2-amino-6-(4-hydroxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester | 358975-84-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-6-(4-hydroxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester
• 英文别名: 2-amino-9-[2-(phosphonomethoxy)ethyl]-6-(4-hydroxyphenylthio)purine bis(2,2,2-trifluoroethyl) ester；4-[2-Amino-9-[2-[bis(2,2,2-trifluoroethoxy)phosphorylmethoxy]ethyl]purin-6-yl]sulfanylphenol
• CAS: 358975-84-5
• 化学式: C₁₈H₁₈F₆N₅O₅PS
• 分子量: 561.402
• InChiKey: BAZWPYPYBNNQRG-UHFFFAOYSA-N

物化性质

• 沸点：
  691.0±65.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-amino-6-(4-hydroxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester 以 ammonia methanol 为溶剂， 生成 2-amino-9-[2-(phosphonomethoxy)ethyl]-6-(4-hydroxyphenylthio)purine methyl(2,2,2-trifluoroethyl) ester
  参考文献：
  名称：

  Phosphonate nucleotide compound

  摘要：

  本发明的2-氨基-6-芳基硫代嘌呤磷酸酯没有骨髓细胞生长抑制和致突变性等毒性，具有较高的抗病毒活性、口服吸收性和安全性。此外，本发明的化合物可以在短过程中生产。因此，本发明可以提供一种能够高效生产的优秀抗病毒剂。

  公开号：

  US20030153534A1
• 作为产物：
  描述：

  bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-6-(4-hydroxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester
  参考文献：
  名称：

  Synthesis of 2-amino-6-(4-[11C]methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester as a novel potential PET gene reporter probe for HBV and HSV-tk in cancers

  摘要：

  Acyclic nucleoside 2-amino-6-(4-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (ABE, 1) is a new hepatitis B virus (HBV) specific antiviral reagent and shows high anti-HBV activity. Carbon-11 labeled ABE may serve as a novel reporter probe for positron emission tomography (PET) to image HBV and herpes simplex virus thymidine kinase (HSV-tk) in cancers. The radiolabeling precursors 2-amino-6-(4-hydroxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (10) and 2-N-Boc protected analogue 2-N-bis(Boc)amino-6-(4-hydroxyphenylthio)9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (12), and the reference standard ABE were synthesized from bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate (5), guanine (6), and 2-amino-6-chloropurine (8). The target radiotracer 2-amino-6-(4-[C-11]methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester ([C-11]ABE, [C-11]1) was prepared by O-[C-11]methylation of the unprotected HO-precursor 10, or 2-N-Boc protected HO-precursor 12 with [C-11]methyl triflate followed by a quick deprotection reaction, and isolated by solid-phase extraction (SPE) purification in 40-55% radiochemical yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.007

文献信息

• US6767900B2
  申请人：——

  公开号：US6767900B2

  公开（公告）日：2004-07-27
• [EN] ANTI-VIRAL AGENTS AND IN-VITRO METHOD FOR THE IDENTIFICATION OF CANDIDATES ABLE TO INHIBIT BINDING OF POLYMERASE TO EPSILON<br/>[FR] AGENTS ANTIVIRAUX ET PROCEDE IN-VITRO D'IDENTIFICATION DE CANDIDATS EMPECHANT LA FIXATION DE LA POLYMERASE A L'EPSILON
  申请人：MITSUBISHI PHARMA CORP

  公开号：WO2003028737A1

  公开（公告）日：2003-04-10

  The object of the present invention is to detect and identify a medicament which inhibits activation of viral polymerase via RNA binding, and also to provide an anti-viral agent using a medicament which inhibits activation of viral polymerase via RNA binding. The present invention provides an anti-viral agent comprising, as an active ingredient, a medicament which inhibits activation of viral polymerase via RNA binding.
• Phosphonate nucleotide compound
  申请人：——

  公开号：US20030153534A1

  公开（公告）日：2003-08-14

  The 2-amino-6-arylthiopurinephosphonate of the present invention has no toxicity such as bone marrow cell growth inhibition and mutagenicity, and has a high anti-viral activity, oral absorbency and safety. Furthermore, the compound of the present invention can be produced in a short process. Therefore, the present invention can provide an excellent anti-viral agent which can efficiently be produced.

  本发明的2-氨基-6-芳基硫代嘌呤磷酸酯没有骨髓细胞生长抑制和致突变性等毒性，具有较高的抗病毒活性、口服吸收性和安全性。此外，本发明的化合物可以在短过程中生产。因此，本发明可以提供一种能够高效生产的优秀抗病毒剂。
• Synthesis of 2-amino-6-(4-[11C]methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester as a novel potential PET gene reporter probe for HBV and HSV-tk in cancers
  作者：Ji-Quan Wang、Xiangshu Fei、Thomas A. Gardner、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmc.2004.10.007

  日期：2005.1

  Acyclic nucleoside 2-amino-6-(4-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (ABE, 1) is a new hepatitis B virus (HBV) specific antiviral reagent and shows high anti-HBV activity. Carbon-11 labeled ABE may serve as a novel reporter probe for positron emission tomography (PET) to image HBV and herpes simplex virus thymidine kinase (HSV-tk) in cancers. The radiolabeling precursors 2-amino-6-(4-hydroxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (10) and 2-N-Boc protected analogue 2-N-bis(Boc)amino-6-(4-hydroxyphenylthio)9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (12), and the reference standard ABE were synthesized from bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate (5), guanine (6), and 2-amino-6-chloropurine (8). The target radiotracer 2-amino-6-(4-[C-11]methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester ([C-11]ABE, [C-11]1) was prepared by O-[C-11]methylation of the unprotected HO-precursor 10, or 2-N-Boc protected HO-precursor 12 with [C-11]methyl triflate followed by a quick deprotection reaction, and isolated by solid-phase extraction (SPE) purification in 40-55% radiochemical yields. (C) 2004 Elsevier Ltd. All rights reserved.