2-methyl-N-((4-sulfamoylphenyl)carbamothioyl)benzamide | 642944-37-4

• 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: 2-methyl-N-((4-sulfamoylphenyl)carbamothioyl)benzamide
• 英文别名: 2-methyl-N-(4-sulfamoylphenylcarbamothioyl)benzamide；2-methyl-N-[(4-sulfamoylphenyl)carbamothioyl]benzamide
• CAS: 642944-37-4
• 化学式: C₁₅H₁₅N₃O₃S₂
• 分子量: 349.434
• InChiKey: UAZPOOZIINZDKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-N-((4-sulfamoylphenyl)carbamothioyl)benzamide 、 3-溴丙炔 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 以75%的产率得到(Z)-N-(3-(4-aminosulfonylphenyl)-4-methylthiazol-2(3H)-ylidene)-2-methylbenzamide
  参考文献：
  名称：

  异噻唑啉-磺酰胺杂种作为杰克豆脲酶抑制剂；合成，动力学机理和计算分子模型。

  摘要：

  本工作报道了几种作为豆荚脲酶抑制剂的磺酰胺（3a-j）的2-亚氨基噻唑啉衍生物的合成。在1,8-二氮杂双环[5.4.0]十一烷基-7-烯为碱的存在下，通过在干燥的乙醇中将丙烯酰胺硫脲与炔丙基溴杂环化来合成标题化合物。所有化合物均显示出比标准硫脲更高的脲酶抑制活性。化合物（3h）和（3i）表现出优异的酶抑制活性，IC 50分别为0.064和0.058μm，而硫脲的IC 50为20.9μm。通过狄克森图分析的动力学机理表明，化合物（3h）是一种混合型抑制剂，而化合物（3i）是一种竞争性抑制剂。对接研究表明，Asp633，Ala636，His492，Ala440，Lue523，Asp494和Arg439是蛋白质结合位点的主要相互作用残基，可能在抑制酶的功能中发挥重要作用。2-iminothiazoline类似物（3a-j）表现出良好的对接分数（-10.6466至-8.7215 Kcal / mol）和结合能（伦敦dG从-14

  DOI：

  10.1111/cbdd.12675
• 作为产物：
  描述：

  邻甲基苯甲酰氯 以 丙酮 为溶剂， 生成 2-methyl-N-((4-sulfamoylphenyl)carbamothioyl)benzamide
  参考文献：
  名称：

  Synthesis, biological evaluation and docking study of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors

  摘要：

  A series of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives containing sulfonamide moiety were designed and synthesized as 15-lipoxygenase (15-LOX) inhibitors. Most synthesized compounds showed potent activity against soybean 15-LOX with IC50 values less than 25 mu M. The most potent compound 4c (3-methylbenzoyl derivative) with IC50 value of 1.8 mu M was 10-fold more potent than quercetin. Interestingly, compound 4c also showed the highest antioxidant activity, as determined by ferric reducing antioxidant power (FRAP) assay. Its capacity for reducing ferric ion was more than ascorbic acid. The viability assay of the selected compound 4c against oxidative stress-induced cell death in differentiated PC12 cells revealed that compound 4c significantly protected neurons against cell death in low concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.054

文献信息

• Synthesis, molecular docking studies, and in vitro screening of sulfanilamide-thiourea hybrids as antimicrobial and urease inhibitors
  作者：Aamer Saeed、Sumera Zaib、Arshid Pervez、Amara Mumtaz、Mohammad Shahid、Jamshed Iqbal

  DOI：10.1007/s00044-012-0376-4

  日期：2013.8

  A series of novel hybrid molecules containing sulfanilamide and thiourea templates was designed and synthesized. These compounds were screened for antimicrobial and urease inhibitory activities. Some of the compounds revealed promising antibacterial and antifungal activities. Fascinatingly, the majority of the compounds exhibited potential urease inhibitory activities with IC50 ranging from 0.20 to

  设计并合成了一系列含有磺胺和硫脲模板的新型杂化分子。筛选了这些化合物的抗微生物和脲酶抑制活性。一些化合物显示出令人鼓舞的抗菌和抗真菌活性。令人着迷的是，大多数化合物都表现出潜在的脲酶抑制活性，IC 50为0.20至7.50μM。化合物2b被确定为最有效的脲酶抑制剂（IC 50为0.20μM），且效力比标准抑制剂硫脲高100倍。化合物的分子对接研究是在Jack bean和幽门螺杆菌脲酶的3D晶体结构上进行的。
• POTENT INHIBITORS OF HUMAN CARBONIC ANHYDRASE II AND BOVINE CARBONIC ANHYDRASE II AND THEIR MECHANISM OF ACTION
  申请人：Choudhary Muhammad Iqbal

  公开号：US20170073306A1

  公开（公告）日：2017-03-16

  Inhibitors of carbonic anhydrase-II derived from sulfanilamide are reported.