3-benzoyl-5-(1,2-O-isopropylidene-3-O-methyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole | 1071856-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-5-(1,2-O-isopropylidene-3-O-methyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole
• 英文别名: [(3aR,5S,6R,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-(2-benzoylimidazo[2,1-b][1,3]thiazol-5-yl)methanone
• CAS: 1071856-28-4
• 化学式: C₂₁H₂₀N₂O₆S
• 分子量: 428.466
• InChiKey: GDVYUAPABYRIHG-FCGDIQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-bromo-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-hexofuranos-5-ulose 、 N'-(5-benzoylthiazol-2-yl)-N,N-dimethylformamidine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以27%的产率得到3-benzoyl-5-(1,2-O-isopropylidene-3-O-methyl-α-D-xylofuranos-5-ulo-5-yl)imidazo[2,1-b]thiazole
  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

文献信息

• Synthesis and antiviral activity of azoles obtained from carbohydrates
  作者：José Sebastián Barradas、María Inés Errea、Norma B. D’Accorso、Claudia S. Sepúlveda、Laura B. Talarico、Elsa B. Damonte

  DOI：10.1016/j.carres.2008.06.028

  日期：2008.9

  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.