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(S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine 3,6,9,12,15,18-hexaoxaeicosyl ester | 1313815-93-8

中文名称
——
中文别名
——
英文名称
(S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine 3,6,9,12,15,18-hexaoxaeicosyl ester
英文别名
[1-[(4-Amino-2-oxo-pyrimidin-1-yl)methyl]-2-hydroxy-ethoxy]methyl-[2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]phosphinic acid;[(2S)-1-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxypropan-2-yl]oxymethyl-[2-[2-[2-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]phosphinic acid
(S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine 3,6,9,12,15,18-hexaoxaeicosyl ester化学式
CAS
1313815-93-8
化学式
C22H42N3O12P
mdl
——
分子量
571.562
InChiKey
LTXCJSZDZXZCNI-FQEVSTJZSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    -3.6
  • 重原子数:
    38
  • 可旋转键数:
    26
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.82
  • 拓扑面积:
    190
  • 氢给体数:
    3
  • 氢受体数:
    12

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

  • 作为产物:
    描述:
    六甘醇四丁基氢氧化铵4-甲基苯磺酸吡啶 、 sodium hydride 、 三乙胺 、 potassium iodide 、 silver(l) oxide 作用下, 以 四氢呋喃甲醇二氯甲烷 、 mineral oil 为溶剂, 反应 134.25h, 生成 (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine 3,6,9,12,15,18-hexaoxaeicosyl ester
    参考文献:
    名称:
    New prodrugs of Adefovir and Cidofovir
    摘要:
    New Adefovir (PMEA) prodrugs with a pro-moiety consisting of decyl or decyloxyethyl chain bearing hydroxyl function(s), hexaethyleneglycol or a (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl unit were prepared starting from the tetrabutylammonium salt of the phosphonate drug and an appropriate alkyl bromide or tosylate. Analogously, two esters of Cidofovir [(S)-HPMPC] bearing a hexaethyleneglycol moiety were prepared. The activity of the prodrugs was evaluated in vitro against different virus families. A loss in the antiviral activities of the hydroxylated decyl or decyloxyethyl esters and hexaethyleneglycol esters of PMEA against human immunodeficiency virus (HIV) and herpesviruses [ including herpes simplex virus (HSV), varicella-zoster virus (VZV), and human cytomegalovirus (CMV)] occurred in comparison with the parent compound. On the other hand, the (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl ester of PMEA showed significant activities against HIV and herpesviruses. (S)-HPMPC prodrugs exhibited anti-cytomegalovirus activities in the same range as the parent drug, whereas the anti-HSV and anti-VZV activities were one-to seven-fold lower than that of Cidofovir. (C) 2011 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2011.04.016
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文献信息

  • New prodrugs of Adefovir and Cidofovir
    作者:Tomáš Tichý、Graciela Andrei、Martin Dračínský、Antonín Holý、Jan Balzarini、Robert Snoeck、Marcela Krečmerová
    DOI:10.1016/j.bmc.2011.04.016
    日期:2011.6
    New Adefovir (PMEA) prodrugs with a pro-moiety consisting of decyl or decyloxyethyl chain bearing hydroxyl function(s), hexaethyleneglycol or a (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl unit were prepared starting from the tetrabutylammonium salt of the phosphonate drug and an appropriate alkyl bromide or tosylate. Analogously, two esters of Cidofovir [(S)-HPMPC] bearing a hexaethyleneglycol moiety were prepared. The activity of the prodrugs was evaluated in vitro against different virus families. A loss in the antiviral activities of the hydroxylated decyl or decyloxyethyl esters and hexaethyleneglycol esters of PMEA against human immunodeficiency virus (HIV) and herpesviruses [ including herpes simplex virus (HSV), varicella-zoster virus (VZV), and human cytomegalovirus (CMV)] occurred in comparison with the parent compound. On the other hand, the (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl ester of PMEA showed significant activities against HIV and herpesviruses. (S)-HPMPC prodrugs exhibited anti-cytomegalovirus activities in the same range as the parent drug, whereas the anti-HSV and anti-VZV activities were one-to seven-fold lower than that of Cidofovir. (C) 2011 Elsevier Ltd. All rights reserved.
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