N-[2-hydroxyethyl]-N-[2-(6-chloro-2-methoxyacridine-9-ylamine)ethyl]-N’,N’-bis[2-(4,4’-dimethoxytrityloxy)ethyl]glutaramide | 1422895-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[2-hydroxyethyl]-N-[2-(6-chloro-2-methoxyacridine-9-ylamine)ethyl]-N’,N’-bis[2-(4,4’-dimethoxytrityloxy)ethyl]glutaramide
• CAS: 1422895-89-3
• 化学式: C₆₉H₇₁ClN₄O₁₀
• 分子量: 1151.8
• InChiKey: HUNBIEIBXGCQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.33
• 重原子数：
  84.0
• 可旋转键数：
  29.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  150.38
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-[2-hydroxyethyl]-N-[2-(6-chloro-2-methoxyacridine-9-ylamine)ethyl]-N’,N’-bis[2-(4,4’-dimethoxytrityloxy)ethyl]glutaramide 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以85%的产率得到N,N-bis[2-(4,4’-dimethoxytrityloxy)ethyl]-N’-[2-(2-cyanoethyloxy-N,N-diisopropyldiisopropylphosphoramiditeoxy)ethyl]-N’-[2-(6-chloro-2-methoxyacridine-9-ylamine)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：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-[2-hydroxyethyl]-N-[2-(6-chloro-2-methoxyacridine-9-ylamine)ethyl]-N’,N’-bis[2-(4,4’-dimethoxytrityloxy)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