(R)-3-(3-fluoro-4-(2-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)oxy)pyrimidin-5-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one | 1188917-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (R)-3-(3-fluoro-4-(2-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)oxy)pyrimidin-5-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one
• 英文别名: (S,R)-3-{3-fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one；(5R)-3-[3-fluoro-4-[2-[[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy]pyrimidin-5-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one
• CAS: 1188917-90-9
• 化学式: C₂₀H₁₇FN₆O₇
• 分子量: 472.389
• InChiKey: PIXHIYPKEKLXQA-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (S)-2-硝基-6,7-二氢-5H-咪唑并[2,1-b][1,3]恶嗪-6-醇 在 sodium hydride 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (R)-3-(3-fluoro-4-(2-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)oxy)pyrimidin-5-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one
  参考文献：
  名称：

  Synergistic Activity of Nitroimidazole-Oxazolidinone Conjugates against Anaerobic Bacteria

  摘要：

  自行车环4-硝基咪唑和噁唑烷酮类抗微生物药物的介绍代表了过去二十年在传染病领域取得的最重要进展。Pretomanid是一种自行车环4-硝基咪唑，而利奈唑是一种噁唑烷酮，它们也是最近被美国食品药品监督管理局批准用于治疗肺部、广泛耐药（XDR）、治疗不耐受或对多药耐药（MDR）结核分枝杆菌（TB）的联合疗法的一部分。为了寻找具有减少耐药发展倾向的新抗微生物药物，设计、合成和评估了一系列双作用硝基咪唑-噁唑烷酮共轭物，以评估它们的抗微生物活性。这种共轭系列中的化合物已显示出对一系列厌氧细菌具有协同作用，包括那些导致严重细菌感染的细菌。

  DOI：

  10.3390/molecules25102431

文献信息

• BICYCLIC NITROIMIDAZOLE-SUBSTITUTED PHENYL OXAZOLIDINONES
  申请人：Ding Charles Z.

  公开号：US20090281088A1

  公开（公告）日：2009-11-12

  The current invention provides a series of bicyclic nitroimidazole-substituted phenyl oxazolidinones in which a bicyclic nitroimidazole pharmacophore is covalently bonded to a phenyl oxazolidinone, their pharmaceutical compositions, and the method of use of the compositions for prevention and treatment of bacterial infections. The bicyclic nitroimidazole-substituted phenyl oxazolidinones possess surprising antibacterial activity against wild-type and resistant strains of pathogens, and are therefore useful for the prevention, control and treatment of a number of human and veterinary bacterial infections caused by these pathogens, such as Mycobacterium tuberculosis.

  本发明提供了一系列双环硝基咪唑取代的苯基噁唑烷酮，其中双环硝基咪唑药效团与苯基噁唑烷酮共价键合，它们的制药组合物以及用于预防和治疗细菌感染的组合物的使用方法。这些双环硝基咪唑取代的苯基噁唑烷酮对野生型和耐药菌株具有惊人的抗菌活性，因此对于预防、控制和治疗由这些病原体引起的许多人类和兽医细菌感染是有用的，如结核分枝杆菌。
• BICYCLIC NITROIMIDAZOLES COVALENTLY LINKED TO SUBSTITUTED PHENYL OXAZOLIDINONES
  申请人：Global Alliance For Tb Drug Development

  公开号：EP2254892B1

  公开（公告）日：2014-04-23
• US7666864B2
  申请人：——

  公开号：US7666864B2

  公开（公告）日：2010-02-23
• [EN] BICYCLIC NITROIMIDAZOLES COVALENTLY LINKED TO SUBSTITUTED PHENYL OXAZOLIDINONES<br/>[FR] NITROIMIDAZOLES BICYCLIQUES LIÉS PAR COVALENCE À DES PHÉNYLOXAZOLIDINONES SUBSTITUÉES
  申请人：GLOBAL ALLIANCE FOR TB DRUG DE

  公开号：WO2009120789A1

  公开（公告）日：2009-10-01

  The current invention provides a series of bicyclic nitroimidazole- substituted phenyl oxazolidinones in which a bicyclic nitroimidazole pharmacophore is covalently bonded to a phenyl oxazolidinone, their pharmaceutical compositions, and the method of use of the compositions for prevention and treatment of bacterial infections. The bicyclic nitroimidazole-substituted phenyl oxazolidinones possess surprising antibacterial activity against wild- type and resistant strains of pathogens, and are therefore useful for the prevention, control and treatment of a number of human and veterinary bacterial infections caused by these pathogens, such as Mycobacterium tuberculosis.
• Synergistic Activity of Nitroimidazole-Oxazolidinone Conjugates against Anaerobic Bacteria
  作者：Zhijun Zhuang、Dawei Wan、Jun Ding、Shijie He、Qian Zhang、Xiaomei Wang、Ying Yuan、Yu Lu、Charles Z. Ding、Anthony Simon Lynch、Anna M. Upton、Christopher B. Cooper、William A. Denny、Zhenkun Ma

  DOI：10.3390/molecules25102431

  日期：——

  The introductions of the bicyclic 4-nitroimidazole and the oxazolidinone classes of antimicrobial agents represented the most significant advancements in the infectious disease area during the past two decades. Pretomanid, a bicyclic 4-nitroimidazole, and linezolid, an oxazolidinone, are also part of a combination regimen approved recently by the US Food and Drug Administration for the treatment of pulmonary, extensively drug resistant (XDR), treatment-intolerant or nonresponsive multidrug-resistant (MDR) Mycobacterium tuberculosis (TB). To identify new antimicrobial agents with reduced propensity for the development of resistance, a series of dual-acting nitroimidazole-oxazolidinone conjugates were designed, synthesized and evaluated for their antimicrobial activity. Compounds in this conjugate series have shown synergistic activity against a panel of anaerobic bacteria, including those responsible for serious bacterial infections.

  自行车环4-硝基咪唑和噁唑烷酮类抗微生物药物的介绍代表了过去二十年在传染病领域取得的最重要进展。Pretomanid是一种自行车环4-硝基咪唑，而利奈唑是一种噁唑烷酮，它们也是最近被美国食品药品监督管理局批准用于治疗肺部、广泛耐药（XDR）、治疗不耐受或对多药耐药（MDR）结核分枝杆菌（TB）的联合疗法的一部分。为了寻找具有减少耐药发展倾向的新抗微生物药物，设计、合成和评估了一系列双作用硝基咪唑-噁唑烷酮共轭物，以评估它们的抗微生物活性。这种共轭系列中的化合物已显示出对一系列厌氧细菌具有协同作用，包括那些导致严重细菌感染的细菌。