3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(azidomethyl)oxazolidin-2-one | 1448255-96-6

• 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-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(azidomethyl)oxazolidin-2-one
• 英文别名: 5-(Azidomethyl)-3-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-1,3-oxazolidin-2-one；5-(azidomethyl)-3-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-1,3-oxazolidin-2-one
• CAS: 1448255-96-6
• 化学式: C₁₃H₁₁FN₆O₃
• 分子量: 318.267
• InChiKey: CHTBEUNDXYYXMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(azidomethyl)oxazolidin-2-one 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(aminomethyl)oxazolidin-2-one
  参考文献：
  名称：

  针对革兰氏阳性多耐药病原体的新型强效抗菌剂：利奈唑胺样1,2,4-恶二唑中侧链修饰和手性的影响

  摘要：

  研究了利奈唑胺样1,2,4-恶二唑中侧链修饰和手性的影响，以设计出针对革兰氏阳性多药耐药病原体的新型有效抗菌剂。所采用的策略涉及分子建模方法，新设计化合物的合成和生物学评估，对映异构体分离和绝对构型分配。设计的（S）-1-（（3-（4-（3-甲基-1,2,4-恶二唑-5-基）苯基）-恶唑烷丁-2-one-5- ））（甲基）-3-甲基硫脲和（S）-1-（（3-（3-氟-4-（3-甲基-1,2,4-恶二唑-5-基）苯基）-恶唑烷-2-一（5-基）甲基）-3-甲基硫脲对耐多药的利奈唑胺菌株的耐药性高于利奈唑胺。

  DOI：

  10.1016/j.bmc.2014.10.037
• 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 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以99%的产率得到3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-5-(azidomethyl)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 potent antibacterials against Gram-positive multiresistant pathogens: Effects of side chain modification and chirality in linezolid-like 1,2,4-oxadiazoles
  作者：Cosimo G. Fortuna、Roberto Berardozzi、Carmela Bonaccorso、Gianluigi Caltabiano、Lorenzo Di Bari、Laura Goracci、Annalisa Guarcello、Andrea Pace、Antonio Palumbo Piccionello、Gennaro Pescitelli、Paola Pierro、Elena Lonati、Alessandra Bulbarelli、Clementina E.A. Cocuzza、Giuseppe Musumarra、Rosario Musumeci

  DOI：10.1016/j.bmc.2014.10.037

  日期：2014.12

  the synthesis and biological evaluation of new designed compounds, enantiomers separation and absolute configuration assignment. Experimental determination of the antibacterial activity of the designed (S)-1-((3-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-oxazolidin-2-one-5-yl)methyl)-3-methylthiourea and (S)-1-((3-(3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-oxazolidin-2-one-5-yl)methyl)-3-methylthiourea

  研究了利奈唑胺样1,2,4-恶二唑中侧链修饰和手性的影响，以设计出针对革兰氏阳性多药耐药病原体的新型有效抗菌剂。所采用的策略涉及分子建模方法，新设计化合物的合成和生物学评估，对映异构体分离和绝对构型分配。设计的（S）-1-（（3-（4-（3-甲基-1,2,4-恶二唑-5-基）苯基）-恶唑烷丁-2-one-5- ））（甲基）-3-甲基硫脲和（S）-1-（（3-（3-氟-4-（3-甲基-1,2,4-恶二唑-5-基）苯基）-恶唑烷-2-一（5-基）甲基）-3-甲基硫脲对耐多药的利奈唑胺菌株的耐药性高于利奈唑胺。
• 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.
• Synthesis of oxazolidinones from N-aryl-carbamate and epichlorohydrin under mild conditions
  作者：Leydi Marcela Moreno、Paola Marzullo、Silvestre Buscemi、Braulio Insuasty、Antonio Palumbo Piccionello

  DOI：10.24820/ark.5550190.p011.706

  日期：——