(Z)-ethyl-2-azido-3-(3-(benzyloxy)-4-methoxyphenyl)acrylate | 1333109-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl-2-azido-3-(3-(benzyloxy)-4-methoxyphenyl)acrylate
• CAS: 1333109-68-4
• 化学式: C₁₉H₁₉N₃O₄
• 分子量: 353.378
• InChiKey: IUWUPCAFHXMMGT-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl-2-azido-3-(3-(benzyloxy)-4-methoxyphenyl)acrylate 以 xylenes 为溶剂， 反应 12.0h， 以76%的产率得到ethyl 5-(benzyloxy)-6-methoxy-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D

  摘要：

  A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a beta-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.056
• 作为产物：
  描述：

  叠氮乙酸乙酯 、 3-苄氧基-4-甲氧基苯甲醛 在 乙醇 、 sodium 作用下， 反应 3.0h， 以88%的产率得到(Z)-ethyl-2-azido-3-(3-(benzyloxy)-4-methoxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D

  摘要：

  A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a beta-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.056