N-1-(2-azidoethyl)thymine | 350228-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-1-(2-azidoethyl)thymine
• 英文别名: 1-(2-Azidoethyl)-5-methylpyrimidine-2,4-dione
• CAS: 350228-44-3
• 化学式: C₇H₉N₅O₂
• 分子量: 195.181
• InChiKey: MKFINIUMBBCJJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-1-(2-azidoethyl)thymine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以90%的产率得到1-(2-氨基乙基)-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Alkylation of thymine with 1,2-dibromoethane

  摘要：

  Alkylation of thymine with 1,2-dibromoethane depends strongly on the reaction conditions. Various alkyl derivatives may be produced, including N-1- or N-5-monosubstituted alkylthymines and products of their cyclisation, as well higher molecular weight products resulting from intermolecular substitution of N-1- and N-3-mono- and N-1,N-3-dialkylthymines. We have identified two cyclic products 5 and 6 and the dialkylated derivative 7, for which detailed structural analyses have been performed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00277-0
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 243.0h， 生成 N-1-(2-azidoethyl)thymine
  参考文献：
  名称：

  Alkylation of thymine with 1,2-dibromoethane

  摘要：

  Alkylation of thymine with 1,2-dibromoethane depends strongly on the reaction conditions. Various alkyl derivatives may be produced, including N-1- or N-5-monosubstituted alkylthymines and products of their cyclisation, as well higher molecular weight products resulting from intermolecular substitution of N-1- and N-3-mono- and N-1,N-3-dialkylthymines. We have identified two cyclic products 5 and 6 and the dialkylated derivative 7, for which detailed structural analyses have been performed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00277-0

文献信息

• Synthesis and Biological Evaluation of 3΄-C-Ethynyl and 3΄-C-(1,4-disubstituted-1,2,3-triazolo) Double-Headed Pyranonucleosides
  作者：Christos Kiritsis、Stella Manta、Ioannis Papasotiriou、Evdoxia Coutouli-Argyropoulou、Sakellarios Trakossas、Jan Balzarini、Dimitri Komiotis

  DOI：10.2174/157340612800786624

  日期：2012.5.1

  respectively and deacetylated to afford the target 1-(3'-C-ethynyl-β-D-allopyranosyl)nucleosides 5a-c,f,g. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) reaction was utilized to couple the 3'-C-ethynyl pyranonucleoside derivatives with azidoethyl adenine, 5-fluorouracil and thymine, respectively to afford novel triazole double-headed nucleoside analogs 8a-h. 3'-C-Ethynyl pyranonucleosides and the new double-headed

  设计并合成了一系列新颖的3'-C-乙炔基和3​​'-C-（1,4-二取代-1,2,3-三唑）双头吡喃核苷。3-酮基葡糖苷1与乙炔基溴化镁的反应得到所需的前体3-C-乙炔基-1,2：5,6-二-O-异亚丙基-α-D-呋喃糖（2）。水解，然后进行乙酰化，得到1,2,4,6-四-O-乙酰基-3-C-乙炔基-β-D-戊基葡萄糖（3）。将化合物3分别与甲硅烷基化的5-氟尿嘧啶，尿嘧啶，胸腺嘧啶，N4-苯甲酰胞嘧啶和N6-苯甲酰腺嘌呤缩合并脱乙酰基，得到目标1-（3'-C-乙炔基-β-D-戊吡喃糖基）核苷5a-c， ，铜催化的叠氮化物-炔烃环加成反应（CuAAC）用于将3'-C-乙炔基吡喃核苷衍生物与叠氮基乙基腺嘌呤，5-氟尿嘧啶和胸腺嘧啶偶联，分别得到新的三唑双头核苷类似物8a-h。评价了3'-C-乙炔基吡喃核苷和新的双头类似物的抗病毒和细胞抑制活性。尽管这些化合物均未显示出明显的细胞抑制活性并且没
• Synthesis of modified triazole nucleosides possessing one or two base moieties via a click chemistry approach
  作者：Sakellarios Trakossas、Evdoxia Coutouli-Argyropoulou、Dimitra J. Hadjipavlou-Litina

  DOI：10.1016/j.tetlet.2011.01.145

  日期：2011.4

  Copper-catalyzed 1,3-dipolar cycloaddition of propargyl and azidoethyl thymine and adenine derivatives afforded triazole nucleosides bearing one or two base moieties. A catalytic role of the adenine nucleus was observed and is explained through copper-adenine coordination in the intermediate copper acetylide-azide complex. The antioxidant activity of the obtained cycloadducts was tested. (c) 2011 Elsevier Ltd. All rights reserved.
• Alkylation of thymine with 1,2-dibromoethane
  作者：B Nawrot、O Michalak、S Olejniczak、M.W Wieczorek、T Lis、W.J Stec

  DOI：10.1016/s0040-4020(01)00277-0

  日期：2001.4

  Alkylation of thymine with 1,2-dibromoethane depends strongly on the reaction conditions. Various alkyl derivatives may be produced, including N-1- or N-5-monosubstituted alkylthymines and products of their cyclisation, as well higher molecular weight products resulting from intermolecular substitution of N-1- and N-3-mono- and N-1,N-3-dialkylthymines. We have identified two cyclic products 5 and 6 and the dialkylated derivative 7, for which detailed structural analyses have been performed. (C) 2001 Elsevier Science Ltd. All rights reserved.