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Stereoselective synthesis of E, E / E, Z isomers based on 1-(4- iodophenyl)-2,5-divinyl-1H-pyrrole core skeleton: A configuration-controlled fluorescence characteristics and highly selective anti-cancer activity
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-08-18 , DOI: 10.1016/j.dyepig.2020.108733
Majeed Irfan , Rong Deng , Idrees Sumra , Xiao-Feng Zhu , Tingting Liu , Zhuo Zeng

The E and Z isomeric intermediates based on ethyl/methyl-2-cyano-3-(5-formyl-1-(4-iodo-phenyl)-1H-pyrrol-2-yl)acrylate have been synthesized and these intermediates (E or Z) were further stereo-selectively converted into their respective E, E or E, Z isomers of diethyl/dimethyl-3,3'-(1-(4-iodophenyl)-1H-pyrrole-2,5-diyl)bis (2-cyanoacrylate) at the first time. The E, E isomers of both 2a and 3a, in solid state displayed higher quantum efficiency with longer fluorescent lifetime as compared to E, Z isomers. Notably, the E, E isomers proved to be better AIEs while, E, Z isomer of 2a has eminent anticancer activity against human nasopharyngeal carcinoma. A simple and straight forward strategy has been firstly developed to utilize the impact of configuration on fluorescence and anti-cancer activity.



中文翻译:

基于1-(4-碘苯基)-2,5-二乙烯基-1H-吡咯核心骨架的E,E / E,Z异构体的立体选择性合成:构型控制的荧光特性和高度选择性的抗癌活性

合成了基于乙基/甲基-2-氰基-3-(5-甲酰基-1-(4-碘-苯基)-1H-吡咯-2-基)丙烯酸酯的E和Z异构中间体,这些中间体(E或Z)进一步立体选择性地转化为二乙基/二甲基-3,3'-(1-(4-碘苯基)-1H-吡咯-2,5-二基)双的各自的E,E或E,Z异构体(2-氰基丙烯酸酯)。与E,Z异构体相比,固态的2a和3a的E,E异构体显示出更高的量子效率和更长的荧光寿命。值得注意的是,E,E异构体被证明是更好的AIE,而2a的E,Z异构体对人鼻咽癌具有显着的抗癌活性。首先开发了一种简单明了的策略,以利用构型对荧光和抗癌活性的影响。

更新日期:2020-09-08
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