2',3',5'-tri-O-acetyl-6-methyl-8-azanebularine | 909907-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',5'-tri-O-acetyl-6-methyl-8-azanebularine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(7-methyltriazolo[4,5-d]pyrimidin-3-yl)oxolan-2-yl]methyl acetate
• CAS: 909907-32-0
• 化学式: C₁₆H₁₉N₅O₇
• 分子量: 393.356
• InChiKey: SNNCPZLWTWJIER-XKVFNRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-6-methyl-8-azanebularine 在 吡啶 、 甲醇 、 氨 、 silver nitrate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-6-methyl-8-azanebularine
  参考文献：
  名称：

  C6-Substituted Analogues of 8-Azanebularine:  Probes of an RNA-Editing Enzyme Active Site

  摘要：

  We describe the synthesis of derivatives of 8-azanebularine, a known inhibitor of adenosine deaminases including the RNA-editing enzyme ADAR2.6-Methyl, 6-hydroxymethyl, 6-cyano, and 6-mercapto derivatives were obtained from 6-bromo precursors using different cross-coupling or substitution reactions. The C6-methyl derivative was incorporated into an RNA substrate for ADAR2 via the phosphoramidite. Quantitative gel mobility shift experiments with the resulting RNA indicate that methylation at C6 dramatically reduces the affinity of 8-azanebularine for ADAR2.

  DOI：

  10.1021/ol061354j
• 作为产物：
  描述：

  四甲基锡 、 2',3',5'-tri-O-acetyl-6-bromo-8-azanebularine 在 四(三苯基膦)钯 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 以57%的产率得到2',3',5'-tri-O-acetyl-6-methyl-8-azanebularine
  参考文献：
  名称：

  C6-Substituted Analogues of 8-Azanebularine:  Probes of an RNA-Editing Enzyme Active Site

  摘要：

  We describe the synthesis of derivatives of 8-azanebularine, a known inhibitor of adenosine deaminases including the RNA-editing enzyme ADAR2.6-Methyl, 6-hydroxymethyl, 6-cyano, and 6-mercapto derivatives were obtained from 6-bromo precursors using different cross-coupling or substitution reactions. The C6-methyl derivative was incorporated into an RNA substrate for ADAR2 via the phosphoramidite. Quantitative gel mobility shift experiments with the resulting RNA indicate that methylation at C6 dramatically reduces the affinity of 8-azanebularine for ADAR2.

  DOI：

  10.1021/ol061354j