5-benzylamino-2'-deoxyuridine | 1239968-06-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-benzylamino-2'-deoxyuridine
• 英文别名: 5-(benzylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1239968-06-9
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: XBFBVHLSLRVSRT-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzylamino-2'-deoxyuridine 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到5-氨基-2'-脱氧尿苷
  参考文献：
  名称：

  Highly Efficient and Facile Synthesis of 5-Azido-2′-Deoxyuridine

  摘要：

  Previously reported syntheses of the photoaffinity label 5-azido-2'-deoxyuridine are rather inefficient and involve the tedious preparation of a 5-nitro intermediate. To overcome these inconveniences, we have developed a new approach from the commercially available 5-bromo-2'-deoxyuridine nucleoside. Our synthetic route makes use of a benzylamination reduction sequence. Using this strategy, the 5-azido-2'-deoxyuridine photolabel is prepared in three steps and quantitative yields.

  DOI：

  10.1080/15257770.2010.487507
• 作为产物：
  描述：

  溴脲苷 、 苄胺 反应 3.0h， 以100%的产率得到5-benzylamino-2'-deoxyuridine
  参考文献：
  名称：

  Highly Efficient and Facile Synthesis of 5-Azido-2′-Deoxyuridine

  摘要：

  Previously reported syntheses of the photoaffinity label 5-azido-2'-deoxyuridine are rather inefficient and involve the tedious preparation of a 5-nitro intermediate. To overcome these inconveniences, we have developed a new approach from the commercially available 5-bromo-2'-deoxyuridine nucleoside. Our synthetic route makes use of a benzylamination reduction sequence. Using this strategy, the 5-azido-2'-deoxyuridine photolabel is prepared in three steps and quantitative yields.

  DOI：

  10.1080/15257770.2010.487507

文献信息

• Perylenyltriazoles inhibit reproduction of enveloped viruses
  作者：Andrey V. Aralov、Gleb V. Proskurin、Alexey A. Orlov、Liubov I. Kozlovskaya、Alexey A. Chistov、Sergey V. Kutyakov、Galina G. Karganova、Vladimir A. Palyulin、Dmitry I. Osolodkin、Vladimir A. Korshun

  DOI：10.1016/j.ejmech.2017.06.014

  日期：2017.9

  1-Substituted 4-perylen-2(3)-y1-1,2,3-triazoles, easily accessible by 'click' reaction and combining in one molecule a polyaromatic unit and a nitrogen heterocycle, were found to strongly inhibit the reproduction of enveloped viruses. 5[4-(Perylen-3-y1)-1,2,3-triazol-1-y1]-uridine and 2-[1-(2-hydroxyethyl)-1,2,3triazol-4-yl]perylene show EC50 of 0.031 and 0.023 mu M, respectively, against tick-borne encephalitis virus (TBEV). Remarkably, the nucleoside unit appears to be not essential for antiviral activity. These results provide deeper understanding of structural basis of activity for this new class of antivirals. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Highly Efficient and Facile Synthesis of 5-Azido-2′-Deoxyuridine
  作者：Stéphanie Gourdain、Christian Petermann、Dominique Harakat、Pascale Clivio

  DOI：10.1080/15257770.2010.487507

  日期：2010.6.28

  Previously reported syntheses of the photoaffinity label 5-azido-2'-deoxyuridine are rather inefficient and involve the tedious preparation of a 5-nitro intermediate. To overcome these inconveniences, we have developed a new approach from the commercially available 5-bromo-2'-deoxyuridine nucleoside. Our synthetic route makes use of a benzylamination reduction sequence. Using this strategy, the 5-azido-2'-deoxyuridine photolabel is prepared in three steps and quantitative yields.