N-acetyl-8-oxo-7,8-dihydroadenosine-,2’,3’,5’-triacetate | 29851-55-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-acetyl-8-oxo-7,8-dihydroadenosine-,2’,3’,5’-triacetate
• 英文别名: [(2R,3R,4R,5R)-5-(6-acetamido-8-oxo-7H-purin-9-yl)-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 29851-55-6
• 化学式: C₁₈H₂₁N₅O₉
• 分子量: 451.393
• InChiKey: SPYOYIKJGBTVIV-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-acetyl-8-oxo-7,8-dihydroadenosine-,2’,3’,5’-triacetate 在 吡啶 、 pyridine amine 作用下， 反应 18.0h， 生成 6-N-acetyl-5'-O-tert-butyldimethylsilyl-8-oxoadenosine
  参考文献：
  名称：

  Synthesis and antitumor activities of phosmidosine A and its N-acetylated derivative

  摘要：

  A new antitumor active phosmidosine A, which was isolated from Streptomyces sp., was successfully synthesized by a series of reactions involving construction of the N-acyl phosphoramidate linkage which was achieved by the reaction of the 5'-O-phosphoramidite derivative with a prolinamide derivative in the presence of 5-(3,5-dinitrophenyl)-1H-tetrazole. The growth inhibitory effect of phosmidosine A and its N-acetyl analog on the various human cell lines was examined. These results showed that both compounds have a significant growth inhibitory activity and that the 6-amino group is not required for the growth inhibitory activity of phosmidosine A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00926-6
• 作为产物：
  描述：

  6-N-2',3',5'-tri-O-tetraacetyladenosine 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以7.6%的产率得到N-acetyl-8-oxo-7,8-dihydroadenosine-,2’,3’,5’-triacetate
  参考文献：
  名称：

  Functionalization Including Fluorination of Nitrogen-Containing Compounds Using Electrochemical Oxidation.

  摘要：

  含氮化合物在以Et3N-3HF为电解质的条件下进行了电化学氧化。咖啡因的氧化产物为8-氟咖啡因，产率为40.3%。鸟苷四乙酸酯和尿苷三乙酸酯分别给出了17.5%和4.6%的氟化化合物。咖啡因与甲醇、KCl或KCN的类似电化学氧化分别得到了8-甲氧基咖啡因、8-氯咖啡因或8-氰基咖啡因。

  DOI：

  10.1248/cpb.44.1141

文献信息

• Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy
  作者：Denis I. Nilov、Dmitry Y. Komarov、Maxim S. Panov、Kanykey E. Karabaeva、Andrey S. Mereshchenko、Alexander N. Tarnovsky、R. Marshall Wilson

  DOI：10.1021/ja3068148

  日期：2013.3.6

  Oxidative damage to purine nucleic acid bases proceeds through quinoidal intermediates derived from their corresponding 8-oxo-7,8-dihydropurine bases. Oxidation studies of 8-oxo-7,8-dihyroadenosine and 8-oxo-7,8-dihydroinosine indicate that these quinoidal species can produce stable cross links with a wide variety of nucleophiles in the 2-positions of the purines. An azide precursor for the adenosine iminoquinone has been synthesized and applied in ultrafast transient absorption spectroscopic studies. Thus, the adenosine iminoquinone can be observed directly, and its susceptibility to nudeophilic attack with various nucleophiles as well as the stability of the resulting cross linked species have been evaluated Finally, these observations indicate that this azide might be a very useful photoaffurity labeling agent, because the reactive intermediate, adenosine iminoquinone, is such a good mimic for the universal purine base adenosine.