N-propargyl-5-acetamidomethyl-2-oxazolidinone | 923276-68-0

• 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: N-propargyl-5-acetamidomethyl-2-oxazolidinone
• 英文别名: N-{[2-Oxo-3-(prop-2-yn-1-yl)-1,3-oxazolidin-5-yl]methyl}acetamide；N-[(2-oxo-3-prop-2-ynyl-1,3-oxazolidin-5-yl)methyl]acetamide
• CAS: 923276-68-0
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: MCPDWRVOOAWOAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  N-propargyl-5-acetamidomethyl-2-oxazolidinone 、 benzyl N-[(2R,3R,4R,5S,6S)-2-[(2R,3S,4R,5S)-2-(azidomethyl)-5-[(1R,2R,3S,5R,6S)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(phenylmethoxycarbonylamino)-6-(phenylmethoxycarbonylaminomethyl)oxan-2-yl]oxy-6-hydroxy-3,5-bis(phenylmethoxycarbonylamino)cyclohexyl]oxy-4-hydroxyoxolan-3-yl]oxy-4,5-dihydroxy-6-(phenylmethoxycarbonylaminomethyl)oxan-3-yl]carbamate 在 copper diacetate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.23h， 生成
  参考文献：
  名称：

  Surprising Alteration of Antibacterial Activity of 5′′-Modified Neomycin against Resistant Bacteria

  摘要：

  A facile synthetic protocol for the production of neomycin B derivatives with various modifications at the 5 '' position has been developed. The structural activity relationship (SAR) against aminoglycoside resistant bacteria equipped with various aminoglycoside-modifying enzymes (AMEs) was investigated. Enzymatic and molecular modeling studies reveal that the superb substrate promiscuity of AMEs allows the resistant bacteria to cope with diverse structural modifications despite the observation that several derivatives show enhanced antibacterial activity compared to the parent neomycin. Surprisingly, when testing synthetic neomycin derivatives against other human pathogens, two leads exhibit prominent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) that are known to exert a high level of resistance against clinically used aminoglycosides. These findings can be extremely useful in developing new aminoglycoside antibiotics against resistant bacteria. Our result also suggests that. new biological and antimicrobial activities can be obtained by chemical modifications of old drugs.

  DOI：

  10.1021/jm800997s

文献信息

• Surprising Alteration of Antibacterial Activity of 5′′-Modified Neomycin against Resistant Bacteria
  作者：Jianjun Zhang、Fang-I. Chiang、Long Wu、Przemyslaw Greg Czyryca、Ding Li、Cheng-Wei Tom Chang

  DOI：10.1021/jm800997s

  日期：2008.12.11

  A facile synthetic protocol for the production of neomycin B derivatives with various modifications at the 5 '' position has been developed. The structural activity relationship (SAR) against aminoglycoside resistant bacteria equipped with various aminoglycoside-modifying enzymes (AMEs) was investigated. Enzymatic and molecular modeling studies reveal that the superb substrate promiscuity of AMEs allows the resistant bacteria to cope with diverse structural modifications despite the observation that several derivatives show enhanced antibacterial activity compared to the parent neomycin. Surprisingly, when testing synthetic neomycin derivatives against other human pathogens, two leads exhibit prominent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) that are known to exert a high level of resistance against clinically used aminoglycosides. These findings can be extremely useful in developing new aminoglycoside antibiotics against resistant bacteria. Our result also suggests that. new biological and antimicrobial activities can be obtained by chemical modifications of old drugs.