2-amino-7-hydroxy-4-(8-nitro-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-chromene-3-carbonitrile | 1427069-90-6

• 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-7-hydroxy-4-(8-nitro-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-7-hydroxy-4-(5-nitro-2,3-dihydro-1,4-benzodioxin-7-yl)-4H-chromene-3-carbonitrile
• CAS: 1427069-90-6
• 化学式: C₁₈H₁₃N₃O₆
• 分子量: 367.318
• InChiKey: GHLMFHBVNZKXNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-amino-7-hydroxy-4-(8-nitro-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-chromene-3-carbonitrile 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 2-amino-7-methoxy-4-(8-nitro-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Comparative in vivo evaluation of polyalkoxy substituted 4H-chromenes and oxa-podophyllotoxins as microtubule destabilizing agents in the phenotypic sea urchin embryo assay

  摘要：

  A series of polyalkoxy substituted 7-hydroxy- and 7-methoxy-4-aryl-4H-chromenes were evaluated using the sea urchin embryo model to yield several compounds exhibiting potent antimitotic microtubule destabilizing activity. Data obtained by the assay were further confirmed in the NCI60 human cancer cell screen. The replacement of methylenedioxy ring A and lactone ring D in podophyllotoxin analogues by 7-methoxy, 2-NH2, and 3-CN groups in 4-aryl-4H-chromenes resulted in potent antimitotic microtubule destabilizing agents. Feasible synthesis and high yields render 7-methoxy-4H-chromenes to be a promising series for further anticancer drug development.

  DOI：

  10.1016/j.bmcl.2014.06.043
• 作为产物：
  描述：

  8-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde 、 丙二腈 、 间苯二酚 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 生成 2-amino-7-hydroxy-4-(8-nitro-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Comparative in vivo evaluation of polyalkoxy substituted 4H-chromenes and oxa-podophyllotoxins as microtubule destabilizing agents in the phenotypic sea urchin embryo assay

  摘要：

  A series of polyalkoxy substituted 7-hydroxy- and 7-methoxy-4-aryl-4H-chromenes were evaluated using the sea urchin embryo model to yield several compounds exhibiting potent antimitotic microtubule destabilizing activity. Data obtained by the assay were further confirmed in the NCI60 human cancer cell screen. The replacement of methylenedioxy ring A and lactone ring D in podophyllotoxin analogues by 7-methoxy, 2-NH2, and 3-CN groups in 4-aryl-4H-chromenes resulted in potent antimitotic microtubule destabilizing agents. Feasible synthesis and high yields render 7-methoxy-4H-chromenes to be a promising series for further anticancer drug development.

  DOI：

  10.1016/j.bmcl.2014.06.043

文献信息

• Comparative in vivo evaluation of polyalkoxy substituted 4H-chromenes and oxa-podophyllotoxins as microtubule destabilizing agents in the phenotypic sea urchin embryo assay
  作者：Marina N. Semenova、Dmitry V. Tsyganov、Oleg R. Malyshev、Oleg V. Ershov、Ivan N. Bardasov、Roman V. Semenov、Alex S. Kiselyov、Victor V. Semenov

  DOI：10.1016/j.bmcl.2014.06.043

  日期：2014.8

  A series of polyalkoxy substituted 7-hydroxy- and 7-methoxy-4-aryl-4H-chromenes were evaluated using the sea urchin embryo model to yield several compounds exhibiting potent antimitotic microtubule destabilizing activity. Data obtained by the assay were further confirmed in the NCI60 human cancer cell screen. The replacement of methylenedioxy ring A and lactone ring D in podophyllotoxin analogues by 7-methoxy, 2-NH2, and 3-CN groups in 4-aryl-4H-chromenes resulted in potent antimitotic microtubule destabilizing agents. Feasible synthesis and high yields render 7-methoxy-4H-chromenes to be a promising series for further anticancer drug development.