4,6-dimethoxy-2-[1-[4-(4-methyl-piperazin-1-yl)-phenyl]-meth-(E)-ylidene]-7-(1-methyl-piperidin-4-yl)-benzofuran-3-one | 426842-21-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 4,6-dimethoxy-2-[1-[4-(4-methyl-piperazin-1-yl)-phenyl]-meth-(E)-ylidene]-7-(1-methyl-piperidin-4-yl)-benzofuran-3-one
• 英文别名: (2Z)-4,6-dimethoxy-2-[[4-(4-methylpiperazin-1-yl)phenyl]methylidene]-7-(1-methylpiperidin-4-yl)-1-benzofuran-3-one
• CAS: 426842-21-9
• 化学式: C₂₈H₃₅N₃O₄
• 分子量: 477.604
• InChiKey: JAIQFQSNOIVDHE-ULJHMMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-2-[1-[4-(4-methyl-piperazin-1-yl)-phenyl]-meth-(E)-ylidene]-7-(1-methyl-piperidin-4-yl)-benzofuran-3-one 在 吡啶盐酸盐 作用下， 反应 3.0h， 生成 Benzofuranone deriv. 8
  参考文献：
  名称：

  Structure-Based Design and Synthesis of 2-Benzylidene-benzofuran-3-ones as Flavopiridol Mimics

  摘要：

  Novel 2-benzylidene-benzofuran-3-ones were designed and synthesized to mimic flavopiridol, a well-established inhibitor of cyclin-dependent kinases (CDKs) which is currently undergoing clinical evaluation. The underlying design concepts as well as the synthesis and structure-activity relationships (CDKs 1, 2, and 4 enzyme assays) of these mimics are described. Inhibitors of CDKs 1 and 2 that are more potent and selective than flavopiridol were obtained.

  DOI：

  10.1021/jm0108348
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 tris(dibenzylideneacetone)dipalladium (0) 、 氢气 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 61.5h， 生成 4,6-dimethoxy-2-[1-[4-(4-methyl-piperazin-1-yl)-phenyl]-meth-(E)-ylidene]-7-(1-methyl-piperidin-4-yl)-benzofuran-3-one
  参考文献：
  名称：

  Structure-Based Design and Synthesis of 2-Benzylidene-benzofuran-3-ones as Flavopiridol Mimics

  摘要：

  Novel 2-benzylidene-benzofuran-3-ones were designed and synthesized to mimic flavopiridol, a well-established inhibitor of cyclin-dependent kinases (CDKs) which is currently undergoing clinical evaluation. The underlying design concepts as well as the synthesis and structure-activity relationships (CDKs 1, 2, and 4 enzyme assays) of these mimics are described. Inhibitors of CDKs 1 and 2 that are more potent and selective than flavopiridol were obtained.

  DOI：

  10.1021/jm0108348