6-(2-deoxy-β-D-ribofuranosyl)-indolo[2,3-b]quinoxaline | 917076-95-0

• 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: 6-(2-deoxy-β-D-ribofuranosyl)-indolo[2,3-b]quinoxaline
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-indolo[3,2-b]quinoxalin-6-yloxolan-3-ol
• CAS: 917076-95-0
• 化学式: C₁₉H₁₇N₃O₃
• 分子量: 335.362
• InChiKey: QQBITHZDKHUMDF-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(2-deoxy-β-D-ribofuranosyl)-indolo[2,3-b]quinoxaline 在 二异丙基铵盐四氮唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-indolo[3,2-b]quinoxalin-6-yloxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

  摘要：

  6H-Indolo[2,3-b]quinoxaline was studied as a covalently bound heteroaromatic intercalator. Six monomers were synthesized and incorporated into DNA oligonucleotides. Through a study of linker length dependence it was concluded that the linker between the oligo and the intercalator must consist of at least five C atoms in order to stabilize a DNA duplex. An intercalator with a 2 '-deoxy-D-riboside linker to the oligo could also stabilize a DNA/RNA duplex, while (S)-4-(6-methylindolo[2,3-b]quinoxalin-3-ylmethoxy)-butane-1,2-diol was able to stabilize both DNA/DNA, DNA/RNA and a DNA/LNA duplex. Mismatch studies revealed a huge sensitivity to the C-C mismatch at the 5'-site of the intercalator. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.017
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 四丁基溴化铵 、 sodium 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 6-(2-deoxy-β-D-ribofuranosyl)-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline

  摘要：

  6H-Indolo[2,3-b]quinoxaline was studied as a covalently bound heteroaromatic intercalator. Six monomers were synthesized and incorporated into DNA oligonucleotides. Through a study of linker length dependence it was concluded that the linker between the oligo and the intercalator must consist of at least five C atoms in order to stabilize a DNA duplex. An intercalator with a 2 '-deoxy-D-riboside linker to the oligo could also stabilize a DNA/RNA duplex, while (S)-4-(6-methylindolo[2,3-b]quinoxalin-3-ylmethoxy)-butane-1,2-diol was able to stabilize both DNA/DNA, DNA/RNA and a DNA/LNA duplex. Mismatch studies revealed a huge sensitivity to the C-C mismatch at the 5'-site of the intercalator. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.017