N²-benzylguanosine | 71171-58-9

• 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: N²-benzylguanosine
• 英文别名: n2-Benzylguanosine；2-(benzylamino)-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 71171-58-9
• 化学式: C₁₇H₁₉N₅O₅
• 分子量: 373.368
• InChiKey: OLFDXOUGVHUWCN-XNIJJKJLSA-N

物化性质

• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-benzylguanosine 在 磷酸三甲酯 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 N2-benzyl-7-methylguanosinium 5'-monophosphate sodium salt
  参考文献：
  名称：

  Synthesis of N2-modified 7-methylguanosine 5′-monophosphates as nematode translation inhibitors

  摘要：

  Preparative scale synthesis of 14 new N-2-modified mononucleotide 5' mRNA cap analogues was achieved. The key step involved use of an SNAr reaction with protected 2-fluoro inosine and various primary and secondary amines. The derivatives were tested in a parasitic nematode, Ascaris suum, cell-free system as translation inhibitors. The most effective compound with IC50 similar to 0.9 mu M was a N-2-p-metoxybenzyl-7-methylguanosine-5'-monophosphate 35. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.078
• 作为产物：
  描述：

  2',3',5'-tris-O-acetyl-O6-<2-(4-nitrophenyl)ethyl>-guanosine 在 吡啶 、 pyridine hydrofluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.33h， 生成 N²-benzylguanosine
  参考文献：
  名称：

  Synthesis of N2-modified 7-methylguanosine 5′-monophosphates as nematode translation inhibitors

  摘要：

  Preparative scale synthesis of 14 new N-2-modified mononucleotide 5' mRNA cap analogues was achieved. The key step involved use of an SNAr reaction with protected 2-fluoro inosine and various primary and secondary amines. The derivatives were tested in a parasitic nematode, Ascaris suum, cell-free system as translation inhibitors. The most effective compound with IC50 similar to 0.9 mu M was a N-2-p-metoxybenzyl-7-methylguanosine-5'-monophosphate 35. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.078

文献信息

• Rapid and Selective Reduction of Amide Group by Borane-Amine Complexes in Acyl Protected Nucleosides
  作者：Zinaida A. Sergueeva、Dmitri S. Sergueev、Barbara Ramsay Shaw

  DOI：10.1080/15257770008033009

  日期：2000.1

  fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.

  硼烷-胺络合物提供了脱氧核苷N-酰基异常快速且选择性的还原为相应的N-烷基。具有三个N-保护基团（苯甲酰基，异丁酰基或乙酰基）之一的三种不同的核苷（dG，dA和dC）用于在温和条件下以高收率制备N-烷基化的核苷。在N-酰基还原的条件下，脱氧核糖O-酰基保护基保持完整。
• Application of Phosphoramidate ProTide Technology for the Synthesis of 5’‐mRNA Cap Analogs Modified on the Exocyclic Amine Group
  作者：Izabela Siekierska、Maciej Lukaszewicz、Remigiusz Worch、Marzena Jankowska‐Anyszka、Karolina Piecyk

  DOI：10.1002/cmdc.202200490

  日期：2023.2.14

  Aryloxy phosphoramidate analogues of the 5’-end of mRNA with enhanced inhibitory properties towards eIF4E were synthesised. Enzymatic activation of presented ProTide cap analogues was confirmed using carboxypeptidase Y assay. Their bioactivation pathway and further inhibitory properties were examined in the rabbit reticulocyte lysate system. Obtained 5’-cap analogues demonstrated promising potential

  合成了具有增强的 eIF4E 抑制特性的 mRNA 5' 末端的芳氧基氨基磷酸酯类似物。使用羧肽酶 Y 测定法确认所呈现的 ProTide 帽类似物的酶促激活。在兔网织红细胞裂解物系统中检查了它们的生物激活途径和进一步的抑制特性。获得的 5'-帽类似物显示出作为帽依赖性翻译的充分抑制剂的有前途的潜力。
• Substituent-induced effects on the stability of benzylated guanosines: model systems for the factors influencing the stability of carcinogen-modified nucleic acids
  作者：Robert C. Moschel、W. Robert Hudgins、Anthony Dipple

  DOI：10.1021/jo00176a028

  日期：1984.1
• Reactivity effects on site selectivity in nucleoside aralkylation: a model for the factors influencing the sites of carcinogen-nucleic acid interactions
  作者：Robert C. Moschel、W. Robert Hudgins、Anthony Dipple

  DOI：10.1021/jo00372a015

  日期：1986.10
• Aralkylation of guanosine by the carcinogen N-nitroso-N-benzylurea
  作者：Robert C. Moschel、W. Robert Hudgins、Anthony Dipple

  DOI：10.1021/jo01291a037

  日期：1980.2