2-[(4,7-Dimethoxy-1,3-benzodioxol-5-yl)methylidene]propanedinitrile | 1043380-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-[(4,7-Dimethoxy-1,3-benzodioxol-5-yl)methylidene]propanedinitrile
• CAS: 1043380-71-7
• 化学式: C₁₃H₁₀N₂O₄
• 分子量: 258.233
• InChiKey: KPDMPYZAMUIICQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(4,7-Dimethoxy-1,3-benzodioxol-5-yl)methylidene]propanedinitrile 在 硝酸 、 乙酸酐 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of new tetraalkoxyquinolines from parsley and dill secondary metabolites

  摘要：

  DOI：

  10.1016/j.mencom.2023.06.013
• 作为产物：
  描述：

  1,3-苯并二噁唑-5-甲醛,4,7-二甲氧基- 、 丙二腈 生成 2-[(4,7-Dimethoxy-1,3-benzodioxol-5-yl)methylidene]propanedinitrile
  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.
• Synthesis of new tetraalkoxyquinolines from parsley and dill secondary metabolites
  作者：Victor E. Kalugin、Olga I. Adaeva、Dmitry V. Demchuk、Victor V. Semenov

  DOI：10.1016/j.mencom.2023.06.013

  日期：2023.7