3'-O-acetyl-N-benzoyl-2'-deoxyadenosine | 25152-95-8

• 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: 3'-O-acetyl-N-benzoyl-2'-deoxyadenosine
• 英文别名: (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl acetate；N(6)-benzoyl-3'-O-acetyldeoxyadenosine；O^3'-acetyl-N⁶-benzoyl-2'-deoxy-adenosine；[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] Acetate
• CAS: 25152-95-8
• 化学式: C₁₉H₁₉N₅O₅
• 分子量: 397.39
• InChiKey: XVUQUPLKBMCYMQ-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-N-benzoyl-2'-deoxyadenosine 在 四氮唑 、 二氯乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 4.36h， 生成 [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[methoxy-[2-(4-nitrophenyl)ethoxy]phosphoryl]oxymethyl]oxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]oxolan-3-yl] acetate
  参考文献：
  名称：

  Rapid and Efficient Syntheses of Phosphorylated Dinucleotides

  摘要：

  Nine or ten-step solution phase syntheses of the dimers dpApA, dApAp, dpTpT and dTpTp in 0.1-0.5 g amounts, in overall yields of 49%, 45%, 32%, and 20% respectively, are described. The synthetic intermediates were characterized by H-1 and P-31 NMR and the structures of the final products were established by hydrolysis with alkaline phosphatase and comparison of the products with authentic samples.

  DOI：

  10.1080/15257779408011881
• 作为产物：
  描述：

  N-苯甲酰基-2’-脱氧腺苷 在 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 反应 20.25h， 生成 3'-O-acetyl-N-benzoyl-2'-deoxyadenosine
  参考文献：
  名称：

  Michels, Winfried; Schlimme, Eckhard, Liebigs Annalen der Chemie, 1982, # 7, p. 1398 - 1402

  摘要：

  DOI：

文献信息

• Molecular recognition of tyrosinyl adenylate analogues by prokaryotic tyrosyl tRNA synthetases
  作者：Pamela Brown、Christine M. Richardson、Lucy M. Mensah、Peter J. O'Hanlon、Neal F. Osborne、Andrew J. Pope、Graham Walker

  DOI：10.1016/s0968-0896(99)00192-3

  日期：1999.11

  modelling and synthetic studies have been carried out on tyrosinyl adenylate and analogues to probe the interactions seen in the active site of the X-ray crystal structure of tyrosyl tRNA synthetase from Bacillus stearothermophilus, and to search for new inhibitors of this enzyme. Micromolar and sub-micromolar inhibitors of tyrosyl tRNA synthetases from both B. stearothermophilus and Staphylococcus aureus have

  已经对酪氨酰腺苷酸及其类似物进行了分子建模和合成研究，以探测在嗜热脂肪芽孢杆菌的酪氨酰tRNA合成酶的X射线晶体结构的活性位点中观察到的相互作用，并寻找该酶的新抑制剂。已经合成了来自嗜热脂肪芽孢杆菌和金黄色葡萄球菌的酪氨酰tRNA合成酶的微摩尔和亚微摩尔抑制剂。腺嘌呤环对酪氨酸腺苷酸与酶结合的重要性以及水介导的氢键相互作用的重要性已得到强调。通过与金黄色葡萄球菌酶的同源性建模以及配体对接研究进一步支持了抑制数据。
• Synthesis and Biological Evaluation of Triazolyl 13α-Estrone–Nucleoside Bioconjugates
  作者：Brigitta Bodnár、Erzsébet Mernyák、János Wölfling、Gyula Schneider、Bianka Herman、Mihály Szécsi、Izabella Sinka、István Zupkó、Zoltán Kupihár、Lajos Kovács

  DOI：10.3390/molecules21091212

  日期：——

  alkyne-azide click reaction (CuAAC). For the introduction of the azido group the 5'-position of the nucleosides and a propargyl ether functional group on the 3-hydroxy group of 13α-estrone were chosen. The best yields were realized in our hands when the 3'-hydroxy groups of the nucleosides were protected by acetyl groups and the 5'-hydroxy groups were modified by the tosyl-azide exchange method. The commonly

  通过应用铜催化的炔-叠氮化物点击反应（CuAAC）合成了13α-雌酮的2'-脱氧核苷共轭物。为了引入叠氮基，选择了核苷的5'-位和13α-雌酮的3-羟基上的炔丙基醚官能团。当核苷的3'-羟基被乙酰基保护并且5'-羟基通过甲苯磺酰叠氮化物交换法进行修饰时，我们的手中获得了最佳收率。受保护的5'-叠氮核苷和甾类炔烃之间单击反应的常用条件通过使用1.5当量的Cu（I）催化剂进行了轻微修饰。所有制备的缀合物均通过MTT分析法在体外评估，其针对一组人类粘附细胞系（HeLa，通过体外放射性底物孵育研究了MCF-7和A2780）以及新缀合物对人17β-羟基类固醇脱氢酶1（17β-HSD1）的潜在抑制活性。一些受保护的缀合物对一组人类粘附癌细胞系表现出中等的抗增殖特性（受保护的胞苷缀合物被证明是最有效的，IC50值为9μM）。胸苷偶联物显示出相当大的17β-HSD1抑制活性（IC50 = 19μM）。一些
• [EN] THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS<br/>[FR] GROUPES PROTECTEURS ET DE LIAISON THERMIQUEMENT CLIVABLES
  申请人：EVONETIX LTD

  公开号：WO2018189546A1

  公开（公告）日：2018-10-18

  The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.

  本发明涉及化学连接剂和保护基团，含有化学连接剂或保护基团的化合物和组合物，以及可用于制备它们的中间体和过程。这些化学连接剂和保护基团基于吡咯烷和哌哆啶活化基团，加热后发生分子内环化，并释放二氧化碳，从而释放有机化合物从底物中。特别是，这些化学连接剂和保护基团在寡核苷酸的固相合成中具有用途，具体方案如下。
• A new method for the phosphorylation of nucleosides
  作者：Michael Taktakishvili、Vasu Nair

  DOI：10.1016/s0040-4039(00)01251-x

  日期：2000.9

  te (1), was developed for the phosphorylation of primary and secondary alcohols of nucleosides. In the many examples studied, yields in the phosphorylation step were excellent (∼80 to 95%). There is potential for wide applicability of this procedure, not only in nucleoside and nucleotide chemistry, but also in the phosphorylation of biomolecules such as carbohydrates and amino acids.

  开发了一种新的磷酸化试剂2- O-（4,4'-二甲氧基三苯甲基）乙基磺酰lethan-2'-基磷酸酯（1），用于磷酸化核苷的伯醇和仲醇。在许多研究的实例中，磷酸化步骤的收率非常好（约80％至95％）。该方法不仅在核苷和核苷酸化学中，而且在诸如碳水化合物和氨基酸的生物分子的磷酸化中都有广泛的应用潜力。
• Synthesis of 1′#,2′,3′,4′#,5′,5″-2H6-β-D-ribonucleosides and 1′#, 2′,2″,3′,4′#,5′,5″-2H7-β-D-2′-deoxyribonucleosides for selective suppression of proton resonances in partially-deuterated oligo-DNA, oligo-RNA and in 2,5A core (1H-NMR window)
  作者：András Földesi、Frans Peder R. Nilson、Corine Glemarec、Carlo Gioeli、Jyoti Chattopadhyaya

  DOI：10.1016/s0040-4020(01)82001-9

  日期：1992.1

  1′#,2′,3′,4′#,5′,5″-2H6-ribonucleosides 13 – 16 were converted in high yields to the corresponding 1′#,2′,2″,3′,4′#,5′,5″-2H7-2′-deoxynucleosides 41 – 44 in the following manner: 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TPDS))-1′#,2′,3′,4#′,5′,5″-2H6-nucleosides 29 – 32 were converted to the corresponding 2′-O-phenoxythiocarbonyl derivatives 33 – 36, which were deoxygenated by tri-n-butyltin

  阮内镍-2 H 2 O在甲基α/β-D-呋喃核糖苷[α/β= 〜3：10] 1的差向异构体混合物上的交换反应产生了甲基1 ＃，2,3,4 ＃，5,5'- 2 H 6 -α/β-呋喃核糖苷2 [在C2，C3，C5 / 5'处为97原子％2 H；C 4（C4 ＃）〜85原子％2 H ；在C1（C1 ＃）]处约20个原子％2 H，以60 – 80％的产率获得，同时还得到了差向异构的木糖和阿拉伯糖副产物。在干燥的吡啶中将粗产物2甲苯磺酸化，并在硅胶柱上小心分离，得到纯的1-O-甲基-2,3,5-三-O-（4-甲苯甲酰基）-α/β-D-1＃，2,3,4 ＃，5,5'- 2 H 6-核呋喃糖苷4（48％）。4转化为1-O-乙酰基-2,3,5-三-O-甲苯甲酰基-α/β-D-1 ＃，2,3,4 ＃，5,5'- 2 H 6-核呋喃糖苷6（ 82％的人提供了合成氘核糖核苷用于RNA或DNA合成的关键组成部分。然后将化合物6与甲硅烷基尿嘧啶，N