摘要
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 scutella- rein by using diethylene glycol dimethyl ether （DME） as solvent under heating condition. The ob- tained compounds and substituted nicotinic acid were condensed to prepare 6,7-diphenylketal protec- ting 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.
出处
《贵阳医学院学报》
CAS
2013年第3期221-225,共5页
Journal of Guiyang Medical College
基金
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
关键词
灯盏乙素苷元
前药
合成
烟酸
scutellarein
prodrug
synthesis
nicotinic acid
