N2-(p-anisyldiphenylmethyl)-9-[(4-fluoro)-3-p-anisyldiphenylmethoxy-methylbutyl]guanine | 206067-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N2-(p-anisyldiphenylmethyl)-9-[(4-fluoro)-3-p-anisyldiphenylmethoxy-methylbutyl]guanine
• 英文别名: N²-(p-anisyldiphenylmethyl)-9-[(4-fluoro)-3-p-anisyldiphenylmethoxy-methylbutyl]guanine；N²-(p-anisyldiphenylmethyl)-9-[(4-fluoro)-3-p-anisyldiphenylmethoxymethylbutyl]guanine；N2-(p-anisyldiphenylmethyl)-9-[3-(p-anisyldiphenylmethoxymethyl)-4-fluorobutyl]guanine
• CAS: 206067-85-8
• 化学式: C₅₀H₄₆FN₅O₄
• 分子量: 799.945
• InChiKey: GFKLKIZOZTWLFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.53
• 重原子数：
  60.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  103.29
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N2-(p-anisyldiphenylmethyl)-9-[(4-fluoro)-3-p-anisyldiphenylmethoxy-methylbutyl]guanine 以 盐酸 、 甲醇 为溶剂， 反应 0.5h， 以85%的产率得到9-(4-fluoro-3-hydroxymethylbutyl)guanine
  参考文献：
  名称：

  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)

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2006.03.002
• 作为产物：
  描述：

  4-甲氧基三苯基氯甲烷 在 吡啶 、 4-二甲氨基吡啶 、 potassium fluoride 、 三乙胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.67h， 生成 N2-(p-anisyldiphenylmethyl)-9-[(4-fluoro)-3-p-anisyldiphenylmethoxy-methylbutyl]guanine
  参考文献：
  名称：

  An Improved Total Synthesis of PET HSV‐tk Gene Reporter Probe 9‐(4‐[¹⁸F]Fluoro‐3‐hydroxymethylbutyl)guanine ([¹⁸F]FHBG)

  摘要：

  An improved total synthesis of [F-18]FHBG starting from triethyl-1,1,2-ethanetricarboxylate and 2-amino-6-chloropurine is reported. [F-18]FHBG 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 20-25% radiochemical yield.

  DOI：

  10.1081/scc-120027717

文献信息

• Efficient synthesis of 9-(4-[18F]fluoro-3-hydroxymethylbutyl)guanine ([18F]FHBG) and 9-[(3-[18F]fluoro-1-hydroxy-2-propoxy)methyl]guanine ([18F]FHPG)
  作者：Jie Liu、Jorge R. Barrio、Nagichettiar Satyamurthy

  DOI：10.1016/j.jfluchem.2017.08.007

  日期：2017.9

  A new, high radiochemical yield synthesis of [18F]FHBG and [18F]FHPG, the most popular imaging agents currently in use for monitoring gene therapy using positron emission tomography (PET), is reported in this work. Protection of sensitive sites in the precursors generally utilized for the preparation of [18F]FHBG and [18F]FHPG using the nucleophilic 18F-fluorination reaction was found to be critical

  这项工作报道了[ 18 F] FHBG和[ 18 F] FHPG的新的高放射化学收率合成，这是目前正用于监测使用正电子发射断层扫描（PET）进行基因治疗的最流行的成像剂。发现通常使用亲核的18 F-氟化反应来保护制备[ 18 F] FHBG和[ 18 F] FHPG的前体中的敏感位点，对于合成方法的良好放射化学收率，可靠性和可重复性至关重要。最初的方法是在当前使用的单甲氧基三苯甲基保护的喷昔洛韦甲苯磺酸酯衍生物9的鸟嘌呤部分的O 6氧处进行保护。与氨基甲酰基一起进行。随后，两者的充分保护ö 6 -氧和Ñ 2 -氮在单甲氧保护喷昔洛韦和更昔洛韦甲苯磺酸酯类似物9和10，通过它们的反应与二-实现叔丁基二碳酸酯，这导致ö 6 -叔-丁基- ñ 2 -Boc单甲氧保护的喷昔洛韦甲苯磺酸酯18和ö 6 -叔丁基- ñ 2 -Boc单甲氧保护的更昔洛韦甲苯磺酸酯19， 分别。首先将新合成的氨基甲酰基和Boc保护的前体与与Kryptofix
• 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.