N-(2-hydroxyethyl)-N'-(6-chloro-2-methoxyacridine-9-yl)ethylenediamine | 35365-89-0

• 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-hydroxyethyl)-N'-(6-chloro-2-methoxyacridine-9-yl)ethylenediamine
• 英文别名: 2-[2-(6-chloro-2-methoxy-acridin-9-ylamino)-ethylamino]-ethanol；2-[2-(6-Chlor-2-methoxy-acridin-9-ylamino)-aethylamino]-aethanol；2-Methoxy-6-chlor-9-<2-(2-hydroxyethylamino)-ethylamino>-acridin；2-[2-[(6-Chloro-2-methoxy-acridin-9-yl)amino]ethylamino]ethanol；2-[2-[(6-chloro-2-methoxyacridin-9-yl)amino]ethylamino]ethanol
• CAS: 35365-89-0
• 化学式: C₁₈H₂₀ClN₃O₂
• 分子量: 345.829
• InChiKey: NFFXOJOBSFGXNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-N'-(6-chloro-2-methoxyacridine-9-yl)ethylenediamine 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 8.0h， 生成
  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 、 羟乙基乙二胺 在 苯酚 作用下， 生成 N-(2-hydroxyethyl)-N'-(6-chloro-2-methoxyacridine-9-yl)ethylenediamine
  参考文献：
  名称：

  New Compounds. 6-Chloro-9-[2'-hydroxethylamino)-ethylamino]-2-methoxyacridine

  摘要：

  DOI：

  10.1021/ja01139a600

文献信息

• Synthetic Amebicides. I. Heterocyclic 2,2-Dichloro-N-(2-hydroxyethyl)-N-substituted Acetamides¹
  作者：Edward F. Elslager、Elinor L. Benton、Franklin W. Short、Frank H. Tendick

  DOI：10.1021/ja01595a052

  日期：1956.7
• New Compounds. 6-Chloro-9-[2'-hydroxethylamino)-ethylamino]-2-methoxyacridine
  作者：John Sheehan、Edgar Steck

  DOI：10.1021/ja01139a600

  日期：1952.10
• Oligonucleotide derivatives in nucleic acid hybridization analysis. III. Synthesis and investigation of properties of oligonucleotides, bearing bifunctional non-nucleotide insertion
  作者：M. S. Kupryushkin、D. V. Pyshnyi

  DOI：10.1134/s106816201206009x

  日期：2012.11

  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.