2,6-difluoro-9,10-dihydro-9,10-[4,5]epidioxoloanthracen-13-one | 81059-30-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2,6-difluoro-9,10-dihydro-9,10-[4,5]epidioxoloanthracen-13-one
• CAS: 81059-30-5
• 化学式: C₁₇H₁₀F₂O₃
• 分子量: 300.261
• InChiKey: OOUALWKHHMVWGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,6-difluoro-9,10-dihydro-9,10-[4,5]epidioxoloanthracen-13-one 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到C₁₆H₁₂F₂O₂
  参考文献：
  名称：

  Antitumor agents. II. Bis(guanylhydrazones) of anthracene-9,10-dicarboxaldehydes

  摘要：

  9,10-Anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone] (bisantrene, VI-1) showed anticancer activity in mice vs. both leukemias and solid tumors. Increases in life span vs. the following neoplasms were: P-388 leukemia, 137%; B-16 melanoma, 122%; Lieberman plasma cell tumor, greater than 85%; colon tumor 26, 150%; Ridgway osteogenic sarcoma, 85%. There were significant numbers of long-term survivors. Both DNA and RNA synthesis were strongly inhibited. The drug was resistant to biodegradation and was bound strongly to tissues; in monkeys the half-life for disappearance from serum was 6 days. Related hydrazones were synthesized, and structure-activity relationships are discussed. Two routes to ring-substituted anthracene-9,10-dicarboxaldehyde intermediates were developed.

  DOI：

  10.1021/jm00347a006
• 作为产物：
  描述：

  碳酸亚乙烯酯 、 2,6-difluoroanthracene 反应 8.0h， 以45%的产率得到2,6-difluoro-9,10-dihydro-9,10-[4,5]epidioxoloanthracen-13-one
  参考文献：
  名称：

  Antitumor agents. II. Bis(guanylhydrazones) of anthracene-9,10-dicarboxaldehydes

  摘要：

  9,10-Anthracenedicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone] (bisantrene, VI-1) showed anticancer activity in mice vs. both leukemias and solid tumors. Increases in life span vs. the following neoplasms were: P-388 leukemia, 137%; B-16 melanoma, 122%; Lieberman plasma cell tumor, greater than 85%; colon tumor 26, 150%; Ridgway osteogenic sarcoma, 85%. There were significant numbers of long-term survivors. Both DNA and RNA synthesis were strongly inhibited. The drug was resistant to biodegradation and was bound strongly to tissues; in monkeys the half-life for disappearance from serum was 6 days. Related hydrazones were synthesized, and structure-activity relationships are discussed. Two routes to ring-substituted anthracene-9,10-dicarboxaldehyde intermediates were developed.

  DOI：

  10.1021/jm00347a006