5-(4-Ethyl-phenyl)-oxazole-4-carboxylic acid methyl ester | 89204-98-8

• 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-(4-Ethyl-phenyl)-oxazole-4-carboxylic acid methyl ester
• 英文别名: Methyl 5-(4-ethylphenyl)-1,3-oxazole-4-carboxylate；methyl 5-(4-ethylphenyl)-1,3-oxazole-4-carboxylate
• CAS: 89204-98-8
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: KYRAYBPVGRBFBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Ethyl-phenyl)-oxazole-4-carboxylic acid methyl ester 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-(4-Ethyl-phenyl)-oxazole-4-carboxylic acid amide
  参考文献：
  名称：

  Syntheses of 5-substituted oxazole-4-carboxylic acid derivatives with inhibitory activity on blood platelet aggregation.

  摘要：

  α-异氰基乙酸甲酯在碱存在下与酰化试剂反应，合成了 5-取代的噁唑-4-羧酸甲酯。噁唑甲酯被转化成羧酸和羧酰胺。然后，通过噁唑-4-羧酰氯制备出 N-烷基噁唑-4-羧酰胺。此外，还通过 N-酰基-α-苯甲酰基甘氨酸甲酯的环化合成了 2-取代的噁唑，这些噁唑甲酯是通过α-苯甲酰基甘氨酸甲酯的酰化，然后对生成的噁唑甲酯进行氨解而得到的。对这些噁唑化合物进行了体外和体内血小板聚集抑制活性评估。其中一些化合物的抑制活性与阿司匹林相当。其中，5-(3, 4, 5-三甲氧基苯基) 恶唑-4-甲酰胺是体内外试验中活性最强的化合物。

  DOI：

  10.1248/cpb.31.4417

文献信息

• Syntheses of 5-substituted oxazole-4-carboxylic acid derivatives with inhibitory activity on blood platelet aggregation.
  作者：YASUHIKO OZAKI、SADAO MAEDA、TAMEO IWASAKI、KAZUO MATSUMOTO、AKIO ODAWARA、YASUHIKO SASAKI、TAKASHI MORITA

  DOI：10.1248/cpb.31.4417

  日期：——

  Methyl 5-substituted oxazole-4-carboxylates were synthesized by the reaction of methyl α-isocyanoacetate with acylating reagents in the presence of bases. The oxazole methyl esters were converted into the carboxylic acids and the carboxamides. Then, N-alkyl-oxazole-4-carboxamides were prepared through the oxazole-4-carboxylic acid chloride. Furthermore, 2-substituted oxazoles were synthesized by cyclization of N-acyl-α-benzoylglycine methyl esters. which were obtained by acylation of α-benzoylglycine methyl ester followed by ammonolysis of the resulting oxazole methyl esters. These oxazole compounds were evaluated for inhibitory activity on blood platelet aggregation in vitro and ex vivo. Some of these compounds showed the inhibitory activity comparable to that of aspirin. Of these, 5-(3, 4, 5-trimethoxyphenyl) oxazole-4-carboxamide was the most active compound in the ex vivo test.

  α-异氰基乙酸甲酯在碱存在下与酰化试剂反应，合成了 5-取代的噁唑-4-羧酸甲酯。噁唑甲酯被转化成羧酸和羧酰胺。然后，通过噁唑-4-羧酰氯制备出 N-烷基噁唑-4-羧酰胺。此外，还通过 N-酰基-α-苯甲酰基甘氨酸甲酯的环化合成了 2-取代的噁唑，这些噁唑甲酯是通过α-苯甲酰基甘氨酸甲酯的酰化，然后对生成的噁唑甲酯进行氨解而得到的。对这些噁唑化合物进行了体外和体内血小板聚集抑制活性评估。其中一些化合物的抑制活性与阿司匹林相当。其中，5-(3, 4, 5-三甲氧基苯基) 恶唑-4-甲酰胺是体内外试验中活性最强的化合物。