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《Journal of Guiyang Medical College》 2013-03
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Design and Synthesis of Nicotinic Acid Ester Derivatives of Scutellarein with Improved Anti-oxidative Activity

XU Qingyun,FU Xiaozhong,YANG Guo,DONG Yongxi,LIU Ying,ZHA Yufeng, LAN Yanyu,WANG Yonglin,ZHENG Lin(School of Pharmacology,Guiyang Medical College,Guiyang 550004,Guizhou,China)  
Objective: To design and synthetize 4′-nicotinic acid ester derivatives of scutellarein with improved free radical scavenging activity and better physiochemical property.Methods: Scutellarein coupled with dichlorodiphenylmethane were adopted to prepare 6,7-diphenylketal protecting scutellarein by using diethylene glycol dimethyl ether(DME) as solvent under heating condition.The obtained compounds and substituted nicotinic acid were condensed to prepare 6,7-diphenylketal protecting scutellarein 4′-nicotinic acid ester derivatives(5a~5e) in the presence of coupling agent DCC/DMAP,and the protecting group was removed by using acetyl chloride/methanol system to generate the target compounds.Results: Five unreported 4′-nicotinic acid ester derivatives of scutellarein(6a~6e) were synthetized.The chemical structure of synthetized compounds and key intermediates were confirmed to have the same structure with the target compound by using methods of 1HNMR,ESI-MS and ESI-HRMS respectively.Conclusions: This synthetic method has good practicality and can be used in synthetizing scutellarein 4′-nicotinic acid ester derivatives.
【Fund】: 国家自然科学基金(81260473 81060359);; 贵州省科技厅攻关计划(2008)3028;; 贵州省中药现代化科技产业研究开发专项(2012)3013
【CateGory Index】: R914
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