ethyl 2-[2-(4-methoxyphenyl)-5-(2-furyl)-4-oxazolyl]acetate | 88352-50-5

• 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-[2-(4-methoxyphenyl)-5-(2-furyl)-4-oxazolyl]acetate
• 英文别名: ethyl 2-[5-(furan-2-yl)-2-(4-methoxyphenyl)-1,3-oxazol-4-yl]acetate
• CAS: 88352-50-5
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: URSTXNUDNQWACG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[2-(4-methoxyphenyl)-5-(2-furyl)-4-oxazolyl]acetate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以82%的产率得到2-[2-(4-Methoxyphenyl)-5-(2-furyl)-4-oxazolyl]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：

  2-氨基-1-(呋喃-2-基)乙-1-酮盐酸盐 在 吡啶 、 氯化亚砜 、 sodium hydride 、 碳酸氢钠 作用下， 以 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 6.83h， 生成 ethyl 2-[2-(4-methoxyphenyl)-5-(2-furyl)-4-oxazolyl]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

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

  公开号：US04642313A1

  公开（公告）日：1987-02-10

  A furyloxazolylacetic acid derivative of the formula: ##STR1## wherein R.sup.1 is alkyl of one to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, phenyl or a substituted phenyl (said substituted phenyl being phenyl group substituted with one or two radicals selected from alkyl of one to 2 carbon atoms, alkoxy of one to 2 carbon atoms and halogen), and R.sup.2 is hydrogen or alkyl of one to 12 carbon atoms. The compound (I) is useful as a hypolipidemic agent.

  公式为：##STR1## 的一种Furyloxazolyl乙酸衍生物，其中R.sup.1是1至6个碳原子的烷基，5至6个碳原子的环烷基，苯基或取代苯基（所述取代苯基为苯基取代基之一或二，所述取代基选自1至2个碳原子的烷基，1至2个碳原子的烷氧基和卤素），R.sup.2是氢或1至12个碳原子的烷基。该化合物（I）可用作降脂药物。
• 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：——
• ——
  作者：MATSUMOTO KAZUO、 TAKASHIMA KOHKI

  DOI：——

  日期：——
• Furyloxazolylacetic acid derivatives, process for preparing same and pharmaceutical compositions containing same
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0087782B1

  公开（公告）日：1986-05-21
• US4642313A
  申请人：——

  公开号：US4642313A

  公开（公告）日：1987-02-10