4-(5-phenyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide | 325749-09-5

• 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-(5-phenyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide
• 英文别名: 4-(5-Phenyltriazol-1-yl)benzenesulfonamide
• CAS: 325749-09-5
• 化学式: C₁₄H₁₂N₄O₂S
• 分子量: 300.341
• InChiKey: ZMTRFTUXNAXKQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-azidobenzenesulfonamide 、 苯乙炔 在 Cp*RuCl 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以4%的产率得到4-(5-phenyl-1H-1,2,3-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Metallocene-Based Inhibitors of Cancer-Associated Carbonic Anhydrase Enzymes IX and XII

  摘要：

  In this study, 20 metallocene-based compounds comprising extensive structural diversity were synthesized and evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. These compounds proved moderate to good CA inhibitors in vitro, with several compounds displaying selectivity for cancer-associated isozymes CA IX and CA XII compared to off-target CA I and CA II. Compound 6 was the most potent ferrocene-based inhibitor with K(i)s of 5.9 and 6.8 nM at CA IX and XII, respectively. A selection of key drug-like parameters comprising Log P, Log D, solubility, and in vitro metabolic stability and permeability were measured for two of the ferrocene-based compounds, regioisomers 1 and S. Compounds.1 and 5 were found to have characteristics consistent with lipophilic compounds, however, our findings show that the lipophilicity of the ferrocene moiety is not well modeled by replacement with either a naphthyl or a phenyl moiety in software prediction tools.

  DOI：

  10.1021/jm300427m

文献信息

• Metallocene-Based Inhibitors of Cancer-Associated Carbonic Anhydrase Enzymes IX and XII
  作者：Adam J. Salmon、Michael L. Williams、Quoc K. Wu、Julia Morizzi、Daniel Gregg、Susan A. Charman、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm300427m

  日期：2012.6.14

  In this study, 20 metallocene-based compounds comprising extensive structural diversity were synthesized and evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. These compounds proved moderate to good CA inhibitors in vitro, with several compounds displaying selectivity for cancer-associated isozymes CA IX and CA XII compared to off-target CA I and CA II. Compound 6 was the most potent ferrocene-based inhibitor with K(i)s of 5.9 and 6.8 nM at CA IX and XII, respectively. A selection of key drug-like parameters comprising Log P, Log D, solubility, and in vitro metabolic stability and permeability were measured for two of the ferrocene-based compounds, regioisomers 1 and S. Compounds.1 and 5 were found to have characteristics consistent with lipophilic compounds, however, our findings show that the lipophilicity of the ferrocene moiety is not well modeled by replacement with either a naphthyl or a phenyl moiety in software prediction tools.