2-(1,2-O-isopropylidene-α-D-xylo-tetrafuranos-4-yl)-5-(o-bromophenyl)-1,3,4-oxadiazole | 1071856-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(1,2-O-isopropylidene-α-D-xylo-tetrafuranos-4-yl)-5-(o-bromophenyl)-1,3,4-oxadiazole
• 英文别名: (3aR,5S,6S,6aR)-5-[5-(2-bromophenyl)-1,3,4-oxadiazol-2-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 1071856-62-6
• 化学式: C₁₅H₁₅BrN₂O₅
• 分子量: 383.198
• InChiKey: QWKFHZMCMIIFHE-KZWBYHQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2-O-isopropylidene-α-D-xylopentadialdo-1,4-furanose (o-bromobenzoyl)hydrazone 在 1,1,3-三甲基-3-苯基二氢化茚-4,5-二甲酸 、 sodium acetate 作用下， 以 甲醇 为溶剂， 以58%的产率得到2-(1,2-O-isopropylidene-α-D-xylo-tetrafuranos-4-yl)-5-(o-bromophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and antiviral activity of azoles obtained from carbohydrates

  摘要：

  Herein we describe the synthesis of 1,2,4-triazolyl-3-thione; 1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-alpha-D-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.028