5-O-(5-amino-5-deoxy-β-D-ribofuranosyl)-6-deoxy-6-(4-octylphenylureido)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronic acid trifluoroacetate salt | 1223563-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(5-amino-5-deoxy-β-D-ribofuranosyl)-6-deoxy-6-(4-octylphenylureido)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronic acid trifluoroacetate salt
• 英文别名: (2S,3S)-3-[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-3-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-[(4-octylphenyl)carbamoylamino]propanoic acid;2,2,2-trifluoroacetic acid
• CAS: 1223563-51-6
• 化学式: C₂HF₃O₂*C₃₁H₄₅N₅O₁₂
• 分子量: 793.749
• InChiKey: GAWLVTVVNULHNG-XRMJVAHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  55
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  300
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  tert-butyl 5-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-6-deoxy-2,3-O-isopropylidene-6-(4-octylphenylureido)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronate 、 三氟乙酸 以 水 为溶剂， 反应 6.0h， 以93%的产率得到5-O-(5-amino-5-deoxy-β-D-ribofuranosyl)-6-deoxy-6-(4-octylphenylureido)-1-(uracil-1-yl)-β-D-glycero-L-talo-heptofuranuronic acid trifluoroacetate salt
  参考文献：
  名称：

  Function-Oriented Synthesis of Simplified Caprazamycins: Discovery of Oxazolidine-Containing Uridine Derivatives as Antibacterial Agents against Drug-Resistant Bacteria

  摘要：

  The rational simplification of the caprazamycin (CPZ) class of nucleoside natural products was carried out to address their molecular complexity. First, analogues 6-8, where the diazepanone ring of the CPZ was removed and a lipophilic side chain was attached to either the C-7' or N(6') atom, were used to investigate the conformation activity relationship. On the basis of this relationship, we designed the oxazolidine-containing uridine derivatives 18-21 by restricting the conformation of 6-8. As a result, the 'Bu ester derivatives 20 were found to be the most active against a range of bacterial strains containing VRE with a potency similar to that of the parent CPZs. This study provides a novel strategy for the development of a new type of antibacterial agent effective against drug-resistant bacteria.

  DOI：

  10.1021/jm100243n