2-amino-6-fluoro-9-(4-hydroxy-3-hydroxy-methylbutyl)purine | 222842-93-5

• 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: 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxy-methylbutyl)purine
• 英文别名: 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl)purine；6-fluoropenciclovir；2-[2-(2-Amino-6-fluoropurin-9-yl)ethyl]propane-1,3-diol
• CAS: 222842-93-5
• 化学式: C₁₀H₁₄FN₅O₂
• 分子量: 255.252
• InChiKey: ZLCJUPDOKKANSY-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C (decomp)
• 沸点：
  596.1±60.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxy-methylbutyl)purine 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以99%的产率得到
  参考文献：
  名称：

  Synthesis and evaluation of 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine mono- and diesters as potential prodrugs of penciclovir

  摘要：

  2-Amino-6-fluoro-9-(4-hydroxy-3-hydroxymethlbut-1-yl)purine (7), and its mono- and diesters 8-15 were prepared and evaluated for their potential as prodrugs of penciclovir. Treatment of 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (5) with trimethylamine in THF followed by a reaction of the resulting trimethylammonium chloride salt 6 with KF in DMF afforded 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (7) in 80% yield. Esterification of 7 with an appropriate acid anhydride [Ac2O, (EtCO)(2)O, (n-PrCO)(2)O, or (i-PrCO)(2)O] in DMF in the presence of a catalytic amount of DMAP produced the mono-esters 8-11 in 42-45% yields and diesters 12-15 in 87-99% yields. Of the prodrugs tested in rats, the monoisobutyrate 11 was the most efficiently absorbed and metabolized to 7, showing the mean maximum total concentration of penciclovir (5.5 mu g/mL) and 7 (10.8 mu g/mL) in the blood was much higher than the mean maximum concentration of penciclovir (11.5 mu g/mL) from famciclovir. However, the mean concentrations of penciclovir from it were lower than those from famciclovir because of the limited conversion of a major metabolite 7 to penciclovir by adenosine deaminase. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00263-6
• 作为产物：
  描述：

  9-(4-乙酰氧基-3-乙酰氧甲基丁基)-2-氨基-6-氯嘌呤 在 potassium fluoride 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxy-methylbutyl)purine
  参考文献：
  名称：

  PET成像报告基因HSV1-tk新探针的合成：2-氨基-6-[18F]氟-9-（4-羟基-3-羟甲基丁基）嘌呤（6-[18F]氟喷昔洛韦）

  摘要：

  报告了 2-氨基-6-[18F] 氟-9-(4-羟基-3-羟甲基丁基) 嘌呤 (6-[18F] 氟代喷昔洛韦) 6 的一步放射合成。放射性标记的产物 6-[18F] 氟喷昔洛韦 6 是通过化合物 4 与 [18F]KF 的放射性氟化制备的，并通过硅胶 Sep-Pak 柱分离。化合物 6 的放射化学产率在六次运行中衰减校正 (dc) 为 45–55%，放射化学纯度 >98%，放射合成时间为从轰击结束 (EOB) 35–42 分钟。版权所有 © 2006 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1080

文献信息

• The new convenient synthesis of fluorinated Penciclovir analogues 9-(4-fluoro-3-hydroxymethylbutyl) guanine (FHBG) and 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxymethylbutyl) purine (6-Fluoropenciclovir)
  作者：Hancheng Cai、Duanzhi Yin、Lan Zhang、Yongxian Wang

  DOI：10.1016/j.jfluchem.2006.03.002

  日期：2006.7

  9-(4-Hydroxy-3-hydroxymethylbutyl) guanine (Penciclovir) is a potent and selective inhibitor of members of the herpes virus family. A new convenient synthesis of fluorinated Penciclovir analogues 9-(4-fluoro-3-hydroxymethylbutyl) guanine (FHBG) and 2-amino-6-fluoro-9-(4-hydroxy-3-hydroxy-methylbutyl) purine (6-Fluoropenciclovir) were described. The structures of the products were characterized by UV, IR, H-1 NMR, F-19 NMR spectra and MS. (c) 2006 Elsevier B.V. All rights reserved.