4-chloro-N-((4-sulfamoylphenyl)carbamothioyl)benzamide | 400872-39-1

• 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: 4-chloro-N-((4-sulfamoylphenyl)carbamothioyl)benzamide
• 英文别名: 4-chloro-N-(4-sulfamoylphenylcarbamothioyl)benzamide；4-chloro-N-[(4-sulfamoylphenyl)carbamothioyl]benzamide
• CAS: 400872-39-1
• 化学式: C₁₄H₁₂ClN₃O₃S₂
• 分子量: 369.853
• InChiKey: PGMCAQXJGRLJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰氯 以 乙腈 为溶剂， 反应 0.5h， 生成 4-chloro-N-((4-sulfamoylphenyl)carbamothioyl)benzamide
  参考文献：
  名称：

  一些新的1-芳酰基-3-(4-氨基磺酰基苯基)硫脲的合成、表征和1-(3,4,5-三甲氧基苯甲酰基)-3-(4-氨基磺酰基苯基)硫脲的晶体结构

  摘要：

  通过磺胺与取代的芳酰基异硫氰酸酯在干燥乙腈中的反应，合成了一个小型的新型 1-芳酰基-3-(4-氨基磺酰基苯基) 硫脲衍生物。反应的范围通过合成 1-undecanoyl-3-(4-aminosulfonylphenyl)thiourea，一种涉及烷酰基异硫氰酸酯的酰基衍生物来表明。所有化合物都通过分析和光谱方法进行了表征，在一种情况下，通过单晶 X 射线衍射数据进行了表征。

  DOI：

  10.1080/17415993.2010.541461

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。
• Novel benzoyl thioureido benzene sulfonamides as highly potent and selective inhibitors of carbonic anhydrase IX: optimization and bioactive studies
  作者：Li Liu、Wanqi Wang、Jin Huang、Zhenjiang Zhao、Honglin Li、Yufang Xu

  DOI：10.1039/c8md00392k

  日期：——

  development of new anticancer agents. In this study, a series of sulfonamide derivatives were designed and synthesized as potential CA IX inhibitors from a lead compound (benzoyl thioureido benzene sulfonamide) discovered by virtual screening. The bioassay demonstrated that some of the synthesized compounds exhibited potent inhibitory activity against CA IX in the subnanomolar range and high selectivity over

  CA IX 作为开发新型抗癌药物的有前景的靶点而备受关注。在本研究中，通过虚拟筛选发现的先导化合物（苯甲酰基硫脲基苯磺酰胺）设计并合成了一系列磺酰胺衍生物作为潜在的 CA IX 抑制剂。生物测定表明，一些合成的化合物对亚纳摩尔范围内的 CA IX 表现出有效的抑制活性，并且对同工酶 CA I 和 CA II 具有高选择性。其中，化合物6a对CA IX表现出抑制活性，IC 50值为0.48 nM，选择性是CA II的约1500倍。还通过分子对接分析了新磺酰胺衍生物的构效关系和CA IX选择性。
• Design and synthesis of some new benzoylthioureido phenyl derivatives targeting carbonic anhydrase enzymes
  作者：Mazin A. A. Najm、Walaa R. Mahmoud、Azza T. Taher、Safinaz E-S. Abbas、Fadi M. Awadallah、Heba Abdelrasheed Allam、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1080/14756366.2022.2126463

  日期：2022.12.31

  Abstract The present study aimed to develop potent carbonic anhydrase inhibitors (CAIs). The design of the target compounds was based on modifying the structure of the ureido-based carbonic anhydrase inhibitor SLC-0111. Six series of a substituted benzoylthioureido core were prepared featuring different zinc-binding groups; the conventional sulphamoyl group 4a–d and 12a–c, its bioisosteric carboxylic

  摘要 本研究旨在开发有效的碳酸酐酶抑制剂 (CAI)。目标化合物的设计基于对脲基碳酸酐酶抑制剂 SLC-0111 的结构的修饰。制备了六个系列的具有不同锌结合基团的取代苯甲酰硫脲基核；常规的氨基磺酸基团4a-d和12a-c，其生物等排羧酸基团5a-d和13a-c或羧酸乙酯基团6a-d和14a-c作为潜在的前药。评估了所有化合物对一组四种生理相关的人 CA 同种型 hCA I 和 hCA II、hCA IX 和 hCA XII 的碳酸酐酶 (CA) 抑制活性。化合物4a、4b、4c、4d、5d、12a和12c显示出对hCA I的显着抑制活性，这将突出这些化合物作为治疗青光眼的有希望的候选药物。
• Synthesis, biological evaluation and docking study of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors
  作者：Mohammad Mahdavi、Maryam Shahzad Shirazi、Raana Taherkhani、Mina Saeedi、Eskandar Alipour、Farshad Homayouni Moghadam、Alireza Moradi、Hamid Nadri、Saeed Emami、Loghman Firoozpour、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2014.05.054

  日期：2014.7

  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.
• 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.