diethyl 2-(2-hydroxyethoxy)propylphosphonate | 1192066-00-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 2-(2-hydroxyethoxy)propylphosphonate
• 英文别名: 2-(1-Diethoxyphosphorylpropan-2-yloxy)ethanol
• CAS: 1192066-00-4
• 化学式: C₉H₂₁O₅P
• 分子量: 240.237
• InChiKey: RJICQAOGTVEIMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-hydroxyethoxy)propylphosphonate 在 甲醇 、 三甲基溴硅烷 、 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 1-[2-(1-phosphonopropan-2-yloxy)ethyl]thymine
  参考文献：
  名称：

  Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity

  摘要：

  Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy) ethyl (PEE) chain bearing various substituents in beta-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE-ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.045
• 作为产物：
  描述：

  ethyl 2-[1-(diethoxyphosphoryl)propan-2-yloxy]acetate 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 生成 diethyl 2-(2-hydroxyethoxy)propylphosphonate
  参考文献：
  名称：

  支链9- [2-（2-膦酰基乙氧基）乙基]嘌呤的合成，作为一类新的无环核苷膦酸酯，可抑制恶性疟原虫次黄嘌呤-鸟嘌呤-黄嘌呤磷酸核糖基转移酶

  摘要：

  疟疾寄生虫恶性疟原虫（Pf）缺乏从头途径，并且依赖挽救酶次黄嘌呤-鸟嘌呤-黄嘌呤磷酸核糖基转移酶（HGXPRT）来合成6-氧代嘌呤核苷一磷酸。特定的无环核苷膦酸酯（ANP）抑制Pf HGXPRT并具有抗疟原虫活性。合成了两个系列的9- [2-（2-膦酰基乙氧基）乙基]嘌呤衍生的新型支链ANP，以研究其对Pf HGXPRT和人HGPRT的抑制作用。Pf HGXPRT的最佳抑制剂具有K i1μM。数据表明，疏水取代基的位置和性质都改变了ANP的效能和选择性。

  DOI：

  10.1016/j.bmc.2009.07.044

文献信息

• Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity
  作者：Dana Hocková、Antonín Holý、Graciela Andrei、Robert Snoeck、Jan Balzarini

  DOI：10.1016/j.bmc.2011.06.045

  日期：2011.8

  Series of novel acyclic nucleoside phosphonates (ANPs) with various nucleobases and 2-(2-phosphonoethoxy) ethyl (PEE) chain bearing various substituents in beta-position to the phosphonate moiety were prepared. The influence of structural alternations on antiviral activity was studied. Several derivatives exhibit antiviral activity against HIV and vaccinia virus (middle micromolar range), HSV-1 and HSV-2 (lower micromolar range) and VZV and CMV (nanomolar range), although the parent unbranched PEE-ANPs are inactive. Adenine as a nucleobase and the methyl group attached to the PEE chain proved to be a prerequisite to afford pronounced antiviral activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of branched 9-[2-(2-phosphonoethoxy)ethyl]purines as a new class of acyclic nucleoside phosphonates which inhibit Plasmodium falciparum hypoxanthine–guanine–xanthine phosphoribosyltransferase
  作者：Dana Hocková、Antonín Holý、Milena Masojídková、Dianne T. Keough、John de Jersey、Luke W. Guddat

  DOI：10.1016/j.bmc.2009.07.044

  日期：2009.9.1

  the salvage enzyme, hypoxanthine–guanine–xanthine phosphoribosyltransferase (HGXPRT), for the synthesis of the 6-oxopurine nucleoside monophosphates. Specific acyclic nucleoside phosphonates (ANPs) inhibit PfHGXPRT and possess anti-plasmodial activity. Two series of novel branched ANPs derived from 9-[2-(2-phosphonoethoxy)ethyl]purines were synthesized to investigate their inhibition of PfHGXPRT and

  疟疾寄生虫恶性疟原虫（Pf）缺乏从头途径，并且依赖挽救酶次黄嘌呤-鸟嘌呤-黄嘌呤磷酸核糖基转移酶（HGXPRT）来合成6-氧代嘌呤核苷一磷酸。特定的无环核苷膦酸酯（ANP）抑制Pf HGXPRT并具有抗疟原虫活性。合成了两个系列的9- [2-（2-膦酰基乙氧基）乙基]嘌呤衍生的新型支链ANP，以研究其对Pf HGXPRT和人HGPRT的抑制作用。Pf HGXPRT的最佳抑制剂具有K i1μM。数据表明，疏水取代基的位置和性质都改变了ANP的效能和选择性。