(S)-N-<<3-(4-acetyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide | 139071-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-<<3-(4-acetyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide
• 英文别名: 5-(S)-Acetamidomethyl-3-[4'-acetyl-3'-fluorophenyl]oxazolidine-2-one；N-(5S)-3-(4-acetyl-3-fluorophenyl)-2-oxooxazolidin-5-ylmethylacetamide；N-[3-(4-acetyl-3-fluoro-phenyI)-2-oxo-oxazolidin-5-ylmethyl]-acetamide；N-[[(5S)-3-(4-acetyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 139071-99-1
• 化学式: C₁₄H₁₅FN₂O₄
• 分子量: 294.283
• InChiKey: SLEXXMGLTJKWNZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-<<3-(4-acetyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide 在 盐酸 、 水 、 溴 、 碳酸氢钠 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 为溶剂， 反应 40.0h， 生成 O-methyl 5-aminomethyl-3-[3-fluoro-4-(2-pyrazol-1-ylmethyl-thiazol-4-yl)-phenyl]-oxazolidin-2-one
  参考文献：
  名称：

  WO2008/143649

  摘要：

  公开号：
• 作为产物：
  描述：

  (S)-N-[3-(3-氟-4-碘-苯基)-2-氧代-唑烷-5-甲基]-乙酰氨 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 甲酸 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (S)-N-<<3-(4-acetyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide
  参考文献：
  名称：

  Carbon–carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria

  摘要：

  In an effort to expand the spectrum of activity of the oxazolidinone class of antibacterial agents to include Gram-negative bacteria, a series of new carbon-carbon linked pyrazolylphenyl analogues has been prepared. The alpha -N-substituted methyl pyrazole (10 alpha) in the C3-linked series exhibited very good Gram-positive activity with MICs less than or equal to 0.5-1 mug/mL and moderate Gramnegative activity with MICs = 2-8 mug/mL against Haemophilus influence and Moraxella catarrhalis. This analogue was also found to have potent in vivo activity with an ED50 = 1.9 mg/kg. beta -Substitution at the C3-linked pyrazole generally results in a loss of activity. The C4-linked pyrazoles are slightly more potent than their counterparts in the C3-linked series. Most of the analogues in the C4-linked series exhibited similar levels of activity in vitro, but lower levels of activity in vivo than 10 alpha. In addition, incorporation of a thioamide moiety in selected C4-linked pyrazole analogues results in an enhancement of in vitro activity leading to compounds several times more potent than eperezolid. linezolid and vancomycin. The thioamide of the N-cyanomethyl pyrazole analogue (34) exhibited an exceptional in vitro activity with MICs of less than or equal to 0.06-0.25 kg/mL against Gram-positive pathogens and with MICs of 1 mug/mL against fastidious Gram-negative pathogens. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00233-4

文献信息

• Aminometyl oxooxazolidinyl benzene derivatives
  申请人：Zeneca Ltd.

  公开号：US06362191B1

  公开（公告）日：2002-03-26

  The invention concerns compounds of formula (I), wherein: A is a 5 membered heteroaryl ring, a bicyclic benzo system containing such a 5 membered heteroaryl ring or a bicyclic or tricyclic heteroaryl ring system with at least one bridgehead nitrogen and optionally a further 1-3 heteroatoms chosen from oxygen, sulfur and nitrogen; R1 is, for example, hydroxy, halo, amino, nitro, cyano, carboxy, thiol, C1-4alkanoyloxy, C1-4alkoxycarbonyl, dimethylaminomethyleneaminocarbonyl, C1-4alkyl, C2-4alkenyl, C2-4alkynyl, C1-4alkoxy, optionally substituted phenyl, an optionally substituted 5- or 6-membered heteroaryl ring or hydroxyC1-4alkyl; n is 0-6; R2 and R3 are independently hydrogen or fluoro; R4 is, for example, C1-4alkyl; pharmaceutically acceptable salts and in vivo hydrolysable ester thereof; processes for their preparation; pharmaceutical compositions containing them and their use as antibacterial agents.

  该发明涉及式(I)的化合物， 其中： A是5元杂环芳基环，含有这样的5元杂环芳基环的双环苯系统，或者带有至少一个桥头氮原子和可选地进一步选择氧、硫和氮中的1-3个杂原子的双环或三环杂环芳基环系统； R1是，例如，羟基、卤素、氨基、硝基、氰基、羧基、硫醇基、C1-4烷酰氧基、C1-4烷氧羰基、二甲氨基甲烷氨基羰基、C1-4烷基、C2-4烯基、C2-4炔基、C1-4烷氧基、可选地取代的苯基、可选地取代的5-或6元杂环芳基环或羟基C1-4烷基； n为0-6； R2和R3独立地是氢或氟； R4是，例如，C1-4烷基；其药学上可接受的盐及体内可水解酯；它们的制备方法；含有它们的药物组合物以及它们作为抗菌剂的用途。
• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 4. Multiply-substituted aryl derivatives
  作者：Chung Ho Park、David R. Brittelli、C. L. J. Wang、Frank D. Marsh、Walter A. Gregory、Mark A. Wuonola、Ronald J. McRipley、Virginia S. Eberly、Andrew M. Slee、Martin Forbes

  DOI：10.1021/jm00084a022

  日期：1992.3

  Antibacterial evaluation of compounds I against Staphylococcus aureus and Enterococcus faecalis gave the following results. The 2,4- and 2,5-disubstituted derivatives have weak or no antibacterial activity. Antibacterial activities of 3,4-disubstituted compounds are comparable to those of the 4-monosubstituted analogues for small 3-substituents (smaller than Br), but decline rapidly for larger 3-substituents

  合成和结构-活性关系（SAR）的研究对5-（乙酰氨基甲基）恶唑烷酮（I）芳香环中不同的多取代模式对抗菌活性的影响。通过先前描述的六步合成法（Gregory，WA；等人，J.Med.Chem。[公式：参见文本] 1989，32，1673），3-取代的化合物的亲电芳族取代反应制备化合物I，和3，4-二取代化合物的官能团互换反应。化合物I对金黄色葡萄球菌和粪肠球菌的抗菌评价给出以下结果。2，4-和2，5-二取代的衍生物具有弱的或没有抗菌活性。抗菌活性3，对于小的3-取代基（小于Br），4-二取代的化合物与4-单取代的类似物相当，但是对于较大的3-取代基则迅速下降。3，4-环氧基衍生物的活性与其开链类似物相当。3，5-二取代的和3，4，5-和2，4，6-三取代的衍生物没有抗菌活性。
• Oxazolidinone combinatorial libraries, compositions and methods of preparation
  申请人：——

  公开号：US20020183371A1

  公开（公告）日：2002-12-05

  Oxazolidinones and methods for their synthesis are provided. Also provided are combinatorial libraries comprising oxazolidinones, and methods to prepare the libraries. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. The methods of library preparation include the attachment of oxazolidinones to a solid support. The methods of compound preparation in one embodiment involve the reaction of an iminophosphorane with a carbonyl containing polymeric support.

  本发明提供了噁唑烷酮及其合成方法。还提供了包含噁唑烷酮的组合式文库以及制备这些文库的方法。此外，还提供了制备生物活性噁唑烷酮以及包含这些噁唑烷酮的药用组合物的方法。文库制备方法包括将噁唑烷酮附着到固体支持上。在一种实施例中，化合物制备方法涉及使用亚胺磷酰胺与含羰基的聚合物支持物反应。
• NOVEL OXAZOLIDINONE COMPOUNDS AS ANTIINFECTIVE AGENTS
  申请人：Takhi Mohamed

  公开号：US20100298384A1

  公开（公告）日：2010-11-25

  The present invention relates to novel oxazolidinone compounds of formula (I) with antibacterial activity, their pharmaceutically acceptable salts, their stereoisomers, their prodrugs, pharmaceutical compositions comprising the same and to their use as therapeutic agents

  本发明涉及具有抗菌活性的新型噁唑烷酮化合物（I）及其药学上可接受的盐、立体异构体、前药、包含其的制药组合物以及将其用作治疗剂的用途。
• Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids
  作者：N. Selvakumar、G. Sunil Kumar、A. Malar Azhagan、G. Govinda Rajulu、Shikha Sharma、M. Sitaram Kumar、Jagattaran Das、Javed Iqbal、Sanjay Trehan

  DOI：10.1016/j.ejmech.2006.10.013

  日期：2007.4

  With an intention to synergise the antibacterial activity of chalcones and oxazolidinones, several hybrid compounds possessing both chalcone and oxazolidinone moieties were synthesized and tested for antibacterial activity. The hybrid molecules containing heterocycles instead of aromatic ring were found to be active. A SAR study with various heterocycles resulted in a lead molecule 20, which was converted to one of the potent antibacterial compounds 27. (c) 2006 Elsevier Masson SAS. All rights reserved.