N-(((5S)-3-(3-fluoro-4-((2R)-oxiran-2-ylmethoxy)phenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide | 1580053-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(((5S)-3-(3-fluoro-4-((2R)-oxiran-2-ylmethoxy)phenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide
• 英文别名: (S)-N-{[3-[4-((R)-epoxypropoxy)]-3-fluorophenyl]-2-oxo-5-oxazolidinyl}methylacetamide
• CAS: 1580053-20-8
• 化学式: C₁₅H₁₇FN₂O₅
• 分子量: 324.309
• InChiKey: LMKPSHKGZWRICW-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.4
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(((5S)-3-(3-fluoro-4-((2R)-oxiran-2-ylmethoxy)phenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide 在 calcium(II) trifluoromethanesulfonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 生成 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：

  左旋环氧氯丙烷 、 (S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以34%的产率得到N-(((5S)-3-(3-fluoro-4-((2R)-oxiran-2-ylmethoxy)phenyl)-2-oxo-1,3-oxazolidin-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

• 噁唑烷酮类化合物及其制备方法和用途
  申请人：四川好医生药业集团有限公司

  公开号：CN104725330B

  公开（公告）日：2017-06-13

  本发明提供了一种噁唑烷酮类化合物或其药学上可接受的盐或水合物。本发明还提供了化合物的制备方法和用途。本发明提供的化合物，对结核分枝杆菌的选择性明显大于其他革兰氏阳性菌和阴性菌，且其选择性优于阳性药物利奈唑胺，说明本发明提供的化合物对结核杆菌具有极强的特异选择性，为临床用药提供了一种更为安全、有效的新选择。