7-[(1,3-dibenzyloxy-2-propoxy)methyl]guanine | 84222-49-1

• 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: 7-[(1,3-dibenzyloxy-2-propoxy)methyl]guanine
• 英文别名: 2-amino-7-[1,3-bis(phenylmethoxy)propan-2-yloxymethyl]-1H-purin-6-one
• CAS: 84222-49-1
• 化学式: C₂₃H₂₅N₅O₄
• 分子量: 435.483
• InChiKey: PLKLVEXRRNLWJY-UHFFFAOYSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-[(1,3-dibenzyloxy-2-propoxy)methyl]guanine 在 钯 乙醇 作用下， 以 环己烯 为溶剂， 反应 18.0h， 以89%的产率得到2-氨基-1,7-二氢-7-[[2-羟基-1-(羟基甲基)乙氧基]甲基]-6H-嘌呤-6-酮
  参考文献：
  名称：

  Biologically active acyclonucleoside analogues. II. The synthesis of 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine (BIOLF-62)

  摘要：

  描述了9-[[2-羟基-1-(羟甲基)乙氧基]甲基]鸟苷的化学合成。这种化合物，被称为BIOLF-62，对抗疱疹病毒有效。这种化合物是一类新型的核苷类似物的成员，它们缺乏刚性的碳水化合物环，但具有所有天然存在的脱氧核苷的功能基团。

  DOI：

  10.1139/v82-430
• 作为产物：
  描述：

  鸟嘌呤 在 硫酸氢铵 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 7-[(1,3-dibenzyloxy-2-propoxy)methyl]guanine
  参考文献：
  名称：

  Novel radiosynthesis of PET HSV-tk gene reporter probes [18F]FHPG and [18F]FHBG employing dual Sep-Pak SPE techniques

  摘要：

  Positron emission tomography (PET) herpes simplex virus thymidine kinase (HSV-tk) gene reporter probes 9-[(3-[F-18]fluoro-1-hydroxy-2-propoxy)methyl]guanine ([F-18]FHPG) and 9-(4-[F-18]fluoro-3-hydroxymethylbutyl)guanine ([F-18]FHBG) were prepared by nucleophilic substitution of the appropriate tosylated precursors with [F-18]KF/Kryptofix 2.2.2 followed by a quick deprotection reaction and purification with a simplified dual Silica Sep-Pak solid-phase extraction (SPE) method in 15-30% radiochemical yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.010

文献信息

• An Improved Total Synthesis of PET HSV‐tk Gene Expression Imaging Agent 9‐[(3‐[¹⁸F]Fluoro‐1‐hydroxy‐2‐propoxy)methyl]guanine ([¹⁸F]FHPG)
  作者：Ji‐Quan Wang、Qi‐Huang Zheng、Xiangshu Fei、Xuan Liu、Thomas A. Gardner、Chinghai Kao、Sudhanshu P. Raikwar、Barbara E. Glick‐Wilson、Michael L. Sullivan、Bruce H. Mock、Gary D. Hutchins

  DOI：10.1081/scc-120028365

  日期：2004.12.31

  An improved total synthesis of [F-18]FHPG starting from 1,3-dibenzyloxy2-propanol and guanine has been developed. [F-18]FHPG was prepared by nucleophilic substitution of the appropriate precursor with [F-18]KF/ Kryptofix 2.2.2 followed by a quick deprotection reaction and purification with a simplified Silica Sep-Pak solid-phase extraction (SPE) method in 10-15% radiochemical yield, and 70 min synthesis time from end of bombardment (EOB).
• US4508898A
  申请人：——

  公开号：US4508898A

  公开（公告）日：1985-04-02
• Biologically active acyclonucleoside analogues. II. The synthesis of 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine (BIOLF-62)
  作者：Kelvin K. Ogilvie、Ukken O. Cheriyan、Bruno K. Radatus、Kendall O. Smith、Karen S. Galloway、Wiebke L. Kennell

  DOI：10.1139/v82-430

  日期：1982.12.15

  The chemical synthesis of 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine is described. This compound, known as BIOLF-62, is active against herpesviruses. This compound is a member of a novel class of nucleoside analogues which lack a rigid carbohydrate ring, but which possess all of the functional groups of naturally occurring deoxynucleosides.

  描述了9-[[2-羟基-1-(羟甲基)乙氧基]甲基]鸟苷的化学合成。这种化合物，被称为BIOLF-62，对抗疱疹病毒有效。这种化合物是一类新型的核苷类似物的成员，它们缺乏刚性的碳水化合物环，但具有所有天然存在的脱氧核苷的功能基团。
• Novel radiosynthesis of PET HSV-tk gene reporter probes [18F]FHPG and [18F]FHBG employing dual Sep-Pak SPE techniques
  作者：Ji-Quan Wang、Qi-Huang Zheng、Xiangshu Fei、Bruce H. Mock、Gary D. Hutchins

  DOI：10.1016/j.bmcl.2003.09.010

  日期：2003.11

  Positron emission tomography (PET) herpes simplex virus thymidine kinase (HSV-tk) gene reporter probes 9-[(3-[F-18]fluoro-1-hydroxy-2-propoxy)methyl]guanine ([F-18]FHPG) and 9-(4-[F-18]fluoro-3-hydroxymethylbutyl)guanine ([F-18]FHBG) were prepared by nucleophilic substitution of the appropriate tosylated precursors with [F-18]KF/Kryptofix 2.2.2 followed by a quick deprotection reaction and purification with a simplified dual Silica Sep-Pak solid-phase extraction (SPE) method in 15-30% radiochemical yield. (C) 2003 Elsevier Ltd. All rights reserved.