2-amino-4-(4,7-dimethoxy-1,3-benzodioxol-5-yl)-7-(dimethylamino)-4H-chromene-3-carbonitrile | 1192655-34-7

• 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-(4,7-dimethoxy-1,3-benzodioxol-5-yl)-7-(dimethylamino)-4H-chromene-3-carbonitrile
• CAS: 1192655-34-7
• 化学式: C₂₁H₂₁N₃O₅
• 分子量: 395.415
• InChiKey: PCKCXOUJKPGAJK-UHFFFAOYSA-N

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：

  1,3-苯并二噁唑-5-甲醛,4,7-二甲氧基- 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(4,7-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

文献信息

• Polyalkoxy Substituted 4<i>H</i>-Chromenes: Synthesis by Domino Reaction and Anticancer Activity
  作者：Anatoliy M. Shestopalov、Yuri M. Litvinov、Lyudmila A. Rodinovskaya、Oleg R. Malyshev、Marina N. Semenova、Victor V. Semenov

  DOI：10.1021/co300062e

  日期：2012.8.13

  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 51,5} and 55,5} featured sesamol-derived ring B and methoxyphenyl or m-methoxymethylenedioxyphenyl ring E. Compounds 53,1}, 51,2}, 55,4}, 51,5}, and 55,5} 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.