3-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-6-[9-(2-methylpropoxy)nonyl]furo[2,3-d]pyrimidin-2-one | 1421336-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 3-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-6-[9-(2-methylpropoxy)nonyl]furo[2,3-d]pyrimidin-2-one
• CAS: 1421336-35-7
• 化学式: C₂₄H₃₈N₂O₅
• 分子量: 434.576
• InChiKey: MZPXAPZQZVELRA-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  undec-10-yn-1-yl methanesulfonate 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.0h， 生成 3-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-6-[9-(2-methylpropoxy)nonyl]furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Novel Antiviral Activity of l-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro

  摘要：

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.

  DOI：

  10.1021/jm301778x

文献信息

• Novel Antiviral Activity of <scp>l</scp>-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro
  作者：Christopher McGuigan、Karen Hinsinger、Laura Farleigh、Ranjith N. Pathirana、Joachim J. Bugert

  DOI：10.1021/jm301778x

  日期：2013.2.14

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.