3-(4-phenyl-1,2,3-triazol-1-yl)-1,8-naphthalic anhydride | 1073775-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 3-(4-phenyl-1,2,3-triazol-1-yl)-1,8-naphthalic anhydride
• 英文别名: 7-(4-phenyltriazol-1-yl)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione
• CAS: 1073775-49-1
• 化学式: C₂₀H₁₁N₃O₃
• 分子量: 341.326
• InChiKey: OIUYYLMWNLSGKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.08
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-氨乙基哌嗪 、 3-(4-phenyl-1,2,3-triazol-1-yl)-1,8-naphthalic anhydride 以 乙醇 为溶剂， 以76%的产率得到N-(2-piperazin-1-yl-ethyl)-3-(4-phenyl-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
• 作为产物：
  描述：

  3-amino-naphthalene-1,8-dicarboxylic acid-anhydride 在 盐酸 、 copper(ll) sulfate pentahydrate 、 溶剂黄146 、 sodium ascorbate 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 11.83h， 生成 3-(4-phenyl-1,2,3-triazol-1-yl)-1,8-naphthalic anhydride
  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