5-(1-adamantyl)uracil | 156899-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(1-adamantyl)uracil
• 英文别名: 5-Adamantyluracil；5-(1-adamantyl)-1H-pyrimidine-2,4-dione
• CAS: 156899-86-4
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: IRPQHEAMCQGUIS-UHFFFAOYSA-N

物化性质

• 密度：
  1.291±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(1-adamantyl)uracil 在 硫酸 、 三氟乙酸酐 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以86%的产率得到5-(3-hydroxyadamantan-1-yl)uracil
  参考文献：
  名称：

  官能化的5-（3 - R -1-金刚烷基）尿嘧啶及其相关化合物的合成

  摘要：

  描述了功能化的5-（3 - R -1-金刚烷基）尿嘧啶和相关化合物（R = OH，COOH，NH 2等）的有效合成方法。在三氟乙酸酐中用H 2 SO 4将5-（1-金刚烷基）尿嘧啶中金刚烷叔C–H键的选择性羟基化用作关键步骤。5-（3-羟基-1-金刚烷基）尿嘧啶与N和C亲核试剂在CF 3 COOH，H 2 SO 4或H 2 SO 4中的随后亲电反应/ AcOH介质制得的金刚烷核中具有酰胺，氨基，芳基，羧基和硫脲基的衍生物。对抗病毒活性的初步评估表明，一些合成的物种在Vero细胞中显示出对HSV-1（SI〜20）的中等抗病毒活性。

  DOI：

  10.1016/j.tet.2010.02.043
• 作为产物：
  描述：

  2-(1-金刚烷基)乙酸甲酯 在 氯乙酸 、 lithium hexamethyldisilazane 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 5-(1-adamantyl)uracil
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines

  摘要：

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.

  DOI：

  10.1080/15257779408013234

文献信息

• Synthesis and antiherpetic activity of adamantyl-containing nucleoside analogs
  作者：É. A. Shokova、L. M. Alimbarova、V. V. Kovalev

  DOI：10.1007/bf02508710

  日期：1999.7

  numerous pyrimidine derivatives (in particular, 2'-deoxyuridine analogs) modified with respect to both the nucleic acid residue and the sugar fragment [4 8]. The synthesis of acyctovir has stimulated the search for new antiviral agents in the series of acyclic ufidine analogs [9]. However, we failed to find any published data on the synthesis and biological properties of nucleoside analogs with framework

  研究人员对合成核苷化合物的兴趣在很大程度上可以通过这些制剂成功用于治疗病毒和肿瘤疾病来解释。尤其是3'-azido-2',3'dideoxythymidine（叠氮胸苷）能够强烈抑制HIV-1感染，在临床条件下被广泛用于治疗艾滋病患者。2-氨基-9-[(2羟基乙氧基)甲基]-6,9-二氢-1H-嘌呤（阿昔洛韦或阿昔洛韦）已被证明是对抗HSV感染的有效药物[1 -3 ]。还合成和测试了许多在核酸残基和糖片段方面都经过修饰的嘧啶衍生物（特别是 2'-脱氧尿苷类似物）[4-8]。acyctovir 的合成刺激了在无环乌定类似物系列中寻找新的抗病毒药物 [9]。然而，我们未能找到有关在核碱基中具有框架取代基的核苷类似物的合成和生物学特性的任何已发表数据。同时，人们可以预期，金刚烷片段会显着改变这些化合物的构象和理化性质，从而影响它们与细胞膜的相互作用，从而显着改变初始物质的底物性质 [10, 11]
• The Synthesis of Some 5-Alkyl (Cycloalkyl)-Substituted 2′ -Deoxy-4′-Thiouridines
  作者：I. Basnak、M. Sun、P. L. Coe、R. T. Walker

  DOI：10.1080/07328319608002375

  日期：1996.1

  The silylated pyrimidine bases IIa-d were condensed with the benzyl 3,5-di-O-benzyl-2-deoxy-1,4-ditkio-D-erythro-pentofuranoside III in acetonitrile under activation by N-iodosuccinimide, giving ca 1.5 : 1/alpha: beta anomeric mixtures of the blocked nucleosides IVa-d and Va-d. in yields of 55-88%. After the separation on a silica column the pure anomers were deprotected by BCl3 or TiCl4, providing the free nucleosides VIa-d and VIIa,c,d in moderate to good overall yields. The beta- or alpha-anomeric configuration, anti-glycosidic conformation and prevailing C2'-endo(S) thiosugar pucker in the synthesized compounds were established by the combined use of the H-1, C-13 NMR and X-ray crystallography.
• Synthesis of functionalized 5-(3-R-1-adamantyl)uracils and related compounds
  作者：Alexander Shmailov、Ludmila Alimbarova、Elvira Shokova、Viktor Tafeenko、Ivan Vatsouro、Vladimir Kovalev

  DOI：10.1016/j.tet.2010.02.043

  日期：2010.4

  synthetic approaches to functionalized 5-(3-R-1-adamantyl)uracils and related compounds (R=OH, COOH, NH2, etc.) are described. The selective hydroxylation of the adamantane tertiary C–H bonds in 5-(1-adamantyl)uracils with H2SO4 in trifluoroacetic anhydride is used as the key step. Subsequent electrophilic reactions of 5-(3-hydroxy-1-adamantyl)uracils with N- and C-nucleophiles in CF3COOH, H2SO4 or H2SO4/AcOH

  描述了功能化的5-（3 - R -1-金刚烷基）尿嘧啶和相关化合物（R = OH，COOH，NH 2等）的有效合成方法。在三氟乙酸酐中用H 2 SO 4将5-（1-金刚烷基）尿嘧啶中金刚烷叔C–H键的选择性羟基化用作关键步骤。5-（3-羟基-1-金刚烷基）尿嘧啶与N和C亲核试剂在CF 3 COOH，H 2 SO 4或H 2 SO 4中的随后亲电反应/ AcOH介质制得的金刚烷核中具有酰胺，氨基，芳基，羧基和硫脲基的衍生物。对抗病毒活性的初步评估表明，一些合成的物种在Vero细胞中显示出对HSV-1（SI〜20）的中等抗病毒活性。
• The Synthesis of Some 5-Substituted and 5,6-Disubstituted 2′-Deoxyuridines
  作者：I. Basnak、A. Balkan、P. L. Coe、R. T. Walker

  DOI：10.1080/15257779408013234

  日期：1994.3

  5-Alkyl(cycloalkyl)-2'-deoxyuridines VIa-VIf were synthesised in high yields by condensation of the corresponding silylated bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform and subsequent deblocking with sodium methoxide in methanol. The beta-configuration, anti-glycosidic conformation and C2'-endo (S) sugar pucker of all of these compounds has been established from their H-1 NMR, C-13 NMR, UV and mass spectra. Under the same conditions, the condensation of silylated 5,6-trimethyleneuracil, resulted in 1:2/alpha:beta anomeric mixture (overall yield 71%) and syn-conformation of the 5,6-trimethylene-2'-deoxyuridine [Xg]. The results of the condensation of the silylated 5,6-dimethyluracil are discussed as well. No significant antiviral activity has been found in testing the synthesised compounds against a range of herpes, influenza and HIV-1 viruses.