3-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-bromofuro[2,3-d]pyrimidin-2(3H)-one | 873325-86-1

• 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-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-bromofuro[2,3-d]pyrimidin-2(3H)-one
• 英文别名: [(2R,3S,5R)-3-acetyloxy-5-(6-bromo-2-oxofuro[2,3-d]pyrimidin-3-yl)oxolan-2-yl]methyl acetate
• CAS: 873325-86-1
• 化学式: C₁₅H₁₅BrN₂O₇
• 分子量: 415.197
• InChiKey: PSDBKTOPOBNTLK-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-bromofuro[2,3-d]pyrimidin-2(3H)-one 在 copper(l) iodide 、 四(三苯基膦)钯 氨 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-[2-(4-propylphenyl)ethynyl]furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core

  摘要：

  Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2'-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl < dec-1-en-1-yl < decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were similar to 20-fold more potent inhibitors of VZV than acyclovir but were similar to 6-fold less potent than BVDU and similar to 60-fold weaker than the most active 6-(4-pentylphenyl) -substituted prototype.

  DOI：

  10.1021/jm070210n
• 作为产物：
  描述：

  5-ethynyl-2'-deoxyuridine 在 copper(l) iodide 、 溴 、 potassium acetate 、 三乙胺 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 3-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-bromofuro[2,3-d]pyrimidin-2(3H)-one
  参考文献：
  名称：

  6-（炔-1-基）呋喃并[2,3-d]嘧啶-2（3H）-一碱基和核苷衍生物的合成及生物学评价。

  摘要：

  在C6处带有长链烷基（或4-烷基苯基）取代基的呋喃[2,3-d]嘧啶-2（3H）-one的2'-脱氧核苷衍生物显示出显着的抗VZV（水痘带状疱疹病毒）效力和选择性，以及类似的2'，3'-二脱氧核苷衍生物显示出抗HCMV（人类巨细胞病毒）活性。我们现在报告一种合成方法，该方法能够制备长链6-（炔基-1-基）呋喃并[2,3-d]嘧啶-2（3H）-，其中棒状乙炔间隔基取代了4-取代基-在C6的苯环。已经制备了在N 3处具有甲基，β-d-呋喃呋喃糖基，β-d-阿拉伯呋喃糖基和2-脱氧β-d-赤-戊呋喃糖基取代基的类似物。2'-脱氧核苷系列中C6处的长链衍生物显示病毒编码的核苷激酶敏感的抗VZV活性。令人惊讶的是，3-甲基-6-（辛基-1-基）呋喃[2，

  DOI：

  10.1021/jm050867d

文献信息

• Parallel-stranded DNA: Enhancing duplex stability by the ‘G-clamp’ and a pyrrolo-dC derivative
  作者：Xin Ming、Ping Ding、Peter Leonard、Simone Budow、Frank Seela

  DOI：10.1039/c2ob06606h

  日期：——

  pure oligonucleotides. Oligonucleotide duplexes with parallel chain orientation were constructed incorporating dA·dT and isoGd·dC base pairs. Replacement of dC-residues by the G-clamp 3 led to extraordinarily stable duplexes (ΔTm = +11 °C for two incorporations) in ps DNA, while the pyrrolo-dC derivative 4 behaved like dC. Surprisingly, the G-clamp 3 forms an even more stable base pair with 2′-deoxyisoguanosine

  合成了通过三唑接头与烷基氨基侧链束缚的新吡咯并-dC衍生物4。制备含有G-钳位3或吡咯并-dC衍生物4的寡核苷酸。在标准条件下寡核苷酸的合成和脱保护导致不需要的副产物形成。副产物被鉴定为氨基烷基侧链的丙烯腈加合物。将合成和后处理条件改变为快速脱保护化学反应并在固体支持物上进行氰基乙基的β-消除，得到纯的寡核苷酸。结合dA·dT和isoG d构建具有平行链取向的寡核苷酸双链体·dC碱基对。用G钳3取代dC残基导致ps DNA中非常稳定的双链体（两次掺入的ΔT m = +11°C），而吡咯并dC衍生物4表现得像dC。出乎意料的是，G-clamp 3与DNA中具有平行链取向的2'-脱氧异鸟苷形成了更稳定的碱基对。2'-脱氧鸟苷 在aps DNA中。