4-(5’-氟尿嘧啶甲基)-3-硝基苯甲酸的合成及光控性能

Synthesis and Photo-control Properties of 4-( 5’-Fluorouracil-methyl)-3-nitrobenzoic Acid

以3-硝基-4-甲基苯甲酸为原料,经酯化、溴化,再与2,4-双-三甲基硅烷氧基-5-氟尿嘧啶反应,最后水解合成了标题化合物,有关中间体及最终产物经NMR、FT-IR和HRMS进行结构表征。通过UV-Vis、HPLC以及1HNMR跟踪监测标题化合物光照分解的过程,研究其光照分解的速率、半衰期、量子产率以及光照对5-氟尿嘧啶(5-FU)的控释效果。结果表明,标题化合物在365 nm紫外光照射下迅速分解并释放出5-FU,分解速度先快后慢,量子产率为0.028;在以水为主体的溶剂中分解速度最快;光照下5-FU持续释放,避光下停止释放,最终约有86%的5-FU被释放。

The title compound was synthesized from 3-nitro-4-methylbenzoic acid by esterification,bromination,reacting with 2,4-bis-trimethylsiloxy-5-fluorouracil and hydrolysis.The structures were confirmed by NMR,FT-IR and HRMS.The photodegradation process of the target molecular was monitored by UV-Vis,HPLC and 1HNMR.The rate of photodegradation,half-life,quantum yield and the effect of illumination on 5-fluorouracil(5-FU)were well investigated.The results showed that the compound rapidly decomposed and released 5-FU under 365 nm ultraviolet light irradiation.The decomposition rate was fast followed by slow and the quantum yield was 0.028.The decomposition rate was the highest in water-based solvent.5-FU sustained release under UV and stopped releasing in the dark.Finally,about 86%of 5-FU was released.