5,12-dihydro-13,14-dihydroxy-5,12-ethanonaphtacene | 71440-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 5,12-dihydro-13,14-dihydroxy-5,12-ethanonaphtacene
• 英文别名: 5,12-Dihydro-5,12-ethanobenz[b]anthracene-13,14-diol；pentacyclo[10.6.2.02,11.04,9.013,18]icosa-2,4,6,8,10,13,15,17-octaene-19,20-diol
• CAS: 71440-74-9
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: SQLSXFHLAZUYKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,12-dihydro-13,14-dihydroxy-5,12-ethanonaphtacene 在 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 并四苯
  参考文献：
  名称：

  Photochemical synthesis of naphthacene and its derivatives for irreversible photo-responsive fluorescent molecules

  摘要：

  Highly fluorescent naphthacene derivatives and their photoconvertible precursors were synthesized for irreversibly photo-responsive fluorescent molecules. The fluorescence quantum yields (Phi(f)) of the precursors were less than 0.02, and the precursors can be converted to the highly fluorescent naphthacene derivatives (Phi(f) = 0.67-0.70) quantitatively by photo-irradiation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.014
• 作为产物：
  描述：

  并四苯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 5,12-dihydro-13,14-dihydroxy-5,12-ethanonaphtacene
  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

• Novel dihydrobenzanthracene derivatives
  申请人：American Cyanamid Company

  公开号：US04187373A1

  公开（公告）日：1980-02-05

  This disclosure describes benzanthracene-5,12(or 7,12)-dicarboxaldehyde-bis-hydrazones and the 5,12(or 7,12)-dihydrobenzanthracene-5,12(or 7,12)-dicarboxaldehyde-bis-hydrazones useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or pallation of leukemia and related cancers.

  本文披露了苯并蒽-5,12（或7,12）-二甲酰肼双酰肼及其5,12（或7,12）-二氢苯并蒽-5,12（或7,12）-二甲酰肼双酰肼，可用作抗菌剂，用于抑制移植小鼠肿瘤的生长，以及诱导白血病和相关癌症的退化和/或缓解。
• US4187373A
  申请人：——

  公开号：US4187373A

  公开（公告）日：1980-02-05
• 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.
• Photochemical synthesis of naphthacene and its derivatives for irreversible photo-responsive fluorescent molecules
  作者：Tatsuya Aotake、Yuko Yamashita、Tetsuo Okujima、Nobuhiko Shirasawa、Yukari Jo、Shigeo Fujimori、Hidemitsu Uno、Noboru Ono、Hiroko Yamada

  DOI：10.1016/j.tetlet.2013.01.014

  日期：2013.4

  Highly fluorescent naphthacene derivatives and their photoconvertible precursors were synthesized for irreversibly photo-responsive fluorescent molecules. The fluorescence quantum yields (Phi(f)) of the precursors were less than 0.02, and the precursors can be converted to the highly fluorescent naphthacene derivatives (Phi(f) = 0.67-0.70) quantitatively by photo-irradiation. (C) 2013 Elsevier Ltd. All rights reserved.