cis-1,4-Dimethoxy-9,10-dihydro-9,10-anthracenedicarboxaldehyde | 71440-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: cis-1,4-Dimethoxy-9,10-dihydro-9,10-anthracenedicarboxaldehyde
• 英文别名: 1,4-Dimethoxy-9,10-cis-dihydroanthracen-9,10-dicarbaldehyd；Cis-1,4-Dimethoxy-9,10-dihydro-9,10-anthracenedicarboxaldehyde；(9R,10S)-1,4-dimethoxy-9,10-dihydroanthracene-9,10-dicarbaldehyde
• CAS: 71440-47-6
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: FIDJTLCYAKXXFY-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-dimethoxy-9,10-dihydro-9,10-ethanoanthracene-11,12-diol 在 lead(IV) acetate 、 溶剂黄146 作用下， 反应 0.17h， 以28%的产率得到cis-1,4-Dimethoxy-9,10-dihydro-9,10-anthracenedicarboxaldehyde
  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

• Bis(2-imida
  申请人：American Cyanamid Company

  公开号：US04235996A1

  公开（公告）日：1980-11-25

  This disclosure describes 9,10-dihydroanthracene-9,10-dicarboxaldehyde-bis-hydrazones and derivatives thereof useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers in mammals.

  本公开描述了9,10-二氢蒽-9,10-二甲醛双肼脒及其衍生物，可用作抗菌剂，用于抑制移植小鼠肿瘤的生长，并用于诱导哺乳动物体内白血病和相关癌症的退缩和/或缓解。
• FR2446285
  申请人：——

  公开号：——

  公开（公告）日：——
• US4235996A
  申请人：——

  公开号：US4235996A

  公开（公告）日：1980-11-25
• 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.