bis(3'-azido-3'-deoxythymidin-5'-yl)carbonate

• 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: bis(3'-azido-3'-deoxythymidin-5'-yl)carbonate
• 英文别名: (AZT-O)2C=O；bis[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl] carbonate
• 化学式: C₂₁H₂₄N₁₀O₉
• 分子量: 560.483
• InChiKey: DYXYYVUBPYLMSC-KPRKPIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  182
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  齐多夫定 在 Candida antarctica lipase B 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 bis(3'-azido-3'-deoxythymidin-5'-yl)carbonate
  参考文献：
  名称：

  Chemoenzymatic Syntheses of Homo‐ and Heterodimers of AZT and d4T, and Evaluation of Their Anti‐HIV Activity

  摘要：

  Homo- and heterodimers of AZT and d4T, possessing carbonate and carbamate linkers, have been synthesized with the aim to enhance the antiviral activity of their components. Homo- and heterodimer carbamates showed weak anti-HIV activity. On the other hand, dinucleoside carbonates showed marked antiviral activity.

  DOI：

  10.1081/ncn-120037749

文献信息

• Synthesis, molecular structure and physicochemical properties of bis(3′-azido-3′-deoxythymidin-5′-yl) carbonate
  作者：Mónica A. Raviolo、Patricia A.M. Williams、Susana B. Etcheverry、Oscar E. Piro、Eduardo E. Castellano、Maria S. Gualdesi、Margarita C. Briñón

  DOI：10.1016/j.molstruc.2010.02.032

  日期：2010.4

  3'-Azido-3'-deoxythymidine (zidovudine, AZT), a synthetic analog of natural nucleoside thymidine, has been used extensively in AIDS treatments. We report here the synthesis. X-ray crystal and molecular structure, NMR, IR and Raman spectra and the thermal behavior of a novel carbonate of AZT [(AZT-O)(2)C=O], prepared by the reaction of zidovudine with carbonyldiimidazole. The carbonate compound, C21H24N10O9, crystallizes in the tetragonal space group P4(1)2(1)2 with a = b = 15.284(1), c = 21.695(1) angstrom, and Z = 8 molecules per unit cell. It consists of two AZT moieties of closely related conformations which are bridged by a carbonyl group to adopt a folded Z-like shape. (C) 2010 Elsevier B.V. All rights reserved.
• Chemoenzymatic Syntheses of Homo‐ and Heterodimers of AZT and d4T, and Evaluation of Their Anti‐HIV Activity
  作者：M. Taourirte、L. Ait Mohamed、A. Rochdi、J.‐J. Vasseur、S. Fernández、M. Ferrero、V. Gotor、C. Pannecouque、E. De Clercq、H. B. Lazrek

  DOI：10.1081/ncn-120037749

  日期：2004.12.31

  Homo- and heterodimers of AZT and d4T, possessing carbonate and carbamate linkers, have been synthesized with the aim to enhance the antiviral activity of their components. Homo- and heterodimer carbamates showed weak anti-HIV activity. On the other hand, dinucleoside carbonates showed marked antiviral activity.