1-(6-bromohexylamino)anthracene-9,10-dione | 200942-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(6-bromohexylamino)anthracene-9,10-dione
• CAS: 200942-24-1
• 化学式: C₂₀H₂₀BrNO₂
• 分子量: 386.288
• InChiKey: OJECRASCSFWODS-UHFFFAOYSA-N

物化性质

• 沸点：
  559.2±50.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-(6-bromohexylamino)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-[(7,7-dicarboxyheptyl)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-(6-hydroxyhexyl-1-amino)anthraquinone 在 吡啶 、 二溴亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到1-(6-bromohexylamino)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

• 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.