9-(2-phosphonylethoxymethyl)adenine | 121149-97-1

• 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: 9-(2-phosphonylethoxymethyl)adenine
• 英文别名: 2-[(6-aminopurin-9-yl)methoxy]ethylphosphonic Acid
• CAS: 121149-97-1
• 化学式: C₈H₁₂N₅O₄P
• 分子量: 273.188
• InChiKey: PSEZOBYOARTIDA-UHFFFAOYSA-N

物化性质

• 沸点：
  632.5±65.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(2-phosphonylethoxymethyl)adenine 在 吡啶 、 2,3,5-三甲基吡啶 、 三氯甲基磺酰氯 、 2,4,6-三异丙基苯磺酰氯 作用下， 反应 27.0h， 生成 9-<2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine-3'-<(methoxyalaninyl)<2-(adenin-9-ylmethoxy)ethyl>phosphonate>
  参考文献：
  名称：

  Design, Synthesis, and Structure-Activity Relationship of Novel Dinucleotide Analogs as Agents against Herpes and Human Immunodeficiency Viruses

  摘要：

  A new acyclic nucleoside phosphonate (13) containing an adenine moiety was synthesized, which acted as an excellent inhibitor of calf mucosal adenosine deaminase. This inhibitory property allows it to exert great synergistic effect on certain antiviral agents (e.g., ara-A, 37). Phosphonate 13 was not phosphorylated by the bovine brain guanylate kinase nor by 5-phosphoribosyl 1-pyrophosphate synthetase. Syntheses of biologically active nucleotide phosphonate 40 and its phosphonoamidate derivative 42 were accomplished, which showed remarkable activity against herpes viruses and exhibited low host cell toxicity. 3'-Azido-nucleoside phosphonate 20 and 3'-fluoronucleoside phosphonate 32, as well as the corresponding dinucleotide analogs 47 and 48, and their respective phosphonoamidates 53-56 were also synthesized as new compounds, among which phosphonoamidates 53-56 showed potent activity against human immunodeficiency virus. Phosphonoamidates 55 and 56 bearing a methyl D-alaninate moiety exhibited less cellular toxicity than 53 and 54 bearing a methyl L-alaninate moiety. Nucleotide phosphonate 40 as well as dinucleotide phosphonates 47 and 48 were found susceptible to degradation by phosphodiesterases. Their respective phosphonoamidates 42 and 53-56, however, were completely resistant to snake venom and spleen enzymes.

  DOI：

  10.1021/jm00023a004
• 作为产物：
  描述：

  1-[(2-羟基乙氧基)甲基]腺嘌呤 在 ammonium hydroxide 、 三甲基氯硅烷 、 三甲基溴硅烷 、 四溴化碳 、 三苯基膦 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 69.0h， 生成 9-(2-phosphonylethoxymethyl)adenine
  参考文献：
  名称：

  Rosenberg, Ivan; Holy, Antonin; Masojidkova, Milena, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2753 - 2777

  摘要：

  DOI：

文献信息

• QSAR Analysis for ADA upon Interaction with a Series of Adenine Derivatives as Inhibitors
  作者：A. A. Moosavi‐Movahedi、S. Safarian、G. H. Hakimelahi、G. Ataei、D. Ajloo、S. Panjehpour、S. Riahi、M. F. Mousavi、S. Mardanyan、N. Soltani、A. Khalafi‐Nezhad、H. Sharghi、H. Moghadamnia、A. A. Saboury

  DOI：10.1081/ncn-120030719

  日期：2004.12.31

  presence of adenine derivatives (R1-R24) in sodium phosphate buffer (50 mM; pH 7.5) solution at 27 degrees C. These kinetic parameters were used for QSAR analysis. As such, we found some theoretical descriptors to which the binding affinity of adenosine deaminase (ADA) towards several adenine nucleosides as inhibitors is correlated. QSAR analysis has revealed that binding affinity of the adenine nucleosides

  在不存在和存在腺嘌呤衍生物（R1-R24）的磷酸钠缓冲液（50 mM; pH 7.5）溶液中，在27摄氏度下测定Km和Ki等腺苷脱氨酶的动力学参数。这些动力学参数用于QSAR分析。因此，我们发现了一些理论上的描述子，腺苷脱氨酶（ADA）对作为抑制剂的几种腺嘌呤核苷的结合亲和力是相关的。QSAR分析表明，腺嘌呤核苷与ADA相互作用时的结合亲和力取决于分子体积，分子的偶极矩，N1原子周围的电荷以及相关分子的最高正电荷。
• Adenylate analogs as potent anti-herpes virus agents
  申请人：National Science Council

  公开号：US05733890A1

  公开（公告）日：1998-03-31

  Novel adenylate analogs having the following formula are synthesized in the present invention, which are found active against herpes simplex viruses: ##STR1## wherein R.sup.1 is hydroxyl, C.sub.1 -C.sub.4 alkoxy, an amino ester radical of --NHR.sup.3 COOR.sup.4, wherein R.sup.3 is a bivalent C.sub.1 -C.sub.4 saturated hydrocarbon and R.sup.4 is C.sub.1 -C.sub.4 alkyl; and R.sup.2 is hydroxyl, --O.sup.+ NH.sub.4 or ##STR2##

  本发明合成了具有以下公式的新型腺苷酸类似物，发现对单纯疱疹病毒具有活性： ##STR1## 其中，R.sup.1是羟基、C.sub.1-C.sub.4烷氧基、--NHR.sup.3 COOR.sup.4的氨基酯基团，其中R.sup.3是双价的C.sub.1-C.sub.4饱和碳氢化合物，R.sup.4是C.sub.1-C.sub.4烷基；而R.sup.2是羟基、--O.sup.+ NH.sub.4或##STR2##。
• HOLY, ANTONIN;ROSENBERG, IVAN;DVORAKOVA, HANA;DECLERCQ, ERIK, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 667-670
  作者：HOLY, ANTONIN、ROSENBERG, IVAN、DVORAKOVA, HANA、DECLERCQ, ERIK

  DOI：——

  日期：——
• ROSENBERG, IVAN;HOLY, ANTONIN;MASOJIDKOVA, MILENA, COLLECT. CZECHOSL. CHEM. COMMUN., 53,(1988) N1B, C. P2753-2777
  作者：ROSENBERG, IVAN、HOLY, ANTONIN、MASOJIDKOVA, MILENA

  DOI：——

  日期：——
• US5733890A
  申请人：——

  公开号：US5733890A

  公开（公告）日：1998-03-31