N-(9-((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-9H-purin-6-yl)benzamide | 1146629-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-9H-purin-6-yl)benzamide
• 英文别名: N-[9-[(4,5,7-trimethoxy-9,10-dioxoanthracen-2-yl)methyl]purin-6-yl]benzamide
• CAS: 1146629-11-9
• 化学式: C₃₀H₂₃N₅O₆
• 分子量: 549.543
• InChiKey: PSGUUMQGNMKWBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(9-((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-9H-purin-6-yl)benzamide 在 氢溴酸 、 溶剂黄146 、 tin(II) chloride dihdyrate 作用下， 以 水 为溶剂， 反应 1.5h， 以57%的产率得到
  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：

  N6-苯甲酰基腺嘌呤 、 6-Bromomethyl-1,3,8-trimethoxy-6-methyl-anthraquinone 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到N-(9-((4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)-9H-purin-6-yl)benzamide
  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