4-(2-(2-hydroxyphenyl)-4,5-diphenyl-1H-imidazol-1-yl)benzenesulfonamide | 1172126-55-4

• 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-(2-(2-hydroxyphenyl)-4,5-diphenyl-1H-imidazol-1-yl)benzenesulfonamide
• 英文别名: 4-[2-(2-hydroxyphenyl)-4,5-diphenylimidazole-1-yl]-benzenesulfonamide；4-[2-(2-Hydroxyphenyl)-4,5-diphenylimidazol-1-yl]benzenesulfonamide
• CAS: 1172126-55-4
• 化学式: C₂₇H₂₁N₃O₃S
• 分子量: 467.548
• InChiKey: UINJLKMAJSNNQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[(2-hydroxybenzylidene)amino]benzenesulfonamide 、 联苯甲酰 在 ammonium acetate 作用下， 反应 0.28h， 以81%的产率得到4-(2-(2-hydroxyphenyl)-4,5-diphenyl-1H-imidazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  微波辅助，无溶剂的平行合成方法，阐明了一些具有生物学意义的新型四芳基咪唑的反应机理

  摘要：

  Abstract The microwave assisted, solvent free, parallel syntheses of title compounds is described in this protocol. Twelve new tetraaryl imidazoles, which are incorporated with the chemotherapeutic pharmacophores, have been synthesized by adopting one pot multicomponent reaction. Attempt has been made to investigate the mechanism behind the formation of tetraaryl imidazoles by product identification method. The synthesized compounds were analyzed by physical and analytical data. The synthesized compounds were evaluated for their antibacterial, antitubercular, and short‐term anticancer activity. Compound 13 was found to be the candidate compound to investigate further for its potential anticancer activity. J. Heterocyclic Chem., 46, 278 (2009).

  DOI：

  10.1002/jhet.68

文献信息

• Design, Synthesis, Biological Evaluation, and Computational Studies of Novel Tri-Aryl Imidazole-Benzene Sulfonamide Hybrids as Promising Selective Carbonic Anhydrase IX and XII Inhibitors
  作者：Lamya H. Al-Wahaibi、Bahaa G. M. Youssif、Ehab S. Taher、Ahmed H. Abdelazeem、Antar A. Abdelhamid、Adel A. Marzouk

  DOI：10.3390/molecules26164718

  日期：——

  designed for their selective inhibitory against hCA IX and XII activity. Six compounds were found to be potent and selective CA IX inhibitors with the order of 5g > 5b > 5d > 5e > 5g > 5n (Ki = 0.3–1.3 μM, and selectivity ratio for hCA IX over hCA XII = 5–12) relative to acetazolamide (Ki = 0.03 μM, and selectivity ratio for hCA IX over hCA XII = 0.20). The previous sixth inhibitors have been further

  设计了一系列带有苯磺酰胺部分的新型三芳基咪唑衍生物5a - n，用于选择性抑制 hCA IX和XII活性。发现六种化合物是有效的选择性 CA IX 抑制剂，顺序为5g > 5b > 5d > 5e > 5g > 5n（Ki = 0.3–1.3 μM，hCA IX 与 hCA XII 的选择性比 = 5–12）相对于乙酰唑胺（Ki = 0.03 μM，hCA IX 与 hCA XII 的选择性比 = 0.20）。已经使用 MTT 测定进一步研究了先前的第六种抑制剂对四种不同癌细胞系的抗增殖活性。与多柔比星 (GI 50 = 1.1 M)相比，化合物5g和5b显示出比其他测试化合物 (GI 50 分别为 2.3 和 2.8 M)更高的抗增殖活性。这两种化合物的对接研究采用取向和结合相互作用，具有更高的进入活性侧袋 CA-IX 的倾向，与配体9FK 的选择性相似. 分子建模模拟显示与获得的生物学评价非常吻合。