1,1'-(1,6,8,10,11,13-hexahydroxy-7,14-dioxo-7,14-dihydrophenanthro[1,10,9,8-opqra]perylene-3,4-diyl)bis(methylene)-bis(5-methylpyrimidine-2,4(1H,3H)-dione) | 1146629-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,1'-(1,6,8,10,11,13-hexahydroxy-7,14-dioxo-7,14-dihydrophenanthro[1,10,9,8-opqra]perylene-3,4-diyl)bis(methylene)-bis(5-methylpyrimidine-2,4(1H,3H)-dione)
• CAS: 1146629-04-0
• 化学式: C₄₀H₂₄N₄O₁₂
• 分子量: 752.65
• InChiKey: WSDDWGYFMRBKEO-UHFFFAOYSA-N

物化性质

• 熔点：
  >350 °C
• 密度：
  1.862±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  56.0
• 可旋转键数：
  4.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  265.24
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  1,1'-(1,3,4,6,8,15-hexahydroxy-7,16-dioxo-7,16-dihydrodibenzo[a,o]perylene-10,13-diyl)bis(methylene)bis(5-methylpyrimidine-2,4(1H,3H)-dione) 以 丙酮 为溶剂， 反应 2.5h， 以77%的产率得到1,1'-(1,6,8,10,11,13-hexahydroxy-7,14-dioxo-7,14-dihydrophenanthro[1,10,9,8-opqra]perylene-3,4-diyl)bis(methylene)-bis(5-methylpyrimidine-2,4(1H,3H)-dione)
  参考文献：
  名称：

  ω,ω′-Appended nucleo-base derivatives of hypericin

  摘要：

  omega,omega'-Disubstituted hypericin derivatives with the nucleo-bases thymine, cytosine, and adenine in these positions were prepared starting from tri-O-methyl-omega-bromoemodin. The most promising derivative proved to be that with a thymine moiety. It displayed the best solubility of the three products together with a potency to produce singlet oxygen and/or reactive oxygen species comparable to the parent compound hypericin. In addition, although no specific interaction with DNA or poly(2'-deoxyadenylic acid) could be detected, it proved to be significantly better accumulating in the nucleus of prostatic cancer LNCaP cells than hypericin making it a promising candidate for a second-generation photodynamic hypericin agent.

  DOI：

  10.1007/s00706-008-0898-0