(E)-5-oxo-3-(prop-1-enyl)cyclopent-3-ene-1,2-diyl dibutyrate | 1246376-99-7

• 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: (E)-5-oxo-3-(prop-1-enyl)cyclopent-3-ene-1,2-diyl dibutyrate
• CAS: 1246376-99-7
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: YWAKCUICJLTVGZ-KBKYZLAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  丁酸酐 、 土曲霉酮 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (E)-5-oxo-3-(prop-1-enyl)cyclopent-3-ene-1,2-diyl dibutyrate
  参考文献：
  名称：

  Studies on terrein as a new class of proteasome inhibitors

  摘要：

  The proteasome is an intracellular multicatalytic protease involved in the cell cycle regulation, signaling response, antigen presentation and apoptosis. Since proteasome inhibitors promote cell death by apoptosis, they have been proposed as new anti-tumoral drugs. Terrein, a secondary metabolite secreted by the fungus Aspergillus terreus, was firstly described in 1935. In the present work we report that terrein isolated through the screening for inhibitors of the 20S proteasome showed inhibitory effect upon both chymotrypsin- and trypsin-like activities of the multicatalytic core particle, the 20S proteasome. Despite of the high inhibitory concentration determined in vitro, that verified by incubating cells (fibroblasts and a pulmonary tumor cell line) in the presence of terrein was 4-fold lower indicating the proteasome as a selective intracellular target. Moreover, terrein promoted apoptotic cell death on both fibroblasts and pulmonary tumor cell line tested. Although terrein concentrations (mM range) necessary to elicit apoptosis in the cellular models herein tried were high when compared to those (mu M and nM range) of other inhibitors recently described, its chemical structure is not correlated to any other inhibitor reported thus far. Therefore, the present results point out for the possibility of exploring terrein as a new molecular fragment for the development of synthetic proteasome inhibitors.

  DOI：

  10.1590/s0103-50532010000200015