(S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine | 198410-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine
• 英文别名: (S)-benzyl 4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate；benzyl 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazine-1-carboxylate
• CAS: 198410-25-2
• 化学式: C₂₂H₂₅FN₄O₄
• 分子量: 428.463
• InChiKey: GWIKZSISGJXSCV-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine 在 palladium on activated charcoal 吡啶 、 二氯甲烷 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-[[(5S)-3-[3-氟-4-[4-(2-羟基乙酰基)-1-哌嗪基]苯基]-2-氧代-5-噁唑烷基]甲基]-乙酰胺
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of U-100592 and U-100766, Two Oxazolidinone Antibacterial Agents for the Potential Treatment of Multidrug-Resistant Gram-Positive Bacterial Infections

  摘要：

  Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones,

  DOI：

  10.1021/jm9509556
• 作为产物：
  描述：

  N-[[(5S)-3-[3-氟-4-[4-(2-羟基乙酰基)-1-哌嗪基]苯基]-2-氧代-5-噁唑烷基]甲基]-乙酰胺 在 sodium azide 、 草酰氯 、 sodium hydride 、 碳酸氢钠 、 sodium carbonate 、 二甲基亚砜 、 三乙胺 、 亚硝基苯 、 三苯基膦 、 D-脯氨酸 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 40.0h， 生成 (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine
  参考文献：
  名称：

  Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation

  摘要：

  An efficient enantioselective synthesis of the antibacterials, linezolid (U-100766), and eperezolid (U-100592) using D-proline-catalyzed asymmetric alpha-aminooxylation of aldehydes as the key step is described here. This is the first report on the enantioselective synthesis of linezolid and eperezolid using asymmetric catalysis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.065

文献信息

• Oxazolidinone antibacterial agents having a thiocarbonyl functionality
  申请人：Pharmacia and Upjohn Company

  公开号：US06342513B1

  公开（公告）日：2002-01-29

  The present invention provides compounds of Formula 1: or pharmaceutical acceptable salts thereof wherein A, G and R1 are as defined in the claims which are antibacterial agents.

  本发明提供了式1化合物： 或药物可接受的盐，其中A，G和R1如权利要求中所定义，它们是抗菌剂。
• [EN] BORON CONTAINING SMALL MOLECULES<br/>[FR] PETITES MOLÉCULES CONTENANT DU BORE
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2011037731A1

  公开（公告）日：2011-03-31

  This invention provides, among other things, novel compounds useful for treating bacterial infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.

  这项发明提供了用于治疗细菌感染的新化合物，包含这些化合物的药物组合物，以及这些化合物与至少一种其他治疗有效剂的组合。
• [EN] GLYCOLOYL-SUBSTITUTED OXAZOLIDINONE-DERIVATIVES AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES D'OXAZOLIDINONE GLYCOLOYL-SUBSTITUEE UTILISES COMME AGENTS ANTI-BACTERIEN
  申请人：UPJOHN CO

  公开号：WO2004002479A1

  公开（公告）日：2004-01-08

  The present invention describes difluororthioacetamide oxazolidinones_of formula I with a glycoloylpiperazine substituent as novel antibacterial agents, and antimicrobial combination therapies for combatting infective diseases caused by gram-positive and gram-negative bacteria.

  本发明描述了一种具有甘氨酰哌嗪取代基的二氟硫代乙酰胺噁唑啉酮I式化合物，作为新型抗菌剂，以及用于对抗由革兰氏阳性和革兰氏阴性细菌引起的感染性疾病的抗微生物联合治疗。
• BORON CONTAINING SMALL MOLECULES
  申请人：HERNANDEZ Vincent S.

  公开号：US20110124597A1

  公开（公告）日：2011-05-26

  This invention provides, among other things, novel compounds useful for treating bacterial infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent.

  这项发明提供了多种新型化合物，用于治疗细菌感染，包括含有这些化合物的药物组合物，以及这些化合物与至少一种其他治疗有效剂的组合。
• An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants
  作者：Wanida Phetsang、Mark A.T. Blaskovich、Mark S. Butler、Johnny X. Huang、Johannes Zuegg、Sreeman K. Mamidyala、Soumya Ramu、Angela M. Kavanagh、Matthew A. Cooper

  DOI：10.1016/j.bmc.2014.05.054

  日期：2014.8

  An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile 'click' chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure-activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy.