2-amino-4-(6,7-dimethoxy-1,3-benzodioxol-5-yl)-7-(dimethylamino)-4H-chromene-3-carbonitrile | 1119393-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-amino-4-(6,7-dimethoxy-1,3-benzodioxol-5-yl)-7-(dimethylamino)-4H-chromene-3-carbonitrile
• CAS: 1119393-84-8
• 化学式: C₂₁H₂₁N₃O₅
• 分子量: 395.415
• InChiKey: JHAPKZPCYGOREM-UHFFFAOYSA-N

物化性质

• 熔点：
  188-191 °C
• 沸点：
  571.0±50.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-dimethoxy-4,5-methylenedioxybenzaldehyde 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(6,7-dimethoxy-1,3-benzodioxol-5-yl)-7-(dimethylamino)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Polyalkoxy Substituted 4H-Chromenes: Synthesis by Domino Reaction and Anticancer Activity

  摘要：

  A series of 4H-chromenes containing various modifications in the ring B and polyalkoxy substituents in the ring E has been synthesized by Knoevenagel-Michael-hetero-Thorpe-Ziegler three-component domino reaction with the overall yield of 45-82%. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antimitotic and microtubule destabilizing activity. The most active compounds 5{1,5} and 5{5,5} featured sesamol-derived ring B and methoxyphenyl or m-methoxymethylenedioxyphenyl ring E. Compounds 5{3,1}, 5{1,2}, 5{5,4}, 5{1,5}, and 5{5,5} exhibited strong cytotoxicity in the NCI60 human tumor cell line anticancer drug screen. Surprisingly, cell growth inhibition caused by these agents was more pronounced in the multidrug resistant NCI/ADR-RES cells than the parent OVCAR-8 cell line. The results suggest that polyalkoxy substited 4H-chromenes may prove to be advantageous for further design as anticancer agents.

  DOI：

  10.1021/co300062e