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bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate | 186345-41-5

中文名称
——
中文别名
——
英文名称
bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate
英文别名
Phosphonic acid, [(2-iodoethoxy)methyl]-, bis(2,2,2-trifluoroethyl) ester;1,1,1-trifluoro-2-[2-iodoethoxymethyl(2,2,2-trifluoroethoxy)phosphoryl]oxyethane
bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate化学式
CAS
186345-41-5
化学式
C7H10F6IO4P
mdl
——
分子量
430.023
InChiKey
FBCPWTURELUJAL-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    294.4±40.0 °C(Predicted)
  • 密度:
    1.799±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.8
  • 重原子数:
    19
  • 可旋转键数:
    8
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    1.0
  • 拓扑面积:
    44.8
  • 氢给体数:
    0
  • 氢受体数:
    10

SDS

SDS:3e647c17b3df3eb0e7dd59ed218d9060
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    2-Amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl]purine Bis(2,2,2-trifluoroethyl) Esters as Novel HBV-Specific Antiviral Reagents
    摘要:
    Novel 2-amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl] purine bis(2,2,2-trifluoroethyl) esters were synthesized and evaluated for antihepatitis B virus (HBV) activity in vitro using HB611, HuH-6 cell line, stably transfected with the HBV genome. Among the compounds synthesized, 2-amino-6-phenylthio-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (8), 2-amino-6-(4-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl] purine bis(2,2,2-trifluoroethyl) ester (16), 2-amino-6-(3-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (17), and 2-amino-6-(2-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (18) showed considerably high anti-HBV activity, as represented by IC50 values of 0.05, 0.03, 0.04, and 0.08 muM, respectively, and exhibited low cytotoxicity, as represented by CC50 values of more than 1000 muM. It was suggested that these compounds did not have anti-HIV activity, and compound 8 showed only weak anti-HSV-1 activity. An antiviral agent, 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), which was used as a control in the present study, showed moderate anti-HBV activity, as represented by an IC50 value of 0.2 muM. Furthermore, compound 16 was administered orally to mice at a dose of 100 mg/kg in order to examine its gastrointestinal absorbability. Consequently, the main active metabolite was observed in mouse plasma, with especially high concentrations in the liver.
    DOI:
    10.1021/jm020036x
  • 作为产物:
    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
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文献信息

  • 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
    申请人:IAF BioChem International, Inc.
    公开号:US05047407A1
    公开(公告)日:1991-09-10
    Methods and compositions for preventing or treating human immunodeficiency virus (HIV) infections characterized by 2-substituted-5-substituted-1,3-oxathiolanes.
    方法和组合物用于预防或治疗2-取代-5-取代-1,3-噻二氢杂环特征的人类免疫缺陷病毒(HIV)感染。
  • 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.
  • J. Med. Chem. 2002, 45, 3138-3142
    作者:
    DOI:——
    日期:——
  • Bioorg. Med. Chem. 2005, 13, 549-556
    作者:
    DOI:——
    日期:——
  • Nucleosides Nucleotides 1993, 12, 225-236
    作者:
    DOI:——
    日期:——
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同类化合物

(1-氨基丁基)磷酸 顺丙烯基磷酸 除草剂BUMINAFOS 阿仑膦酸 阻燃剂 FRC-1 铵甲基膦酸盐 钠甲基乙酰基膦酸酯 钆1,5,9-三氮杂环十二烷-N,N',N''-三(亚甲基膦酸) 钆-1,4,7-三氮杂环壬烷-N,N',N''-三(亚甲基膦酸) 重氮甲基膦酸二乙酯 辛基膦酸二丁酯 辛基膦酸 辛基-膦酸二钾盐 辛-1-烯-2-基膦酸 试剂12-Azidododecylphosphonicacid 英卡膦酸 苯胺,4-乙烯基-2-(1-甲基乙基)- 苯甲基膦酸二甲酯 苯基膦酸二甲酯 苯基膦酸二仲丁酯 苯基膦酸二乙酯 苯基膦酸二乙酯 苯基磷酸二辛酯 苯基二异辛基亚磷酸酯 苯基(1H-1,2,4-三唑-1-基)甲基膦酸二乙酯 苯丁酸,b-氨基-g-苯基- 苄基膦酸苄基乙酯 苄基亚甲基二膦酸 膦酸,[(2-乙基己基)亚氨基二(亚甲基)]二,triammonium盐(9CI) 膦酸叔丁酯乙酯 膦酸单十八烷基酯钾盐 膦酸二辛酯 膦酸二(二十一烷基)酯 膦酸,辛基-,单乙基酯 膦酸,甲基-,单(2-乙基己基)酯 膦酸,甲基-,二(苯基甲基)酯 膦酸,甲基-,2-甲氧基乙基1-甲基乙基酯 膦酸,丁基乙基酯 膦酸,[苯基[(苯基甲基)氨基]甲基]-,二甲基酯 膦酸,[[羟基(苯基甲基)氨基]苯基甲基]-,二(苯基甲基)酯 膦酸,[2-(环丙基氨基)-2-羰基乙基]-,二乙基酯 膦酸,[2-(二甲基亚肼基)丙基]-,二乙基酯,(E)- 膦酸,[1-甲基-2-(苯亚氨基)乙烯基]-,二乙基酯 膦酸,[1-(乙酰基氨基)-1-甲基乙基]-(9CI) 膦酸,[(环己基氨基)苯基甲基]-,二乙基酯 膦酸,[(二乙氧基硫膦基)(二甲氨基)甲基]- 膦酸,[(2S)-2-氨基-2-苯基乙基]-,二乙基酯 膦酸,[(1Z)-2-氨基-2-(2-噻嗯基)乙烯基]-,二乙基酯 膦酸,P-[(二乙胺基)羰基]-,二乙基酯 膦酸,(氨基二环丙基甲基)-