6-N-benzoyl-P-(2-cyanoethyl)-1'-deoxy-2'-isoadenylyl-(3'->5')-4-N,3'-O-dibenzoyl-1'-deoxy-2'-isocytidine | 917598-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-N-benzoyl-P-(2-cyanoethyl)-1'-deoxy-2'-isoadenylyl-(3'->5')-4-N,3'-O-dibenzoyl-1'-deoxy-2'-isocytidine
• CAS: 917598-82-4
• 化学式: C₄₃H₄₀N₉O₁₂P
• 分子量: 905.817
• InChiKey: ODDOGDYYYDFXCQ-HCDQUKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  65.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  270.23
• 氢给体数：
  3.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-P-(2-cyanoethyl)-1'-deoxy-2'-isoadenylyl-(3'->5')-4-N,3'-O-dibenzoyl-1'-deoxy-2'-isocytidine 在 吡啶 、 四氮唑 、 ammonium hydroxide 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 28.17h， 生成 5'-O-phosphoryl-1'-deoxy-2'-isoadenylyl-(3'->5')-1'-deoxy-2'-isocytidine
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.

  DOI：

  10.1080/15257770500265703
• 作为产物：
  描述：

  6-N-benzoyl-1'-deoxy-2'-isoadenosine 在 吡啶 、 四氮唑 、 二氯乙酸 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 6-N-benzoyl-P-(2-cyanoethyl)-1'-deoxy-2'-isoadenylyl-(3'->5')-4-N,3'-O-dibenzoyl-1'-deoxy-2'-isocytidine
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.

  DOI：

  10.1080/15257770500265703