1-(3-bromopropylamino)anthracene-9,10-dione | 200942-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(3-bromopropylamino)anthracene-9,10-dione
• CAS: 200942-23-0
• 化学式: C₁₇H₁₄BrNO₂
• 分子量: 344.208
• InChiKey: HEEDEYPYELPULK-UHFFFAOYSA-N

物化性质

• 沸点：
  538.506±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.532±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-bromopropylamino)anthracene-9,10-dione 在 氢氧化钾 、 potassium tert-butylate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-[(4,4-dicarboxybutyl)amino]anthraquinone dipotassium salt
  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-[(3-hydroxypropyl)amino]-9,10-anthracenedione 在 吡啶 、 二溴亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到1-(3-bromopropylamino)anthracene-9,10-dione
  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

• The preparation and characterisation of cyclam/anthraquinone macrocyle/intercalator complexes and their interactions with DNA
  作者：Leanne T. Ellis、David F. Perkins、Peter Turner、Trevor W. Hambley

  DOI：10.1039/b302123h

  日期：——

  A new series of macrocycle/intercalator adducts have been prepared from cyclam (1,4,8,11-tetraazacyclotetradecane) and the 1- and 2-substituted anthraquinones (1-[(2-aminoethyl)amino]anthracene-9,10-dione (1C2mac), 1-[(3-aminopropyl)amino]anthracene-9,10-dione (1C3mac), 2-[(3-aminopropyl)amino]anthracene-9,10-dione (2C3mac)). The copper complexes of two of these adducts were prepared and the crystal structure of the complex of 1C2mac ([Cu(1C2mac)(CH3CN)2](PF6)2.0.2H2O) was determined as the hexafluorophosphate salt. The equilibrium constants for the binding to DNA of 1C2-mac, with and without the copper added, were found by UV titrations to be 4.7 × 103 M−1 and 6.2 × 103 M−1, respectively. Reaction with plasmid DNA allowed comparison between the effects of the cyclam/anthraquinone adducts, their copper complexes and the intercalators alone. Addition of the macrocycle increased the extent and effect of DNA intercalation and addition of copper increased the effect still further. The adducts with the longer side chains caused substantially more unwinding of the DNA. None of the adducts inhibited cleavage at dGpG or dGpC sites by restriction enzymes. Molecular modelling was used to investigate the effects of the side chain for a number of possible DNA binding modes. These models reveal that intercalation is not significantly interfered with by the presence of the macrocycle, irrespective of the position of attachment. The increased unwinding caused by adducts with the longer side chain is therefore most likely to be due to specific interactions between the macrocycle and the DNA.

  一系列新的宏环/插层剂加合物是由环四氮烷（1,4,8,11-四氮杂环十四烷）和1-、2-取代的蒽醌（1-[(2-氨乙基)氨基]蒽醌-9,10-二酮（1C2mac）、1-[(3-氨丙基)氨基]蒽醌-9,10-二酮（1C3mac）、2-[(3-氨丙基)氨基]蒽醌-9,10-二酮（2C3mac））制备的。两种这些加合物的铜复合物已被制备，并且1C2mac的复合物（[Cu(1C2mac)(CH3CN)2](PF6)2·0.2H2O）的晶体结构被确定为六氟磷酸盐。通过UV滴定法，发现1C2mac与DNA结合的平衡常数分别为4.7 × 10³ M−1（未添加铜）和6.2 × 10³ M−1（添加铜）。与质粒DNA反应使得可以比较宏环/蒽醌加合物、它们的铜复合物以及单独插层剂的影响。添加宏环增加了DNA插层的程度和影响，而添加铜则进一步增强了效果。具有较长侧链的加合物导致DNA的解旋显著增加。没有任何加合物抑制限制酶在dGpG或dGpC位点的切割。分子模拟用于研究侧链对多种可能DNA结合模式的影响。这些模型显示，无论附着位置如何，宏环的存在并不明显干扰插层。因此，侧链较长的加合物所引起的增加的解旋最可能是由于宏环与DNA之间的特定相互作用。
• Thiol-functionalized anthraquinones: mass spectrometry and electrochemical studies
  作者：Paweł Niedziałkowski、Tadeusz Ossowski、Radosław Majewski、Zdzisława Nowakowska、Grzegorz Schroeder

  DOI：10.1007/s00706-011-0623-2

  日期：2011.11

  In this work, the synthesis of various thiol-functionalized anthraquinone compounds is presented. The studied compounds were characterized by mass spectrometry and the main fragmentation pathways are discussed. The compounds studied formed stable self-assembled monolayers (SAMs) in the gold surface. The parameters for the reduction processes in the gold surface of the studied new anthraquinones were determined by cyclic voltamperometry tests.
• US4088661A
  申请人：——

  公开号：US4088661A

  公开（公告）日：1978-05-09
• 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.