3-[5-(4-methoxy-phenylamino)-[1,3,4]oxadiazol-2-yl]-chromen-2-one | 1350468-43-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-[5-(4-methoxy-phenylamino)-[1,3,4]oxadiazol-2-yl]-chromen-2-one
• CAS: 1350468-43-7
• 化学式: C₁₈H₁₃N₃O₄
• 分子量: 335.319
• InChiKey: YBWBPAVUPFSMAW-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  在 碘 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以53%的产率得到3-[5-(4-methoxy-phenylamino)-[1,3,4]oxadiazol-2-yl]-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity

  摘要：

  Dual cyclooxygenase/lipoxygenase (COX/LOX) inhibitors constitute a valuable alternative to classical nonsteroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors for the treatment of inflammatory diseases. A series of 3-(5-phenyl/phenylamino-[1,3,4]oxadiazol-2-yl)-chromen-2-one and N-[5-(2-oxo-2H-chromen-3-yl)-[1,3,4] oxadiazol-2-yl]-benzamide derivatives were synthesized and screened for anti-inflammatory, analgesic activity. All the derivatives prepared are active in inhibiting oedema induced by carrageenan. Compound 4e was found more potent with 89% of inhibition followed by compound 4b (86%). Compounds with >70% of anti-inflammatory activity were tested for analgesic, ulcerogenic, and lipid peroxidation profile. Selected compounds were also evaluated for inhibition of COXs (COX-1 and COX-2) and LOXs (LOX-5, LOX-12, and LOX-15). Compound 4e was comparatively selective for COX-2, LOX-5, and LOX-15. Study revealed that these derivatives were more effective than ibuprofen with reduced side effects. It can be suggested that these derivatives could be used to develop more potent and safer NSAIDs.

  DOI：

  10.3109/14756366.2010.550890