3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one | 215178-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: N-[3-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]-2-methylpropanamide
• CAS: 215178-26-0
• 化学式: C₁₄H₁₈BrN₅O₅
• 分子量: 416.231
• InChiKey: GLIKTTOUVVJFLF-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 3-bromo-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1,5-dihydro-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Stabilisation of duplex DNA by 7-halogenated 8-aza-7-deazaguanines

  摘要：

  含有 7 卤化 8-aza-7-deaza-2′-deoxyguanosine (c7z8Gd) 衍生物的寡核苷酸，如 d(Br7c7z8 G-C)4 8（Tm = 88 ℃）和 d(I7c7z8 G-C)4 9（Tm = 84 ℃），比 d(G-C)4 5（Tm = 59 ℃）稳定得多。

  DOI：

  10.1039/a804414g
• 作为产物：
  描述：

  异丁酸酐 、 6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazole<3,4-d>pyrimidin-4-one 在 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以64%的产率得到3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Stabilisation of duplex DNA by 7-halogenated 8-aza-7-deazaguanines

  摘要：

  含有 7 卤化 8-aza-7-deaza-2′-deoxyguanosine (c7z8Gd) 衍生物的寡核苷酸，如 d(Br7c7z8 G-C)4 8（Tm = 88 ℃）和 d(I7c7z8 G-C)4 9（Tm = 84 ℃），比 d(G-C)4 5（Tm = 59 ℃）稳定得多。

  DOI：

  10.1039/a804414g

文献信息

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

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1640::aid-hlca1640>3.0.co;2-n

  日期：1999.10.6

  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.