贵州医科大学学报

2013, v.38;No.162(03) 221-225

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基于抗氧化活性增强的新型灯盏乙素苷元烟酸酯类衍生物的设计与合成
Design and Synthesis of Nicotinic Acid Ester Derivatives of Scutellarein with Improved Anti-oxidative Activity

徐青云;傅晓钟;杨果;董永喜;刘影;查雨锋;兰燕宇;王永林;郑林;
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)

摘要(Abstract):

目的:合成并设计具有较好清除自由基作用及较好理化性质的灯盏乙素苷元4'-烟酸酯类衍生物。方法:灯盏乙素苷元与二氯二苯甲烷在二乙二醇二甲醚为溶剂,加热条件下制备6,7-二苯缩酮保护灯盏乙素苷元,所得产物与取代烟酸在偶联剂DCC/DMAP的条件下缩合制备6,7-二苯缩酮保护灯盏乙素苷元4'-烟酸酯(5a~5e),后者经过乙酰氯/甲醇体系脱去保护基,获得目标化合物。结果:合成了5个未见报道的灯盏乙素苷元4'-烟酸酯(6a~6e),合成的化合物及重要中间体均经过1HNMR,ESI-MS以及ESI-HRMS进行了结构表征,确证结构与目标产物一致。结论:该方法具有较好的实用性,能用于灯盏乙素苷元4'-烟酸酯的制备。
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.

关键词(KeyWords): 灯盏乙素苷元;前药;合成;烟酸
scutellarein;prodrug;synthesis;nicotinic acid

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基金项目(Foundation): 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

作者(Author): 徐青云;傅晓钟;杨果;董永喜;刘影;查雨锋;兰燕宇;王永林;郑林;
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)

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DOI: 10.19367/j.cnki.1000-2707.2013.03.002

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