N,N-(2-hydroxy-4-nitrophenyl)dimethanesulfonamide | 198626-60-7

• 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,N-(2-hydroxy-4-nitrophenyl)dimethanesulfonamide
• 英文别名: N-(2-hydroxy-4-nitrophenyl)-N-methylsulfonylmethanesulfonamide
• CAS: 198626-60-7
• 化学式: C₈H₁₀N₂O₇S₂
• 分子量: 310.309
• InChiKey: ZCGZOEAYWWBRFU-UHFFFAOYSA-N

物化性质

• 熔点：
  249-253 °C (decomp)(Solv: water (7732-18-5); chloroform (67-66-3))
• 沸点：
  528.9±60.0 °C(Predicted)
• 密度：
  1.726±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-(2-hydroxy-4-nitrophenyl)dimethanesulfonamide 在 sodium hydroxide 、 水 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[2-(2'-phenylbenzyloxy)-4-nitrophenyl]methanesulfonamide
  参考文献：
  名称：

  WO2007/120379

  摘要：

  公开号：
• 作为产物：
  描述：

  2-(苄氧基)-4-硝基苯胺 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 二甲基硫 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-(2-hydroxy-4-nitrophenyl)dimethanesulfonamide
  参考文献：
  名称：

  WO2007/120379

  摘要：

  公开号：

文献信息

• Radiosynthesis of New Carbon-11-labeled Nimesulide Analogs as Potential PET SAER Tracers for Imaging of Aromatase Expression in Breast Cancer
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、George W. Sledge、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1080/00397910903013747

  日期：2010.2.12

  Carbon-11-labeled nimesulide analogs, N-[11C]methyl-N-(2-benzyloxy-4-nitrophenyl)methanesulfonamide ([11C]4a), N-[11C]methyl-N-[2-(4'-methylbenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]4b), N-[11C]methyl-N-[2-(4'-fluorobenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]4c), N-[11C]methyl-N-[2-(4'-nitrobenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]8a), N-[11C]methyl-N-[2-(-naphthylmethoxy)-4-nitrophenyl]methanesulfonamide ([11C]8b), and N-[11C]methyl-N-[2-(2'-phenylbenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]8c), have been synthesized as new potential positron emission tomography (PET) selective aromatase expression regulator (SAER) radiotracers for imaging of aromatase expression in breast cancer. The target tracers were prepared by N-[11C]methylation of their corresponding precursors using [11C]CH3OTf under basic conditions (NaH) and isolated by reversed-phase high-pressure liquid chromatography (HPLC) method in 30-50% radiochemical yields decay corrected to end of bombardment (EOB) with 25-30min overall synthesis time and 111-148 GBq/mol specific activity at end of synthesis (EOS).
• Synthesis and Biological Evaluation of Selective Aromatase Expression Regulators in Breast Cancer Cells
  作者：Bin Su、Serena Landini、Danyetta D. Davis、Robert W. Brueggemeier

  DOI：10.1021/jm061133j

  日期：2007.4.1

  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.