4-((7-nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)benzonitrile | 1415679-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 4-((7-nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)benzonitrile
• 英文别名: 4-[(6-Nitro-2,3-dihydro-1,4-benzodioxin-3-yl)methoxy]benzonitrile；4-[(6-nitro-2,3-dihydro-1,4-benzodioxin-3-yl)methoxy]benzonitrile
• CAS: 1415679-99-0
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: UGNXTDCFOZQSHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-((7-nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)benzonitrile 在 盐酸 、 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、2.5 MPa 条件下， 反应 64.0h， 生成 ethyl 2-(benzyl(2-((4-carbamimidoylphenoxy)methyl)-2,3-dihydrobenzo[b][1,4]dioxin-7-yl)amino)-2-oxoacetate trifluoroacetate
  参考文献：
  名称：

  Novel 1,4-benzoxazine and 1,4-benzodioxine inhibitors of angiogenesis

  摘要：

  Esters of 1,4-benzoxazine and 1,4-benzodioxine compounds 1 and 10, which combine thrombin inhibitory and GPIIb/IIIa antagonistic activity in one molecule are shown to inhibit endothelial cell migration and tube formation in vitro and angiogenesis in the chicken chorioallantoic membrane (CAM) assay. The corresponding carboxylic acids 1 (R-2 = H) and 11 were devoid of anti-angiogenic activity, most probably due to their insufficient entry into the cell. Although thrombin inhibition remains the most probable explanation for their inhibition of angiogenesis, VEGFR2 kinase assay suggest that other targets such as VEGFR2 might be involved. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.001
• 作为产物：
  描述：

  4-羟基苯甲腈 、 2-羟甲基-7-硝基苯并-1,4-二氧杂环己烷 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 以43%的产率得到4-((7-nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methoxy)benzonitrile
  参考文献：
  名称：

  Novel 1,4-benzoxazine and 1,4-benzodioxine inhibitors of angiogenesis

  摘要：

  Esters of 1,4-benzoxazine and 1,4-benzodioxine compounds 1 and 10, which combine thrombin inhibitory and GPIIb/IIIa antagonistic activity in one molecule are shown to inhibit endothelial cell migration and tube formation in vitro and angiogenesis in the chicken chorioallantoic membrane (CAM) assay. The corresponding carboxylic acids 1 (R-2 = H) and 11 were devoid of anti-angiogenic activity, most probably due to their insufficient entry into the cell. Although thrombin inhibition remains the most probable explanation for their inhibition of angiogenesis, VEGFR2 kinase assay suggest that other targets such as VEGFR2 might be involved. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.001