4-methoxy-6-methyl-5-(1-trimethylsiloxyvinyl)-α-pyrone | 80928-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methoxy-6-methyl-5-(1-trimethylsiloxyvinyl)-α-pyrone
• 英文别名: 4-Methoxy-6-methyl-5-(1-trimethylsilyloxyethenyl)pyran-2-one
• CAS: 80928-00-3
• 化学式: C₁₂H₁₈O₄Si
• 分子量: 254.358
• InChiKey: NIVZVJMSCFMLRV-UHFFFAOYSA-N

物化性质

• 沸点：
  324.0±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-6-methyl-5-(1-trimethylsiloxyvinyl)-α-pyrone 在 四氯化钛 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-hydroxy-4-methoxy-5,7-dimethyl-7,8-dihydro-2H,5H-pyrano[4,3-b]pyran-2-one
  参考文献：
  名称：

  Synthesis of pyrenocines A, B and pyrenochaetic acid A

  摘要：

  DOI：

  10.1016/s0040-4020(01)87700-0
• 作为产物：
  描述：

  乙酰丙酮 在 三乙烯二胺 、 三乙胺 、 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 55.33h， 生成 4-methoxy-6-methyl-5-(1-trimethylsiloxyvinyl)-α-pyrone
  参考文献：
  名称：

  Synthesis of pyrenocines A, B and pyrenochaetic acid A

  摘要：

  DOI：

  10.1016/s0040-4020(01)87700-0

文献信息

• Synthesis of pyrenocine A and B
  作者：Akitami Ichihara、Kazuo Murakami、Sadao Sakamura

  DOI：10.1016/s0040-4039(01)82049-9

  日期：1981.1
• ICHIHARA, AKITAMI;MURAKAMI, KAZUO;SAKAMURA, SADAO, TETRAHEDRON, 43,(1987) N 22, 5245-5250
  作者：ICHIHARA, AKITAMI、MURAKAMI, KAZUO、SAKAMURA, SADAO

  DOI：——

  日期：——
• Pyrenocine A induces monopolar spindle formation and suppresses proliferation of cancer cells
  作者：Yusuke Myobatake、Shinji Kamisuki、Senko Tsukuda、Tsunehito Higashi、Takumi Chinen、Kenji Takemoto、Masami Hachisuka、Yuka Suzuki、Maya Takei、Yukine Tsurukawa、Hiroaki Maekawa、Toshifumi Takeuchi、Tomoko M. Matsunaga、Hiroeki Sahara、Takeo Usui、Sachihiro Matsunaga、Fumio Sugawara

  DOI：10.1016/j.bmc.2019.115149

  日期：2019.12

  Pyrenocine A, a phytotoxin, was found to exhibit cytotoxicity against cancer cells with an IC50 value of 2.6-12.9 mu M. Live cell imaging analysis revealed that pyrenocine A arrested HeLa cells at the M phase with characteristic ring-shaped chromosomes. Furthermore, as a result of immunofluorescence staining analysis, we found that pyrenocine A resulted in the formation of monopolar spindles in HeLa cells. Monopolar spindles are known to be induced by inhibitors of the kinesin motor protein Eg5 such as monastrol and STLC. Monastrol and STLC induce monopolar spindle formation and M phase arrest via inhibition of the ATPase activity of Eg5. Interestingly, our data revealed that pyrenocine A had no effect on the ATPase activity of Eg5 in vitro, which suggested the compound induces a monopolar spindle by an unknown mechanism. Structure-activity relationship analysis indicates that the enone structure of pyrenocine A is likely to be important for its cytotoxicity. An alkyne-tagged analog of pyrenocine A was synthesized and suppressed proliferation of HeLa cells with an IC50 value of 2.3 mu M. We concluded that pyrenocine A induced monopolar spindle formation by a novel mechanism other than direct inhibition of Eg5 motor activity, and the activity of pyrenocine A may suggest a new anticancer mechanism.