(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-bromophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 2872-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-bromophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-bromophenoxy)oxan-2-yl]methyl acetate
• CAS: 2872-69-7
• 化学式: C₂₀H₂₃BrO₁₀
• 分子量: 503.301
• InChiKey: WNZWHRKLWFAYMS-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-bromophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 四(三苯基膦)钯 、 caesium carbonate 、 甲胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 N-(2'-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-[1,1'-biphenyl]-3-yl)methanesulfonamide
  参考文献：
  名称：

  Biphenyl Gal and GalNAc FmlH Lectin Antagonists of Uropathogenic E. coli (UPEC): Optimization through Iterative Rational Drug Design

  摘要：

  The F9/Yde/Fml pilus, tipped with the FmlH adhesin, has been shown to provide uropathogenic Escherichia coli (UPEC) a fitness advantage in urinary tract infections (UTIs). Here, we used X-ray structure guided design to optimize our previously described ortho-biphenyl Gal and GalNAc FmlH antagonists such as compound 1 by replacing the carboxylate with a sulfonamide as in 50. Other groups which can accept H-bonds were also tolerated. We pursued further modifications to the biphenyl aglycone resulting in significantly improved activity. Two of the most potent compounds, 86 (IC50 = 0.051 mu M) and 90 (IC50 = 0.034 mu M), exhibited excellent metabolic stability in mouse plasma and liver microsomes but showed only limited oral bioavailability (<1%) in rats. Compound 84 also showed a good pharmacokinetic (PK) profile in mice after IP dosing with compound exposure above the IC50 for 6 h. These new FmlH antagonists represent new antivirulence drugs for UTIs.

  DOI：

  10.1021/acs.jmedchem.8b01561
• 作为产物：
  描述：

  2-溴苯酚 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 以200 mg的产率得到(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-bromophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS
  [FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT D'INFECTIONS BACTÉRIENNES

  摘要：

  本发明涉及各种化合物、组合物和治疗细菌感染（如尿路感染）的方法。

  公开号：

  WO2019094631A1

文献信息

• COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS
  申请人：Washington University

  公开号：US20210171563A1

  公开（公告）日：2021-06-10

  The present invention is directed to various compounds, compositions, and methods for treating bacterial infections such as urinary tract infections.