N-[2-(tert-butyldimethylsilyloxy)ethyl]-N’-[6-chloro-2-methoxyacridine-9-yl]ethylenediamine | 1397705-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-[2-(tert-butyldimethylsilyloxy)ethyl]-N’-[6-chloro-2-methoxyacridine-9-yl]ethylenediamine
• 英文别名: N¹-(2 (tert-butyldimethylsiloxy)ethyl)-N²-(6-chloro-2-methoxyacridine-9-yl)ethylenediamine
• CAS: 1397705-18-8
• 化学式: C₂₄H₃₄ClN₃O₂Si
• 分子量: 460.091
• InChiKey: IAIVRFGJHOGJBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.41
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[2-(tert-butyldimethylsilyloxy)ethyl]-N’-[6-chloro-2-methoxyacridine-9-yl]ethylenediamine 在 吡啶 、 四氮唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 17.53h， 生成 N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[2-(6-chloro-2-methoxyacridine-9-ylamine)ethyl]-N’-[2-(4,4’-dimethoxytrityloxy)ethyl]-N’-[2-(2-cyano-ethyloxy-N,N-iisopropylphosphoramiditeoxy)ethyl]glutaramide
  参考文献：
  名称：

  Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion

  摘要：

  Non-nucleotide phosporamidites were synthetized, having a branching backbone with different positions for functional groups. Phosphoramidite monomers obtained contain intercalator moiety, 6-chloro-2-methoxyacridine, and additional hydroxyl residue protected with dimethoxytrityl group or with the tert-butyldimethylsilyl group for post-synthetic modification. Oligothymidilates containing one or more modified units in different positions of the sequence were synthesized. The melting point and thermodynamic parameters of the formation of complementary duplexes formed by modified oligonucleotides were defined (change in enthalpy and entropy). The introduction of intercalating residue causes a significant stabilization of DNA duplexes. It is shown that the efficiency of the fluorescence of acridine residue in the oligonucleotide conjugate significantly changes upon hybridization with DNA.

  DOI：

  10.1134/s106816201206009x
• 作为产物：
  描述：

  6,9-二氯-2-甲氧基吖啶 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 33.0h， 生成 N-[2-(tert-butyldimethylsilyloxy)ethyl]-N’-[6-chloro-2-methoxyacridine-9-yl]ethylenediamine
  参考文献：
  名称：

  Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion

  摘要：

  Non-nucleotide phosporamidites were synthetized, having a branching backbone with different positions for functional groups. Phosphoramidite monomers obtained contain intercalator moiety, 6-chloro-2-methoxyacridine, and additional hydroxyl residue protected with dimethoxytrityl group or with the tert-butyldimethylsilyl group for post-synthetic modification. Oligothymidilates containing one or more modified units in different positions of the sequence were synthesized. The melting point and thermodynamic parameters of the formation of complementary duplexes formed by modified oligonucleotides were defined (change in enthalpy and entropy). The introduction of intercalating residue causes a significant stabilization of DNA duplexes. It is shown that the efficiency of the fluorescence of acridine residue in the oligonucleotide conjugate significantly changes upon hybridization with DNA.

  DOI：

  10.1134/s106816201206009x

文献信息

• A convenient method for the synthesis of phosphoramidite non-nucleotide inserts for preparation of functionalized oligonucleotides
  作者：M. S. Kupryushkin、D. V. Pyshnyi

  DOI：10.1134/s1068162012060106

  日期：2012.11

  A simple approach to the synthesis of amidophosphite synthons of achiral non-nucleotide inserts using 4-(2-(4,4'-dimethoxytrityloxy)ethyl)morpholine-2,3-dione as a backbone of key precursor was suggested. Non-nucleotide synthons were synthesized using this approach that were suitable for synthesis of acridine-containing oligonucleotide derivatives, as well as oligonucleotides with branched carbohydrate-phosphate backbone.