2-[2-(4-Chlorophenyl)-5-(furan-2-yl)-1,3-oxazol-4-yl]propanoic acid | 94797-19-0

• 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-[2-(4-Chlorophenyl)-5-(furan-2-yl)-1,3-oxazol-4-yl]propanoic acid
• CAS: 94797-19-0
• 化学式: C₁₆H₁₂ClNO₄
• 分子量: 317.729
• InChiKey: ROFMOVBDYDLIEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙基[2-(4-氯苯基)-5-(2-呋喃基)-1,3-恶唑-4-基]乙酸酯 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 10.0h， 生成 2-[2-(4-Chlorophenyl)-5-(furan-2-yl)-1,3-oxazol-4-yl]propanoic 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

文献信息

• Furyloxazolylacetic acid derivative, processes for preparing same and pharmaceutical composition
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0120270A2

  公开（公告）日：1984-10-03

  A furyloxazolylacetic acid derivative of the formula: wherein R' is lower alkyl, R2 is hydrogen atom or lower alkyl, R3 is hydrogen atom or lower alkyl and ring A is phenyl or halogenophenyl, processes for preparing same and pharmaceutical compositions containing the new compounds, which are useful as a hypolipidemic agent are disclosed.

  一种式中R'为低级烷基，R2为氢原子或低级烷基，R3为氢原子或低级烷基，环A为苯基或卤素苯基的呋喃恶唑乙酸衍生物，其制备方法以及含有该衍生物的药物组合物： 其中R'为低级烷基，R2为氢原子或低级烷基，R3为氢原子或低级烷基，环A为苯基或卤代苯基，公开了制备这些新化合物的工艺和含有这些新化合物的药物组合物，它们可用作降血脂剂。
• 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：——
• Synthesis of ethyl 2-(4-chlorophenyl)-5-(2-furyl)-4-oxazoleacetate, a hypolipidemic agent, and related compounds
  作者：Tamon Moriya、Masahiko Seki、Seiichi Takabe、Kazuo Matsumoto、Kohki Takashima、Tetsuji Mori、Akio Odawara、Shigeyuki Takeyama

  DOI：10.1021/jm00401a021

  日期：1988.6

  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.