N-benzoyl-N'-(p-aminophenyl)thiourea

• 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'-(p-aminophenyl)thiourea
• 英文别名: N-{[(4-aminophenyl)amino]carbonothioyl}benzamide；N-[(4-aminophenyl)carbamothioyl]benzamide
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: ARJXDDNJBILCHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 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：
  99.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl-N'-(p-aminophenyl)thiourea 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (4-amino-phenyl)-thiourea
  参考文献：
  名称：

  基于结构的药物设计和合成新型 N-Aryl-2,4-联噻唑-2-胺 CYP1B1 选择性抑制剂克服 A549 细胞的紫杉醇耐药性

  摘要：

  作为一个有前途的癌症治疗靶点，CYP1B1 在紫杉醇耐药的 A549 细胞中过表达；然而，其在耐药性中的作用仍不清楚。生物信息学分析数据表明，CYP1B1与AKT/ERK1/2和粘着斑通路密切相关，从而在紫杉醇耐药和癌症迁移/侵袭中发挥重要作用。沿着类似的思路，AhR 激动剂 7,12-二甲基苯并[ a ]蒽 (DMBA) 增强了紫杉醇抗性并促进了可能源于 CYP1B1 上调的 A549 和 H460 细胞的迁移/侵袭。此外，还设计合成了 83 种新型N -芳基-2,4-联噻唑-2-胺 CYP1B1 选择性抑制剂，以验证 CYP1B1 在紫杉醇抗性 A549 细胞中的作用。令人印象深刻的是，最有效和最具选择性的一个，即77显着抑制 AKT/ERK1/2 和 FAK/SRC 通路，从而逆转紫杉醇抗性并抑制 A549/紫杉醇细胞的迁移和侵袭。总的来说，这项研究不仅展示了 CYP1B1 在紫杉醇

  DOI：

  10.1021/acs.jmedchem.2c01306
• 作为产物：
  描述：

  benzoyl isothiocyanate 、 对苯二胺 以 乙腈 为溶剂， 反应 4.0h， 以78%的产率得到N-benzoyl-N'-(p-aminophenyl)thiourea
  参考文献：
  名称：

  Metal complexes of the nanosized ligand N-benzoyl-N′-(p-amino phenyl) thiourea: Synthesis, characterization, antimicrobial activity and the metal uptake capacity of its ligating resin

  摘要：

  The new nanosized N-benzoyl-N'-(p-amino phenyl) thiourea ligand H2L was synthesized by nano-precipitation method. The [Cu (H2L)(2) Cl]center dot 2H(2)O, [Zn (H2L)(2)(OAc)(2)], [Cd (H2L)(2)Cl-2] and [Hg (H2L)2Cl(2)] complexes were synthesized and characterized by various physicochemical methods. Results revealed that the ligand act as hypodentate and bonded to the metal ion via the sulfur atom forming mononuclear non-electrolyte diamagnetic complex. Magnetic moment results indicated a reduction of Cu (II) to Cu (I) during the coordination process. Thermal studies demonstrated variable stabilities of the complexes and [Zn (H2L)(2)(OAc)(2)] exhibited the highest thermal stability while [Hg (H2L)(2)Cl-2] was volatile. The prepared compounds were screened against different pathogenic microorganisms. The ligand performed high antibacterial activity against certain bacterial strain compared to its complexes, and the standard bacteriocide in use. The ligand was successfully immobilized on modified Amberlite XAD-16 forming the hypodentate ligating resin PS-SO2-H2L. The new resin was characterized and the extent of metal adsorption reached maximum at pH 6.0 for Cu (II), Cd (II) and Ag (I), with an adsorption amount of 43, 4.0 and 3.7 mmol g(-1) respectively. The nanosized H2L represents a new category of promising adsorbent that would have a practical impact on biological and water treatment applications. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.07.049

文献信息

• SARKIS, G. Y.;FAISAL, E. D., J. HETEROCYCL. CHEM., 1985, 22, N 1, 137-140
  作者：SARKIS, G. Y.、FAISAL, E. D.

  DOI：——

  日期：——
• ADHESIVE COMPOSITIONS
  申请人：Henkel AG & Co. KGaA

  公开号：EP3612609B1

  公开（公告）日：2022-12-28
• Metal complexes of the nanosized ligand N-benzoyl-N′-(p-amino phenyl) thiourea: Synthesis, characterization, antimicrobial activity and the metal uptake capacity of its ligating resin
  作者：Amel F. Elhusseiny、Ali Eldissouky、Ahmed M. Al-Hamza、Hammed H.A.M. Hassan

  DOI：10.1016/j.molstruc.2015.07.049

  日期：2015.11

  The new nanosized N-benzoyl-N'-(p-amino phenyl) thiourea ligand H2L was synthesized by nano-precipitation method. The [Cu (H2L)(2) Cl]center dot 2H(2)O, [Zn (H2L)(2)(OAc)(2)], [Cd (H2L)(2)Cl-2] and [Hg (H2L)2Cl(2)] complexes were synthesized and characterized by various physicochemical methods. Results revealed that the ligand act as hypodentate and bonded to the metal ion via the sulfur atom forming mononuclear non-electrolyte diamagnetic complex. Magnetic moment results indicated a reduction of Cu (II) to Cu (I) during the coordination process. Thermal studies demonstrated variable stabilities of the complexes and [Zn (H2L)(2)(OAc)(2)] exhibited the highest thermal stability while [Hg (H2L)(2)Cl-2] was volatile. The prepared compounds were screened against different pathogenic microorganisms. The ligand performed high antibacterial activity against certain bacterial strain compared to its complexes, and the standard bacteriocide in use. The ligand was successfully immobilized on modified Amberlite XAD-16 forming the hypodentate ligating resin PS-SO2-H2L. The new resin was characterized and the extent of metal adsorption reached maximum at pH 6.0 for Cu (II), Cd (II) and Ag (I), with an adsorption amount of 43, 4.0 and 3.7 mmol g(-1) respectively. The nanosized H2L represents a new category of promising adsorbent that would have a practical impact on biological and water treatment applications. (C) 2015 Elsevier B.V. All rights reserved.
• Structure-Based Drug Design and Synthesis of Novel <i>N</i>-Aryl-2,4-bithiazole-2-amine CYP1B1-Selective Inhibitors in Overcoming Taxol Resistance in A549 Cells
  作者：Jianping Mao、Dong Wang、Ping Xu、Ying Wang、Haoyu Zhang、Shiyu Wang、Feng Xu、Jian Wang、Fengjiao Zhang

  DOI：10.1021/acs.jmedchem.2c01306

  日期：2022.12.22

  12-dimethylbenz[a]anthracene (DMBA) enhanced Taxol resistance and promoted migration/invasion of A549 and H460 cells likely stemming from CYP1B1 upregulation. Moreover, 83 novel N-aryl-2,4-bithiazole-2-amine CYP1B1-selective inhibitors were designed and synthesized to verify the role of CYP1B1 in Taxol-resistant A549 cells. Impressively, the most potent and selective one, namely, 77, remarkably inhibited AKT/ERK1/2

  作为一个有前途的癌症治疗靶点，CYP1B1 在紫杉醇耐药的 A549 细胞中过表达；然而，其在耐药性中的作用仍不清楚。生物信息学分析数据表明，CYP1B1与AKT/ERK1/2和粘着斑通路密切相关，从而在紫杉醇耐药和癌症迁移/侵袭中发挥重要作用。沿着类似的思路，AhR 激动剂 7,12-二甲基苯并[ a ]蒽 (DMBA) 增强了紫杉醇抗性并促进了可能源于 CYP1B1 上调的 A549 和 H460 细胞的迁移/侵袭。此外，还设计合成了 83 种新型N -芳基-2,4-联噻唑-2-胺 CYP1B1 选择性抑制剂，以验证 CYP1B1 在紫杉醇抗性 A549 细胞中的作用。令人印象深刻的是，最有效和最具选择性的一个，即77显着抑制 AKT/ERK1/2 和 FAK/SRC 通路，从而逆转紫杉醇抗性并抑制 A549/紫杉醇细胞的迁移和侵袭。总的来说，这项研究不仅展示了 CYP1B1 在紫杉醇