2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine | 107037-21-8

• 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: 2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
• 英文别名: 2-Amino-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-aminopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 107037-21-8
• 化学式: C₁₆H₁₉N₅O₇
• 分子量: 393.356
• InChiKey: VSOAGZSAGYPMQM-RGCMKSIDSA-N

物化性质

• 沸点：
  613.9±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 oxone 、 亚硝酸正戊酯 、 sodium methylate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 41.0h， 生成 2-cyano-9-β-D-ribofuranosylpurine
  参考文献：
  名称：

  Sulfone of the antibiotic, nebularine: synthesis and conversion to novel analogues of nebularlne

  摘要：

  DOI：

  10.1016/s0040-4020(01)86068-3
• 作为产物：
  描述：

  鸟苷 在 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 三乙胺 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.0h， 生成 2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  2-Halogenated purine nucleosides: synthesis and reactivity

  摘要：

  DOI：

  10.1021/jo00383a034

文献信息

• Photochemical Behavior of 2-Azidopurine Tri-<i>O</i>-Acetylribonucleoside in Aqueous Solution: Unprecedented Transformation into 1-(5′-<i>O</i>-Acetyl-<i>β</i>-D-Ribofuranosyl)-5-[(2-Oxo-1,3,5-Oxadiazocan-4-Ylidene)Amino]-1<i>H</i>-Imidazole-4-Carbaldehyde
  作者：Krzysztof Komodziński、Zofia Gdaniec、Bohdan Skalski

  DOI：10.1080/15257770.2014.981342

  日期：2015.4.3

  The photochemical behavior of 2-azidopurine 2′,3′,5′-tri-O-acetylribonucleoside has been investigated in aqueous solution under aerobic and anaerobic conditions. The two major processes under anaerobic irradiation of 2-azidopurine 2′,3′,5′-tri-O-acetylribonucleoside involve unprecedented transformation into 1-(5′-O-acetyl-β-D-ribofuranosyl)-5-[(2-oxo-1,3,5-oxadiazocan-4-ylidene)amino]-1H-imidazole-4-carbaldehyde

  在有氧和无氧条件下，研究了2-叠氮嘌呤2'，3'，5'-tri-O-乙酰核糖核苷的光化学行为。2-叠氮嘌呤2'，3'，5'-tri-O-乙酰核糖核苷在厌氧照射下的两个主要过程涉及到前所未有的转化成1-（5'-O-乙酰基-β-D-核呋喃呋喃糖基）-5-[（ 2-oxo-1,3,5-oxadiazocan-4-ylidene）amino] -1H-imidazole-4-carbaldehyde和光还原成各自的2-aminopurine衍生物，而在有氧条件下，这两个过程的发生程度和光氧化程度都小得多以各自的2-硝基嘌呤衍生物为主。通过NMR和高分辨率电喷雾电离质谱数据证实了所形成的光产物的结构。
• <i>N</i>²-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA
  作者：Hayden Peacock、Olena Maydanovych、Peter A. Beal

  DOI：10.1021/ol100019r

  日期：2010.3.5

  Nucleoside analogs that project substituents into the minor groove when incorporated into duplex RNA perturb the binding of proteins and can affect base pairing specificity. The synthesis of 2-aminopurine ribonucleoside analogs and their phosphoramidites, their incorporation into duplex RNA, their postsynthetic modification via Cu-catalyzed azide−alkyne cycloaddition (CuAAC), and their effect on duplex

  当掺入双链 RNA 时，将取代基投射到小沟中的核苷类似物会扰乱蛋白质的结合，并会影响碱基配对的特异性。描述了 2-氨基嘌呤核糖核苷类似物及其亚磷酰胺的合成、它们与双链 RNA 的结合、通过铜催化的叠氮化物-炔环加成 (CuAAC) 进行的合成后修饰，以及它们对双链稳定性和碱基配对特异性的影响。
• Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors
  作者：Irina Gillerman、Bilha Fischer

  DOI：10.1021/jm101286g

  日期：2011.1.13

  Inhibitors of adenosine deaminase (ADA, EC 3 5 4 4) are potential therapeutic agents for the treatment of various health disorders Several highly potent inhibitors were previously identified, yet they exhibit unacceptable toxicities We performed a SAR study involving a series of C2 or C8 substituted purine-riboside analogues with a view to discover less potent inhibitors with a lesser toxicity We found that any substitution at C8 position of nebularine resulted in total loss of activity toward calf intestinal ADA However several 2-substituted-adenosine, 8-aza-adenosine, and nebularine analogues exhibited inhibitory activity Specifically, 2-Cl-purine riboside, 8-aza-2-thiohexyl adenosine, 2-thiohexyl adenosine, and 2-MeS-purine riboside were found to be competitive inhibitors of ADA with K-i values of 25, 22, 6, and 3 mu M, respectively We concluded that electronic parameters are not major recognition determinants of ADA but rather steric parameters A C2 substituent which fits ADA hydrophobic pocket and improves H-bonding with the enzyme makes a good inhibitor In addition, a gg rotamer about C4'-C5' bond is apparently an important recognition determinant
• Zinic, Biserka; Krizmanic, Irena; Vikic-Topic, Drazen, Croatica Chemica Acta, 2001, vol. 74, # 2, p. 399 - 414
  作者：Zinic, Biserka、Krizmanic, Irena、Vikic-Topic, Drazen、Srzic, Dunja、Zinic, Mladen

  DOI：——

  日期：——
• NAIR, VASU;HETTRICK, BRIAN J., TETRAHEDRON, 44,(1988) N 23, C. 70001-7006
  作者：NAIR, VASU、HETTRICK, BRIAN J.

  DOI：——

  日期：——