6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazole<3,4-d>pyrimidin-4-one | 183274-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazole<3,4-d>pyrimidin-4-one
• 英文别名: 6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one；6-amino-3-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 183274-52-4
• 化学式: C₁₀H₁₂BrN₅O₄
• 分子量: 346.14
• InChiKey: BXXBFAKOTMFIJS-VPENINKCSA-N

物化性质

• 密度：
  2.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazole<3,4-d>pyrimidin-4-one 在 吡啶 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 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：

  4-氯-1H-吡唑并[3,4-D]嘧啶-6-胺 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium isopropylate 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 异丙醇 、 乙腈 为溶剂， 反应 8.0h， 生成 6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazole<3,4-d>pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of 7-Halogenated 8-Aza-7-deaza-2′-deoxyguanosines and Related Pyrazolo[3,4-d]pyrimidine 2′-Deoxyribonucleosides

  摘要：

  描述了8-氮杂-7-脱氮-2′-去氧鸟苷（2, 3）的7-溴和7-碘衍生物的合成，以及卤化的4-烷氧基衍生物4a-c和5a-c。将7a-c或8a-c的卤化吡唑[3,4-d]嘧啶阴离子与2-去氧-3,5-二-O-(对甲苯酰基)-α-d-赤糖善氟糖氯化物（9）进行糖苷化反应，得到区域异构糖苷化产物，N(1)-异构体10a-c和11a-c，以及N(2)-化合物12a-c。后者异构体在无水氢氧化钾存在下糖苷化时失去卤素。在无水条件下（氢化钠）生成了10c、11c以及卤化的N(2)-异构体13a,b。化合物10a-c和11a-c被去保护并转化为4-烷氧基核糖苷4a-c和5a-c。N(1)-核糖苷4c和5c被水解，得到8-氮杂-7-脱氮-2′-去氧鸟苷的7-溴或7-碘衍生物2和3。与常规的2′-去氧核糖核苷不同，吡唑[3,4-d]嘧啶2′-去氧核糖核苷的糖部分在溶液中显示出优先的N型扭曲（3T2），这种构象在固态中也得到了验证。

  DOI：

  10.1055/s-1998-4483

文献信息

• TheHigh-Anti Conformation of 7-Halogenated 8-Aza-7-deaza-2′-deoxy-guanosines: A Study of the Influence of Modified Bases on the Sugar Structure of Nucleosides
  作者：Frank Seela、Georg Becher、Helmut Rosemeyer、Hans Reuter、Guido Kastner、Igor A. Mikhailopulo

  DOI：10.1002/(sici)1522-2675(19990113)82:1<105::aid-hlca105>3.0.co;2-3

  日期：1999.1.13

  The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.
• 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.
• Seela, Frank; Ramzaeva, Natalya; Becher, Georg, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S258 - S261
  作者：Seela, Frank、Ramzaeva, Natalya、Becher, Georg

  DOI：——

  日期：——