benzyl 2-(2-(4-methoxyphenylthio)phenyl)acetate | 1191112-15-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: benzyl 2-(2-(4-methoxyphenylthio)phenyl)acetate
• 英文别名: Benzyl 2-[2-(4-methoxyphenyl)sulfanylphenyl]acetate
• CAS: 1191112-15-8
• 化学式: C₂₂H₂₀O₃S
• 分子量: 364.465
• InChiKey: KSGZEBCBAONVIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2-(2-(4-methoxyphenylthio)phenyl)acetate 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以682 mg的产率得到benzyl 2-(2-(4-methoxyphenylsulfonyl)phenyl)acetate
  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-methoxy-phenylsulfanyl)-phenyl acetic acid 、 溴甲苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 benzyl 2-(2-(4-methoxyphenylthio)phenyl)acetate
  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

• THIOARYL SUBSTITUTED INHIBITORS OF ZINC PROTEASES AND THEIR USE
  申请人：Rossello Armando

  公开号：US20090239829A1

  公开（公告）日：2009-09-24

  There are described compounds having the general formula (I) below and their pharmaceutically acceptable salts thereof, wherein E, X, m, q, R 1 , R 2 , n and ZBG have the meanings reported in the description useful, in therapy, as inhibitors of zinc metalloproteinases.

  描述了具有下面一般式（I）的化合物及其药学上可接受的盐，其中E、X、m、q、R1、R2、n和ZBG的含义如描述中所述，在治疗中作为锌金属蛋白酶的抑制剂。
• US8093386B2
  申请人：——

  公开号：US8093386B2

  公开（公告）日：2012-01-10
• 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.