李靖,周雯,刘影,傅晓钟,欧瑜,兰燕宇,王爱民,王永林
LI Jing,ZHOU Wen,LIU Ying,FU Xiaozhong,OU Yu,LAN Yanyu,WANG Aimin,WANG Yonglin (School of Pharmacology

• 1:贵阳医学院药学院

摘要(Abstract)：

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 star-ting material to synthesize scutellarein aglycone 4'-hydroxyethyl ether(4a-4c) protected by 6,7-diethy-lenebenzene 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(8a-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 me-thod is practical and can be used in synthesizing scutellarein aglycone 4'-N,N-bis-substituted aminome-thylation benzoate ether derivatives.

关键词(KeyWords)： 氨甲基苯甲酸类;药物前体;色谱法,液相
aminobenzoic acids;prodrugs;chromatography,liquid

Abstract:

Keywords:

基金项目(Foundation): 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;;

作者(Author): 李靖,周雯,刘影,傅晓钟,欧瑜,兰燕宇,王爱民,王永林
LI Jing,ZHOU Wen,LIU Ying,FU Xiaozhong,OU Yu,LAN Yanyu,WANG Aimin,WANG Yonglin (School of Pharmacology

DOI: 10.19367/j.cnki.1000-2707.2011.05.002

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