1-[(3-carboxypropyl)amino]-9,10-anthracenedione | 5525-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-[(3-carboxypropyl)amino]-9,10-anthracenedione
• 英文别名: 4-Anthrachinonyl-(1)-amino-buttersaeure；4-[(9,10-Dioxoanthracen-1-yl)amino]butanoic acid
• CAS: 5525-26-8
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: MGYXMRDXTKZIKY-UHFFFAOYSA-N

物化性质

• 熔点：
  203-204 °C
• 沸点：
  601.9±55.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(3-carboxypropyl)amino]-9,10-anthracenedione 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[[4-[4-[(9,10-Dioxoanthracen-1-yl)amino]butanoylamino]phenyl]methyl]propanedioic acid
  参考文献：
  名称：

  Anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs

  摘要：

  A series of complexes PtAm2L [where Am-2 = (NH3)(2), ethylenediamine(en), 1,2-diaminocyclohexane (DACH) or (NH3)(c-C6H11NH2) and where L is a bidentate 1,1-dicarboxylate ligand tethered to 1-aminoanthraquinone by various spacers] was prepared and screened in vitro against P388 leukemia cells. The free ligands displayed moderate activity and the corresponding platinum complexes were tenfold more active. The nature of the linker chain does not seem to affect the potency of the complexes. The potency depends on the nature of the inert amine ligand [NH3 > DACH > en]. The low aqueous solubility of these complexes prevented any in vivo studies and the preparation of water soluble analogs is currently under way.

  DOI：

  10.1016/s0223-5234(99)80068-3
• 作为产物：
  描述：

  1-氯蒽醌 、 4-氨基丁酸 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以22%的产率得到1-[(3-carboxypropyl)amino]-9,10-anthracenedione
  参考文献：
  名称：

  Anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs

  摘要：

  A series of complexes PtAm2L [where Am-2 = (NH3)(2), ethylenediamine(en), 1,2-diaminocyclohexane (DACH) or (NH3)(c-C6H11NH2) and where L is a bidentate 1,1-dicarboxylate ligand tethered to 1-aminoanthraquinone by various spacers] was prepared and screened in vitro against P388 leukemia cells. The free ligands displayed moderate activity and the corresponding platinum complexes were tenfold more active. The nature of the linker chain does not seem to affect the potency of the complexes. The potency depends on the nature of the inert amine ligand [NH3 > DACH > en]. The low aqueous solubility of these complexes prevented any in vivo studies and the preparation of water soluble analogs is currently under way.

  DOI：

  10.1016/s0223-5234(99)80068-3

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.
• Anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs
  作者：D Gibson、I Binyamin、M Haj、I Ringel、A Ramu、J Katzhendler

  DOI：10.1016/s0223-5234(99)80068-3

  日期：1997.10

  A series of complexes PtAm2L [where Am-2 = (NH3)(2), ethylenediamine(en), 1,2-diaminocyclohexane (DACH) or (NH3)(c-C6H11NH2) and where L is a bidentate 1,1-dicarboxylate ligand tethered to 1-aminoanthraquinone by various spacers] was prepared and screened in vitro against P388 leukemia cells. The free ligands displayed moderate activity and the corresponding platinum complexes were tenfold more active. The nature of the linker chain does not seem to affect the potency of the complexes. The potency depends on the nature of the inert amine ligand [NH3 > DACH > en]. The low aqueous solubility of these complexes prevented any in vivo studies and the preparation of water soluble analogs is currently under way.