4-methyl-N-((1,1,3-trioxo-2,3-dihydrobenzo[d]isothiazol-2yl)carbonyl)benzenesulfonamide | 28946-24-9

• 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-methyl-N-((1,1,3-trioxo-2,3-dihydrobenzo[d]isothiazol-2yl)carbonyl)benzenesulfonamide
• 英文别名: 1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazole-2-carboxylic acid toluene-4-sulfonylamide；N-(4-methylphenyl)sulfonyl-1,1,3-trioxo-1,2-benzothiazole-2-carboxamide
• CAS: 28946-24-9
• 化学式: C₁₅H₁₂N₂O₆S₂
• 分子量: 380.402
• InChiKey: CRPHBJOSYNZUSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲苯磺酰氨基甲酸甲酯 、 糖精 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以59%的产率得到4-methyl-N-((1,1,3-trioxo-2,3-dihydrobenzo[d]isothiazol-2yl)carbonyl)benzenesulfonamide
  参考文献：
  名称：

  EGFR tyrosine kinase targeted compounds: synthesis, docking study, and in vitro antitumor activity of some new quinazoline and benzo[d]isothiazole derivatives

  摘要：

  The preparation of new quinazoline and benzo[d]isothiazole-based antitumor agents is described. The target compounds fall into three groups including the N-substituted derivatives 2a-d, the substituted amino derivatives 4-6a-d, and the dimeric compounds 7-9a,b. Docking study of the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) tyrosine kinase was performed to compare the binding mode of these compounds to the known EGFR inhibitor, lapatinib. All compounds were tested, in vitro, for their activity against human mammary carcinoma cell line (MCF7) in which EGFR is highly expressed. All compounds showed significant growth inhibitory activity. The remarkable activity of the bis quinazoline derivative 8a (IC50 = 0.06 mu g/ml; 1.64 nmol/ml) is to be noted.

  DOI：

  10.1007/s00044-010-9437-8

文献信息

• EGFR tyrosine kinase targeted compounds: synthesis, docking study, and in vitro antitumor activity of some new quinazoline and benzo[d]isothiazole derivatives
  作者：Kamelia M. Amin、Hanan H. Georgey、Fadi M. Awadallah

  DOI：10.1007/s00044-010-9437-8

  日期：2011.9

  The preparation of new quinazoline and benzo[d]isothiazole-based antitumor agents is described. The target compounds fall into three groups including the N-substituted derivatives 2a-d, the substituted amino derivatives 4-6a-d, and the dimeric compounds 7-9a,b. Docking study of the designed compounds into the ATP binding site of epidermal growth factor receptor (EGFR) tyrosine kinase was performed to compare the binding mode of these compounds to the known EGFR inhibitor, lapatinib. All compounds were tested, in vitro, for their activity against human mammary carcinoma cell line (MCF7) in which EGFR is highly expressed. All compounds showed significant growth inhibitory activity. The remarkable activity of the bis quinazoline derivative 8a (IC50 = 0.06 mu g/ml; 1.64 nmol/ml) is to be noted.