Ethyl 2-[5-(furan-2-yl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]acetate | 113598-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 2-[5-(furan-2-yl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]acetate
• CAS: 113598-12-2
• 化学式: C₁₈H₁₄F₃NO₄
• 分子量: 365.309
• InChiKey: HDLVWCTUDZROIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  455.1±55.0 °C(predicted)
• 密度：
  1.297±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[5-(furan-2-yl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]acetate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以76%的产率得到2-[5-(Furan-2-yl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]acetic acid
  参考文献：
  名称：

  Synthesis of ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate, a hypolipidemic agent, and related compounds

  摘要：

  A series of 2-aryl and 2-alkyl derivatives of 5-furyl-4-oxazoleacetic acid and their homologues having alkyl groups at the alpha-position of the acids were synthesized and evaluated for their hypolipidemic activities in Sprague-Dawley rats. On the basis of the structure-activity relationships and subacute toxicities, ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate (35) was selected as a candidate compound for development. Compound 35 reduced serum cholesterol and triglyceride levels by 23% and 35%, respectively, at a dose of 0.05% in a diet in normal rats, and it was about 10 times more active in hereditary hyperlipidemic rats (THLR/1) than in normal rats. Compound 35 inhibited platelet aggregation in vitro and also normalized hyperaggregability of hyperlipidemic plasma platelet ex vivo.

  DOI：

  10.1021/jm00401a021
• 作为产物：
  描述：

  3-(三氟甲基)苯甲酰氯 在 sodium hydride 、 碳酸氢钠 、 三氯氧磷 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 8.83h， 生成 Ethyl 2-[5-(furan-2-yl)-2-[3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]acetate
  参考文献：
  名称：

  Synthesis of ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate, a hypolipidemic agent, and related compounds

  摘要：

  A series of 2-aryl and 2-alkyl derivatives of 5-furyl-4-oxazoleacetic acid and their homologues having alkyl groups at the alpha-position of the acids were synthesized and evaluated for their hypolipidemic activities in Sprague-Dawley rats. On the basis of the structure-activity relationships and subacute toxicities, ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate (35) was selected as a candidate compound for development. Compound 35 reduced serum cholesterol and triglyceride levels by 23% and 35%, respectively, at a dose of 0.05% in a diet in normal rats, and it was about 10 times more active in hereditary hyperlipidemic rats (THLR/1) than in normal rats. Compound 35 inhibited platelet aggregation in vitro and also normalized hyperaggregability of hyperlipidemic plasma platelet ex vivo.

  DOI：

  10.1021/jm00401a021

文献信息

• MORIYA, TAMON;SEKI, MASAHIKO;TAKABE, SEIICHI;MATSUMOTO, KAZUO;TAKASHIMA, +, J. MED. CHEM., 31,(1988) N 6, 1197-1204
  作者：MORIYA, TAMON、SEKI, MASAHIKO、TAKABE, SEIICHI、MATSUMOTO, KAZUO、TAKASHIMA, +

  DOI：——

  日期：——