2-methylene-3-(triethylsilanyloxy)-trans,trans-4,6-octadienoic acid methyl ester | 1097679-68-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methylene-3-(triethylsilanyloxy)-trans,trans-4,6-octadienoic acid methyl ester
• 英文别名: methyl (4E,6E)-2-methylidene-3-triethylsilyloxyocta-4,6-dienoate
• CAS: 1097679-68-9
• 化学式: C₁₆H₂₈O₃Si
• 分子量: 296.482
• InChiKey: YRDWAYWLETVUOI-FREZGGHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-methylene-octa-4,6-dienoic acid methyl ester 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-methylene-3-(triethylsilanyloxy)-trans,cis-4,6-octadienoic acid methyl ester 、 2-methylene-3-(triethylsilanyloxy)-trans,trans-4,6-octadienoic 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