2-Amino-7-hydroxy-4-(7-methoxy-benzo[1,3]dioxol-5-yl)-4H-chromene-3-carbonitrile

• 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-(7-methoxy-benzo[1,3]dioxol-5-yl)-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-7-hydroxy-4-(7-methoxy-1,3-benzodioxol-5-yl)-4H-chromene-3-carbonitrile
• 化学式: C₁₈H₁₄N₂O₅
• 分子量: 338.32
• InChiKey: AXQQFUIYRITDQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Amino-7-hydroxy-4-(7-methoxy-benzo[1,3]dioxol-5-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-(7-methoxy-benzo[1,3]dioxol-5-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：

  肉豆蔻醛 、 丙二腈 、 间苯二酚 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-Amino-7-hydroxy-4-(7-methoxy-benzo[1,3]dioxol-5-yl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 2. Structure–activity relationships of the 7- and 5-, 6-, 8-positions

  摘要：

  As a continuation of our efforts to discover and develop the apoptosis inducing 4-aryl-4H-chromenes as novel anticancer agents, we explored the SAR of 4-aryl-4H-chromenes with modifications at the 7- and 5-, 6-, 8-positions. It was found that a small hydrophobic group, such as NMe2, NH2, NHEt, and OMe, is preferred at the 7-position. Di-substitution at either the 5,7-positions or the 6,7-positions generally led to a large decrease in potency. Di-substitution at the 7,8-positions, in general, was found to result in potent compounds. 7-NMe2, 7-NHEt, 7-OMe, and 7,8-di-NH2 analogs were found to have similar SAR for the 4-aryl group, and several 7-substituted and 7,8-di-substituted analogs were found to have similar potencies as the lead compound MX58151 (2a) both as caspase activators and inhibitors of cell proliferation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.066