N-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydropyran-2-yl]oxyphenyl]acetamide | 1231607-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydropyran-2-yl]oxyphenyl]acetamide
• 英文别名: N-(4-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)acetamide；N-[4-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]acetamide；N-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetamide
• CAS: 1231607-60-5
• 化学式: C₁₄H₁₉NO₇
• 分子量: 313.307
• InChiKey: DCCJHZKQNIFNNA-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(4-((2R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-yloxy)phenyl)acetamide 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以71%的产率得到N-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydropyran-2-yl]oxyphenyl]acetamide
  参考文献：
  名称：

  Glycosylated Acetaminophen Pro-Drug Analogs

  摘要：

  本发明涉及一种用于合成、生产和使用镇痛药扑热息痛的前药类似物的方法和组合物。本发明涉及一种用于生产扑热息痛衍生物的广泛群体的糖苷类物质的方法。

  公开号：

  US20120022012A1

文献信息

• Structure-Based Drug Design and Optimization of Mannoside Bacterial FimH Antagonists
  作者：Zhenfu Han、Jerome S. Pinkner、Bradley Ford、Robert Obermann、William Nolan、Scott A. Wildman、Doug Hobbs、Tom Ellenberger、Corinne K. Cusumano、Scott J. Hultgren、James W. Janetka

  DOI：10.1021/jm100438s

  日期：2010.6.24

  FimH-mediated cellular adhesion to mannosylated proteins is critical in the ability of uropathogenic E. coli (UPEC) to colonize and invade the bladder epithelium during urinary tract infection. We describe the discovery and optimization of potent small-molecule FimH bacterial adhesion antagonists based on alpha-D-mannose 1-position anomeric glycosides using X-ray structure-guided drug design. Optimized biarylmannosides display low nanomolar binding affinity for FimH in a fluorescence polarization assay and submicromolar cellular activity in a hemagglutination (HA) functional cell assay of bacterial adhesion. X-ray crystallography demonstrates that the biphenyl moiety makes several key interactions with the outer surface of FimH including pi-pi interactions with Tyr-48 and an H-bonding electrostatic interaction with the Arg-98/Glu-50 salt bridge. Dimeric analogues linked through the biaryl ring show an impressive 8-fold increase in potency relative to monomeric matched pairs and represent the most potent FimH antagonists identified to date. The FimH antagonists described herein hold great potential for development as novel therapeutics for the effective treatment of urinary tract infections.
• GLYCOSYLATED ACETAMINOPHEN PRO-DRUG
  申请人：Shull Brian

  公开号：US20130217640A1

  公开（公告）日：2013-08-22

  The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug analogs of the analgesic acetaminophen. This invention relates to a method for the production of a broad group of glycosides of acetaminophen derivatives.
• US8722864B2
  申请人：——

  公开号：US8722864B2

  公开（公告）日：2014-05-13
• [EN] GLYCOSYLATED ACETAMINOPHEN PRO-DRUG ANALOGS<br/>[FR] PRO-MÉDICAMENTS À BASE D'ANALOGUES GLYCOSYLÉS D'ACÉTAMINOPHÈNE
  申请人：NUTEK PHARMA LTD

  公开号：WO2012012339A2

  公开（公告）日：2012-01-26

  The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug analogs of the analgesic acetaminophen. This invention relates to a method for the production of a broad group of glycosides of acetaminophen derivatives.
• Glycosylated Acetaminophen Pro-Drug Analogs
  申请人：Shull Brian

  公开号：US20120022012A1

  公开（公告）日：2012-01-26

  The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug analogs of the analgesic acetaminophen. This invention relates to a method for the production of a broad group of glycosides of acetaminophen derivatives.

  本发明涉及一种用于合成、生产和使用镇痛药扑热息痛的前药类似物的方法和组合物。本发明涉及一种用于生产扑热息痛衍生物的广泛群体的糖苷类物质的方法。