3-[N'-(4-chloro-benzoyl)-thioureido]-benzoic acid | 109569-26-8

• 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: 3-[N'-(4-chloro-benzoyl)-thioureido]-benzoic acid
• 英文别名: 3-[N'-(4-Chlor-benzoyl)-thioureido]-benzoesaeure；3-({[(4-Chlorobenzoyl)amino]carbonothioyl}amino)benzoic acid；3-[(4-chlorobenzoyl)carbamothioylamino]benzoic acid
• CAS: 109569-26-8
• 化学式: C₁₅H₁₁ClN₂O₃S
• 分子量: 334.783
• InChiKey: CZSMCBWKEOAYML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 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：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰氯 以 乙腈 为溶剂， 反应 12.0h， 生成 3-[N'-(4-chloro-benzoyl)-thioureido]-benzoic acid
  参考文献：
  名称：

  Structure–Activity Relationships and Anti-inflammatory Activities of N-Carbamothioylformamide Analogues as MIF Tautomerase Inhibitors

  摘要：

  Macrophage migration inhibitory factor (MIF), a proinflammatory cytokine, is an attractive therapeutic target for the treatment of inflammatory diseases. In our previous study, 3-[(biphenyl-4-ylcarbonyl)carbamothioyl] amino benzoic acid (compound 1) was discovered as a potent inhibitor of MIF by docking-based virtual screening and bioassays. Here, a series of analogues of compound 1 derived from similarity search and chemical synthesis were evaluated for their MIF tautomerase activities, and their structure activity relationships were then analyzed. The most potent inhibitor (compound 5) with an IC50 of 370 nM strongly suppressed lipopolysaccharide (LPS)-induced production of TNF-alpha and IL-6 in a dose-dependent manner and significantly enhanced the survival rate of mice with LPS-induced endotoxic shock from 0 to 35% at 0.5 mg/kg and to 45% at 1 mg/kg, highlighting the therapeutic potential of the MIF tautomerase inhibition in inflammatory diseases.

  DOI：

  10.1021/acs.jcim.5b00445

文献信息

• p-Chlorbenzoylisothiocyanat als Reagens zur Charakterisierung von primÄren und sekundÄren Aminen
  作者：M. Tišler

  DOI：10.1007/bf00459135

  日期：1959.7
• Structure–Activity Relationships and Anti-inflammatory Activities of <i>N</i>-Carbamothioylformamide Analogues as MIF Tautomerase Inhibitors
  作者：Yu Zhang、Lei Xu、Zhiqiang Zhang、Zhiyu Zhang、Longtai Zheng、Dan Li、Youyong Li、Feng Liu、Kunqian Yu、Tingjun Hou、Xuechu Zhen

  DOI：10.1021/acs.jcim.5b00445

  日期：2015.9.28

  Macrophage migration inhibitory factor (MIF), a proinflammatory cytokine, is an attractive therapeutic target for the treatment of inflammatory diseases. In our previous study, 3-[(biphenyl-4-ylcarbonyl)carbamothioyl] amino benzoic acid (compound 1) was discovered as a potent inhibitor of MIF by docking-based virtual screening and bioassays. Here, a series of analogues of compound 1 derived from similarity search and chemical synthesis were evaluated for their MIF tautomerase activities, and their structure activity relationships were then analyzed. The most potent inhibitor (compound 5) with an IC50 of 370 nM strongly suppressed lipopolysaccharide (LPS)-induced production of TNF-alpha and IL-6 in a dose-dependent manner and significantly enhanced the survival rate of mice with LPS-induced endotoxic shock from 0 to 35% at 0.5 mg/kg and to 45% at 1 mg/kg, highlighting the therapeutic potential of the MIF tautomerase inhibition in inflammatory diseases.