2-<(Diethylphosphonyl)methoxy>ethyl methanesulfonate | 117087-22-6

• 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: 2-<(Diethylphosphonyl)methoxy>ethyl methanesulfonate
• 英文别名: diethyl (2-mesyloxyethoxy)methylphosphonate；1-Methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane；2-(diethoxyphosphorylmethoxy)ethyl methanesulfonate
• CAS: 117087-22-6
• 化学式: C₈H₁₉O₇PS
• 分子量: 290.274
• InChiKey: UJRVYFSGHYCOKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  420.5±30.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-<(Diethylphosphonyl)methoxy>ethyl methanesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以93%的产率得到diethyl (2-azidoethoxy)methylphosphonate
  参考文献：
  名称：

  Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain

  摘要：

  Acyclic 2'-azanucleosides with a phosphonomethoxy function in the side chain were obtained by coupling of diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl} phosphonate with the pyrimidine nucleobases via the Vorbruggen-type protocol. The compounds were evaluated in vitro for activity against a broad variety of RNA and DNA viruses. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.054
• 作为产物：
  描述：

  二乙基((2-羟基乙氧基)甲基)膦酸基酯 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以96%的产率得到2-<(Diethylphosphonyl)methoxy>ethyl methanesulfonate
  参考文献：
  名称：

  Synthesis and antiviral activity of the nucleotide analog (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cystosine

  摘要：

  The acyclic nucleotide analogue (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl] cytosine (2, HPMPC) was prepared on a multigram scale in 18% overall yield starting from (R)-2,3-O-isopropylideneglycerol. The key step in the nine-step synthetic route is coupling of cytosine with the side-chain derivative 8 which bears a protected phosphonylmethyl ether group. In vitro data showed that HPMPC has good activity against herpes simplex virus types 1 and 2, although it was 10-fold less potent than acyclovir [AVC, 9-[(2-hydroxyethoxy)methyl]guanine]. By comparison, HPMPC exhibited greater activity than ACV against a thymidine kinase deficient strain of HSV 1 and was more potent than ganciclovir [DHPG, 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine] against human cytomegalovirus. In vivo, HPMPC showed exceptional potency against HSV 1 systemic infection in mice, having an ED50 of 0.1 mg/kg per day (ip) compared with 50 mg/kg per day for ACV. HPMPC was also more efficacious than ACV in the topical treatment of HSV 1 induced cutaneous lesions in guinea pigs.

  DOI：

  10.1021/jm00127a010

文献信息

• Synthesis and antiviral activity of methyl derivatives of 9-[2-(phosphonomethoxy)ethyl]guanine
  作者：Kuo Long Yu、Joanne J. Bronson、Hyekyung Yang、Amy Patick、Masud Alam、Vera Brankovan、Roelf Datema、Michael J. M. Hitchcock、John C. Martin

  DOI：10.1021/jm00094a005

  日期：1992.8

  A number of methyl derivatives of 9-[2-(phosphonomethoxy)ethyl]guanine (PMEG, 1) have been synthesized and tested in vitro for anti-herpes and anti-human immunodeficiency virus (HIV) activity. Among these analogues, (R)-2'-methyl-PMEG [(R)-3] and 2',2'-dimethyl-PMEG (7) demonstrated potent anti-HIV activity in the XTT assay with EC50 values of 1.0 and 2.6 microM, respectively. The corresponding (S)-2'-methyl-PMEG

  已经合成了许多9- [2-（膦甲氧基）乙基]鸟嘌呤的甲基衍生物（PMEG，1），并在体外测试了其抗疱疹和抗人免疫缺陷病毒（HIV）的活性。在这些类似物中，（R）-2'-甲基-PMEG [[R] -3]和2'，2'-二甲基-PMEG（7）在XTT分析中显示出有效的抗HIV活性，EC50值为1.0和分别为2.6 microM。发现相应的（S）-2'-甲基-PMEG [（S）-3]对HIV的效力较低。另外，制备9- [3-羟基-2-（膦甲氧基）丙基]鸟嘌呤的（R）和（S）对映异构体（HPMPG，8）用于比较生物学活性，并显示出对疱疹病毒的活性和等效性。 ，但对HIV无效。
• Antiviral phosphonomethoxyalkylene purine and pyrimidine derivatives
  申请人：Institute of Organic Chemistry and Biochemistry of the Academy of

  公开号：US05650510A1

  公开（公告）日：1997-07-22

  A series of compounds of Formula I which have anti-tumor activity, and are useful in treating viral infections, their compositions and use. ##STR1## In Formula I B is a purine or pyrimidine base; alk.sub.1 alk.sub.2 and alk.sub.3 are chemical bonds or alkylene groups; Q is hydrogen or hydroxyl; and R.sub.1 -R.sub.4 are hydrogen or alkyl.

  一系列具有抗肿瘤活性的I式化合物，可用于治疗病毒感染，其组成和用途。## STR1 ## 在公式I中，B是嘌呤或嘧啶碱基; alk.sub.1，alk.sub.2和alk.sub.3是化学键或烷基; Q是氢或羟基; R.sub.1-R.sub.4是氢或烷基。
• BRONSON, JOANNE J.;GHAZZOULI, ISMAIL;HITCHCOOCK, MICHAEL J. M.;WEBB, ROBE+, J. MED. CHEM., 32,(1989) N, C. 1457-1463
  作者：BRONSON, JOANNE J.、GHAZZOULI, ISMAIL、HITCHCOOCK, MICHAEL J. M.、WEBB, ROBE+

  DOI：——

  日期：——
• US5650510A
  申请人：——

  公开号：US5650510A

  公开（公告）日：1997-07-22
• US5854228A
  申请人：——

  公开号：US5854228A

  公开（公告）日：1998-12-29