6-N-benzoyl-5'-O-[di(2-cyanoethoxy)phosphinyl]-P-(2-cyanoethyl)-2'-deoxyadenylyl-(3'->5')-6-N,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine | 787552-80-1

• 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-5'-O-[di(2-cyanoethoxy)phosphinyl]-P-(2-cyanoethyl)-2'-deoxyadenylyl-(3'->5')-6-N,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine
• CAS: 787552-80-1
• 化学式: C₅₀H₄₇N₁₃O₁₄P₂
• 分子量: 1115.95
• InChiKey: RFDLPDPBECYTSJ-YZTFJACTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  79.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  351.05
• 氢给体数：
  2.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-5'-O-[di(2-cyanoethoxy)phosphinyl]-P-(2-cyanoethyl)-2'-deoxyadenylyl-(3'->5')-6-N,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine 在 ammonium hydroxide 作用下， 反应 24.0h， 以69.4%的产率得到5'-O-phosphoryl-2'-deoxyadenylyl-(3'->5')-1'-deoxy-2'-isoadenosine
  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：

  双(2-氰乙基)-N,N-二异丙基亚磷酰胺 在 吡啶 、 四氮唑 、 水 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-N-benzoyl-5'-O-[di(2-cyanoethoxy)phosphinyl]-P-(2-cyanoethyl)-2'-deoxyadenylyl-(3'->5')-6-N,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine
  参考文献：
  名称：

  Inhibition of the strand transfer step of HIV-1 integrase by non-natural dinucleotides

  摘要：

  New, non-natural dinucleotide 5'-monophosphates, with a surrogate isonucleoside component Of L-related stereochemistry at the 'terminal' position, have been synthesized. Structures of 2a-c were confirmed by multinuclear NMR spectra (H-1, C-13, (31)p, COSY), UV hypochromicity and FAB HRMS data. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. The dinucleotides 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 selective strand transfer inhibitors of HIV integrase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.050