3-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-((pyrazol-1-yl)methyl)oxazolidin-2-one | 1448256-01-6

• 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-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-((pyrazol-1-yl)methyl)oxazolidin-2-one
• 英文别名: 3-[4-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]-5-(pyrazol-1-ylmethyl)-1,3-oxazolidin-2-one；3-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-5-(pyrazol-1-ylmethyl)-1,3-oxazolidin-2-one
• CAS: 1448256-01-6
• 化学式: C₁₆H₁₅N₅O₃
• 分子量: 325.327
• InChiKey: GRIUBUMTCNSKIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-allyl-4-(3'-methyl-1,2,4-oxadiazol-5'-yl)-aniline 在 4-二甲氨基吡啶 、 碘 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 72.5h， 生成 3-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-((pyrazol-1-yl)methyl)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

• New linezolid-like 1,2,4-oxadiazoles active against Gram-positive multiresistant pathogens
  作者：Cosimo G. Fortuna、Carmela Bonaccorso、Alessandra Bulbarelli、Gianluigi Caltabiano、Laura Rizzi、Laura Goracci、Giuseppe Musumarra、Andrea Pace、Antonio Palumbo Piccionello、Annalisa Guarcello、Paola Pierro、Clementina E.A. Cocuzza、Rosario Musumeci

  DOI：10.1016/j.ejmech.2013.03.069

  日期：2013.7

  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.