1-<5-O-trityl-2-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine | 124355-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-<5-O-trityl-2-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine
• 英文别名: 5-methyl-1-[(2R,3R,5S)-3-(1,2,4-triazol-1-yl)-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 124355-39-1
• 化学式: C₃₁H₂₉N₅O₄
• 分子量: 535.602
• InChiKey: WXFHTCUSPTXUDP-YIKNKFAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<5-O-trityl-2-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到1-<2-(1,2,4-triazol-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
• 作为产物：
  描述：

  Imidazole-1-carboxylic acid (2R,3R,4R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-[1,2,4]triazol-1-yl-2-trityloxymethyl-tetrahydro-furan-3-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到1-<5-O-trityl-2-(1,2,4-triazol-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：——