3-((4-(4-chlorophenyl)phthalazin-1-yl)amino)benzenesulfonamide | 1402423-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-((4-(4-chlorophenyl)phthalazin-1-yl)amino)benzenesulfonamide
• 英文别名: 3-[[4-(4-Chlorophenyl)phthalazin-1-yl]amino]benzenesulfonamide；3-[[4-(4-chlorophenyl)phthalazin-1-yl]amino]benzenesulfonamide
• CAS: 1402423-49-7
• 化学式: C₂₀H₁₅ClN₄O₂S
• 分子量: 410.884
• InChiKey: IEJQTMUBLSCUGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻苯二甲酰肼 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 、 三溴氧磷 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.0h， 生成 3-((4-(4-chlorophenyl)phthalazin-1-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  Optimization of heterocyclic substituted benzenesulfonamides as novel carbonic anhydrase IX inhibitors and their structure activity relationship

  摘要：

  In this study, starting from a lead compound discovered by virtual screening, a series of novel hetero-cyclic substituted benzenesulfonamides were designed and synthesized as new carbonic anhydrase IX (CA IX) inhibitors. Some compounds exhibited potent inhibitory effects against CA IX (in the low nanomolar range) as well as high selectivity against other carbonic anhydrase isozymes (CA I and CA II). The most potent and selective compound 27 could inhibit CA IX in the subnanomolar level with IC50 of 0.48 nM, which increased the potency by about 40-fold against CA IX compared with the lead compound 26, and presented more than 10(3) fold selectivity over CA I and CA II. The structure activity relationship (SAR) based on the docking experiments further elucidated the effects of the compounds on the bioactivity and selectivity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.030

文献信息

• Optimization of heterocyclic substituted benzenesulfonamides as novel carbonic anhydrase IX inhibitors and their structure activity relationship
  作者：Rui Gao、Sha Liao、Chen Zhang、Weilong Zhu、Liyan Wang、Jin Huang、Zhenjiang Zhao、Honglin Li、Xuhong Qian、Yufang Xu

  DOI：10.1016/j.ejmech.2013.01.030

  日期：2013.4

  In this study, starting from a lead compound discovered by virtual screening, a series of novel hetero-cyclic substituted benzenesulfonamides were designed and synthesized as new carbonic anhydrase IX (CA IX) inhibitors. Some compounds exhibited potent inhibitory effects against CA IX (in the low nanomolar range) as well as high selectivity against other carbonic anhydrase isozymes (CA I and CA II). The most potent and selective compound 27 could inhibit CA IX in the subnanomolar level with IC50 of 0.48 nM, which increased the potency by about 40-fold against CA IX compared with the lead compound 26, and presented more than 10(3) fold selectivity over CA I and CA II. The structure activity relationship (SAR) based on the docking experiments further elucidated the effects of the compounds on the bioactivity and selectivity. (C) 2013 Elsevier Masson SAS. All rights reserved.