(6-methyl-6H-indolo[2,3-b]quinoxalin-3-yl)methanol | 917077-15-7

• 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-methyl-6H-indolo[2,3-b]quinoxalin-3-yl)methanol
• 英文别名: (6-Methylindolo[3,2-b]quinoxalin-3-yl)methanol；(6-methylindolo[3,2-b]quinoxalin-3-yl)methanol
• CAS: 917077-15-7
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: XYQPYVDFZMPSOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-methyl-6H-indolo[2,3-b]quinoxalin-3-yl)methanol 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到3-chloromethyl-6-methyl-6H-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
• 作为产物：
  描述：

  6H-indolo[2,3-b]quinoxaline-3-carboxylic acid 、 碘甲烷 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 二甲基亚砜 、 四氢呋喃 为溶剂， 反应 53.0h， 以44%的产率得到(6-methyl-6H-indolo[2,3-b]quinoxalin-3-yl)methanol
  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

文献信息

• Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline
  作者：Michael C. Wamberg、Allam A. Hassan、Andrew D. Bond、Erik B. Pedersen

  DOI：10.1016/j.tet.2006.09.017

  日期：2006.11

  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.