4-甲氧基-3H-咪唑并[2,1-b]嘌呤 | 62962-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 4-甲氧基-3H-咪唑并[2,1-b]嘌呤
• 英文名称: N²,3-etheno-O⁶-methylguanine
• 英文别名: 4-methoxy-3H-imidazo[2,1-b]purine
• CAS: 62962-40-7
• 化学式: C₈H₇N₅O
• 分子量: 189.176
• InChiKey: KCTFIUPJRAPVQN-UHFFFAOYSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基-3H-咪唑并[2,1-b]嘌呤 在 盐酸 作用下， 以 水 为溶剂， 生成 3,5-二氢咪唑并[2,1-b]嘌呤-4-酮
  参考文献：
  名称：

  三环核苷类似物及其核苷作为嘌呤核苷磷酸化酶的底物。II 鸟嘌呤和异鸟嘌呤衍生物

  摘要：

  使用标准方法制备和纯化鸟嘌呤、O6-甲基鸟嘌呤和异鸟嘌呤的乙烯衍生物。在反向（合成）途径中，将标题化合物作为来自各种来源的嘌呤核苷磷酸化酶的潜在底物进行检测。发现 1,N2-乙烯-鸟嘌呤和 1,N6-乙烯-异鸟嘌呤是大肠杆菌嘌呤核苷磷酸化酶 (PNP) 的优良底物，而 O6-甲基-N2,3-乙烯-鸟嘌呤表现出中等活性与这种酶。后两种化合物在中性水性介质中显示出强烈的荧光，相应的核糖基化产物也是如此。相比之下，来自小牛脾脏的 PNP 对 1,N6-乙烯异鸟嘌呤仅表现出适度的活性；其余的化合物没有被这种酶核糖基化。1的酶促核糖基化，N6-乙烯异鸟嘌呤使用两种形式的小牛 PNP（野生型和 N243D）和大肠杆菌 PNP（野生型和 D204N）得到三种不同的产物，根据 NMR 分析和与异鸟苷产物的比较进行鉴定与氯乙醛反应，得到基本上单一的化合物，明确鉴定为 N9-核糖苷。以野生型大肠杆菌酶为催化剂

  DOI：

  10.3390/molecules24081493
• 作为产物：
  描述：

  鸟苷 在 吡啶 、 咪唑 、 三甲基氯硅烷 、 sodium acetate 、 溶剂黄146 、 三氟乙酸酐 、 potassium iodide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 126.25h， 生成 4-甲氧基-3H-咪唑并[2,1-b]嘌呤
  参考文献：
  名称：

  N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization

  摘要：

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).

  DOI：

  10.1021/jo00061a033

文献信息

• Tri-Cyclic Nucleobase Analogs and their Ribosides as Substrates of Purine-Nucleoside Phosphorylases. II Guanine and Isoguanine Derivatives
  作者：Stachelska-Wierzchowska、Wierzchowski、Górka、Bzowska、Wielgus-Kutrowska

  DOI：10.3390/molecules24081493

  日期：——

  displayed intense fluorescence in neutral aqueous medium, and so did the corresponding ribosylation products. By contrast, PNP from calf spleens exhibited only modest activity towards 1,N6-etheno-isoguanine; the remaining compounds were not ribosylated by this enzyme. The enzymatic ribosylation of 1,N6-etheno-isoguanine using two forms of calf PNP (wild type and N243D) and E. coli PNP (wild type and D204N)

  使用标准方法制备和纯化鸟嘌呤、O6-甲基鸟嘌呤和异鸟嘌呤的乙烯衍生物。在反向（合成）途径中，将标题化合物作为来自各种来源的嘌呤核苷磷酸化酶的潜在底物进行检测。发现 1,N2-乙烯-鸟嘌呤和 1,N6-乙烯-异鸟嘌呤是大肠杆菌嘌呤核苷磷酸化酶 (PNP) 的优良底物，而 O6-甲基-N2,3-乙烯-鸟嘌呤表现出中等活性与这种酶。后两种化合物在中性水性介质中显示出强烈的荧光，相应的核糖基化产物也是如此。相比之下，来自小牛脾脏的 PNP 对 1,N6-乙烯异鸟嘌呤仅表现出适度的活性；其余的化合物没有被这种酶核糖基化。1的酶促核糖基化，N6-乙烯异鸟嘌呤使用两种形式的小牛 PNP（野生型和 N243D）和大肠杆菌 PNP（野生型和 D204N）得到三种不同的产物，根据 NMR 分析和与异鸟苷产物的比较进行鉴定与氯乙醛反应，得到基本上单一的化合物，明确鉴定为 N9-核糖苷。以野生型大肠杆菌酶为催化剂
• N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization
  作者：Rajesh Khazanchi、Pei Lin Yu、Francis Johnson

  DOI：10.1021/jo00061a033

  日期：1993.4

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).