3,4-bis((6-amino-9H-purin-9-yl)methyl)-1,6,8,10,11,13-hexahydroxyphenanthro[1,10,9,8-opqra]perylene-7,14-dione | 1146629-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3,4-bis((6-amino-9H-purin-9-yl)methyl)-1,6,8,10,11,13-hexahydroxyphenanthro[1,10,9,8-opqra]perylene-7,14-dione
• 英文别名: 5,24-bis[(6-aminopurin-9-yl)methyl]-7,11,13,16,18,22-hexahydroxyoctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,7,10,12,14(28),15(27),16,18,21,23-tridecaene-9,20-dione
• CAS: 1146629-17-5
• 化学式: C₄₀H₂₂N₁₀O₈
• 分子量: 770.677
• InChiKey: MFHXNJLDWKVQNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  58
• 可旋转键数：
  4
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  295
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  以 甲醇 、 氨 、 水 、 丙酮 为溶剂， 反应 0.75h， 以36%的产率得到3,4-bis((6-amino-9H-purin-9-yl)methyl)-1,6,8,10,11,13-hexahydroxyphenanthro[1,10,9,8-opqra]perylene-7,14-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