diisopropyl{2-[2-amino-6-(diethylamino)-9H-purine-9-yl]ethoxy}methylphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: diisopropyl{2-[2-amino-6-(diethylamino)-9H-purine-9-yl]ethoxy}methylphosphonate
• 英文别名: diisopropyl (2-(2-amino-6-diethylamino-9H-purin-9-yl)ethoxy)methylphosphonate；9-[2-[di(propan-2-yloxy)phosphorylmethoxy]ethyl]-6-N,6-N-diethylpurine-2,6-diamine
• 化学式: C₁₈H₃₃N₆O₄P
• 分子量: 428.472
• InChiKey: VETFOLKSPWJECS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  氯乙醛 、 diisopropyl{2-[2-amino-6-(diethylamino)-9H-purine-9-yl]ethoxy}methylphosphonate 以 1,4-二氧六环 、 水 为溶剂， 反应 7.0h， 以48%的产率得到diisopropyl (2-(4-diethylamino-1H-imidazo[2,1-b]purin-1-yl)ethoxy)methylphosphonate
  参考文献：
  名称：

  Tricyclic etheno analogs of PMEG and PMEDAP: Synthesis and biological activity

  摘要：

  A series of novel 9-substituted (2-(3H-imidazo[1,2-a]purin-3-yl)ethoxy)methylphosphonic and 4-substituted (2-(1H-imidazo[2,1-b]purin-1-yl)ethoxy)methylphosphonic acids as tricyclic etheno analogs of potent antivirals and cytostatics PMEG and PMEDAP was synthesized and evaluated for their biological activity. Most of the compounds showed modest activity against varicella-zoster virus (VZV) and human cytomegalovirus (HCMV) except for (2-(9-oxo-5,9-dihydro-3H-imidazo[1,2-a]purin-3-yl)ethoxy)methylphosphonic acid 8 which proved markedly active against VZV and HCMV. None of the compounds tested exhibited any significant cytostatic effect.

  DOI：

  10.1016/j.bmc.2006.07.036
• 作为产物：
  描述：

  2-[(diisopropoxyphosphoryl)methoxy]ethyl 4-methylbenzene-1-sulfonate 在 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 diisopropyl{2-[2-amino-6-(diethylamino)-9H-purine-9-yl]ethoxy}methylphosphonate
  参考文献：
  名称：

  通过顺序区域选择性Mitsunobu偶联和基于S N Ar的C 6功能化，以多样性为导向的三取代嘌呤的有效利用

  摘要：

  据报道，从鸟嘌呤前体2-氨基-6-氯嘌呤核苷开始，通过随后的区域选择性，高产率的Mitsunobu偶联和亲核取代，可以合成多种2,6,7-和2,6,9-三取代嘌呤的有效方案。在C 6下具有通用的伯胺和仲胺。各种各样的2,6,7-和2,6,9-三取代嘌呤可以良好的收率获得，并且具有出色的官能团耐受性。此外，还以优异的产率完成了无溶剂的前体2和3的大规模合成以及有机磷侧链4和5的简便制备。

  DOI：

  10.1016/j.tet.2012.10.079

文献信息

• Diversity oriented efficient access of trisubstituted purines via sequential regioselective Mitsunobu coupling and SNAr based C6 functionalizations
  作者：Atul Manvar、Anamik Shah

  DOI：10.1016/j.tet.2012.10.079

  日期：2013.1

  An efficient protocol for the syntheses of diverse 2,6,7- and 2,6,9-trisubstituted purines is reported starting from the guanine precursor, 2-amino-6-chloropurine nucleoside through subsequent regioselective, high yielding Mitsunobu coupling and nucleophilic substitutions at C6 with versatile primary and secondary amines. A wide range of 2,6,7- and 2,6,9-trisubstituted purines were accessible in good

  据报道，从鸟嘌呤前体2-氨基-6-氯嘌呤核苷开始，通过随后的区域选择性，高产率的Mitsunobu偶联和亲核取代，可以合成多种2,6,7-和2,6,9-三取代嘌呤的有效方案。在C 6下具有通用的伯胺和仲胺。各种各样的2,6,7-和2,6,9-三取代嘌呤可以良好的收率获得，并且具有出色的官能团耐受性。此外，还以优异的产率完成了无溶剂的前体2和3的大规模合成以及有机磷侧链4和5的简便制备。
• Tricyclic etheno analogs of PMEG and PMEDAP: Synthesis and biological activity
  作者：Kateřina Hořejší、Graciela Andrei、Erik De Clercq、Robert Snoeck、Radek Pohl、Antonín Holý

  DOI：10.1016/j.bmc.2006.07.036

  日期：2006.12

  A series of novel 9-substituted (2-(3H-imidazo[1,2-a]purin-3-yl)ethoxy)methylphosphonic and 4-substituted (2-(1H-imidazo[2,1-b]purin-1-yl)ethoxy)methylphosphonic acids as tricyclic etheno analogs of potent antivirals and cytostatics PMEG and PMEDAP was synthesized and evaluated for their biological activity. Most of the compounds showed modest activity against varicella-zoster virus (VZV) and human cytomegalovirus (HCMV) except for (2-(9-oxo-5,9-dihydro-3H-imidazo[1,2-a]purin-3-yl)ethoxy)methylphosphonic acid 8 which proved markedly active against VZV and HCMV. None of the compounds tested exhibited any significant cytostatic effect.