Dykellic acid | 248951-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Dykellic acid
• 英文别名: 3-(5-methylene-2-oxo-6-penta-1,3-dienyl-5,6-dihydro-2H-pyran-3-yl)propionic acid；3-[5-methylidene-2-oxo-6-[(1E,3E)-penta-1,3-dienyl]pyran-3-yl]propanoic acid
• CAS: 248951-83-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: XMBYWWHLSMXSPA-VNKDHWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dykellic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 以57%的产率得到3-(5-methylene-2-oxo-6-penta-1,3-dienyl-5,6-dihydro-2H-pyran-3-yl)propionic acid methyl ester
  参考文献：
  名称：

  Total Synthesis and Cytoprotective Properties of Dykellic Acid

  摘要：

  Small molecule inhibitors of apoptosis hold considerable promise for the treatment of a host of diseases, including neurodegeneration, myocardial infarction, and stroke. Many compounds that delay or prevent apoptotic death either reduce the amount of cellular reactive oxygen species (ROS) or are direct inhibitors of caspases. With the goal of using small molecules to identify novel antiapoptotic targets, we have investigated the cytoprotective activity of the natural product dykellic acid. Described herein is the first total synthesis of dykellic acid, the synthesis of several dykellic acid derivatives, and the evaluation of these, compounds in assays related to cell death. We have found that dykellic acid protects cells from death as induced by etoposide and rotenone. Further experiments strongly Suggest that dykellic acid does not scavenge ROS or directly inhibit caspase enzymes, and analysis of synthetic derivatives establishes key functional groups of the molecule that are essential for its cytoprotective activity.

  DOI：

  10.1021/jm801169s
• 作为产物：
  描述：

  3-(5-methylene-2-oxo-6-penta-1,3-dienyl-5,6-dihydro-2H-pyran-3-yl)propionaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以60%的产率得到Dykellic acid
  参考文献：
  名称：

  Total Synthesis and Cytoprotective Properties of Dykellic Acid

  摘要：

  Small molecule inhibitors of apoptosis hold considerable promise for the treatment of a host of diseases, including neurodegeneration, myocardial infarction, and stroke. Many compounds that delay or prevent apoptotic death either reduce the amount of cellular reactive oxygen species (ROS) or are direct inhibitors of caspases. With the goal of using small molecules to identify novel antiapoptotic targets, we have investigated the cytoprotective activity of the natural product dykellic acid. Described herein is the first total synthesis of dykellic acid, the synthesis of several dykellic acid derivatives, and the evaluation of these, compounds in assays related to cell death. We have found that dykellic acid protects cells from death as induced by etoposide and rotenone. Further experiments strongly Suggest that dykellic acid does not scavenge ROS or directly inhibit caspase enzymes, and analysis of synthetic derivatives establishes key functional groups of the molecule that are essential for its cytoprotective activity.

  DOI：

  10.1021/jm801169s