1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-3-(3-trifluoroacetamidopropynyl)-4H-pyrazolo[3,4-d]-pyrimidin-4-one | 1403243-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-3-(3-trifluoroacetamidopropynyl)-4H-pyrazolo[3,4-d]-pyrimidin-4-one
• CAS: 1403243-79-7
• 化学式: C₁₉H₂₁F₃N₆O₆
• 分子量: 486.408
• InChiKey: KSWRRADMHVDFLY-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  171.46
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-3-(3-trifluoroacetamidopropynyl)-4H-pyrazolo[3,4-d]-pyrimidin-4-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 以98%的产率得到1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-3-(3-trifluoroacetamidoprop-yl)-4H-pyrazolo[3,4-d]-pyrimidin-4-one
  参考文献：
  名称：

  8–17 DNAzyme modified with purine analogs in its catalytic core: The conservation of the five-membered moieties of purine residues

  摘要：

  8-17 DNAzyme is characterized by its recurrence in different in vitro selections and versatile cleavage sites, leading to extensive studies on its structural properties and applications. We evaluated the purine residues (A6, G7, G11, A12, G14, and A15) in the catalytic core of 8-17 DNAzyme of their five-membered ring moiety with purine analogs 1-5 to have an insight into the conservation of the residues at the level of functional groups. The 7-nitrogen atom in the AGC loop was demonstrated to be strictly conserved for the cleavage reaction. But such modifications exerted favorable effect at G11 of the base-pair stem and A12 in the single-strand loop, directing toward more efficient DNAzymes. Even the most conserved G14 could tolerate such modifications. These results demonstrated that chemical modification on the functional groups is a feasible approach to gain an insight into the structural requirement in the catalytic reaction of DNAzymes. It also provided modification sites for introduction of signaling molecules used for mechanistic and folding studies of 8-17 DNAzyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.044
• 作为产物：
  描述：

  N-三氟乙酰基炔丙基胺 、 1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95.3%的产率得到1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-6-[(2-methylpropanoyl)amino]-3-(3-trifluoroacetamidopropynyl)-4H-pyrazolo[3,4-d]-pyrimidin-4-one
  参考文献：
  名称：

  8–17 DNAzyme modified with purine analogs in its catalytic core: The conservation of the five-membered moieties of purine residues

  摘要：

  8-17 DNAzyme is characterized by its recurrence in different in vitro selections and versatile cleavage sites, leading to extensive studies on its structural properties and applications. We evaluated the purine residues (A6, G7, G11, A12, G14, and A15) in the catalytic core of 8-17 DNAzyme of their five-membered ring moiety with purine analogs 1-5 to have an insight into the conservation of the residues at the level of functional groups. The 7-nitrogen atom in the AGC loop was demonstrated to be strictly conserved for the cleavage reaction. But such modifications exerted favorable effect at G11 of the base-pair stem and A12 in the single-strand loop, directing toward more efficient DNAzymes. Even the most conserved G14 could tolerate such modifications. These results demonstrated that chemical modification on the functional groups is a feasible approach to gain an insight into the structural requirement in the catalytic reaction of DNAzymes. It also provided modification sites for introduction of signaling molecules used for mechanistic and folding studies of 8-17 DNAzyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.044