3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(N-(thioacetyl)aminomethyl)oxazolidin-2-one | 1448256-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(N-(thioacetyl)aminomethyl)oxazolidin-2-one
• 英文别名: N-[[3-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide
• CAS: 1448256-00-5
• 化学式: C₁₅H₁₅FN₄O₃S
• 分子量: 350.374
• InChiKey: WJMUXBODIOAGNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(iodomethyl)oxazolidin-2-one 在 劳森试剂 、 吡啶 、 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(N-(thioacetyl)aminomethyl)oxazolidin-2-one
  参考文献：
  名称：

  New linezolid-like 1,2,4-oxadiazoles active against Gram-positive multiresistant pathogens

  摘要：

  The synthesis and the in vitro antibacterial activity of novel linezolid-like oxadiazoles are reported. Replacement of the linezolid morpholine C-ring with 1,2,4-oxadiazole results in an antibacterial activity against Staphylococcus aureus both methicillin-susceptible and methicillin-resistant comparable or even superior to that of linezolid. While acetamidomethyl or thioacetoamidomethyl moieties in the C(5) side-chain are required, fluorination of the phenyl B ring exhibits a slight effect on an antibacterial activity but its presence seems to reduce the compounds cytotoxicity. Molecular modeling performed using two different approaches - FLAP and Amber software - shows that in the binding pose of the newly synthesized compounds as compared with the crystallographic pose of linezolid, the 1,2,4-oxadiazole moiety seems to perfectly mimic the function of the morpholinic ring, since the H-bond interaction with U2585 is retained. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.069

文献信息

• NOVEL 1, 2, 4-OXADIAZOL COMPOUNDS ACTIVE AGAINST GRAM-POSITIVE PATHOGENS
  申请人：Università degli Studi di Milano - Bicocca

  公开号：EP2970244B1

  公开（公告）日：2019-05-29