8-乙基腺苷 | 69359-47-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 8-乙基腺苷
• 英文名称: 8-ethyl-adenosine
• 英文别名: 8-ethyladenosine；8-Aethyladenosin；(2R,3R,4S,5R)-2-(6-amino-8-ethylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 69359-47-3
• 化学式: C₁₂H₁₇N₅O₄
• 分子量: 295.298
• InChiKey: OOOZBXHUEHEQJT-JJNLEZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-乙基腺苷 在 氯化亚砜 作用下， 以 吡啶 、 乙腈 为溶剂， 以37%的产率得到5'chloro-5'-deoxy-8-ethyladenosine
  参考文献：
  名称：

  New Insights into the Design of Inhibitors of Human S-Adenosylmethionine Decarboxylase: Studies of Adenine C⁸ Substitution in Structural Analogues of S-Adenosylmethionine

  摘要：

  S-adenosylmethionine decarboxylase (AdoMetDC) is a critical enzyme in the polyamine biosynthetic pathway and depends on a pyruvoyl group for the decarboxylation process. The crystal structures of the enzyme with various inhibitors at the active site have shown that the adenine base of the ligands adopts an unusual syn conformation when bound to the enzyme. To determine whether compounds that favor the syn conformation in solution would be more potent AdoMetDC inhibitors, several series of AdoMet substrate analogues with a variety of substituents at the 8-position of adenine were synthesized and analyzed for their ability to inhibit hAdoMetDC. The biochemical analysis indicated that an 8-methyl substituent resulted in more potent inhibitors, yet most other 8-substitutions provided no benefit over the parent compound. To understand these results, we used computational modeling and X-ray crystallography to study C(8)-substituted adenine analogues bound in the active site.

  DOI：

  10.1021/jm801126a
• 作为产物：
  描述：

  5'-O-acetyl-2',3'-O-isopropylidene-8-methylsulfonyladenosine 在 sodium hydroxide 、 甲酸 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 8-乙基腺苷
  参考文献：
  名称：

  Nucleosides and nucleotides. LVIII. Synthesis of 8-alkyladenosines, 8,2'-anhydro-8-hydroxymethyl-9-(.BETA.-D-arabinofuranosyl)adenine and related compounds.

  摘要：

  介绍了 8-烷基腺苷和相关核苷的合成。将 5'-O-乙酰基-2'，3'-O-异亚丙基-8-甲磺酰基腺苷与钠基乙酰乙酸乙酯进行处理，可得到 8-乙氧羰基甲基衍生物（1）。对 1 进行水解脱羧，然后进行脱乙酰基反应，可得到高产率的 8-甲基腺苷（2）。用甲基或乙基碘对 1 进行烷基化，然后进行水解脱羧，可分别得到 8-乙基和 8-丙基腺苷。尝试对 1 的 8-亚甲基进行二甲基化会生成 N6-二甲基腺苷衍生物。使用甲基碘和氢化钠的组合，可以选择性地对 2'-脱氧腺苷和 2'-脱氧胞苷的氨基进行二甲基化，而不会对这些核苷的糖羟基进行甲基化。8, 2'-脱水-9-β-D-阿拉伯呋喃糖基-8-羟甲基腺嘌呤是由 8-氰基腺苷衍生物通过碱处理 8-羟甲基-2'-对甲苯磺酰基腺苷形成氢键的过程制备的。讨论了 8-烷基腺苷的圆二色性光谱特征。

  DOI：

  10.1248/cpb.33.3263

文献信息

• Straightforward C-8 alkylation of adenosine analogues with tetraalkyltin reagents
  作者：Petros Mamos、Arthur A. Van Aerschot、nancy J. Weyns、Piet A. Herdewijn

  DOI：10.1016/s0040-4039(00)74226-2

  日期：1992.4

  A one step synthesis of the 8-methyl-, 8-ethyl -and 8-vinyl derivatives of adenosine, 2′-deoxyadenosine and 2′,3′-dideoxyadenosine starting from the readily available 8-bromo congeners is described. This reaction makes use of a transient silylation procedure and a Pd(0) catalysed cross-coupling with tetraorganotin reagents.

  描述了从容易获得的8-溴同源物开始的腺苷，2'-脱氧腺苷和2'，3'-二脱氧腺苷的8-甲基，8-乙基和8-乙烯基衍生物的一步合成。该反应利用了瞬态甲硅烷基化程序和Pd（0）催化与四有机锡试剂的交叉偶联。
• Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents
  作者：Arthur A. Van Aerschot、Petros Mamos、Nancy J. Weyns、Satoru Ikeda、Erik De Clercq、Piet A. Herdewijn

  DOI：10.1021/jm00072a013

  日期：1993.10

  2-, 6-, And 8-alkylated (methyl, ethyl, and vinyl) adenosine analogues were synthesized by a palladium-catalyzed cross-coupling of a tetraalkyltin with the halogenated purine nucleosides. The synthesis of the 8-substituted analogues was accomplished using a transient protection procedure. The 6-alkylated-9-beta-D-ribofuranosylpurines as well as 2-ethyladenosine were cytotoxic at relatively low concentrations

  通过将四烷基锡与卤代嘌呤核苷进行钯催化的交叉偶联，可合成2-，6-和8-烷基化（甲基，乙基和乙烯基）的腺苷类似物。8-取代类似物的合成使用瞬态保护程序完成。6烷基化的9-β-D-呋喃呋喃糖基嘌呤以及2-乙基腺苷在相对较低的浓度（0.8-10微克/ mL）下具有细胞毒性。8-甲基腺苷是牛痘病毒的有效和选择性抑制剂，而8-乙基和8-乙烯基腺苷对呼吸道合胞病毒具有特异性抑制作用。8-Vinyladenosine显示出对单纯疱疹病毒（1型）的特殊活性。
• Purine Nucleotide Derivatives
  申请人：Undheim Kjell

  公开号：US20080293665A1

  公开（公告）日：2008-11-27

  This invention provides novel 8-carbyl substituted Camps (adenosine 3′,5′-cyclic monophosphorothioate) and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.

  本发明提供了新颖的8-烷基取代的Camps（腺苷3'，5'-环磷酸单硫酸酯）以及制备8-Br-cAMP（一种关键起始物质）的新型程序。
• INHIBITORS OF S-ADENOSYL-L-METHIONINE DECARBOXYLASE
  申请人：Xiang Yibin

  公开号：US20100261668A1

  公开（公告）日：2010-10-14

  Novel mechanism-based inhibitors of S-adenosyl-L-methionine decarboxylase are provided. These compounds of formula (1) inhibit the life cycle of trypanosomes, and are useful to treat subjects infected with African trypanosomes. The invention includes pharmaceutical compositions and methods of using the compounds of formula (1).

  提供了一种基于机理的S-腺苷基-L-甲硫氨酸脱羧酶抑制剂。这些化合物的公式（1）抑制锥虫的生命周期，并且可用于治疗感染非洲锥虫的受试者。该发明包括制备公式（1）化合物的制药组合物和使用方法。
• Inhibitors of S-adenosyl-L-methionine decarboxylase
  申请人：Xiang Yibin

  公开号：US08633168B2

  公开（公告）日：2014-01-21

  Novel mechanism-based inhibitors of S-adenosyl-L-methionine decarboxylase are provided. These compounds of formula (1) inhibit the life cycle of trypanosomes, and are useful to treat subjects infected with African trypanosomes. The invention includes pharmaceutical compositions and methods of using the compounds of formula (1).

  提供了一种基于机理的S-腺苷基-L-甲硫氨酸脱羧酶抑制剂。这些化合物的化学式（1）可以抑制锥虫的生命周期，并且可用于治疗感染非洲锥虫的受试者。该发明包括制备药物组合物和使用化合物的方法（1）。