N-(2-((4-isopropylbenzyl)oxy)-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide | 1021926-23-7

• 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: N-(2-((4-isopropylbenzyl)oxy)-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide
• CAS: 1021926-23-7
• 化学式: C₁₈H₂₂N₂O₇S₂
• 分子量: 442.514
• InChiKey: FIRCGUGRFOTGBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123.89
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(2-((4-isopropylbenzyl)oxy)-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide 在 sodium hydroxide 作用下， 生成 N-[2-(4'-isopropylbenzyloxy)-4-nitrophenyl]-methanesulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Selective Aromatase Expression Regulators in Breast Cancer Cells

  摘要：

  Aromatase converts androgens to estrogens and is a particularly attractive target in the treatment of estrogen receptor positive breast cancer. The enzyme is encoded by the CYP19 gene, which is expressed in a tissue-specific manner. Prostaglandin E-2 (PGE(2)), the major product of cyclooxygenase-2 (COX-2), stimulates aromatase gene expression via protein kinase A and C signaling pathways. Our previous study demonstrated that COX-2 selective inhibitor nimesulide decreased aromatase activity from the transcriptional level in breast cancer cells. In this manuscript, the synthesis and biological evaluation of a series of nimesulide analogues as potential selective aromatase expression regulators are described. Several novel sulfonanilide compounds demonstrate IC50 values from 0.33 to 2.68 mu M in suppressing aromatase enzyme activity in SK-BR-3 breast cancer cells and are 10- to 80-fold more active than nimesulide. Also, the sulfonanilide compounds selectively decrease aromatase gene expression in breast cancer cells, without exhibiting cytotoxic or apoptotic effects at low micromole concentrations.

  DOI：

  10.1021/jm061133j
• 作为产物：
  描述：

  2-氨基-5-硝基苯酚 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 N-(2-((4-isopropylbenzyl)oxy)-4-nitrophenyl)-N-(methylsulfonyl)methanesulfonamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Selective Aromatase Expression Regulators in Breast Cancer Cells

  摘要：

  Aromatase converts androgens to estrogens and is a particularly attractive target in the treatment of estrogen receptor positive breast cancer. The enzyme is encoded by the CYP19 gene, which is expressed in a tissue-specific manner. Prostaglandin E-2 (PGE(2)), the major product of cyclooxygenase-2 (COX-2), stimulates aromatase gene expression via protein kinase A and C signaling pathways. Our previous study demonstrated that COX-2 selective inhibitor nimesulide decreased aromatase activity from the transcriptional level in breast cancer cells. In this manuscript, the synthesis and biological evaluation of a series of nimesulide analogues as potential selective aromatase expression regulators are described. Several novel sulfonanilide compounds demonstrate IC50 values from 0.33 to 2.68 mu M in suppressing aromatase enzyme activity in SK-BR-3 breast cancer cells and are 10- to 80-fold more active than nimesulide. Also, the sulfonanilide compounds selectively decrease aromatase gene expression in breast cancer cells, without exhibiting cytotoxic or apoptotic effects at low micromole concentrations.

  DOI：

  10.1021/jm061133j