5-benzyloxy-6-methanesulfonyloxymethyl-2-methyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester | 1151788-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-benzyloxy-6-methanesulfonyloxymethyl-2-methyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester
• CAS: 1151788-53-2
• 化学式: C₁₈H₂₀O₈S
• 分子量: 396.418
• InChiKey: RVCRIBHWCRJSNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  109.11
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-6-methanesulfonyloxymethyl-2-methyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester 、 4-氨基乙基联苯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以73%的产率得到5-benzyloxy-6-{[(biphenyl-4-ylmethyl)-amino]-methyl}-2-methyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of hydroxypyrone- and hydroxythiopyrone-based matrix metalloproteinase inhibitors: Developing a structure–activity relationship

  摘要：

  The zinc(II)-dependent matrix metalloproteinases (MMPs) are associated with a variety of diseases. Development of inhibitors to modulate MMP activity has been an active area of investigation for therapeutic development. Hydroxypyrones and hydroxythiopyrones are alternative zinc-binding groups (ZBGs) that, when combined with peptidomimetic backbones, comprise a novel class of MMP inhibitors (MMPi). In this report, a series of hydroxypyrone- and hydroxythiopyrone-based MMPi with aryl backbones at the 2-, 5-, and 6- positions of the hydroxypyrone ring have been synthesized. Synthetic routes for developing inhibitors with substituents at two of these positions (so-called double-handed inhibitors) are also explored. The MMP inhibition profiles and structure-activity relationship of synthesized hydroxypyrones and hydroxythiopyrones have been analyzed. The results here show that the ZBG, the position of the backbone on the ZBG, and the nature of the linker between the ZBG and backbone are critical for MMPi activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.044
• 作为产物：
  描述：

  5-benzyloxy-6-hydroxymethyl-2-methyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到5-benzyloxy-6-methanesulfonyloxymethyl-2-methyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of hydroxypyrone- and hydroxythiopyrone-based matrix metalloproteinase inhibitors: Developing a structure–activity relationship

  摘要：

  The zinc(II)-dependent matrix metalloproteinases (MMPs) are associated with a variety of diseases. Development of inhibitors to modulate MMP activity has been an active area of investigation for therapeutic development. Hydroxypyrones and hydroxythiopyrones are alternative zinc-binding groups (ZBGs) that, when combined with peptidomimetic backbones, comprise a novel class of MMP inhibitors (MMPi). In this report, a series of hydroxypyrone- and hydroxythiopyrone-based MMPi with aryl backbones at the 2-, 5-, and 6- positions of the hydroxypyrone ring have been synthesized. Synthetic routes for developing inhibitors with substituents at two of these positions (so-called double-handed inhibitors) are also explored. The MMP inhibition profiles and structure-activity relationship of synthesized hydroxypyrones and hydroxythiopyrones have been analyzed. The results here show that the ZBG, the position of the backbone on the ZBG, and the nature of the linker between the ZBG and backbone are critical for MMPi activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.044