4-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamide | 1580456-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamide
• CAS: 1580456-71-8
• 化学式: C₈H₉N₅O₂S₂
• 分子量: 271.324
• InChiKey: WGSQFZIGDXTEDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  119.79
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamide 在 三氯氧磷 作用下， 生成 N-[(Z)-(dimethylamino)methylidene]-4-[6-(4-methylphenyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Benzenesulfonamide bearing 1,2,4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII

  摘要：

  Three series of novel heterocyclic compounds (3a-3g, 4a-4g and 5a-5g) containing benzenesulfonamide moiety and incorporating a 1,2,4-triazole ring, have been synthesized and investigated as inhibitors against four isomers of the alpha-class carbonic anhydrases (CAs, EC 4.2.1.1), comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (transmembrane, tumor associated isozymes). Against the human isozymes hCA I and II, compounds of two series (3a-3g and 4a-4g) showed K-i values in the range of 84-868 nM and 5.6-390 nM, respectively whereas compounds of series 5a-5g were found to be poor inhibitors (K-i values exceeding 10,000 nM in some cases). Against hCA IX and XII, all the tested compounds exhibited excellent to moderate inhibitory potential with K-i values in the range of 2.8-431 nM and 1.3-63 nM, respectively. Compounds 3d, 3f and 4f exhibited excellent inhibitory potential against all of the four isozymes hCA I, II, IX and XII, even better than the standard drug acetazolamide (AZA) whereas compound of the series 5a-5g were comparatively less potent but more selective towards hCA IX and XII. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.055
• 作为产物：
  描述：

  在 一水合肼 作用下， 以 水 为溶剂， 反应 20.0h， 生成 4-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Benzenesulfonamide bearing 1,2,4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII

  摘要：

  Three series of novel heterocyclic compounds (3a-3g, 4a-4g and 5a-5g) containing benzenesulfonamide moiety and incorporating a 1,2,4-triazole ring, have been synthesized and investigated as inhibitors against four isomers of the alpha-class carbonic anhydrases (CAs, EC 4.2.1.1), comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (transmembrane, tumor associated isozymes). Against the human isozymes hCA I and II, compounds of two series (3a-3g and 4a-4g) showed K-i values in the range of 84-868 nM and 5.6-390 nM, respectively whereas compounds of series 5a-5g were found to be poor inhibitors (K-i values exceeding 10,000 nM in some cases). Against hCA IX and XII, all the tested compounds exhibited excellent to moderate inhibitory potential with K-i values in the range of 2.8-431 nM and 1.3-63 nM, respectively. Compounds 3d, 3f and 4f exhibited excellent inhibitory potential against all of the four isozymes hCA I, II, IX and XII, even better than the standard drug acetazolamide (AZA) whereas compound of the series 5a-5g were comparatively less potent but more selective towards hCA IX and XII. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.055

文献信息

• Triazole-benzenesulfonamide hybrids: Synthesis, biological evaluation, and molecular docking study as non-toxic antimicrobial and antioxidant agents
  作者：Chander、Monika、Deepansh Sharma、Pawan K. Sharma、Sita Ram

  DOI：10.1016/j.molstruc.2024.139045

  日期：2024.12

  growth of seven bacterial and one fungal pathogens. Free radical scavenging activities were also determined for the synthesized series of compounds using DPPH method. Furthermore, cytotoxicity studies of the target compounds were performed against mouse fibroblast animal cell lines and plant seed germination cell lines. To identify the binding modes, molecular docking of the most active antibacterial

  我们合成了二十种骨架中具有苯磺酰胺和三唑部分的新型杂环化合物库。测试了合成的目标化合物对七种细菌和一种真菌病原体生长的抑制潜力。还使用DPPH方法测定了合成的系列化合物的自由基清除活性。此外，针对小鼠成纤维细胞动物细胞系和植物种子萌发细胞系进行了目标化合物的细胞毒性研究。为了确定结合模式，在目标酶的活性位点进行了最活跃的抗菌化合物和最活跃的抗真菌化合物的分子对接。所有测试的化合物均具有良好的抗菌（MIC 值 = 4.9 – 37.8 µM）和抗真菌（MIC 值 = 5.4 – 37.8 µM）剂。抗氧化剂研究结果表明，所有测试的化合物都是中等到优秀的自由基清除剂（% RSA 值 = 75.45 – 95.34）。此外，在细胞毒性研究中，所有这些都被发现对两种测试的细胞系都是安全的。