(S)-3-(2,3-dichloro-indolo[2,3-b]quinoxalin-6-yl)-propane-1,2-diol | 917076-92-7

• 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: (S)-3-(2,3-dichloro-indolo[2,3-b]quinoxalin-6-yl)-propane-1,2-diol
• 英文别名: (2S)-3-(2,3-dichloroindolo[3,2-b]quinoxalin-6-yl)propane-1,2-diol
• CAS: 917076-92-7
• 化学式: C₁₇H₁₃Cl₂N₃O₂
• 分子量: 362.215
• InChiKey: CEWSYMLVBUSRCQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(2,3-dichloro-indolo[2,3-b]quinoxalin-6-yl)-propane-1,2-diol 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 Diisopropyl-phosphoramidous acid (S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-(2,3-dichloro-indolo[2,3-b]quinoxalin-6-ylmethyl)-ethyl ester 2-cyano-ethyl ester
  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：

  2,3-dichloro-6H-indolo[2,3-b]quinoxaline 在 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (S)-3-(2,3-dichloro-indolo[2,3-b]quinoxalin-6-yl)-propane-1,2-diol
  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.