5-(5-bromo-5-deoxy-β-D-ribofuranosyl)-3-benzyl-1-methyluracil | 110419-26-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 5-(5-bromo-5-deoxy-β-D-ribofuranosyl)-3-benzyl-1-methyluracil
• 英文别名: 3-benzyl-5-[(2S,3S,4S,5S)-5-(bromomethyl)-3,4-dihydroxyoxolan-2-yl]-1-methylpyrimidine-2,4-dione
• CAS: 110419-26-6
• 化学式: C₁₇H₁₉BrN₂O₅
• 分子量: 411.252
• InChiKey: PLSNPQRXSSMGRP-KBXIAJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(5-bromo-5-deoxy-β-D-ribofuranosyl)-3-benzyl-1-methyluracil 生成 [(2S,3S,4S,5S)-4-acetyloxy-5-(3-benzyl-1-methyl-2,4-dioxopyrimidin-5-yl)-2-(bromomethyl)oxolan-3-yl] acetate
  参考文献：
  名称：

  PANKIEWICZ, KRZYSZTOF W.;NAWROT, BARBARA;GADLER, HAKAN;PRICE, RICHARD W.;+, J. MED. CHEM., 30,(1987) N 12, 2314-2316

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,10R,11R,12S)-11,12-dihydroxy-4-methyl-8,13-dioxa-4,6-diazatricyclo[8.2.1.02,7]trideca-2,6-dien-5-one 生成 5-(5-bromo-5-deoxy-β-D-ribofuranosyl)-3-benzyl-1-methyluracil
  参考文献：
  名称：

  PANKIEWICZ, KRZYSZTOF W.;NAWROT, BARBARA;GADLER, HAKAN;PRICE, RICHARD W.;+, J. MED. CHEM., 30,(1987) N 12, 2314-2316

  摘要：

  DOI：

文献信息

• Nucleosides. 146. 1-Methyl-5-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil, the C-nucleoside isostere of the potent antiviral agent, 1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)thymine (FMAU). Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides. 6
  作者：Krzysztof W. Pankiewicz、Barbara Nawrot、Hakan Gadler、Pichard W. Price、Kyoichi A. Watanabe

  DOI：10.1021/jm00395a023

  日期：1987.12

  The synthesis of 5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil (1, C-FMAU), an isostere of the potent antiviral and antitumor nucleoside 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)thymine (2'-fluoro-5-methyl-ara-U or FMAU), was achieved. Pseudouridine (2) was converted into 4,5'-anhydro-3'-O-acetyl-2'-O-triflylpseudouridine (4), which was treated with tris(dimethylamino)sulfur (1+) difluorotrimethylsilicate (TASF) to give 4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1- methyluracil (5b) in 40% yield. Acid hydrolysis of the 4,5'-anhydro linkage of 5b with Dowex 50 (H+) afforded C-FMAU. The inhibitory activity of C-FMAU against HSV-1 and HSV-2 was about 10-fold less than that of FMAU in tissue culture. This compound, however, did not show significant activity in mice inoculated with HSV-1 or HSV-2.