(S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide | 96800-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide
• 英文别名: (S)-N-(3-phenyl-2-oxo-5-oxazolidinylmethyl)acetamide；N-[[(5S)-2-oxo-3-phenyl-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 96800-17-8
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: ZWTBIVLRHWDITL-NSHDSACASA-N

物化性质

• 沸点：
  436.6±14.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide 在 bis(triphenylphosphine)palladium(II)-chloride 、 碘 、 silver trifluoroacetate 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 24.0h， 生成 (S)-N-<<3-(4-carbomethoxyphenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide
  参考文献：
  名称：

  抗菌药。3-芳基-2-氧代恶唑烷的合成及结构活性研究。2.“ A”组。

  摘要：

  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

  DOI：

  10.1021/jm00171a035
• 作为产物：
  描述：

  (R)-(3-phenyl-2-oxo-5-oxazolidinyl)methyl azide 在 sodium hydroxide 、 三甲氧基磷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 1.5h， 生成 (S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide
  参考文献：
  名称：

  Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group

  摘要：

  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.

  DOI：

  10.1021/jm00128a003

文献信息

• 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。
• A short synthesis of oxazolidinone derivatives linezolid and eperezolid: A new class of antibacterials
  作者：Braj B. Lohray、Sundarababu Baskaran、B. Srinivasa Rao、B. Yadi Reddy、I. Nageswara Rao

  DOI：10.1016/s0040-4039(99)00893-x

  日期：1999.6

  Oxazolidinone derivatives such as Linezolid and Eperazolid, which are a new class of antibacterials, have been synthesized from 1,2,5,6-dianhydro-3,4-isopropylidine-D-mannitol in good yield.

  由1,2,5,6-二脱水-3,4-异丙基吡啶-D-甘露糖醇合成的新型抗菌剂恶唑烷酮衍生物（如Linezolid和Eperazolid）是高收率的。
• Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04705799A1

  公开（公告）日：1987-11-10

  Novel aminomethyl oxooxazolidinyl benzene derivatives, including the sulfides, sulfoxides, sulfones and sulfonamides, such as (l)-N-[3-[4-(methylsulfinyl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.

  新型氨甲基氧噁唑啉基苯衍生物，包括硫醚、亚硫醚、磺酰和磺酰胺衍生物，如（l）-N-[3-[4-(甲基亚磺基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。
• GREGOR, WALTER A.;BRITTELLI, DAVID R.;WANG, C. -L. J.;KEZAR, HOLLIS S. (I+, J. MED. CHEM., 33,(1990) N, C. 2569-2578
  作者：GREGOR, WALTER A.、BRITTELLI, DAVID R.、WANG, C. -L. J.、KEZAR, HOLLIS S. (I+

  DOI：——

  日期：——
• 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.