6-N-,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine | 787552-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-N-,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine
• CAS: 787552-75-4
• 化学式: C₂₄H₂₁N₅O₅
• 分子量: 459.461
• InChiKey: CGVYDUWEHUUCQU-GGPKGHCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  128.46
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-N-,3'-O-dibenzoyl-1'-deoxy-2'-isoadenosine 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  Benzoic acid (2R,3S,4R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(6-dibenzoylamino-purin-9-yl)-tetrahydro-furan-3-yl ester 在 吡啶 、 ammonium hydroxide 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 6-N-,3'-O-dibenzoyl-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

文献信息

• Inhibition of the strand transfer step of HIV-1 integrase by non-natural dinucleotides
  作者：Guochen Chi、Nouri Neamati、Vasu Nair

  DOI：10.1016/j.bmcl.2004.07.050

  日期：2004.10

  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.