2-methoxy-5-methyl-N-(pyridin-3-yl)benzenesulfonamide | 332388-80-4

• 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-methoxy-5-methyl-N-(pyridin-3-yl)benzenesulfonamide
• 英文别名: 2-Methoxy-5-methyl-N-pyridin-3-yl-benzenesulfonamide；2-methoxy-5-methyl-N-pyridin-3-ylbenzenesulfonamide
• CAS: 332388-80-4
• 化学式: C₁₃H₁₄N₂O₃S
• 分子量: 278.332
• InChiKey: OLSQAIQMPKVMBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氨基吡啶 、 2-甲氧基-5-甲基-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43%的产率得到2-methoxy-5-methyl-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

• Tissue non-specific alkaline phosphatase inhibitors and uses thereof for treating vascular calcification
  申请人：Burnham Institute for Medical Research

  公开号：EP2433496A1

  公开（公告）日：2012-03-28

  Disclosed herein are compounds that are tissue-nonspecific alkaline phosphatase inhibitors. The disclosed compounds are used to treat, prevent, or abate vascular calcification, arterial calcification and other cardiovascular diseases.

  本文公开的化合物是组织非特异性碱性磷酸酶抑制剂。所公开的化合物可用于治疗、预防或减轻血管钙化、动脉钙化和其他心血管疾病。
• TISSUE NON-SPECIFIC ALKALINE PHOSPHATASE INHIBITORS AND USES THEREOF FOR TREATING VASCULAR CALCIFICATION
  申请人：The Burnham Institute for Medical Research

  公开号：EP2164329A2

  公开（公告）日：2010-03-24
• US8119693B2
  申请人：——

  公开号：US8119693B2

  公开（公告）日：2012-02-21
• [EN] TISSUE NON-SPECIFIC ALKALINE PHOSPHATASE INHIBITORS AND USES THEREOF FOR TREATING VASCULAR CALCIFICATION<br/>[FR] INHIBITEURS DE LA PHOSPHATASE ALCALINE NON SPÉCIFIQUES À UN TISSU ET LEURS UTILISATIONS POUR TRAITER UNE CALCIFICATION VASCULAIRE
  申请人：BURNHAM INST MEDICAL RESEARCH

  公开号：WO2009017863A2

  公开（公告）日：2009-02-05

  Disclosed herein are compounds that are tissue-nonspecific alkaline phosphatase inhibitors. The disclosed compounds are used to treat, prevent, or abate vascular calcification, arterial calcification and other cardiovascular diseases.
• 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.