6-N-benzoyl-1',3'-dideoxy-2'-isoadenosine | 172603-77-9

• 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-1',3'-dideoxy-2'-isoadenosine
• CAS: 172603-77-9
• 化学式: C₁₇H₁₇N₅O₃
• 分子量: 339.354
• InChiKey: FKWGOEPHVMMDIR-STQMWFEESA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102.16
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-1',3'-dideoxy-2'-isoadenosine 在 四氮唑 、 碘 、 苯硫酚 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 Phosphoric acid bis-[(2S,4S)-4-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  Dinucleotides Incorporating Isomeric Nucleosides: Synthesis, Structural and Stereochemical Characterization, and Enzymology

  摘要：

  The synthesis, stability toward nucleases, and conformational properties of 3'-->5' and 5'--> 5' dinucleotides bearing an isomeric nucleoside component is described.

  DOI：

  10.1080/07328319708006138
• 作为产物：
  描述：

  Imidazole-1-carbothioic acid O-[(2R,3S,4R)-4-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 6-N-benzoyl-1',3'-dideoxy-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.