2-((benzoyloxy)methyl)-5-(4,5-diamino-2-oxopyrimidin-1(2H)yl)tetrahydrofuran-3,4-diyl dibenzoate | 914801-62-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2-((benzoyloxy)methyl)-5-(4,5-diamino-2-oxopyrimidin-1(2H)yl)tetrahydrofuran-3,4-diyl dibenzoate
• 英文别名: 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-5-aminocytidine；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4,5-diamino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 914801-62-0
• 化学式: C₃₀H₂₆N₄O₈
• 分子量: 570.558
• InChiKey: NHNJLYROQJFNEK-PMHJDTQVSA-N

物化性质

• 熔点：
  153-157 °C
• 沸点：
  735.0±70.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-((benzoyloxy)methyl)-5-(4,5-diamino-2-oxopyrimidin-1(2H)yl)tetrahydrofuran-3,4-diyl dibenzoate 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-(p-tolyl)-1H-purin-2(9H)-one
  参考文献：
  名称：

  荧光对取代苯基-咪唑并胞苷类似物

  摘要：

  此处描述了修饰的胞苷类似物的合成和光谱性质。为了赋予荧光特性，胞苷荧光团在胞嘧啶5位上通过肉桂基部分扩展（类似物1a – c），或在苯基咪唑环上扩展（类似物3a – d）。这些化合物分别通过Suzuki-Miyaura偶联反应和5-氨基胞苷与对位取代的苯甲醛的缩合反应合成。所有的类似物在蓝色区域为荧光（λ EM：402-436纳米）。在上述类似物中，对-CF 3-苯基-咪唑并胞苷3d被发现是一种很有前途的荧光探针，其量子产率比胞苷大7000倍（Φ = 0.617），并且红移约为。最大发射108 nm（411 nm）。其保留的Watson-Crick氢键键合面使3d可以与鸟苷特异性碱基配对，类似于胞苷。另外，苯基-咪唑并胞苷类似物优选反构象和C 3'-内切（N）糖折叠。这些特性使3d成为吸引人的荧光探针，可潜在地用于核酸化学的各个方面。

  DOI：

  10.1016/j.tet.2013.03.005
• 作为产物：
  描述：

  2-(4-amino-5-nitro-2-oxopyrimidin-1(2H)-yl)-5((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 7.0h， 以38%的产率得到2-((benzoyloxy)methyl)-5-(4,5-diamino-2-oxopyrimidin-1(2H)yl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  荧光对取代苯基-咪唑并胞苷类似物

  摘要：

  此处描述了修饰的胞苷类似物的合成和光谱性质。为了赋予荧光特性，胞苷荧光团在胞嘧啶5位上通过肉桂基部分扩展（类似物1a – c），或在苯基咪唑环上扩展（类似物3a – d）。这些化合物分别通过Suzuki-Miyaura偶联反应和5-氨基胞苷与对位取代的苯甲醛的缩合反应合成。所有的类似物在蓝色区域为荧光（λ EM：402-436纳米）。在上述类似物中，对-CF 3-苯基-咪唑并胞苷3d被发现是一种很有前途的荧光探针，其量子产率比胞苷大7000倍（Φ = 0.617），并且红移约为。最大发射108 nm（411 nm）。其保留的Watson-Crick氢键键合面使3d可以与鸟苷特异性碱基配对，类似于胞苷。另外，苯基-咪唑并胞苷类似物优选反构象和C 3'-内切（N）糖折叠。这些特性使3d成为吸引人的荧光探针，可潜在地用于核酸化学的各个方面。

  DOI：

  10.1016/j.tet.2013.03.005

文献信息

• Synthesis and Antiviral Activity of 5-Substituted Cytidine Analogues:  Identification of a Potent Inhibitor of Viral RNA-Dependent RNA Polymerases
  作者：Daniel A. Harki、Jason D. Graci、Jessica E. Galarraga、William J. Chain、Craig E. Cameron、Blake R. Peterson

  DOI：10.1021/jm060872x

  日期：2006.10.1

  As part of our studies of lethal viral mutagens, a series of 5-substituted cytidine analogues were synthesized and evaluated for antiviral activity. Among the compounds examined, 5-nitrocytidine was effective against poliovirus (PV) and coxsackievirus B3 (CVB3) and exhibited greater activity than the clinically employed drug ribavirin. Instead of promoting viral mutagenesis, 5-nitrocytidine triphosphate inhibited PV RNA-dependent RNA polymerase (K-d = 1.1 +/- 0.1 mu M), and this inhibition is sufficient to explain the observed antiviral activity.
• Phenyl-imidazolo-cytidine Analogues: Structure–Photophysical Activity Relationship and Ability To Detect Single DNA Mismatch
  作者：Marina Kovaliov、Michal Weitman、Dan Thomas Major、Bilha Fischer

  DOI：10.1021/jo5011944

  日期：2014.8.1

  To expand the arsenal of fluorescent cytidine analogues for the detection of genetic material, we synthesized para-substituted phenyl-imidazolo-cytidine ((Ph)ImC) analogues 5a-g and established a relationship between their structure and fluorescence properties. These analogues were more emissive than cytidine (λem 398-420 nm, Φ 0.009-0.687), and excellent correlation was found between Φ of 5a-g and σp(-) of the substituent on the phenyl-imidazolo moiety (R(2) = 0.94). Calculations suggested that the dominant tautomer of (Ph)ImC in methanol solution is identical to that of cytidine. DFT calculations of the stable tautomer of selected (Ph)ImC analogues suggested a relationship between the HOMO-LUMO gap and Φ and explained the loss of fluorescence in the nitro analogue. Incorporation of the CF3-(Ph)ImdC analogue into a DNA probe resulted in 6-fold fluorescence quenching of the former. A 17-fold reduction of fluorescence was observed for the G-matched duplex vs ODN(CF3-(Ph)ImdC), while for A-mismatched duplex, only a 2-fold decrease was observed. Furthermore, since the quantum yield of ODN(CF3-(Ph)ImdC):ODN(G) was reduced 17-fold vs that of a single strand, whereas that of ODN(CF3-(Ph)ImdC):ORN(G) was reduced only 3.8-fold, ODN(CF3-(Ph)ImdC) appears to be a DNA-selective probe. We conclude that the ODN(CF3-(Ph)ImdC) probe, exhibiting emission sensitivity upon single nucleotide replacement, may be potentially useful for DNA single nucleotide polymorphism (SNP) typing.
• Fluorescent p-substituted-phenyl-imidazolo-cytidine analogues
  作者：Marina Kovaliov、Meirav Segal、Bilha Fischer

  DOI：10.1016/j.tet.2013.03.005

  日期：2013.5

  The synthesis and spectral properties of modified cytidine analogues are described here. To confer fluorescent properties, the cytidine fluorophore was extended by a cinnamyl moiety at the cytidine 5-position, (analogues 1a–c), or extended by a phenyl-imidazolo ring, (analogues 3a–d). Those compounds were synthesized via the Suzuki–Miyaura coupling reaction and via condensation of 5-amino-cytidine

  此处描述了修饰的胞苷类似物的合成和光谱性质。为了赋予荧光特性，胞苷荧光团在胞嘧啶5位上通过肉桂基部分扩展（类似物1a – c），或在苯基咪唑环上扩展（类似物3a – d）。这些化合物分别通过Suzuki-Miyaura偶联反应和5-氨基胞苷与对位取代的苯甲醛的缩合反应合成。所有的类似物在蓝色区域为荧光（λ EM：402-436纳米）。在上述类似物中，对-CF 3-苯基-咪唑并胞苷3d被发现是一种很有前途的荧光探针，其量子产率比胞苷大7000倍（Φ = 0.617），并且红移约为。最大发射108 nm（411 nm）。其保留的Watson-Crick氢键键合面使3d可以与鸟苷特异性碱基配对，类似于胞苷。另外，苯基-咪唑并胞苷类似物优选反构象和C 3'-内切（N）糖折叠。这些特性使3d成为吸引人的荧光探针，可潜在地用于核酸化学的各个方面。