N²,N²-diethylguanosine | 236389-18-7

• 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,N²-diethylguanosine
• 英文别名: 2-(diethylamino)-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 236389-18-7
• 化学式: C₁₄H₂₁N₅O₅
• 分子量: 339.351
• InChiKey: QBEGKMQUBGYMLS-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²,N²-diethylguanosine 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,N2-diethyl-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,N²-diethylguanosine
  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

• A Convenient Method for the Preparation of <i>N</i>²-Ethylguanine Nucleosides and Nucleotides
  作者：Magoichi Sako、Hiroyoshi Kawada、Kosaku Hirota

  DOI：10.1021/jo990500e

  日期：1999.7.1
• Tautomers of One-Electron-Oxidized Guanosine
  作者：Chryssostomos Chatgilialoglu、Clara Caminal、Maurizio Guerra、Quinto G. Mulazzani

  DOI：10.1002/anie.200501087

  日期：2005.9.19
• 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.