7-二乙氨基香豆素-3-烯丙端基化合物的合成及其荧光性质研究  

Synthesis and Fluorescence Properties of 7-Diethylamino Coumarin-3-allyl End Group Compounds

作　　者：卜明 王海君[1] 马玉坤 王静[1] 李爽[1] 陈颂[1] 刘磊[1] 孙靖文 BU Ming;WANG Hai-jun;MA Yu-kun;WANG Jing;LI Shuang;CHEN Song;LIU-Lei;SUN Jing-wen(1.College of Pharmacy,Qiqihar Medical University,Qiqihar 161006,China;Research Institute of Medicine & Pharmacy,Qiqihar Medical University,Qiqihar 161006,China)

机构地区：[1]齐齐哈尔医学院药学院,黑龙江齐齐哈尔161006 [2]齐齐哈尔医学院医药科学研究院,黑龙江齐齐哈尔161006

出　　处：《化学试剂》2019年第6期572-576,共5页Chemical Reagents

基　　金：齐齐哈尔医学科学院项目(QMSI2017M-14)

摘　　要：以4-二乙氨基水杨醛、丙二酸环亚异丙酯为原料,经Knoevenagel反应生成7-二乙氨基香豆素-3-羧酸,与氨基酸发生缩合反应后与3-溴丙烯反应,设计合成了3个目标化合物。结构经1HNMR、^13CNMR、ESI-MS等加以表征,并对其荧光性质进行测定。结果表明,3种烯丙端基化合物收率均超过70%,荧光发射峰波长分别为489、498、508nm,其中7-二乙氨基香豆素-3-酰胺-N-丁酸烯丙酯具有相对较大的Stokes位移,对A549细胞进行染色,绿光激发时,细胞呈现出强烈的绿色荧光,成功实现细胞内荧光成像,具有良好的生物应用前景。7-Diethylamino-coumarin 3-carboxylic acid was synthesized from 4-diethylamino-salicylaldehyde and cycloisopropyl malonate via Knoevenagel reaction.Three 7-diethylamine coumarin-3-allyl terminal compounds were designed and synthesized by 7-diethylamino-coumarin 3-carboxylic acid reacting with amino acid first and then with 3-bromopropene.The structures were confirmed by 1HNMR,^13CNMR and ESI-MS,and their fluorescence properties were measured.The results showed that the yields of all three allyl end compounds were over 70%,and the fluorescence emission peaks were 489,498 and 508 nm,respectively.A549 cells stained by 7-diethylamine coumarin-3-carboxamido-N-allyl butyrate with a relatively large Stokes shift showed strong green fluorescence when stimulated by green light.Therefore,it has been successfully realized the fluorescence imaging in cells,which has a good prospect of the biological application.

关 键 词：7-二乙氨基香豆素-3-羧酸 3-溴丙烯 荧光 细胞成像 

分 类 号：O626.2[理学—有机化学]