2-Anilino-5-aryloxazole 13

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Anilino-5-aryloxazole 13
• 英文别名: N-(3-ethylsulfonylphenyl)-5-phenyl-1,3-oxazol-2-amine
• 化学式: C₁₇H₁₆N₂O₃S
• 分子量: 328.392
• InChiKey: ZSUBOTGCWWCVOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯乙酮盐酸盐 在 sodium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 18.0h， 生成 2-Anilino-5-aryloxazole 13
  参考文献：
  名称：

  Discovery and Evaluation of 2-Anilino-5-aryloxazoles as a Novel Class of VEGFR2 Kinase Inhibitors

  摘要：

  A series of derivatives of 2-anilino-5-phenyloxazole (5) has been identified as inhibitors of VEGFR2 kinase. Herein we describe the structure-activity relationship (SAR) of this novel template. Optimization of both aryl rings led to very potent inhibitors at both the enzymatic and cellular levels. Oxazole 39 had excellent solubility and good oral PK when dosed as the bis-mesylate salt and demonstrated moderate in vivo efficacy against HT29 human colon tumor xenografts. X-ray crystallography confirmed the proposed binding mode, and comparison of oxazoles 39 and 46 revealed interesting differences in orientation of 2-pyridyl and 3-pyridyl rings, respectively, attached at the meta position of the 5-phenyl ring.

  DOI：

  10.1021/jm049538w