1-(3-pyrazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine | 124379-59-5

• 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: 1-(3-pyrazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine
• 英文别名: 1-(3-Pyrazol-1-yl-3-deoxy-beta-D-arabinofuranosyl)thymine；1-[(2R,3S,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-pyrazol-1-yloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 124379-59-5
• 化学式: C₁₃H₁₆N₄O₅
• 分子量: 308.294
• InChiKey: KCAFXBRTKGRNCU-MWGHHZFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine 在 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 1-(3-pyrazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines

  摘要：

  Various 3'-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'-erythro position have been synthesized. The pyrrol-1-yl (3) and the 1,2,4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine. The pyrazol-1-yl (16a), imidazol-1-yl (16b), and 1,2,4-triazol-1-yl (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2,3-anhydro-beta-D-lyxofuranosyl)thymines followed by 2'-deoxygenation. Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.

  DOI：

  10.1021/jm00164a063

文献信息

• Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines
  作者：Piet Wigerinck、Arthur Van Aerschot、Gerard Janssen、Paul Claes、Jan Balzarini、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jm00164a063

  日期：1990.2

  Various 3'-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'-erythro position have been synthesized. The pyrrol-1-yl (3) and the 1,2,4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine. The pyrazol-1-yl (16a), imidazol-1-yl (16b), and 1,2,4-triazol-1-yl (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2,3-anhydro-beta-D-lyxofuranosyl)thymines followed by 2'-deoxygenation. Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.