(5-Ethyl-2-phenyl-quinolin-4-yloxy)-acetic acid ethyl ester | 336100-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5-Ethyl-2-phenyl-quinolin-4-yloxy)-acetic acid ethyl ester
• 英文别名: Ethyl 2-(5-ethyl-2-phenylquinolin-4-yl)oxyacetate
• CAS: 336100-73-3
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: WHOVLUODIQYOST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲胺 、 (5-Ethyl-2-phenyl-quinolin-4-yloxy)-acetic acid ethyl ester 生成 2-(5-Ethyl-2-phenyl-quinolin-4-yloxy)-N-methyl-acetamide
  参考文献：
  名称：

  Synthesis of 4-alkoxy-2-phenylquinoline derivatives as potent antiplatelet agents

  摘要：

  In our continuing search for novel antiplatelet agents, 4-alkoxy derivatives of 2-phenylquinoline as well as related compounds were prepared. Through biological screening, a preliminary structure-antiplatelet activity relationship was established. Compounds 5-ethyl-4-methoxy-2-phenylquinoline (8), 4-ethoxy-5-ethvl-2-phenylquinoline (9), 4-ethoxycarbonylmethoxy-5-ethyl-2phenylquinoline (10), 4-ethoxycarbonylbutoxy-5-ethyl-2-phenylquinoline (12) and 5-ethyl-4-(N-ethylcarboxido)methoxy-2-phenyl-quinoline (17) all demonstrated potent antiplatelet activity. Among them, compound 8 was the most potent with an IC50 value of 0.08 muM and was about 3-fold more active than indomethacin. The mechanism of antiplatelet action of 8 is possibly through its inhibition on cyclooxygenase or thromboxane synthetase. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00652-1
• 作为产物：
  描述：

  5-Ethyl-2-phenyl-1H-quinolin-4-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (5-Ethyl-2-phenyl-quinolin-4-yloxy)-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4-alkoxy-2-phenylquinoline derivatives as potent antiplatelet agents

  摘要：

  In our continuing search for novel antiplatelet agents, 4-alkoxy derivatives of 2-phenylquinoline as well as related compounds were prepared. Through biological screening, a preliminary structure-antiplatelet activity relationship was established. Compounds 5-ethyl-4-methoxy-2-phenylquinoline (8), 4-ethoxy-5-ethvl-2-phenylquinoline (9), 4-ethoxycarbonylmethoxy-5-ethyl-2phenylquinoline (10), 4-ethoxycarbonylbutoxy-5-ethyl-2-phenylquinoline (12) and 5-ethyl-4-(N-ethylcarboxido)methoxy-2-phenyl-quinoline (17) all demonstrated potent antiplatelet activity. Among them, compound 8 was the most potent with an IC50 value of 0.08 muM and was about 3-fold more active than indomethacin. The mechanism of antiplatelet action of 8 is possibly through its inhibition on cyclooxygenase or thromboxane synthetase. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00652-1

文献信息

• Synthesis of 4-alkoxy-2-phenylquinoline derivatives as potent antiplatelet agents
  作者：Ting-Chia Ko、Mann-Jen Hour、Jin-Cherng Lien、Che-Ming Teng、Kuo-Hsiung Lee、Sheng-Chu Kuo、Li-Jiau Huang

  DOI：10.1016/s0960-894x(00)00652-1

  日期：2001.2

  In our continuing search for novel antiplatelet agents, 4-alkoxy derivatives of 2-phenylquinoline as well as related compounds were prepared. Through biological screening, a preliminary structure-antiplatelet activity relationship was established. Compounds 5-ethyl-4-methoxy-2-phenylquinoline (8), 4-ethoxy-5-ethvl-2-phenylquinoline (9), 4-ethoxycarbonylmethoxy-5-ethyl-2phenylquinoline (10), 4-ethoxycarbonylbutoxy-5-ethyl-2-phenylquinoline (12) and 5-ethyl-4-(N-ethylcarboxido)methoxy-2-phenyl-quinoline (17) all demonstrated potent antiplatelet activity. Among them, compound 8 was the most potent with an IC50 value of 0.08 muM and was about 3-fold more active than indomethacin. The mechanism of antiplatelet action of 8 is possibly through its inhibition on cyclooxygenase or thromboxane synthetase. (C) 2001 Published by Elsevier Science Ltd.