摘要
目的:合成灯盏乙素苷元4'N,N-双取代氨甲基苯甲酸醚类衍生物。方法:以灯盏乙素苷元与2-溴乙醇为原料,在偶联剂1.8-二氮杂二环(5.4.0)十一稀-7(DBU)的作用下制备6,7-二苯缩酮保护灯盏乙素苷元4'-羟乙基醚(4a～4c),后者与N,N-双取代氨甲基苯甲酰氯在以4分子筛(MS)为脱水剂条件下缩合制备6,7-二苯缩酮,保护灯盏乙素苷元4'-N,N-双取代氨甲基苯甲酸醚(7a-c),后者经乙酰氯/甲醇体系脱去保护基,获得目标化合物灯盏乙素苷元4'-N,N-双取代氨甲基苯甲酸醚衍生物(8a-c)。结果:合成的化合物及中间体均经过1H NMR,ESI-MS进行了结构表征,确证结构与目标产物一致。结论:采用的合成方法具有较好的实用性,能用于灯盏乙素苷元4'-L-氨基酸酯的制备。
Objective： To synthesize 4＇-N, N-bis-substituted aminomethylation benzoate ether derivatives of scutellarein aglycone. Methods： Scutellarein aglycone and 2-bromo-ethanol were used as starting material to synthesize scutellarein aglycone 4＇-hydroxyethyl ether （4a-4c） protected by 6,7-diethylenebenzene ketal in the presence of 1, 8-dinitroge mixed bicyclic （5.4.0） hendecene-7- （DBU）. The product was used to synthesize scutellarein aglycone 4＇-N, N-Bis-substituted aminomethylation benzoate ether with N, N-Bis-substituted aminomethylation benzoyl chloride using 4＇ molecular sieves （MS） as dehydrater. The protective group was then removed by using acetyl chloride/methanol system and target compounds （Sa-c） were obtained. Results： The structure of synthesized compounds 8a-c and intermediate were confirmed by methods of 1H NMR, ESI-MS. Conclusions： The synthetic method is practical and can be used in synthesizing scutellarein aglycone 4 ＇-N, N-bis-substituted aminomethylation benzoate ether derivatives.
出处
《贵阳医学院学报》
CAS
2011年第5期441-445,共5页
Journal of Guiyang Medical College
基金
国家自然科学基金资助项目(81060359)
贵州省中药现代化科技产业研究开发专项[黔科合社字(2010)5019]
贵州省社会发展攻关计划[黔科合SY(2010)3046号]
贵州省科技厅科技计划[黔科合计工字(2009)4001]
贵州省科技厅攻关计划黔科合GY字(2008)3028
贵阳医学院科研项目基金资助项目(2009)54
