6-amino-3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one | 214770-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-amino-3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 6-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-5H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile
• CAS: 214770-07-7
• 化学式: C₁₁H₁₂N₆O₄
• 分子量: 292.254
• InChiKey: FQPSWZOHCOYORL-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-amino-3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 3-cyano-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1,5-dihydro-6-{[(dimethylamino)methylidene]amino}-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Oligonucleotides Containing Pyrazolo[3,4-d]pyrimidines: The Influence of 7-Substituted 8-Aza-7-deaza-2′-deoxyguanosines on the Duplex Structure and Stability

  摘要：

  Oligonucleotides containing 7-substituted 8-aza-7-deazaguanines (= 6-amino-1,5-dihydro-4H-pyrazolo[3.4-d]pyrimidin-4-ones) were prepared by automated solid-phase synthesis. A series of 7-alkynylated 8-aza-7-deaza-2'-deoxyguanosines (see 4a-d)were synthesized with the 7-iodonucleoside 3c as starting material and by the Pd-0/Cu-I-catalyzed cross-coupling reaction with various alkynes. Phosphoramidites were prepared from the 7-substituted 8-aza-7-deaza-2'-deoxyguanosine derivatives carrying halogeno, cyano, and hexynyl substituents. From the melting profiles of oligonucleotide duplexes. the T-m values as well as the thermodynamic data were determined. A significant duplex stabilization by the 7-substituents was observed for the DNA . DNA duplexes, but not in the case of DNA . RNA hybrids.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1640::aid-hlca1640>3.0.co;2-n
• 作为产物：
  描述：

  氰化亚铜 、 6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-4H-pyrazolo[3,4-d]pyrimidin-4-one 以 吡啶 为溶剂， 反应 7.0h， 以49%的产率得到6-amino-3-cyano-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Facile Synthesis of 2'-Deoxynucleoside Analogs of preQ

  摘要：

  DOI：

  10.1055/s-1998-6088