2-chloro-4-[(2-(4-methylpiperazin-1-yl)-3,4-dioxocyclobuten-1-yl)amino]phenyl α-D-mannopyranoside | 1403988-91-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-4-[(2-(4-methylpiperazin-1-yl)-3,4-dioxocyclobuten-1-yl)amino]phenyl α-D-mannopyranoside
• 英文别名: 2-Chloro-4-{[2-(4-Methylpiperazin-1-Yl)-3,4-Dioxocyclobut-1-En-1-Yl]amino}phenyl Alpha-D-Mannopyranoside；3-[3-chloro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanilino]-4-(4-methylpiperazin-1-yl)cyclobut-3-ene-1,2-dione
• CAS: 1403988-91-9
• 化学式: C₂₁H₂₆ClN₃O₈
• 分子量: 483.906
• InChiKey: OVFSRWMGARZIAS-YVNBQAQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-氯-4-硝基苯基-a-D-吡喃甘露糖苷 在 吗啉 、 platinum(IV) oxide 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 42.75h， 生成 2-chloro-4-[(2-(4-methylpiperazin-1-yl)-3,4-dioxocyclobuten-1-yl)amino]phenyl α-D-mannopyranoside
  参考文献：
  名称：

  Target Selectivity of FimH Antagonists

  摘要：

  Mannose-based FimH antagonists are considered new therapeutics for the treatment of urinary tract. infections (UTIs). They prevent the adhesion of uropathogenic Escherichia coli (UPEC) to urothelial cell surfaces triggered by the lectin FimH, which is located at the tip of bacterial type I pili. Because all reported FimH antagonists are alpha-D-mannosides, they are also potential ligands of mannose receptors of the human host system. We therefore investigated the selectivity range of five FimH antagonists belonging to different compound families by comparing their affinities for FimH and eight human mannose receptors. On the basis of the detected selectivity range of approximately 5 orders of magnitude, no adverse side effects resulting from nonselective binding to the human receptors have to be expected. FimH antagonists can therefore be further considered as potential therapeutics for the., treatment of UTI.

  DOI：

  10.1021/jm3010338