9-phenyl-4H,6H-benzo[4,5]isochromeno[7,6-d]oxazole-4,6-dione | 1097136-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-phenyl-4H,6H-benzo[4,5]isochromeno[7,6-d]oxazole-4,6-dione
• CAS: 1097136-49-6
• 化学式: C₁₉H₉NO₄
• 分子量: 315.285
• InChiKey: NRBVJFMWUJJWJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-phenyl-4H,6H-benzo[4,5]isochromeno[7,6-d]oxazole-4,6-dione 、 (S)-2-(氨甲基)-1-乙基吡咯烷 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到(S)-5-((1-ethylpyrrolidin-2-yl)methyl)-9-phenyl-4H-benzo[de]oxazolo[5,4-g]isoquinoline-4,6(5H)-dione
  参考文献：
  名称：

  Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

  摘要：

  Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more ef.ciently than their R-enantiomers. S-enantiomer B-3 could photodamage DNA at 0.2 mu M and cleave supercoiled plasmid DNA from form I to form II completely at 50 mu M. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.104
• 作为产物：
  描述：

  、 苯甲酸 在 PPA 作用下， 反应 4.0h， 以62%的产率得到9-phenyl-4H,6H-benzo[4,5]isochromeno[7,6-d]oxazole-4,6-dione
  参考文献：
  名称：

  Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

  摘要：

  Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more ef.ciently than their R-enantiomers. S-enantiomer B-3 could photodamage DNA at 0.2 mu M and cleave supercoiled plasmid DNA from form I to form II completely at 50 mu M. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.104