2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine | 667411-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine
• 英文别名: N-(5-Iodo-4-oxo-1,4-dihydropyrimidin-2-yl)benzamide；N-(5-iodo-6-oxo-1H-pyrimidin-2-yl)benzamide
• CAS: 667411-75-8
• 化学式: C₁₁H₈IN₃O₂
• 分子量: 341.108
• InChiKey: ZBRDVNKTPJXKNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine 在 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 三乙酰氧基硼氢化钠 、 氟化氢吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 59.0h， 生成 N-(5-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-1,6-dihydro-pyrimidin-2-yl)-benzamide
  参考文献：
  名称：

  A Short, Efficient Synthesis of 2′-Deoxypseudoisocytidine Based on Heck-Chemistry

  摘要：

  A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.

  DOI：

  10.1081/ncn-120025239
• 作为产物：
  描述：

  2-氨基-5-碘嘧啶-4(1H)-酮 、 苯甲酸酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以76%的产率得到2-(N-benzoylamino)-5-iodo-4-oxo-3,4-dihydropyrimidine
  参考文献：
  名称：

  Synthesis and triplex forming properties of pyrrolidino pseudoisocytidine containing oligodeoxynucleotides

  摘要：

  吡咯烷假C-核苷是天然脱氧核苷的电子等排体，其在生理条件下在吡咯烷环氮处质子化。作为形成三链体的寡脱氧核苷酸 (TFO) 的组成部分，正电荷有望通过与目标 DNA 的磷酸二酯主链的静电相互作用来稳定 DNA 三螺旋。我们描述了吡咯烷异胞苷假核苷和相应的亚磷酰胺结构单元的合成以及将其掺入 TFO 中。与未修饰的寡脱氧核苷酸相比，此类 TFO 显示出显着增加的 DNA 亲和力。亲和力的增加被证明是由于吡咯烷亚基上的正电荷。

  DOI：

  10.1039/b502799c

文献信息

• Synthesis and triplex forming properties of pyrrolidino pseudoisocytidine containing oligodeoxynucleotides
  作者：Alain Mayer、Adrian Häberli、Christian J. Leumann

  DOI：10.1039/b502799c

  日期：——

  Pyrrolidino pseudo-C-nucleosides are isosteres of natural deoxynucleosides which are protonated at the pyrrolidino ring nitrogen under physiological conditions. As constituents of a triplex forming oligodeoxynucleotide (TFO), the positive charge is expected to stabilise DNA triple helices via electrostatic interactions with the phosphodiester backbone of the target DNA. We describe the synthesis of the pyrrolidino isocytidine pseudonucleoside and the corresponding phosphoramidite building block and its incorporation into TFOs. Such TFOs show substantially increased DNA affinity compared to unmodified oligodeoxynucleotides. The increase in affinity is shown to be due to the positive charge at the pyrrolidino subunit.

  吡咯烷假C-核苷是天然脱氧核苷的电子等排体，其在生理条件下在吡咯烷环氮处质子化。作为形成三链体的寡脱氧核苷酸 (TFO) 的组成部分，正电荷有望通过与目标 DNA 的磷酸二酯主链的静电相互作用来稳定 DNA 三螺旋。我们描述了吡咯烷异胞苷假核苷和相应的亚磷酰胺结构单元的合成以及将其掺入 TFO 中。与未修饰的寡脱氧核苷酸相比，此类 TFO 显示出显着增加的 DNA 亲和力。亲和力的增加被证明是由于吡咯烷亚基上的正电荷。
• A Short, Efficient Synthesis of 2′-Deoxypseudoisocytidine Based on Heck-Chemistry
  作者：Alain Mayer、Christian J. Leumann

  DOI：10.1081/ncn-120025239

  日期：2003.10.1

  A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.