3',4-anhydro-5-(2-deoxy-β-D-threo-pentofuranosyl)-1-methyluracil | 127517-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3',4-anhydro-5-(2-deoxy-β-D-threo-pentofuranosyl)-1-methyluracil
• 英文别名: (1R,9R,10R)-10-(hydroxymethyl)-4-methyl-8,11-dioxa-4,6-diazatricyclo[7.2.1.02,7]dodeca-2,6-dien-5-one
• CAS: 127517-30-0
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: WVGJDSFQCBFXLX-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-methyl-5-(2-deoxy-5-O-trityl-β-D-glycero-pentofuranos-3-ulosyl)uracil 在 吡啶 、 sodium tetrahydroborate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 3',4-anhydro-5-(2-deoxy-β-D-threo-pentofuranosyl)-1-methyluracil
  参考文献：
  名称：

  Nucleosides. 153. Synthesis of 1-methyl-5-(3-azido-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)uracil and 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil. The C-nucleoside isostere of 3'-azido-3'-deoxythymidine and its 2'-"up"-fluoro analog

  摘要：

  1-Methyl-5-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)uracil (C-AZT), a C-nucleoside isostere of the potent anti-AIDS nucleoside 3'-azido-3'-deoxythymidine (AZT), was synthesized. 1-Methyl-2'-deoxy-5'-O-tritylpseudouridine (2a) was oxidized with CrO3/pyridine/Ac2O complex to 1-methyl-5-(5-O-trityl-beta-D-glycero-pentofuranos-3-ulosyl) uracil (12a), which was selectively reduced to 1-methyl-5-(5-O-trityl-beta-D-threo-pentofuranosyl)uracil (13a). Mesylation of 13a to 14a followed by nucleophilic displacement of the mesyloxy group with azide afforded 3'-azido-2',3'-dideoxy-5'-O-trityl-1-methylpseudoridine (15a), which was detritylated to C-AZT. In a similar manner, 1-methyl-5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (C-FMAU, a potent antiherpetic nucleoside) was converted into the 3'-azido analogue (3'-azido-C-FMAU). Both C-AZT and 3'-azido-C-FMAU, however, did not exhibit any significant inhibitory activity against HIV in H9 cells.

  DOI：

  10.1021/jm00169a030

文献信息

• SOCHACKA, ELZBIETA;NAWROT, BARBARA;PANKIEWICZ, KRZYSZTOF W.;WATANABE, KYO+, J. MED. CHEM., 33,(1990) N, C. 1995-1999
  作者：SOCHACKA, ELZBIETA、NAWROT, BARBARA、PANKIEWICZ, KRZYSZTOF W.、WATANABE, KYO+

  DOI：——

  日期：——