新型布洛芬衍生物的合成及其抗炎活性.pdfVIP

学兔兔 2014年第22卷 合成 化学 Vo1．22，2014 第6期，781~784 Chinese Journal of Synthetic Chemistry No．6，781—784 · 快递论文· 新型布洛芬衍生物的合成及其抗炎活性 陈诗语，杭 琪，敖桂珍，候丙波，绪广林 (苏州大学药学院，江苏苏州 215123) 摘要：以布洛芬为原料，依次与草酰氯和氨基酸(2a一2d)反应制得中间体布洛芬衍生物(3a一3d)；3与可缓 慢释放H：S的5一对羟基苯基-1，2-二硫杂环戊烯-3-硫酮(4)经酯化反应，合成了4个新型的s-(+)-布洛芬衍生 物(5a一5d)。 -溴乙酰氯与4经酯化反应制得5一(4- -溴乙酰氧基)一苯基一1，2-二硫杂环戊烯-3．-硫酮(6)；6与 1经偶联反应合成了一个新型的S-(+)-布洛芬衍生物(7)，5和7的结构经 H NMR，IR和HR．MS表征。二 甲苯致小鼠耳肿胀试验结果表明：5a，5c，5d和7均有较强的抗炎活性。 关 键 词：S一(十)．布洛芬衍生物；硫化氢供体；合成；抗炎活性 中图分类号：0626．2；R914．5 文献标识码：A 文章编号：1005-1511(2014)06-0781-04 Synthesis and Anti—inflammatory Activities of Novel Ibuprofen Derivatives CHEN Shi—yu，HANG Qi， AO Gui-zhen，HOU Bing-bo，XU Guang—lin (College of Pharmaceutical Science，Soochow University，Suzhou 215123，China) Abstract：Four intermediates(3a一3d)，ibruprofen derivatives，were prepared by reaction of ibupro— fen with oxalyl chloride then amino acid(2a一2d)，respectively．Four novel Is-(+)-ibuprofen defiv— atives(ga一5d)were synthesized by the esterification reaction of3 with H2S con~oHed—release donor (5-p—hydroxyphenyl一1，2-dithieydopentene-3一thione)(4)．An intermediate 5-4一(Ot—bromoacetoxy)一 phenyl一1，2一dithio—cyclopentene-3一thione(6)was prepared by esferificationtion reaction of bro— moacetyl chloride with 4．A novel S一(+)一ibuprofen derivative(7)was synthesized by the coupling reaction of 6 with 1．The structures of5 and 7 were characterized by H NMR，IR and HR．MS．The results of anti—inflammation by xylene—induced mice eB／swelling showed that 5a，5c，5d and 7 exhib— ited better anti-inflammatory activities． ’ Keywords：S一(4-)