2,5-dimethoxy-N-(pyridin-3-yl)benzenesulfonamide | 693270-38-1

• 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: 2,5-dimethoxy-N-(pyridin-3-yl)benzenesulfonamide
• 英文别名: 2,5-dimethoxy-N-pyridin-3-ylbenzenesulfonamide
• CAS: 693270-38-1
• 化学式: C₁₃H₁₄N₂O₄S
• 分子量: 294.331
• InChiKey: VORBWNVMSMVSMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氨基吡啶 、 2,5-二甲氧基苯磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以72%的产率得到2,5-dimethoxy-N-(pyridin-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Discovery and Validation of a Series of Aryl Sulfonamides as Selective Inhibitors of Tissue-Nonspecific Alkaline Phosphatase (TNAP)

  摘要：

  We report the characterization and optimization of drug-like small molecule inhibitors of tissue-nonspecific alkaline phosphatase (TNAP), an enzyme critical for the regulation of extracellular matrix calcification during bone formation and growth. High-throughput screening (HTS) of a small molecule library led to the identification of arylsulfonamides as potent and selective inhibitors of TNAP. Critical structural requirements for activity were determined, and the compounds were subsequently profiled for in vitro activity and bioavailability parameters including metabolic stability and permeability. The plasma levels following subcutaneous administration of a member of the lead series in rat was determined, demonstrating the potential of these TNAP inhibitors as systemically active therapeutic agents to target various diseases involving soft tissue calcification. A representative member of the series was also characterized in mechanistic and kinetic studies.

  DOI：

  10.1021/jm900383s

文献信息

• INTESTINAL ALKALINE PHOSPHATASE MODULATORS AND USES THEREOF
  申请人：Millan Jose Luis

  公开号：US20100016313A1

  公开（公告）日：2010-01-21

  Disclosed are modulators, i.e., activators and inhibitors, of Intestinal Alkaline Phosphatase (IAP). Also disclosed are methods for treating bacterial infections of the intestinal tract and methods for maintaining the health of the intestinal tract using IAP activators. Further disclosed are methods to assist in weight gain of emaciated patients and those having reduced or negligible fat absorption using IAP inhibitors.
• Discovery and Validation of a Series of Aryl Sulfonamides as Selective Inhibitors of Tissue-Nonspecific Alkaline Phosphatase (TNAP)
  作者：Russell Dahl、Eduard A. Sergienko、Ying Su、Yalda S. Mostofi、Li Yang、Ana Maria Simao、Sonoko Narisawa、Brock Brown、Arianna Mangravita-Novo、Michael Vicchiarelli、Layton H. Smith、W. Charles O’Neill、José Luis Millán、Nicholas D. P. Cosford

  DOI：10.1021/jm900383s

  日期：2009.11.12

  We report the characterization and optimization of drug-like small molecule inhibitors of tissue-nonspecific alkaline phosphatase (TNAP), an enzyme critical for the regulation of extracellular matrix calcification during bone formation and growth. High-throughput screening (HTS) of a small molecule library led to the identification of arylsulfonamides as potent and selective inhibitors of TNAP. Critical structural requirements for activity were determined, and the compounds were subsequently profiled for in vitro activity and bioavailability parameters including metabolic stability and permeability. The plasma levels following subcutaneous administration of a member of the lead series in rat was determined, demonstrating the potential of these TNAP inhibitors as systemically active therapeutic agents to target various diseases involving soft tissue calcification. A representative member of the series was also characterized in mechanistic and kinetic studies.