3-(4-fluorophenyl)-3-hydroxy-9-chloro-2,3-dihydrobenzo[de]benzopyran-7,8-dione | 1314798-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4-fluorophenyl)-3-hydroxy-9-chloro-2,3-dihydrobenzo[de]benzopyran-7,8-dione
• 英文别名: 12-Chloro-4-(4-fluorophenyl)-4-hydroxy-2-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13)-tetraene-10,11-dione
• CAS: 1314798-27-0
• 化学式: C₁₈H₁₀ClFO₄
• 分子量: 344.726
• InChiKey: CEOSMEHKVJXEEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-3-hydroxy-9-chloro-2,3-dihydrobenzo[de]benzopyran-7,8-dione 在 polyphosphoric acid 作用下， 反应 0.5h， 以94%的产率得到3-(4-fluorophenyl)-9-chlorobenzo[de]benzopyran-7,8-dione
  参考文献：
  名称：

  Synthesis and evaluation of mansonone F derivatives as topoisomerase inhibitors

  摘要：

  A series of mansonone F (MF) derivatives were designed and synthesized. These compounds were found to be strong inhibitors for topoisomerases, with much more significant inhibition for topoisomerase II rather than topoisomerase I. The best inhibitor showed 20 times stronger anti-topoisomerase II activity than a positive control Etoposide. The cytotoxic activity of these MF derivatives was evaluated against human cancer cell lines CNE-2 and Glc-82, which showed that these compounds were potent antitumor agents. The structure activity relationships (SARs) study revealed that o-quinone group and pyran ring are important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.059
• 作为产物：
  描述：

  10-Amino-12-chloro-4-(4-fluorophenyl)-2-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-4-ol 在 sodium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 水 为溶剂， 生成 3-(4-fluorophenyl)-3-hydroxy-9-chloro-2,3-dihydrobenzo[de]benzopyran-7,8-dione
  参考文献：
  名称：

  Synthesis and evaluation of mansonone F derivatives as topoisomerase inhibitors

  摘要：

  A series of mansonone F (MF) derivatives were designed and synthesized. These compounds were found to be strong inhibitors for topoisomerases, with much more significant inhibition for topoisomerase II rather than topoisomerase I. The best inhibitor showed 20 times stronger anti-topoisomerase II activity than a positive control Etoposide. The cytotoxic activity of these MF derivatives was evaluated against human cancer cell lines CNE-2 and Glc-82, which showed that these compounds were potent antitumor agents. The structure activity relationships (SARs) study revealed that o-quinone group and pyran ring are important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.059