5-iodo-5'-chloro-2',5'-dideoxyuridine | 219556-74-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 5-iodo-5'-chloro-2',5'-dideoxyuridine
• 英文别名: 1-[(2R,4S,5S)-5-(chloromethyl)-4-hydroxy-tetrahydrofuran-2-yl]-5-iodo-pyrimidine-2,4-dione；1-[(2R,4S,5S)-5-(chloromethyl)-4-hydroxyoxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 219556-74-8
• 化学式: C₉H₁₀ClIN₂O₄
• 分子量: 372.547
• InChiKey: QWEPVWJYHVUGRC-RRKCRQDMSA-N

物化性质

• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-iodo-5'-chloro-2',5'-dideoxyuridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-((2R,4S,5S)-5-Chloromethyl-4-hydroxy-tetrahydro-furan-2-yl)-6-octyl-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Bicyclic Nucleoside Inhibitors of Varicella-Zoster Virus: 5′-Chloro and 3′-Chloro Derivatives

  摘要：

  We have recently discovered bicyclic furopyrimidines as potent and selective inhibitors of VZV. In order to investigate the structural requirements for antiviral activity we have succesfully synthesised some 3'-chloro and 5'-chloro derivatives. The compounds have been tested against VZV and CMV, but displayed no significant in vitro activity.

  DOI：

  10.1081/ncn-120022688
• 作为产物：
  描述：

  碘苷 在 四氯化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-iodo-5'-chloro-2',5'-dideoxyuridine
  参考文献：
  名称：

  Modified oligonucleotides with a 5′-5′ interbase semi-rigid junction for alternate strand triplex formation

  摘要：

  Solid-phase synthesis of 5'-5'-linked oligonucleotides with opposite polarities tethered via nucleic bases has been performed using a modified dinucleoside bearing an H-phosphonate group at the 3'-position of one nucleoside and a dimethoxytrityl group-at the 3'-position of the second nucleoside. This system is aimed at forming a base tetrad at the junction in order to provide better stabilization. The linker used between the two 5'-terminal bases in the same plane involves a triple bond in order to rigidify the junction. The two oligonucleotide :chains are either made of natural nucleosides or one of them is built With N3' -->P5' phosphoramidates. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02035-8

文献信息

• Bicyclic Nucleoside Inhibitors of Varicella-Zoster Virus: 5′-Chloro and 3′-Chloro Derivatives
  作者：G. Luoni、C. McGuigan、G. Andrei、R. Snoeck、E. De Clercq、J. Balzarini

  DOI：10.1081/ncn-120022688

  日期：2003.10

  We have recently discovered bicyclic furopyrimidines as potent and selective inhibitors of VZV. In order to investigate the structural requirements for antiviral activity we have succesfully synthesised some 3'-chloro and 5'-chloro derivatives. The compounds have been tested against VZV and CMV, but displayed no significant in vitro activity.
• Modified oligonucleotides with a 5′-5′ interbase semi-rigid junction for alternate strand triplex formation
  作者：Ulysse Asseline、Victoria Roig、Nguyen T. Thuong

  DOI：10.1016/s0040-4039(98)02035-8

  日期：1998.12

  Solid-phase synthesis of 5'-5'-linked oligonucleotides with opposite polarities tethered via nucleic bases has been performed using a modified dinucleoside bearing an H-phosphonate group at the 3'-position of one nucleoside and a dimethoxytrityl group-at the 3'-position of the second nucleoside. This system is aimed at forming a base tetrad at the junction in order to provide better stabilization. The linker used between the two 5'-terminal bases in the same plane involves a triple bond in order to rigidify the junction. The two oligonucleotide :chains are either made of natural nucleosides or one of them is built With N3' -->P5' phosphoramidates. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.