N-(2-hydroxyethyl)-3-(1,2,3-triazol-1-yl)-1,8-naphthalimide | 1073775-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(2-hydroxyethyl)-3-(1,2,3-triazol-1-yl)-1,8-naphthalimide
• 英文别名: 2-(2-Hydroxyethyl)-5-(triazol-1-yl)benzo[de]isoquinoline-1,3-dione
• CAS: 1073775-70-8
• 化学式: C₁₆H₁₂N₄O₃
• 分子量: 308.296
• InChiKey: VWOPISMYSMKQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-azido-1,8-naphthalic anhydride 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 生成 N-(2-hydroxyethyl)-3-(1,2,3-triazol-1-yl)-1,8-naphthalimide
  参考文献：
  名称：

  Novel efficient anticancer agents and DNA-intercalators of 1,2,3-triazol-1,8-naphthalimides: design, synthesis, and biological activity

  摘要：

  Two novel series of 3-1,2,3-triazol-1,8-naphthalimides 5a-e, 7a-e were synthesized easily by employing 'click reaction'. Their bioactivities were evaluated. Compounds 5a-e were found to be more toxic against MCF-7 cells while 7a-e were more potent against 7721 cells, in particular 7a, the IC50 value of which against cell lines of MCF-7 and 7721 was 0.348 mu M and 0.258 mu M, respectively. Due to the phenyl group linked to 1,2,3-triazole, compound 5a not only showed higher DNA affinity but also more efficient DNA damaging ability than compound 7a. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.063

文献信息

• Novel efficient anticancer agents and DNA-intercalators of 1,2,3-triazol-1,8-naphthalimides: design, synthesis, and biological activity
  作者：Xiaolian Li、Yanjie Lin、Yukun Yuan、Kai Liu、Xuhong Qian

  DOI：10.1016/j.tet.2011.01.063

  日期：2011.3

  Two novel series of 3-1,2,3-triazol-1,8-naphthalimides 5a-e, 7a-e were synthesized easily by employing 'click reaction'. Their bioactivities were evaluated. Compounds 5a-e were found to be more toxic against MCF-7 cells while 7a-e were more potent against 7721 cells, in particular 7a, the IC50 value of which against cell lines of MCF-7 and 7721 was 0.348 mu M and 0.258 mu M, respectively. Due to the phenyl group linked to 1,2,3-triazole, compound 5a not only showed higher DNA affinity but also more efficient DNA damaging ability than compound 7a. (C) 2011 Elsevier Ltd. All rights reserved.