5-methyl-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione | 1146629-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methyl-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1146629-02-8
• 化学式: C₂₀H₁₆N₂O₆
• 分子量: 380.357
• InChiKey: AIXTYHUPDQLLGD-UHFFFAOYSA-N

物化性质

• 熔点：
  275 °C (decomp)
• 密度：
  1.555±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  132.62
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-methyl-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione 在 哌啶 、 吡啶 、 吡啶-N-氧化物 、 ferrous(II) sulfate heptahydrate 作用下， 反应 1.0h， 以88%的产率得到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)
  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
• 作为产物：
  描述：

  3-benzoyl-5-methyl-1-((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione 在 tin(II) chloride dihdyrate 、 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 以92%的产率得到5-methyl-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-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