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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (22): 2553-2557. 上一篇    下一篇

研究论文

萘普生2-芳基吗啉乙酯的合成及其对环氧合酶-2的抑制活性

胡艾希* 董敏宇 谢艳丽 曹 高 叶 姣

  

  1. (湖南大学化学化工学院 长沙 410082)

  • 投稿日期:2008-04-07 修回日期:2008-05-19 发布日期:2008-11-28
  • 通讯作者: 胡艾希

Synthesis and Cyclooxygenase-2 Inhibitory Activity of 2-(2-Arylmorpholino)ethyl Ester of Naproxen

HU, Ai-Xi* DONG, Min-Yu XIE, Yan-Li CAO, Gao YE, Jiao   

  1. (College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
  • Received:2008-04-07 Revised:2008-05-19 Published:2008-11-28
  • Contact: HU, Ai-Xi

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1443

被引次数

20 | 1

基于萘普生的构效关系对其羧基进行结构修饰, 设计合成了萘普生2-芳基吗啉乙酯类化合物. 芳基乙酮经过溴代、胺化、还原得到的2-芳基-4-羟乙基吗啉在三乙胺作缚酸剂存在下与萘普生酰氯反应得到萘普生2-芳基吗啉乙酯类化合物, 收率24.2%～76.5%. 新化合物结构经1H NMR确认. 生物活性实验结果表明: 在10 μmol/L质量浓度时, 化合物1d对COX-2的抑制率达96.32%.

关键词: 萘普生, 环氧合酶-2, 抑制剂, 吗啉衍生物, 合成

The 2-(2-arylmorpholino)ethyl esters of naproxen were designed and synthesized according to the structure-activity relationship by the reaction of 2-aryl-4-(2-hydroxyethyl)morpholine with 2-(6-meth-
oxy-2-naphthyl)propionyl chloride in yields of 24.2%～76.5%. 2-Aryl-4-(2-hydroxylethyl)morpholine intermediates were synthesized from arylethanones by bromination, amination and deoxidization. Their structures were confirmed by 1H NMR. The preliminary bioassays indicated that compound 1d exhibited a 96.32% inhibition rate against COX-2 in vitro at 10 μmol/L.

Key words: naproxen, cyclooxygenase-2, inhibitor, morpholine derivative, synthesis