9-<(2-phosphonoethyl)aminocarboxymethyl>adenine | 168696-31-9

• 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-phosphonoethyl)aminocarboxymethyl>adenine
• 英文别名: 2-[[2-(6-aminopurin-9-yl)acetyl]amino]ethylphosphonic acid
• CAS: 168696-31-9
• 化学式: C₉H₁₃N₆O₄P
• 分子量: 300.214
• InChiKey: XKFCUWAOVIDFKD-UHFFFAOYSA-N

物化性质

• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156.25
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-<(2-phosphonoethyl)aminocarboxymethyl>adenine 在 三丁基焦磷酸铵 、 N,N'-羰基二咪唑 作用下， 生成 9-<<2-(β,γ-diphospho)phosphonoethyl>aminocarbonylmethyl>adenine
  参考文献：
  名称：

  Acyclic Nucleoside and Nucleotide Analogues with Amide Bond

  摘要：

  A series of acyclic nucleosides and related alpha-phosphonyl acyclic analogues of dNTP with an amide bond have been prepared. Their antiviral and substrate properties were investigated.New acyclic nucleoside analogues with a rigid structural element, amide bond, have been synthesized in two stages. Alkylation of bis- trimethylsilylated thymine, cytosine and sodium salt of adenine by ethyl bromoacetate gave ethoxycarbonylmethyl derivatives ($) under bar 1a-c. Reaction of ($) under bar 1a-c with aminoalcohols afforded acyclic nucleosides ($) under bar 2-($) under bar 4 in good yields (Scheme 1), These analogues were found to be inactive against HIV-1 (CEM-SS cells) and HSV -1, HSV-2, HCMV, VZV (HFF cells) at concentrations up to 100 mu g/ml and were nontoxic towards CEM and HFF cells. However, it was shown that triphosphate of ($) under bar 2c is incorporated into the DNA chain by DNA polymerase from HSV-1(1). The absence of antiviral activity and cytotoxicity is probably due to the fact that ($) under bar 2-($) under bar 4 are not recognized by cellular and viral kinases.

  DOI：

  10.1080/15257779508012386
• 作为产物：
  描述：

  6-乙基水杨酸甲酯 在 吡啶 、 氢氧化钾 、 ammonium hydroxide 、 三甲基溴硅烷 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.33h， 生成 9-<(2-phosphonoethyl)aminocarboxymethyl>adenine
  参考文献：
  名称：

  Malakhov, D. V.; Semizarov, D. G.; Yas'ko, M. V., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 7, p. 464 - 469

  摘要：

  DOI：