[1-(6-Amino-purin-9-ylmethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester | 169514-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: [1-(6-Amino-purin-9-ylmethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester
• 英文别名: 2-[3-(6-Aminopurin-9-yl)-2-[di(propan-2-yloxy)phosphorylmethoxy]propyl]isoindole-1,3-dione
• CAS: 169514-91-4
• 化学式: C₂₃H₂₉N₆O₆P
• 分子量: 516.494
• InChiKey: XJMHGWXZLLHKFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [1-(6-Amino-purin-9-ylmethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester 生成 N-[3-(6-Amino-purin-9-yl)-2-phosphonomethoxy-propyl]-phthalamic acid
  参考文献：
  名称：

  Acyclic Nucleotide Analogues and Related Compounds

  摘要：

  Acyclic nucleotide analogues bearing amino- and N-substituted amino groups in the side chain were prepared by alkylation of the bases with corresponding oxiranes and subsequent introduction of phosphonomethyl ether function. Novel enantiomeric synthons for the preparation of HPMP-compounds were prepared from a common intermediate and applied to syntheses of novel compounds (e.g. 8-azaguanine derivatives).

  DOI：

  10.1080/15257779508012452
• 作为产物：
  描述：

  9-(3-phthalimido-2-hydroxypropyl)adenine 在 ammonium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 [1-(6-Amino-purin-9-ylmethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester
  参考文献：
  名称：

  N-（2-（膦酰基甲氧基）乙基）核苷酸类似物的2'-氨基甲基衍生物的合成作为潜在的抗病毒剂。

  摘要：

  合成了一系列在2'位带有氨基甲基，（二甲基氨基）甲基，吗啉代甲基和（三甲基铵基）甲基的嘌呤和嘧啶N-（2-（膦酰基甲氧基）乙基）衍生物。通过用适当取代的（氨基烷基）环氧乙烷将杂环碱烷基化，然后将所得的中间体与（对甲苯磺酰基磺酰基）氧基）烷基膦酸二烷基酯缩合，然后用溴代三甲基硅烷处理所得的二酯，来制备化合物。9-（3-氨基-2-（膦酰基甲氧基）丙基）腺嘌呤（2a）在7-35微克的浓度范围内被证明对水痘带状疱疹病毒（VZV），巨细胞病毒（CMV）和莫洛尼鼠肉瘤病毒（MSV）具有活性/毫升

  DOI：

  10.1021/jm9601314

文献信息

• Synthesis of 2‘-Aminomethyl Derivatives of <i>N</i>-(2-(Phosphonomethoxy)ethyl) Nucleotide Analogues as Potential Antiviral Agents
  作者：Hana Dvořáková、Milena Masojídková、Antonín Holý、Jan Balzarini、Graciela Andrei、Robert Snoeck、Erik De Clercq

  DOI：10.1021/jm9601314

  日期：1996.1.1

  A series of purine and pyrimidine N-(2-(phosphonomethoxy)ethyl) derivatives bearing aminomethyl, (dimethylamino)methyl, morpholinomethyl, and (trimethylammonio)methyl groups at the 2'-position were synthesized. The compounds were prepared by alkylation of the heterocyclic bases with appropriately substituted (aminoalkyl)oxiranes followed by condensation of the resulting intermediates with dialkyl

  合成了一系列在2'位带有氨基甲基，（二甲基氨基）甲基，吗啉代甲基和（三甲基铵基）甲基的嘌呤和嘧啶N-（2-（膦酰基甲氧基）乙基）衍生物。通过用适当取代的（氨基烷基）环氧乙烷将杂环碱烷基化，然后将所得的中间体与（对甲苯磺酰基磺酰基）氧基）烷基膦酸二烷基酯缩合，然后用溴代三甲基硅烷处理所得的二酯，来制备化合物。9-（3-氨基-2-（膦酰基甲氧基）丙基）腺嘌呤（2a）在7-35微克的浓度范围内被证明对水痘带状疱疹病毒（VZV），巨细胞病毒（CMV）和莫洛尼鼠肉瘤病毒（MSV）具有活性/毫升
• Acyclic Nucleotide Analogues and Related Compounds
  作者：Antonín Holý、Hana Dvoráková

  DOI：10.1080/15257779508012452

  日期：1995.5.1

  Acyclic nucleotide analogues bearing amino- and N-substituted amino groups in the side chain were prepared by alkylation of the bases with corresponding oxiranes and subsequent introduction of phosphonomethyl ether function. Novel enantiomeric synthons for the preparation of HPMP-compounds were prepared from a common intermediate and applied to syntheses of novel compounds (e.g. 8-azaguanine derivatives).