5-Methyl-2-(4-nitro-phenyl)-4-carboxy-oxazol | 2940-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Methyl-2-(4-nitro-phenyl)-4-carboxy-oxazol
• 英文别名: 5-Methyl-3-<4-nitro-phenyl>-oxazol-4-carbonsaeure；5-methyl-2-(4-nitrophenyl)-1,3-oxazole-4-carboxylic acid；5-methyl-2-(4-nitrophenyl)oxazole-4-carboxylic acid
• CAS: 2940-25-2
• 化学式: C₁₁H₈N₂O₅
• 分子量: 248.195
• InChiKey: MTFFQEVXXGGPMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Methyl-2-(4-nitro-phenyl)-4-carboxy-oxazol 、 N-(2-吡啶甲基)甘氨酸乙酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

  摘要：

  Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.021
• 作为产物：
  描述：

  1-[5-methyl-2-(4-nitro-phenyl)-oxazol-4-yl]-ethanone 在 sodium hypobromide 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-Methyl-2-(4-nitro-phenyl)-4-carboxy-oxazol
  参考文献：
  名称：

  一些取代的4-乙酰基恶唑及其相应酸的合成

  摘要：

  在干燥的氯化氢存在下，通过芳族醛与羟基亚氨基-β-二酮的缩合和中间体N-氧化物的还原，已经制备了几种乙酰基-恶唑。用次溴酸钠将乙酰基-恶唑氧化为相应的酸。

  DOI：

  10.1039/j39680001397

文献信息

• Solution versus Fluorous versus Solid-Phase Synthesis of 2,5-Disubstituted 1,3-Azoles. Preliminary Antibacterial Activity Studies
  作者：Juan F. Sanz-Cervera、Raül Blasco、Julio Piera、Michael Cynamon、Ignacio Ibáñez、Marcelo Murguía、Santos Fustero

  DOI：10.1021/jo9016265

  日期：2009.12.4

  A small library of compounds with an oxa(thia)zole scaffold and structural diversity in both positions 2 and 5 has been synthesized. Double acylation of a protected glycine affords intermediate alpha-amido-beta-ketoesters, which in turn can be dehydrated to afford 1,3-oxazoles or reacted with Lawesson's reagent to furnish 1,3-thiazoles. This procedure was designed with its adaptation to fluorous techniques in mind. Thus, when a protected glycine With a fluorous tag in the ester moiety IS used as a starting material, the synthesis can be easily completed Without column chromatography purification of intermediate compounds with good to excellent yields, thus affording a Suitable entry to the preparation of small libraries of these bioactive compounds. The prepared oxa(thia)zoles were assayed for their antibacterial activity, and several of them were active against Staphylococcus aureus.