20,22-Dioxahexacyclo[10.6.5.02,11.03,8.013,18.019,23]tricosa-2(11),3,5,7,9,13,15,17-octaen-21-one | 27525-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 20,22-Dioxahexacyclo[10.6.5.02,11.03,8.013,18.019,23]tricosa-2(11),3,5,7,9,13,15,17-octaen-21-one
• CAS: 27525-64-0
• 化学式: C₂₁H₁₄O₃
• 分子量: 314.34
• InChiKey: CALDUTDXAKUVKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  576.1±50.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  20,22-Dioxahexacyclo[10.6.5.02,11.03,8.013,18.019,23]tricosa-2(11),3,5,7,9,13,15,17-octaen-21-one 在 lead(IV) acetate 、 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.17h， 生成 7,12-Dialdehyd-7,12-dihydrobenzanthracen
  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 、 苯并[a]蒽 反应 8.0h， 以80%的产率得到20,22-Dioxahexacyclo[10.6.5.02,11.03,8.013,18.019,23]tricosa-2(11),3,5,7,9,13,15,17-octaen-21-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

文献信息

• Antitumor agents. II. Bis(guanylhydrazones) of anthracene-9,10-dicarboxaldehydes
  作者：K. C. Murdock、R. G. Child、Yang I Lin、J. D. Warren、P. F. Fabio、Ving J. Lee、P. T. Izzo、S. A. Lang、Robert B. Angier

  DOI：10.1021/jm00347a006

  日期：1982.5

  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.