3'-azido-3'-deoxy-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine | 174571-55-2

• 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: 3'-azido-3'-deoxy-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine
• 英文别名: N-[5-[3-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]pentyl]-2,2,2-trifluoroacetamide
• CAS: 174571-55-2
• 化学式: C₁₇H₂₃F₃N₆O₅
• 分子量: 448.402
• InChiKey: MOAQDNGMSPEONA-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-azido-3'-deoxy-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine 在 三甲基溴硅烷 、 偶氮二甲酸二异丙酯 、 氨 、 三苯基膦 作用下， 以 甲醇 、 水 为溶剂， 生成 3'-azido-3'-deoxy-5'-O-(dihydroxyphosphoryl)-N³-[1-(5-aminopentyl)]thymidine
  参考文献：
  名称：

  Synthesis of Analogues of 5′-Mono-,5′-Di-, and 5′-Triphosphate-AZT for the Development of Specific Enzyme Immunoassay for Monitoring of Intracellular Levels of AZT-MP, AZT-DP, and AZT-TP

  摘要：

  The synthesis of analogue compounds of polyphosphorylated AZT is described. The compounds are designed to raise specific antibodies against AZT-MP, -DP and -TP in rabbits.

  DOI：

  10.1080/15257779908041604
• 作为产物：
  描述：

  3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 3'-azido-3'-deoxy-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine
  参考文献：
  名称：

  Synthesis of Polyphosphorylated AZT Derivatives for the Development of Specific Enzyme Immunoassays

  摘要：

  The synthesis of a series of analogues of the different polyphosphorylated metabolites of AZT has been carried out. The compounds were designed in order to raise specific antibodies for the development of highly sensitive titration kits for the intracellular metabolites of AZT. The pyrophosphate moiety in AZT-DP and AZT-TP analogues is mimicked by the methylene bisphosphonate group to provide in vivo stability of the compounds. An omega-amino linker was introduced at the N-3 position on the base to allow the further anchoring of the compounds to a carrier protein before immunization, tentitatively focusing the specificity of the immune response toward the phosphate mimic moiety and the nonnatural sugar.

  DOI：

  10.1021/jo982502p

文献信息

• Design, synthesis and studies of triphosphate analogues for the production of anti AZT-TP antibodies
  作者：Camille Roucairol、Stéphane Azoulay、Marie-Claire Nevers、Jérôme Golebiowski、Christophe Créminon、Jacques Grassi、Alain Burger、Danièle Duval

  DOI：10.1016/j.bmcl.2009.12.053

  日期：2010.2

  Triphosphates anabolites are the active chemical species of nucleosidic reverse transcriptase inhibitors in HIV-therapy. Herein, we describe (i) the design of stable triphosphate analogues of AZT using molecular modelling, (ii) their synthesis and (iii) their use for producing anti AZT-TP antibodies in the aim of developing an immunoassay for therapeutic drug monitoring. (c) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Analogues of 5′-Mono-,5′-Di-, and 5′-Triphosphate-AZT for the Development of Specific Enzyme Immunoassay for Monitoring of Intracellular Levels of AZT-MP, AZT-DP, and AZT-TP
  作者：T. Brossette、M-C. Nevers、C. Creminon、C. Mioskowski、J. Grassi、L. Lebeau

  DOI：10.1080/15257779908041604

  日期：1999.4

  The synthesis of analogue compounds of polyphosphorylated AZT is described. The compounds are designed to raise specific antibodies against AZT-MP, -DP and -TP in rabbits.
• Synthesis of a non-hydrolyzable AZT-triphosphate analogue designed for the production of anti-AZT-TP antibodies
  作者：Thierry Brossette、Alain Valleix、Laure Goujon、Christophe Cre´minon、Jacques Grassi、Charles Mioskowski、Luc Lebeau

  DOI：10.1016/s0040-4039(99)00497-9

  日期：1999.4

  An enzymatically stable analogue of AZT-triphosphate is prepared in 7 steps starting from thymidine. The thymine moiety is Functionalized at N-3 to allow the Further cross-linking to a carrier protein for subsequent immunization of rabbits in order to raise specific antibodies directed against AZT-TP. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of Polyphosphorylated AZT Derivatives for the Development of Specific Enzyme Immunoassays
  作者：Thierry Brossette、Anne Le Faou、Laure Goujon、Alain Valleix、Christophe Créminon、Jacques Grassi、Charles Mioskowski、Luc Lebeau

  DOI：10.1021/jo982502p

  日期：1999.7.1

  The synthesis of a series of analogues of the different polyphosphorylated metabolites of AZT has been carried out. The compounds were designed in order to raise specific antibodies for the development of highly sensitive titration kits for the intracellular metabolites of AZT. The pyrophosphate moiety in AZT-DP and AZT-TP analogues is mimicked by the methylene bisphosphonate group to provide in vivo stability of the compounds. An omega-amino linker was introduced at the N-3 position on the base to allow the further anchoring of the compounds to a carrier protein before immunization, tentitatively focusing the specificity of the immune response toward the phosphate mimic moiety and the nonnatural sugar.