N-benzoyl-N′-(2,4,6-trichlorophenyl)-thiourea | 96938-54-4

• 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′-(2,4,6-trichlorophenyl)-thiourea
• 英文别名: N-(2,4,6-trichlorophenyl)-N'-benzoylthiourea；1-benzoyl-3-(2,4,6-trichlorophenyl)thiourea；N-benzoyl-N'-(2,4,6-trichlorophenyl)thiourea；N-[(2,4,6-trichlorophenyl)carbamothioyl]benzamide
• CAS: 96938-54-4
• 化学式: C₁₄H₉Cl₃N₂OS
• 分子量: 359.663
• InChiKey: HFEXTAKSAJFCKR-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C(Solv: benzene (71-43-2))
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 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′-(2,4,6-trichlorophenyl)-thiourea 在 N,N-二甲基甲酰胺 作用下， 反应 180.0h， 以46%的产率得到2-benzoylamino-4,6-dichloro-benzothiazole
  参考文献：
  名称：

  Dual Roles of N,N-Dimethylformamide in Benzothiazoles Synthesis from N-Benzoyl-N′-(2,4,6-trichlorophenyl)thiourea

  摘要：

  N,N-二甲基甲酰胺（DMF）不仅是化学中常用的极性溶剂，还是反应试剂、催化剂和稳定剂。本文意外发现了一种新的反应，其中 DMF 既作为溶剂又作为催化剂。通过将 N-苯甲酰基-N′-(2,4,6-三氯苯基)-硫脲（BAD）溶解在 DMF 中并缓慢蒸发溶剂，获得了单晶，但其组成被确定为 2-苯甲酰胺基-4,6-二氯苯并噻唑（BTT）与 DMF 分子（BTT–DMF），而非 BAD。BAD 的单晶可以通过从乙腈或乙醇等溶剂中结晶获得。测定了 BAD 和 BTT–DMF 的晶体结构并进行了分析。基于它们晶体结构中的氢键相互作用，提出了一种可能的反应机理。总之，DMF 是一种真正的多功能化学品，它可能还具有其他有趣的潜在功能，值得开发。通过将 N-苯甲酰基-N′-(2,4,6-三氯苯基)-硫脲（BAD）溶解在 DMF 中并缓慢蒸发溶剂以生长单晶，发现了一种新的反应。

  DOI：

  10.1007/s10870-019-00796-3
• 作为产物：
  描述：

  苯甲酸 在 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 N-benzoyl-N′-(2,4,6-trichlorophenyl)-thiourea
  参考文献：
  名称：

  Dual Roles of N,N-Dimethylformamide in Benzothiazoles Synthesis from N-Benzoyl-N′-(2,4,6-trichlorophenyl)thiourea

  摘要：

  N,N-二甲基甲酰胺（DMF）不仅是化学中常用的极性溶剂，还是反应试剂、催化剂和稳定剂。本文意外发现了一种新的反应，其中 DMF 既作为溶剂又作为催化剂。通过将 N-苯甲酰基-N′-(2,4,6-三氯苯基)-硫脲（BAD）溶解在 DMF 中并缓慢蒸发溶剂，获得了单晶，但其组成被确定为 2-苯甲酰胺基-4,6-二氯苯并噻唑（BTT）与 DMF 分子（BTT–DMF），而非 BAD。BAD 的单晶可以通过从乙腈或乙醇等溶剂中结晶获得。测定了 BAD 和 BTT–DMF 的晶体结构并进行了分析。基于它们晶体结构中的氢键相互作用，提出了一种可能的反应机理。总之，DMF 是一种真正的多功能化学品，它可能还具有其他有趣的潜在功能，值得开发。通过将 N-苯甲酰基-N′-(2,4,6-三氯苯基)-硫脲（BAD）溶解在 DMF 中并缓慢蒸发溶剂以生长单晶，发现了一种新的反应。

  DOI：

  10.1007/s10870-019-00796-3

文献信息

• Synthesis and spectroscopic properties of some new<i>N,N'</i>-disubstituted thiorueas of potential biological interest
  作者：George Y. Sarkis、Essam D. Faisal

  DOI：10.1002/jhet.5570220134

  日期：1985.1

  Thirty-six new N,N'-disubstituted thioureas have been synthesized by the reaction of phenyl-, p-fluorophenyl- and benzoylisothiocyanates with various substituted anilines, aminopyridines and 4-aminoquinolines. The uv, ir and nmr spectral data are presented and discussed.

  通过使苯基，对氟苯基和苯甲酰基异硫氰酸酯与各种取代的苯胺，氨基吡啶和4-氨基喹啉反应，已经合成了三十六种新的N，N′-二取代的硫脲。介绍并讨论了uv，ir和nmr光谱数据。
• Mononuclear copper(I) complexes with triphenylphosphine and <i>N,N′-</i>disubstituted thioureas: synthesis, characterization, and biological evaluation
  作者：Syed Ishtiaq Khan、Inayat Ali Khan、Amin Badshah、Fouzia Perveen Malik、Saira Tabassum、Ikram Ullah、Davit Zargarian、Muhammad Khawar Rauf

  DOI：10.1080/00958972.2018.1538504

  日期：2018.12.17

  Abstract Twelve new complexes, of the general formula CuCl(TPP)2Tu1–12 (Tu = thiourea), were synthesized by the reaction of CuCl(TPP)3 (TPP = triphenylphosphine) and various N,N′-disubstituted thioureas. The structures of the synthesized complexes were characterized by different techniques such as Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy (1H, 13C

  摘要 通过 CuCl(TPP)3 (TPP = 三苯基膦) 和各种 N,N'-二取代硫脲反应合成了 12 种新的配合物，通式为 CuCl(TPP)2Tu1-12 (Tu = 硫脲)。合成配合物的结构通过傅里叶变换红外 (FTIR) 光谱、核磁共振 (NMR) 光谱 (1H、13C、31P 和 19F) 和代表性配合物 (1、2 和 12) 等不同技术进行表征通过单晶 X 射线衍射分析。单晶 X 射线分析表明，铜 (I) 与氯、两个 TPP 和硫脲配体以单核扭曲四面体模式通过硫原子配位。测试了这些化合物的抗菌、抗真菌、细胞毒性、抗利什曼原虫和抗氧化活性。结果表明，合成的配合物比游离配体和商业参考化合物的活性明显更高。配合物相对于游离配体的高生物活性可归因于氯化铜 (I) 与硫脲配体的络合。合成的复合物也进行了实验和理论评估，用于 DNA 结合研究。紫外-可见光谱和分子对接研究表明，复合物通过凹槽结合模式与
• A Study on the Stability of 5,5-Diamino-substituted-1,4,2-oxathiazoline Derivatives
  作者：Keum Shin Jung、Hong Jung Lee、Hyun Nam Song、Jae Nyoung Kim

  DOI：10.1080/00397919808007019

  日期：1998.5

  5,5-Diamino-substituted-1,4,2-oxathiazoline derivatives 3 as potential prodrugs, which were easily prepared from hydroximoyl chlorides 1 and the appropriate thiourea derivatives 2, were decomposed instantaneously into isothiocyanates 4 and the corresponding urea derivatives 5 irrespective of the substituents.
• Solution-phase microwave assisted parallel synthesis of N,N′-disubstituted thioureas derived from benzoic acid: Biological evaluation and molecular docking studies
  作者：Muhammad Khawar Rauf、Ammara Talib、Amin Badshah、Sumera Zaib、Khurram Shoaib、Mohammad Shahid、Ulrich Flörke、Imtiaz-ud-Din、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2013.10.012

  日期：2013.12

  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.
• New ferrocenyl guanidines as potent antioxidants, protein kinase inhibitors and cytotoxic agents against human leukemia THP-1 cell line
  作者：R. Gul、A. Badshah、A. Ali Altaf、S. Tabassum、M. Zia

  DOI：10.1134/s1070363217110251

  日期：2017.11

  Six new ferrocenyl guanidines were synthesized and characterized by elemental analysis, FT-IR and H-1 and C-13 NMR. Compounds 1-6 were screened for antioxidant, protein kinase inhibition, lethality of brine shrimp, and cytotoxicity against the human leukemia THP-1 cell line. The compounds demonstrated moderate to significant activities. Antioxidant activity of the synthesized compounds was evaluated by DPPH % inhibition with IC50 values. All compounds 1-6 showed notable antioxidant activity with DPPH having IC50 values between 23.2-15.1 and noteworthy brine shrimp lethality. Compound 6 demonstrated the highest cytotoxicity against brine shrimps with LC50 of 9.09 mu g/mL. Protein kinase inhibition activity showed significant hyphea formation inhibition at 100 mu g/disc with 10 to 13 mm clear zone of inhibition for the compounds 2-6. The compounds were screened for in vitro cytotoxicity using human leukemia cell line (THP-1 ATCC#TIB-202). Among all compounds, the most significant activity was demonstrated by compounds 6 and 5 with IC50 of 3.88 and 5.59 mu g/mL which was comparable with the standard 5-flourouracil and vincristine drugs.