4-amino-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidin-2(1H)-one | 1146629-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-amino-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidin-2(1H)-one
• 英文别名: 4-amino-1-[(4,5,7-trihydroxy-10-oxo-9H-anthracen-2-yl)methyl]pyrimidin-2-one
• CAS: 1146629-07-3
• 化学式: C₁₉H₁₅N₃O₅
• 分子量: 365.345
• InChiKey: UDTHZXAQRZCYJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidin-2(1H)-one 在 哌啶 、 吡啶 、 吡啶-N-氧化物 、 ferrous(II) sulfate heptahydrate 作用下， 以48%的产率得到10,13-bis((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3,4,6,8,15-hexahydroxydibenzo[a,o]perylene-7,16-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：

  N-(2-oxo-1-((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-1,2-dihydropyrimidin-4-yl)benzamide 在 溶剂黄146 、 tin(II) chloride dihdyrate 、 氢溴酸 作用下， 以 水 为溶剂， 以89%的产率得到4-amino-1-((4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidin-2(1H)-one
  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