3-(1-(5-bromo-4-(4-chlorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide | 1403880-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1-(5-bromo-4-(4-chlorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide
• 英文别名: 3-[1-[5-Bromo-4-(4-chlorophenyl)-1,3-oxazol-2-yl]-2-hydroxyethoxy]-2,6-difluorobenzamide
• CAS: 1403880-94-3
• 化学式: C₁₈H₁₂BrClF₂N₂O₄
• 分子量: 473.658
• InChiKey: XEHMZJXZTRXASU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  C₁₃H₁₁BrClNO₃ 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-(1-(5-bromo-4-(4-chlorophenyl)oxazol-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationships of substituted oxazole–benzamide antibacterial inhibitors of FtsZ

  摘要：

  The design, synthesis and structure-activity relationships of a series of oxazole-benzamide inhibitors of the essential bacterial cell division protein FtsZ are described. Compounds had potent anti-staphylococcal activity and inhibited the cytokinesis of the clinically-significant bacterial pathogen Staphylococcus aureus. Selected analogues possessing a 5-halo oxazole also inhibited a strain of S. aureus harbouring the glycine-to-alanine amino acid substitution at residue 196 of FtsZ which conferred resistance to previously reported inhibitors in the series. Substitutions to the pseudo-benzylic carbon of the scaffold improved the pharmacokinetic properties by increasing metabolic stability and provided a mechanism for creating pro-drugs. Combining multiple substitutions based on the findings reported in this study has provided small-molecule inhibitors of FtsZ with enhanced in vitro and in vivo antibacterial efficacy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.002

文献信息

• [EN] AROMATIC AMIDES AND USES THEREOF<br/>[FR] AMIDES AROMATIQUES ET LEURS UTILISATIONS
  申请人：BIOTA SCIENT MANAGEMENT

  公开号：WO2012142671A1

  公开（公告）日：2012-10-26

  The present invention provides compounds of Formula (I): and salts, racemates, isomers, diastereoisomers, enantiomers, hydrates, solvates, N-oxides, pharmaceutically acceptable derivatives or prodrugs thereof. Also provided the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

  本发明提供了化合物的结构式(I)：以及它们的盐、消旋体、异构体、对映异构体、立体异构体、水合物、溶剂合物、N-氧化物、药学上可接受的衍生物或前药。还提供了这些化合物作为抗菌剂的用途，包括它们的组合物和制造过程。
• AROMATIC AMIDES AND USES THEREOF
  申请人：Haydon David John

  公开号：US20140135332A1

  公开（公告）日：2014-05-15

  The present invention provides compounds of Formula (I): and salts, racemates, isomers, diastereoisomers, enantiomers, hydrates, solvates, N-oxides, pharmaceutically acceptable derivatives or prodrugs thereof. Also provided the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.

  本发明提供了式（I）的化合物及其盐、外消旋体、异构体、对映异构体、水合物、溶剂化物、N-氧化物、药学上可接受的衍生物或前药。同时提供了这些化合物作为抗菌剂的用途、包含它们的组合物以及它们的制造过程。
• EP2699557B1
  申请人：——

  公开号：EP2699557B1

  公开（公告）日：2017-08-16
• COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
  申请人：TAXIS Pharmaceuticals, Inc.

  公开号：US20170305943A1

  公开（公告）日：2017-10-26

  Compounds and methods are provided for treating bacterial infections.
• US9511073B2
  申请人：——

  公开号：US9511073B2

  公开（公告）日：2016-12-06