7-(2-deoxy-β-D-erythropentofuranosyl)imidazo[1,2-c]-7H-pyrazolo[4,3-e]pyrimidine | 736138-67-3

• 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: 7-(2-deoxy-β-D-erythropentofuranosyl)imidazo[1,2-c]-7H-pyrazolo[4,3-e]pyrimidine
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(3,6,8,10,11-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl)oxolan-3-ol
• CAS: 736138-67-3
• 化学式: C₁₂H₁₃N₅O₃
• 分子量: 275.267
• InChiKey: URLJFIJPHMMCGT-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(2-deoxy-β-D-erythropentofuranosyl)imidazo[1,2-c]-7H-pyrazolo[4,3-e]pyrimidine 在 吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 sodium acetate buffer 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.58h， 生成 7-[2-deoxy-5-O-(4,4'-dimethoxytriphenyl)methyl-β-D-erythropentofuranosyl]-4-isobutyrylamino-7H-pyrazolo[3,4-d][1,2,3]triazine-3'-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]
  参考文献：
  名称：

  Pyrazolo[3,4-d][1,2,3]triazine DNA:  Synthesis and Base Pairing of 7-Deaza-2,8-diaza-2‘-deoxyadenosine

  摘要：

  7-Deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N-6-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced "etheno" moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which was employed in solid-phase oligonucleotide synthesis. Base pairing studies on 4, incorporated in a 12-mer duplex, showed that this adenine nucleoside analogue forms a strong base pair with dG but not with dT. This novel base pair is as stable as that of the canonical dA-dT pair. As a result of the absence of nitrogen-7 compound 4 is expected to form a face to face base pair with dG.

  DOI：

  10.1021/jo040150i
• 作为产物：
  描述：

  氯乙醛 、 8-aza-7-deaza-2'-deoxyadenosine 在 sodium acetate buffer 作用下， 以 水 为溶剂， 反应 70.0h， 以82%的产率得到7-(2-deoxy-β-D-erythropentofuranosyl)imidazo[1,2-c]-7H-pyrazolo[4,3-e]pyrimidine
  参考文献：
  名称：

  Pyrazolo[3,4-d][1,2,3]triazine DNA:  Synthesis and Base Pairing of 7-Deaza-2,8-diaza-2‘-deoxyadenosine

  摘要：

  7-Deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N-6-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced "etheno" moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which was employed in solid-phase oligonucleotide synthesis. Base pairing studies on 4, incorporated in a 12-mer duplex, showed that this adenine nucleoside analogue forms a strong base pair with dG but not with dT. This novel base pair is as stable as that of the canonical dA-dT pair. As a result of the absence of nitrogen-7 compound 4 is expected to form a face to face base pair with dG.

  DOI：

  10.1021/jo040150i

文献信息

• Pyrazolo[3,4-<i>d</i>][1,2,3]triazine DNA:  Synthesis and Base Pairing of 7-Deaza-2,8-diaza-2‘-deoxyadenosine
  作者：Frank Seela、Meike Lindner、Virginie Glaçon、Wenqing Lin

  DOI：10.1021/jo040150i

  日期：2004.7.1

  7-Deaza-2,8-diaza-2'-deoxyadenosine (4) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1) via the 1,N-6-etheno derivative 5. Ring opening with sodium hydroxide followed by ring closure in the presence of sodium nitrite formed the tricyclic intermediate 5 from which the transiently introduced "etheno" moiety was removed with NBS. Compound 4 was converted to the phosphoramidite 11, which was employed in solid-phase oligonucleotide synthesis. Base pairing studies on 4, incorporated in a 12-mer duplex, showed that this adenine nucleoside analogue forms a strong base pair with dG but not with dT. This novel base pair is as stable as that of the canonical dA-dT pair. As a result of the absence of nitrogen-7 compound 4 is expected to form a face to face base pair with dG.