1,7-di-9-anthracene-1,6-heptadiene-3,5-dione | 1251734-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,7-di-9-anthracene-1,6-heptadiene-3,5-dione
• 英文别名: (1E,6E)-1,7-di(anthracen-9-yl)hepta-1,6-diene-3,5-dione
• CAS: 1251734-77-6
• 化学式: C₃₅H₂₄O₂
• 分子量: 476.574
• InChiKey: XQTSYNGMUCVUTL-XPWSMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₅₁H₆₂B₂O₈ 在 正丁胺 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 生成 1,7-di-9-anthracene-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  Copper Curcuminoids Containing Anthracene Groups: Fluorescent Molecules with Cytotoxic Activity

  摘要：

  The coordination chemistry of the new curcuminoid ligand, 1,7-(di-9-anthracene-1,6-heptadiene-3,5-dione), abbreviated 9Accm has been studied, resulting in two new copper-9Accm compounds. Compound 1, [Cu(phen)Cl(9Accm)], was synthesized by reacting 9Accm with [Cu(phen)Cl(2)) in a 1:1 ratio (M:L) and compound 2, [Cu(9Accm)(2)], was prepared from Cu(OAc)(2) and 9Accm (1:2). UV-vis, electron paramagnetic resonance (ERR), and superconducting quantum interference device (SQUID) measurements were some of the techniques employed to portray these species; studies on single crystals of free 9Accm, [Cu(phen)Cl(9Accm)] and [Cu(9Accm)(2)(py)] provided detailed structural information about compounds 1 and 2.py, being the first two copper-curcuminoids crystallographically described. In addition the antitumor activity of the new compounds was studied and compared with free 9Accm for a number of human tumor cells. To provide more insight on the mode of action of these compounds under biological conditions, additional experiments were accomplished, including studies on the nature of their interactions with calf thymus DNA by UV-vis titration and Circular Dichroism. These experiments together with DNA-binding studies indicate electrostatic interactions between some of these species and the double helix, pointing out the weak nature of the interaction of the compounds with CT-DNA. The intrinsic fluorescence of the free ligand and both copper compounds provided valuable information over the cellular process and therefore, fluorescence microscopy studies were performed using a human osteosarcoma cell line. Studies in vitro using this technique suggest that the action of these molecules seems to occur outside the nuclei.

  DOI：

  10.1021/ic101331c