1-[(3-aminopropyl)amino]-4-[[2-(dimethylamino)ethyl]amino]-9,10-anthracenedione | 93184-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-[(3-aminopropyl)amino]-4-[[2-(dimethylamino)ethyl]amino]-9,10-anthracenedione
• 英文别名: 1-<(3-Aminopropyl)amino>-4-<<(2-dimethylamino)ethyl>amino>anthracene-9,10-dione；1-(3-aminopropylamino)-4-(2-dimethylaminoethylamino)anthracene-9,10-dione；1-(3-Aminopropylamino)-4-[2-(dimethylamino)ethylamino]anthracene-9,10-dione
• CAS: 93184-46-4
• 化学式: C₂₁H₂₆N₄O₂
• 分子量: 366.463
• InChiKey: AUVXLKSDMKWNKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(3-aminopropyl)amino]-4-[[2-(dimethylamino)ethyl]amino]-9,10-anthracenedione 、 对硝基苯甲酸 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 以65%的产率得到N-{3-[4-(2-Dimethylamino-ethylamino)-9,10-dioxo-9,10-dihydro-anthracen-1-ylamino]-propyl}-4-nitro-benzamide
  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：

  1,4-二羟基蒽醌 在 potassium carbonate 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 30.0h， 生成 1-[(3-aminopropyl)amino]-4-[[2-(dimethylamino)ethyl]amino]-9,10-anthracenedione
  参考文献：
  名称：

  Synthesis of unsymmetrical 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones for antineoplastic evaluation

  摘要：

  DOI：

  10.1021/jo00200a049

文献信息

• KRAPCHO, A. PAUL;HACKER, MILES P;LANDI, JOHN J.;MCCORMACK, J. J.;SHAW, KE+
  作者：KRAPCHO, A. PAUL、HACKER, MILES P、LANDI, JOHN J.、MCCORMACK, J. J.、SHAW, KE+

  DOI：——

  日期：——
• US4894451A
  申请人：——

  公开号：US4894451A

  公开（公告）日：1990-01-16
• 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.
• Synthesis of unsymmetrical 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones for antineoplastic evaluation
  作者：A. Paul Krapcho、Kenneth J. Shaw、John J. Landi、Donald G. Phinney

  DOI：10.1021/jo00200a049

  日期：1984.12