中心配位。我们分离出了复杂的配体，其中配体与Ru涉及S供体原子单配或双齿配位，而出乎意料的是，在双齿配位模式下，去质子化的硫脲氮在金属中心周围形成4元环结构。DFT计算被用来解释协调行为的差异。这些都得到了该化合物作为抗癌药的稳定性研究和生物学研究的补充。几种合成的衍生物表现出显着的细胞生长抑制活性，具有双齿配体的复合物比其单齿配体更有效。
• Synthesis of aryloxyacetylthiourea derivatives for the development of radicle elongation inhibitor of parasitic weeds
  作者：Motohiro Sonoda、Yusuke Mimura、Shizuki Noda、Atsushi Okazawa

  DOI：10.1016/j.tet.2023.133333

  日期：2023.4

  yl)thiourea (PI-28), has attracted attention as a lead compound for the development of radicle elongation inhibitors in Orobanche minor seeds germination. In this study, we synthesized PI-28 and its derivatives in two steps using commercially available phenols, 2-chloroacetamide, and N-aryl isothiocyanates. In this method, 2-aryloxyacetanilides, which are also attractive as bioactive compounds, were

  芳氧基乙酰基硫脲，1-(3,4-二氯苯基)-3-(2-苯氧基乙酰基)硫脲 (PI-28) 作为先导化合物引起了人们的关注，该化合物用于开发列班列小种子萌发中的胚根伸长抑制剂。在这项研究中，我们使用市售的酚类、2-氯乙酰胺和N分两步合成了 PI-28 及其衍生物-芳基异硫氰酸酯。在该方法中，获得作为生物活性化合物也很有吸引力的 2-芳氧基乙酰苯胺作为副产物。根据对照实验的结果，副产物的形成是由于在反应过程中另一种芳基异硫氰酸酯的作用导致形成的芳酰氧基乙酰硫脲中异硫氰酸酯部分的损失。此外，我们还开发了一种 PI-28 衍生物的一锅法合成方法，总收率相当。
• The Preparation and Hydrolysis of Mono- and Disubstituted Benzoylthioureas¹
  作者：Irwin B. Douglass、F. B. Dains

  DOI：10.1021/ja01321a061

  日期：1934.6