N²-(p-methoxybenzyl)guanosine | 78907-25-2

• 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-(p-methoxybenzyl)guanosine
• 英文别名: N-[(4-Methoxyphenyl)methyl]guanosine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-[(4-methoxyphenyl)methylamino]-1H-purin-6-one
• CAS: 78907-25-2
• 化学式: C₁₈H₂₁N₅O₆
• 分子量: 403.395
• InChiKey: RIDPFWBCOQAKEG-LSCFUAHRSA-N

物化性质

• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²-(p-methoxybenzyl)guanosine 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-p-methoxybenzyl-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'-三乙酰鸟苷 在 吡啶 、 pyridine hydrofluoride 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 14.08h， 生成 N²-(p-methoxybenzyl)guanosine
  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

• 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
• Dissociation of O6-(p-methoxybenzyl)guanosine in aqueous solution to yield guanosine, p-methoxybenzylguanosines, and 4-(p-methoxybenzyl)-5-guanidino-1-.beta.-D-ribofuranosylimidazole
  作者：Robert C. Moschel、W. Robert Hudgins、Anthony Dipple

  DOI：10.1021/ja00408a035

  日期：1981.9
• Synthesis of N2-modified 7-methylguanosine 5′-monophosphates as nematode translation inhibitors
  作者：Karolina Piecyk、Richard E. Davis、Marzena Jankowska-Anyszka

  DOI：10.1016/j.bmc.2012.05.078

  日期：2012.8

  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.