5-Hydroxy-3H-anthra[1,2-b]furan-2,6,11-trione | 81086-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-Hydroxy-3H-anthra[1,2-b]furan-2,6,11-trione
• 英文别名: 5-hydroxy-3H-naphtho[2,3-g][1]benzofuran-2,6,11-trione
• CAS: 81086-05-7
• 化学式: C₁₆H₈O₅
• 分子量: 280.237
• InChiKey: NVLGXQJEVYWZEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-3H-anthra[1,2-b]furan-2,6,11-trione 、 2-氨基-5-二乙基氨基戊烷 以 甲苯 为溶剂， 反应 1.0h， 生成 N-(4-(二乙胺)-1-甲基丁基)-9,10-二氢-1,4-二羟基-9,10-二氧代-2-蒽乙酰胺单盐酸盐
  参考文献：
  名称：

  Preparation and evaluation of 2-substituted anthraquinones based on the anthracyclines

  摘要：

  Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated. All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds. Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.

  DOI：

  10.1021/jm00346a008
• 作为产物：
  描述：

  1,4-二羟基蒽醌 在 sodium dithionite 、 氧气 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 5-Hydroxy-3H-anthra[1,2-b]furan-2,6,11-trione
  参考文献：
  名称：

  Preparation and evaluation of 2-substituted anthraquinones based on the anthracyclines

  摘要：

  Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated. All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds. Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.

  DOI：

  10.1021/jm00346a008