3-5-β-D-ribofuranosylfuro<2,3-d>pyrimidin-2(3H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-5-β-D-ribofuranosylfuro<2,3-d>pyrimidin-2(3H)-one
• 英文别名: 3-(β-D-ribofuranos-1'-yl)furo[2,3-d]pyrimidin-2(3H)-one；1-(β-D-ribofuranosyl)furo[2,3-d]pyrimidin-2(1H)-one；3-(β-D-ribofuranosyl)furo[2,3-d]pyrimidin-2(3H)-one；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]furo[2,3-d]pyrimidin-2-one
• 化学式: C₁₁H₁₂N₂O₆
• 分子量: 268.226
• InChiKey: FCUFHCTWFBZBSV-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2',3',5'-三乙酰尿苷 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 ammonium hydroxide 、 copper(l) iodide 、 四丁基溴化铵 、 一氯化碘 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 39.0h， 生成 3-5-β-D-ribofuranosylfuro<2,3-d>pyrimidin-2(3H)-one
  参考文献：
  名称：

  Fluorescent Nucleoside Derivatives as a Tool for the Detection of Concentrative Nucleoside Transporter Activity Using Confocal Microscopy and Flow Cytometry

  摘要：

  The abundance and function of transporter proteins at the plasma membrane are likely to be crucial in drug responsiveness. Functional detection of human concentrative nucleoside transporters (hCNTs) is of interest for predicting drug sensitivity because of their ability to transport most nucleoside-derived drugs. In the present study, two fluorescent nucleoside analogues, uridine-furan and etheno-cytidine, were evaluated as tools to study in vivo nucleoside transporter-related functions. These two molecules showed high affinity interactions with hCNT1 and hCNT3 and were shown to be substrates of both transporters. Both fluorescence microscopy and flow cytometry experiments showed that uridine-furan uptake was better suited for distinguishing cells that express hCNT1 or hCNT3. These data highlight the usefulness of fluorescent nucleoside derivatives, as long as they fulfill the requirements of confocal microscopy and flow cytometry, for in vivo analysis of hCNT-related function.

  DOI：

  10.1021/acs.molpharmaceut.5b00142

文献信息

• Autofluorescent fused-pyrimidine nucleosides: Synthesis and evaluation as permeants and inhibitors of human nucleoside transporters
  作者：Ireneusz Nowak、Vijaya L. Damaraju、Carol E. Cass、James D. Young、Morris J. Robins

  DOI：10.1135/cccc2011061

  日期：——

  Nucleosides with an aromatic five-membered ring heterocycle (N, O, or S) fused at C4–C5 of pyrimidin-2-one were prepared by ring closures with 5-(alkyn-1-yl)pyrimidin-2-one intermediates, heterocyclic atom replacements, and ring closure with a 5-aminocytidine derivative. Ultraviolet absorption and emission properties of the autofluorescent products enabled studies on permeation and inhibition of the trans-cellular trafficking effected by human equilibrative nucleoside transporters (hENTs). Some of the autofluorescent nucleosides were shown to be potent and selective inhibitors of human concentrative nucleoside transporters (hCNTs) in a companion study reported elsewhere.

  在嘧啶-2-酮的C4-C5位置上，通过使用5-(炔基)-嘧啶-2-酮中间体进行环合、杂环原子替换以及与5-氨基胞嘧啶衍生物进行环合，制备了带有芳香五元环杂环（N、O或S）的核苷。这些自发荧光产物的紫外吸收和发射特性使得可以研究人类平衡核苷转运体（hENTs）介导的跨细胞运输的渗透和抑制作用。在另一项相关研究中，一些自发荧光核苷被证明是人类浓缩核苷转运体（hCNTs）的有效和选择性抑制剂。
• Steric fixation of bromovinyluracil: Synthesis of furo[2,3-<i>d</i>]pyrimidine nucleosides
  作者：Kurt Eger、Mohammad Jalalian、Mathias Schmidt

  DOI：10.1002/jhet.5570320135

  日期：1995.1

  preparation of 5,6-dihydrofuro[2,3-d]pyrimidin-2(3H)-one (3) and its deoxyriboside 8 is reported. Compound 3 undergoes nucleophilic reactions with various agents to yield 5-substituted uracil derivatives. The dehydro derivative of 3, furo[2,3-d]pyrimidin-2(3H)-one (18) was synthesized by cyclization of BVU 15, which made us develop a reproducible and high yield method for the synthesis of BV(D)U. Starting from

  报道了一种合成5,6-二氢呋喃并[2,3- d ]嘧啶-2（3 H）-one（3）及其脱氧核糖核苷8的新方法。化合物3与各种试剂进行亲核反应以产生5-取代的尿嘧啶衍生物。BVU 15的环化反应合成了3，furo [2,3- d ]嘧啶-2（3 H）-one（18）的脱氢衍生物，这为开发BV（ D）U 从18开始，α-脱氧核糖核苷20和β-核糖核苷22 准备好了。
• Fluorescent Nucleoside Derivatives as a Tool for the Detection of Concentrative Nucleoside Transporter Activity Using Confocal Microscopy and Flow Cytometry
  作者：Ana Claudio-Montero、Itziar Pinilla-Macua、Paula Fernández-Calotti、Carlos Sancho-Mateo、Marı́a Pilar Lostao、Dolors Colomer、Anna Grandas、Marçal Pastor-Anglada

  DOI：10.1021/acs.molpharmaceut.5b00142

  日期：2015.6.1

  The abundance and function of transporter proteins at the plasma membrane are likely to be crucial in drug responsiveness. Functional detection of human concentrative nucleoside transporters (hCNTs) is of interest for predicting drug sensitivity because of their ability to transport most nucleoside-derived drugs. In the present study, two fluorescent nucleoside analogues, uridine-furan and etheno-cytidine, were evaluated as tools to study in vivo nucleoside transporter-related functions. These two molecules showed high affinity interactions with hCNT1 and hCNT3 and were shown to be substrates of both transporters. Both fluorescence microscopy and flow cytometry experiments showed that uridine-furan uptake was better suited for distinguishing cells that express hCNT1 or hCNT3. These data highlight the usefulness of fluorescent nucleoside derivatives, as long as they fulfill the requirements of confocal microscopy and flow cytometry, for in vivo analysis of hCNT-related function.