(R)-N-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinylmethyl>azide | 114992-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinylmethyl>azide
• 英文别名: (R)-5-azidomethyl-3-p-acetylphenyl-1,3-oxazolidin-2-one；(R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl azide；(R)-3-(4-acetylphenyl)-5-(azidomethyl)oxazolidin-2-one；(5R)-3-(4-acetylphenyl)-5-(azidomethyl)-1,3-oxazolidin-2-one
• CAS: 114992-53-9
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: LRCJJYOMQSDMAQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinylmethyl>azide 在 盐酸 、 sodium hydroxide 、 三甲氧基磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 N-[(S)-3-(4-Acetyl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
  参考文献：
  名称：

  新型抗菌剂dup 721的手性合成

  摘要：

  描述了由4-乙酰基异氰酸酯（）和（R）-丁酸缩水甘油酯（）合成DuP 721 [（S）-N- [3-（4-乙酰苯基）-2-氧代-5-恶唑烷基甲基]乙酰胺]的手性合成方法。。

  DOI：

  10.1016/0040-4020(89)80130-9
• 作为产物：
  描述：

  (R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl methanesulfonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以87%的产率得到(R)-N-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinylmethyl>azide
  参考文献：
  名称：

  新型抗菌剂dup 721的手性合成

  摘要：

  描述了由4-乙酰基异氰酸酯（）和（R）-丁酸缩水甘油酯（）合成DuP 721 [（S）-N- [3-（4-乙酰苯基）-2-氧代-5-恶唑烷基甲基]乙酰胺]的手性合成方法。。

  DOI：

  10.1016/0040-4020(89)80130-9

文献信息

• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 2. The "A" group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Hollis S. Kezar、Randall K. Carlson、Chung Ho Park、Peter F. Corless、Steven J. Miller、P. Rajagopalan

  DOI：10.1021/jm00171a035

  日期：1990.9

  Chem. 1989, 32, 1673) or by elaboration of the synthetic intermediate 2 (A = H) via electrophilic aromatic substitution or elaboration of the intermediate 2 (A = I) by transition metal catalyzed carbon-carbon bond-forming reactions. Antibacterial evaluation of compounds 2 with A = alkyl, ethenyl, ethynyl, hydroxyalkyl, aldo and keto, oximinoakyl, carboalkoxy, nitro, amino, halo and psi-halo, alkylthio

  描述了一系列5-（乙酰氨基甲基）恶唑烷酮抗菌药（2）中改变“ A”基团的作用的合成和构效关系（SAR）研究。化合物2主要通过前述的六步合成法（J. Med。Chem。1989，32，1673）或通过亲电子芳族取代合成中间体2（A = H）或中间体2制备而制备。 （A ＝ I）通过过渡金属催化的碳-碳键形成反应。化合物2的A =烷基，乙烯基，乙炔基，羟烷基，醛基和酮基，氧亚氨基烷基，碳烷氧基，硝基，氨基，卤素和psi-卤代，烷硫基，烷基亚磺酰基和烷基磺酰基的抗菌评估，导致金黄色葡萄球菌和粪肠球菌的鉴定SAR趋势。在几个系列的同系物（烷基，酮基，轴氨基烷基，氨基，卤素和psi-卤代和烷硫基）中，抗菌活性随亲脂性的增加而增加。但是在A是一个三或四取代（大于H的取代基）季原子直接连接于芳环（羟烷基，烷基亚磺酰基，烷基磺酰基）的取代基上，其活性在具有“叔丁基”的系列成员处达到峰值连接模式。相对于具有
• Bifunctional heterocyclic compounds and methods of making and using same
  申请人：Wang Deping

  公开号：US20080119419A1

  公开（公告）日：2008-05-22

  The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional heterocyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.

  本发明提供了一系列双功能杂环化合物，可作为抗感染、抗增殖、抗炎和促动力药物使用。本发明还提供了制备双功能杂环化合物的方法，以及使用这些化合物作为抗感染、抗增殖剂、抗炎剂和/或促动力剂的方法。
• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Mark A. Wuonola、Ronald J. McRipley、David C. Eustice、Virginia S. Eberly、Andrew M. Slee、Martin Forbes、P. T. Bartholomew

  DOI：10.1021/jm00128a003

  日期：1989.8

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.
• Synthesis of Oxazolidinones by a Solid-Phase/Activation Cycloelimination (SP/ACE) Methodology
  作者：Peter ten Holte、Bart C. J. van Esseveldt、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/1099-0690(200108)2001:15<2965::aid-ejoc2965>3.0.co;2-z

  日期：2001.8

  A versatile method for the solid-phase synthesis of oxazolidinones is described, An appropriate 1,2-diol is attached to immobilized sulfonyl chloride, resulting in the selective activation of one of the alcohol functions, The subsequent reaction of the other alcohol group with an isocyanate, followed by a base-promoted cycloelimination gives an oxazolidinone, By proper choice of isocyanates, functionalities can be introduced which are essential for antibiotic activity.
• [EN] BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSES HETEROCYCLIQUES BIFONCTIONNELS ET PROCEDES DE FABRICATION ET D'UTILISATION DE CES COMPOSES
  申请人：RIB X PHARMACEUTICALS INC

  公开号：WO2004029066A3

  公开（公告）日：2004-08-26