1-Chloro-5-[(pyridin-2-ylmethyl)-amino]-anthraquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Chloro-5-[(pyridin-2-ylmethyl)-amino]-anthraquinone
• 英文别名: 1-Chloro-5-(pyridin-2-ylmethylamino)anthracene-9,10-dione
• 化学式: C₂₀H₁₃ClN₂O₂
• 分子量: 348.788
• InChiKey: QAWXMOLXDCLBQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲基乙二胺 、 1-Chloro-5-[(pyridin-2-ylmethyl)-amino]-anthraquinone 反应 72.0h， 以72%的产率得到1-(2-Dimethylamino-ethylamino)-5-[(pyridin-2-ylmethyl)-amino]-anthraquinone
  参考文献：
  名称：

  Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity?

  摘要：

  The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)80029-x
• 作为产物：
  描述：

  2-氨甲基吡啶 、 1,5-二氯蒽醌 反应 36.0h， 以53%的产率得到1-Chloro-5-[(pyridin-2-ylmethyl)-amino]-anthraquinone
  参考文献：
  名称：

  Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity?

  摘要：

  The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)80029-x

文献信息

• Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: are free radicals essential for cytotoxicity?
  作者：Dinorah Barasch、Omer Zipori、Israel Ringel、Isaac Ginsburg、Amram Samuni、Jehoshua Katzhendler

  DOI：10.1016/s0223-5234(00)80029-x

  日期：1999.7

  The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones. (C) 1999 Editions scientifiques et medicales Elsevier SAS.