Synthesis of Aryl-pyridazinone Acid and Curcumin Ester

VernacularTitle:芳基哒嗪酮酸姜黄素酯的合成
Author: Lei LIU ; Kai SUN ; Song CHEN ; Xin WANG ; Jing WANG
Publication Type:Journal Article
Keywords: Curcumin; Aryl-pyridazinone acid; Esterification; Synthesis
From: China Pharmacy 2015;(19):2670-2672
CountryChina
Language:Chinese
Abstract: OBJECTIVE:To synthesize the aryl-pyridazinone acid and curcumin ester. METHODS:With the raw material of 5-methyl-2-(3-chloro-4-fluorophenyl)-2-oxo-pyridazine acid (compound 1) and curcumin,there was ester-forming in the two sides of a phenolic hydroxyl and pyridazin-6-one carboxyl in curcumin by the catalysis of N,N-dicyclohexyl carbodiimide(DCC)/4- dimethylaminopyridine (DMAP). The targeted product,MS and NMR characterization of the structure were obtained through column chromatographic separation. Single factor was adopted to detect the effect of mixture ratio of curcumin and compound 1,re-action temperature and time and catalyst on the reactions. RESULTS:The productivity of targeted product (aryl-pyridazinone acid and curcumin ester)was 56.3%(in curcumin),the content by HPLC was 98.1%. The optimum conditions were as follows as the mixture ratio of curcumin and compound 1 was 1∶3,reaction temperature was 50 ℃,reaction time was 10 h and the catalyst was DCC/DMAP. CONCLUSIONS:The aryl-pyridazinone acid and curcumin ester is successfully synthesized with stable process.