2-(4-methoxy-benzenesulfonyl)benzoic acid | 39980-79-5

• 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-(4-methoxy-benzenesulfonyl)benzoic acid
• 英文别名: o-(p-Methoxyphenylsulfonyl)benzoesaeure；2-(4-Methoxyphenyl)sulfonylbenzoic acid
• CAS: 39980-79-5
• 化学式: C₁₄H₁₂O₅S
• 分子量: 292.312
• InChiKey: HFCHHUJIRDIHFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-(叔丁基二甲基硅烷)羟胺 、 2-(4-methoxy-benzenesulfonyl)benzoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到N-((tert-butyldimethylsilyl)oxy)-2-((4-methoxyphenyl)sulfonyl)benzamide
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and NMR Studies of a New Series of Arylsulfones As Selective and Potent Matrix Metalloproteinase-12 Inhibitors

  摘要：

  Overexpression of macrophage-elastase (MMP-12), a member of the matrix metalloproteinases family, can be linked to tissue remodeling and degradation in some inflammatory processes, such as chronic obstructive pulmonary disease (COPD), emphysema, rheumatoid arthritis (RA), and atherosclerosis. On this basis, MMP-12 can be considered an attractive target for studying selective inhibitors that are useful in the development of new therapies for COPD and other inflammatory diseases. We report herein the design, synthesis, and in vitro evaluation of a new series of compounds, possessing an arylsulfonyl scaffold, for their potential as selective inhibitors of MMP-12. The best compound in the series showed an IC50 value of 0.2 nM, with good selectivity over MMP-1 and MMP-14. A docking study was carried out on this compound in order to investigate its binding interactions with MMP-12, and NMR studies on the complex with the MMP-12 catalytic domain were able to validate the proposed binding mode.

  DOI：

  10.1021/jm900335a
• 作为产物：
  描述：

  2-((4-methoxyphenyl)thio)benzoic acid 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以60%的产率得到2-(4-methoxy-benzenesulfonyl)benzoic acid
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and NMR Studies of a New Series of Arylsulfones As Selective and Potent Matrix Metalloproteinase-12 Inhibitors

  摘要：

  Overexpression of macrophage-elastase (MMP-12), a member of the matrix metalloproteinases family, can be linked to tissue remodeling and degradation in some inflammatory processes, such as chronic obstructive pulmonary disease (COPD), emphysema, rheumatoid arthritis (RA), and atherosclerosis. On this basis, MMP-12 can be considered an attractive target for studying selective inhibitors that are useful in the development of new therapies for COPD and other inflammatory diseases. We report herein the design, synthesis, and in vitro evaluation of a new series of compounds, possessing an arylsulfonyl scaffold, for their potential as selective inhibitors of MMP-12. The best compound in the series showed an IC50 value of 0.2 nM, with good selectivity over MMP-1 and MMP-14. A docking study was carried out on this compound in order to investigate its binding interactions with MMP-12, and NMR studies on the complex with the MMP-12 catalytic domain were able to validate the proposed binding mode.

  DOI：

  10.1021/jm900335a

文献信息

• Design, Synthesis, Biological Evaluation, and NMR Studies of a New Series of Arylsulfones As Selective and Potent Matrix Metalloproteinase-12 Inhibitors
  作者：Elisa Nuti、Laura Panelli、Francesca Casalini、Stanislava I. Avramova、Elisabetta Orlandini、Salvatore Santamaria、Susanna Nencetti、Tiziano Tuccinardi、Adriano Martinelli、Giovanni Cercignani、Nicola D’Amelio、Alessandro Maiocchi、Fulvio Uggeri、Armando Rossello

  DOI：10.1021/jm900335a

  日期：2009.10.22

  Overexpression of macrophage-elastase (MMP-12), a member of the matrix metalloproteinases family, can be linked to tissue remodeling and degradation in some inflammatory processes, such as chronic obstructive pulmonary disease (COPD), emphysema, rheumatoid arthritis (RA), and atherosclerosis. On this basis, MMP-12 can be considered an attractive target for studying selective inhibitors that are useful in the development of new therapies for COPD and other inflammatory diseases. We report herein the design, synthesis, and in vitro evaluation of a new series of compounds, possessing an arylsulfonyl scaffold, for their potential as selective inhibitors of MMP-12. The best compound in the series showed an IC50 value of 0.2 nM, with good selectivity over MMP-1 and MMP-14. A docking study was carried out on this compound in order to investigate its binding interactions with MMP-12, and NMR studies on the complex with the MMP-12 catalytic domain were able to validate the proposed binding mode.