1,4-bis[(3-aminopropyl)amino]-9,10-anthracenedione | 72705-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis[(3-aminopropyl)amino]-9,10-anthracenedione
• 英文别名: 1.4-Bis-(γ-amino-propylamino)-anthrachinon；1,4-Bis-(3-aminopropylamino)-anthrachinon；1,4-Bis[(3-aminopropyl)amino]-anthracene-9,10-dione；1,4-bis(3-aminopropylamino)anthracene-9,10-dione
• CAS: 72705-28-3
• 化学式: C₂₀H₂₄N₄O₂
• 分子量: 352.436
• InChiKey: SVMMAGQWEQUXRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-bis[(3-aminopropyl)amino]-9,10-anthracenedione 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,4-bis[(3-aminopropyl)amino]-9,10-anthracenedione dihydrochloride
  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：

  2,3-二氢-9,10-二羟基-1,4-蒽二酮 、 1,3-丙二胺 在 air 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 1,4-bis[(3-aminopropyl)amino]-9,10-anthracenedione
  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

• Anthracene derivatives for use as anticancer agents
  申请人：Napier University Ventures Limited

  公开号：US05733880A1

  公开（公告）日：1998-03-31

  A compound having the structural formula, ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen or hydroxyl. R.sup.2 and R.sup.3 are independently oxo or hydrogen, one of R.sup.5 and R.sup.6 is A--B and the other is hydrogen, hydroxyl, or a group A, wherein each A is a spacer group providing --NH-- or --CO-- in the bond with B (if present); at least one A group does not provide the residue of an .alpha.-amino acid adjacent the anthraquinone nucleus and the A of any A--B moiety is joined to the anthraquinone nucleus via an --NH-- bond, and each B is a peptide group or a physiologically acceptable derivative thereof. The compounds are useful as antitumor compounds.

  一种具有结构式##STR1##的化合物，其中R.sup.1和R.sup.2独立地为氢或羟基。R.sup.2和R.sup.3独立地为氧代或氢，R.sup.5和R.sup.6中的一个为A-B，另一个为氢，羟基或A基团，其中每个A为间隔基团，在与B（如果存在）的键中提供--NH--或--CO--；至少一个A基团不提供与蒽醌核相邻的α-氨基酸残基，任何A-B基团中的A通过--NH--键连接到蒽醌核，并且每个B为肽基团或其生理上可接受的衍生物。这些化合物可用作抗肿瘤化合物。
• ANTHRACENE DERIVATIVES FOR USE AS ANTICANCER AGENT OR DYE
  申请人：NAPIER UNIVERSITY VENTURES LIMITED

  公开号：EP0721447B1

  公开（公告）日：1998-02-25
• US4189429A
  申请人：——

  公开号：US4189429A

  公开（公告）日：1980-02-19
• [EN] ANTHRACENE DERIVATIVES FOR USE AS ANTICANCER AGENT OR DYE<br/>[FR] DERIVES D'ANTHRACENE UTILISES EN TANT QU'AGENT ANTICANCEREUX OU EN TANT QUE TEINTURE
  申请人：NAPIER UNIVERSITY VENTURES LIMITED

  公开号：WO1995009149A1

  公开（公告）日：1995-04-06

  (EN) A compound having structural formula (I), where R1 and R2 are independently hydrogen or hydroxyl, R2 and R3 are independently oxo or hydrogen, one of R5 and R6 is A-B and the other is hydrogen, hydroxyl, or a group A, wherein the or each A is independently a spacer group providing -NH- or -CO- in the bond with B (if present), at least one A group does not provide the residue of an $g(a)-amino acid adjacent the anthraquinone nucleus and the A of any A-B moiety is joined to the anthraquinone nucleus via an -NH- bond, and the or or each B is a peptide group; or a physiologically acceptable derivative thereof. The compounds are useful as dyes or anti-tumour compounds. The compounds are useful as anticancer drugs and dyes.(FR) Composé de formule structurelle (I), ou un de ses dérivés physiologiquement acceptables, dans laquelle R1 et R2 représentent indépendamment hydrogène ou hydroxyle, R2 et R3 représentent indépendamment oxo ou hydrogène, un parmi R5 et R6 est A-B et l'autre représente hydrogène ou hydroxyle, ou un groupe A, dans lequel le ou chaque A est indépendamment un groupe bifonctionnel apportant -NH- ou -CO- dans la liaison avec B (si celui-ci est présent), et au moins un groupe A ne donne pas le résidu d'un acide $g(a)-aminé adjacent au noyau anthraquinone, le A de n'importe quelle fraction A-B étant joint au noyau anthraquinone via une liaison -NH-, et le B ou chaque B étant un groupe peptide. Ces composés sont utiles en tant que composés tinctoriaux ou antitumoraux, et en tant que teintures et médicaments anticancéreux.
• 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.