1-(3-pyrrol-1-yl-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine | 124355-24-4

• 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-pyrrol-1-yl-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine
• 英文别名: 3'-Deoxy-3'-pyrrolthymidine；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-pyrrol-1-yloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 124355-24-4
• 化学式: C₁₄H₁₇N₃O₄
• 分子量: 291.307
• InChiKey: SGHAPKYTEJEBPH-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Benzoic acid (2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-pyrrol-1-yl-tetrahydro-furan-2-ylmethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1-(3-pyrrol-1-yl-2,3-dideoxy-β-D-erythro-pentofuranosyl)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

• WIGERINCK, PIET;VAN, AERSCHOT ARTHUR;JANSSEN, GERARD;CLAES, PAUL;BALZARIN+, J. MED. CHEM., 33,(1990) N, C. 868-873
  作者：WIGERINCK, PIET、VAN, AERSCHOT ARTHUR、JANSSEN, GERARD、CLAES, PAUL、BALZARIN+

  DOI：——

  日期：——
• 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.