N-(((S)-3-(3-fluoro-4-((R)-2-hydroxy-3-((4-methoxyphenyl)amino)propoxy)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide | 1580052-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(((S)-3-(3-fluoro-4-((R)-2-hydroxy-3-((4-methoxyphenyl)amino)propoxy)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
• 英文别名: (S)-N-{3-[4-((R)-2-hydroxy-3-(4-methoxyaniline)propoxy)-3-fluorophenyl]-2-oxo-5-oxazolidinyl}methylacetamide；N-[[(5S)-3-[3-fluoro-4-[(2R)-2-hydroxy-3-(4-methoxyanilino)propoxy]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 1580052-95-4
• 化学式: C₂₂H₂₆FN₃O₆
• 分子量: 447.463
• InChiKey: DVMZUUWMDRDQEF-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(((S)-3-(3-fluoro-4-((R)-2-hydroxy-3-((4-methoxyphenyl)amino)propoxy)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 、 N,N'-羰基二咪唑 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以88%的产率得到N-(((5S)-3-(3-fluoro-4-(((5R)-3-(4-methoxyphenyl)-2-oxooxazolidin-5-yl)methoxy)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  Discovery of novel bis-oxazolidinone compounds as potential potent and selective antitubercular agents

  摘要：

  A variety of new mono-oxazolidinone molecules by modifying the C-ring of Linezolid, a marketed antibiotic for MRSA, were synthesized and tested for their in vitro antibacterial activities against several Staphylococcus aureus, Mycobacterium smegmatis and two Gram-negative bacteria strains (Escherichia coli and Pseudomonas aeruginosa). Among them, compounds 4-7 displayed moderate antimicrobial activities. After development of a second oxazolidinone ring in the western part of the mono-oxazolidinone compounds 4-7 by a ring closure reaction with N, N'-carbonyldiimidazole (CDI), we found thus obtained bis-oxazolidinone compounds 22-25 possess excellently inhibitory activities against H(37)Rv but poor or no effects on other test bacteria. Among them, bis-oxazolidinone compound 22 and 24 are the most potent two compounds with a same MIC value of 0.125 mu g/mL against H(37)Rv virulent strain. Compound 22 also exhibited extremely low cytotoxicity on monkey kidney Vero cells with a selective index (IC50/MIC) over 40,000, which suggested bis-oxazolidinone compound 22 is a promising lead compound for subsequent investigation in search of new antitubercular agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.025
• 作为产物：
  描述：

  (S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 在 potassium carbonate 、 calcium(II) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 N-(((S)-3-(3-fluoro-4-((R)-2-hydroxy-3-((4-methoxyphenyl)amino)propoxy)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  Discovery of novel bis-oxazolidinone compounds as potential potent and selective antitubercular agents

  摘要：

  A variety of new mono-oxazolidinone molecules by modifying the C-ring of Linezolid, a marketed antibiotic for MRSA, were synthesized and tested for their in vitro antibacterial activities against several Staphylococcus aureus, Mycobacterium smegmatis and two Gram-negative bacteria strains (Escherichia coli and Pseudomonas aeruginosa). Among them, compounds 4-7 displayed moderate antimicrobial activities. After development of a second oxazolidinone ring in the western part of the mono-oxazolidinone compounds 4-7 by a ring closure reaction with N, N'-carbonyldiimidazole (CDI), we found thus obtained bis-oxazolidinone compounds 22-25 possess excellently inhibitory activities against H(37)Rv but poor or no effects on other test bacteria. Among them, bis-oxazolidinone compound 22 and 24 are the most potent two compounds with a same MIC value of 0.125 mu g/mL against H(37)Rv virulent strain. Compound 22 also exhibited extremely low cytotoxicity on monkey kidney Vero cells with a selective index (IC50/MIC) over 40,000, which suggested bis-oxazolidinone compound 22 is a promising lead compound for subsequent investigation in search of new antitubercular agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.025

文献信息

• Discovery of novel bis-oxazolidinone compounds as potential potent and selective antitubercular agents
  作者：Wei Ang、Weiwei Ye、Zitai Sang、Yuanyuan Liu、Tao Yang、Yong Deng、Youfu Luo、Yuquan Wei

  DOI：10.1016/j.bmcl.2014.02.025

  日期：2014.3

  A variety of new mono-oxazolidinone molecules by modifying the C-ring of Linezolid, a marketed antibiotic for MRSA, were synthesized and tested for their in vitro antibacterial activities against several Staphylococcus aureus, Mycobacterium smegmatis and two Gram-negative bacteria strains (Escherichia coli and Pseudomonas aeruginosa). Among them, compounds 4-7 displayed moderate antimicrobial activities. After development of a second oxazolidinone ring in the western part of the mono-oxazolidinone compounds 4-7 by a ring closure reaction with N, N'-carbonyldiimidazole (CDI), we found thus obtained bis-oxazolidinone compounds 22-25 possess excellently inhibitory activities against H(37)Rv but poor or no effects on other test bacteria. Among them, bis-oxazolidinone compound 22 and 24 are the most potent two compounds with a same MIC value of 0.125 mu g/mL against H(37)Rv virulent strain. Compound 22 also exhibited extremely low cytotoxicity on monkey kidney Vero cells with a selective index (IC50/MIC) over 40,000, which suggested bis-oxazolidinone compound 22 is a promising lead compound for subsequent investigation in search of new antitubercular agents. (C) 2014 Elsevier Ltd. All rights reserved.