6-(2,2-dibromovinyl)-4-methoxy-2H-pyran-2-one | 1255528-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(2,2-dibromovinyl)-4-methoxy-2H-pyran-2-one
• 英文别名: 6-(2,2-Dibromoethenyl)-4-methoxypyran-2-one；6-(2,2-dibromoethenyl)-4-methoxypyran-2-one
• CAS: 1255528-78-9
• 化学式: C₈H₆Br₂O₃
• 分子量: 309.942
• InChiKey: MTQMEVJPJGUOJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2,2-dibromovinyl)-4-methoxy-2H-pyran-2-one 在 N-甲基吡咯烷酮 、 tris-(dibenzylideneacetone)dipalladium(0) 、 亚磷酸氢二甲酯 、 三苯胂 、 氢溴酸 、 溶剂黄146 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 4-hydroxy-6-((1E,3E,5E)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexa-1,3,5-trienyl)-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polyenylpyrrole Derivatives as Anticancer Agents Acting through Caspases-Dependent Apoptosis

  摘要：

  A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC50 of 0.6 and 0.01 mu M, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC50 > 80 mu M), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.

  DOI：

  10.1021/jm100619x
• 作为产物：
  描述：

  4-甲氧基-6-甲基-2H-吡喃酮 在 selenium(IV) oxide 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 6-(2,2-dibromovinyl)-4-methoxy-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Polyenylpyrrole Derivatives as Anticancer Agents Acting through Caspases-Dependent Apoptosis

  摘要：

  A class of polyenylpyrroles and their analogues were designed from a hit compound identified in a fungus. The compounds synthesized were evaluated for their cell cytotoxicity against human non-small-cell lung carcinoma cell lines A549. Two compounds were found to exhibit high cytotoxicity against A549 cells with IC50 of 0.6 and 0.01 mu M, respectively. The underlying mechanisms for the anticancer activity were demonstrated as caspases activation dependent apoptosis induction through loss of mitochondrial membrane potential, release of cytochrome c, increase in B-cell lymphoma-2-associated X protein (Bax) level, and decrease in B-cell lymphoma-2 (Bcl-2) level. The two compounds were nontoxic to normal human lung Beas-2b cells (IC50 > 80 mu M), indicating that they are highly selective in their cytotoxicity activities. Furthermore, one compound showed in vivo anticancer activity in human-lung-cancer-cell-bearing mice. These results open promising insights on how these conjugated polyenes mediate cytotoxicity and may provide a molecular rationale for future therapeutic interventions in carcinogenesis.

  DOI：

  10.1021/jm100619x