3-bromo-2-(2-deoxy-β-D-erythro-pentafuranosyl)-4-[(dimethylamino)ethylidene]-2H-pyrazolo[3,4-d]pyrimidin-4-amine | 296800-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-bromo-2-(2-deoxy-β-D-erythro-pentafuranosyl)-4-[(dimethylamino)ethylidene]-2H-pyrazolo[3,4-d]pyrimidin-4-amine
• 英文别名: N'-[3-bromo-2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethylethanimidamide
• CAS: 296800-34-5
• 化学式: C₁₄H₁₉BrN₆O₃
• 分子量: 399.247
• InChiKey: AFKDBJAAMHIMFG-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  108.89
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-bromo-2-(2-deoxy-β-D-erythro-pentafuranosyl)-4-[(dimethylamino)ethylidene]-2H-pyrazolo[3,4-d]pyrimidin-4-amine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.5h， 生成 3-bromo-2-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentafuranosyl]-4-[(dimethylamino)ethylidene]-2H-pyrazolo[3,4-d]pyrimidin-4-amine 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Base-Pairing Properties of 8-Aza-7-deazaadenine Linked via the 8-Position to the DNA Backbone

  摘要：

  The base-pairing properties of oligonucleotides containing the unusual N-8-linked 8-aza-7-deazaadenine 2'-deoxyribonucleoside (2a) as well as its 7-bromo derivative 2b are described. The oligonucleotides were prepared by solid-phase synthesis employing phosphoramidite chemistry. Compound 2a forms a strong base pair with T-d for which a reverse Watson-Crick pair is suggested (Fig. 9). Compound 2a displays a lower N-glycosylic-bond stability than its Ng-nucleoside and shows strong stacking interactions when incorporated into oligonucleotides. The replacement of 2'-deoxyadenosine by 2a does not significantly influence the duplex stability. However, this behavior depends on the position of the incorporation.

  DOI：

  10.1002/1522-2675(20000705)83:7<1437::aid-hlca1437>3.0.co;2-u
• 作为产物：
  描述：

  3-溴-4-甲氧基-1H-吡唑并[3,4-d]嘧啶 在 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 3-bromo-2-(2-deoxy-β-D-erythro-pentafuranosyl)-4-[(dimethylamino)ethylidene]-2H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Base-Pairing Properties of 8-Aza-7-deazaadenine Linked via the 8-Position to the DNA Backbone

  摘要：

  The base-pairing properties of oligonucleotides containing the unusual N-8-linked 8-aza-7-deazaadenine 2'-deoxyribonucleoside (2a) as well as its 7-bromo derivative 2b are described. The oligonucleotides were prepared by solid-phase synthesis employing phosphoramidite chemistry. Compound 2a forms a strong base pair with T-d for which a reverse Watson-Crick pair is suggested (Fig. 9). Compound 2a displays a lower N-glycosylic-bond stability than its Ng-nucleoside and shows strong stacking interactions when incorporated into oligonucleotides. The replacement of 2'-deoxyadenosine by 2a does not significantly influence the duplex stability. However, this behavior depends on the position of the incorporation.

  DOI：

  10.1002/1522-2675(20000705)83:7<1437::aid-hlca1437>3.0.co;2-u