文献类型：期刊文献

中文题名：2-苯甲酰基嘧啶类化合物的合成与生物活性

英文题名：Synthesis and Bioactivity of 2-Benzoyl Pyrimidine Derivatives

作者：吕强[1,2];芦昕婷[2];戴明[2];刘世梦[2];朱为宏[1];杜葩[3];吕龙[2]

机构：[1]华东理工大学化学与分子工程学院,上海200237;[2]中国科学院上海有机化学研究所有机氟化学重点实验室,上海200032;[3]上海应用技术学院化学与环境工程学院,上海201418

年份：2015

卷号：35

期号：6

起止页码：1260

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000359274400007)】；北大核心:【北大核心2014】；CSCD:【CSCD2015_2016】；

基金：Project supported by the National Key Technologies R&D Program (No. 2011BAE06B02).

语种：中文

中文关键词：2-苯甲酰基嘧啶;合成;结构优化;生物活性

外文关键词：2-benzoyl pyrimidine; synthesis; structral optimization; biological activity

摘要：2-嘧啶氧基-N-芳基苄胺类化合物结构经过两次骨架结构优化后得到2-苯甲酰基嘧啶类化合物二次先导结构.在二次先导结构基础上,共设计并合成了36个化合物,所有化合物结构经1H NMR、13C NMR、HRMS确认,并进行了室内杀菌活性筛选,对各部位取代基进行了逐次优化.结果表明2-苯甲酰基嘧啶类化合物中R1取代基以2位卤素或烷基取代的苯环或杂环活性最好;中间苯环6位引入氟原子活性保持;嘧啶环4,6位甲氧基取代活性较好,5位甲基取代活性大大降低;羰基被还原为羟基后活性消失.其中2,3-二氯-N-[2-(4,6-二甲氧基嘧啶-2-甲酰基)苯氧基]-N-甲基苯甲酰胺(4AHl)、2,5-二氯-N-[2-(4,6-二甲氧基嘧啶-2-甲酰基)苯氧基]-N-甲基苯甲酰胺(4AHn)及N-[2-(4,6-二甲氧基嘧啶-2-甲酰基)-3-氟苯氧基]-N,2-二甲基苯甲酰胺(4AFd)对黄瓜白粉病的杀菌活性与对照样苯菌酮相当.
2-Benzoyl pyrimidine as a secondary leading structure is developed by twice optimization of 2-pyrimidinoxy-Naryl benzylamine. Based on this structure, thirty six 2-benzoyl pyrimidine derivatives have been designed and synthesized. All compounds are determined by 1H NMR, 13 C NMR and HRMS. Their interior fungicidal activities show that R1 substituent prefers phenyl or heterocyclic group with 2-halo or 2-alkyl group. When introducing fluoride to 6-position on benzene ring, the fungicidal activity is maintained at a similar level. 4,6-Dimethoxy group on pyrimidine ring was recognized as a best substituent by far. The activity is seriously decreased when methyl group is fixed on 5-position of pyrimidine. Even the fungicidal activities become completely disappeared when the ketone group is reduced to hydroxyl group. Among them, three compounds 2,3-dichloro-N-（2-（4,6-dimethoxypyrimidine-2-carbonyl）phenoxy）-N-methylbenzamide（4AHl）, 2,5-dichloro-N-（2-（4,6-dimethoxypyrimidine-2-carbonyl）phenoxy）-N-methylbenzamide（4AHn） and N-（2-（4,6-dimethoxypyrimidine-2-carbonyl）-3-fluorophenoxy）-N,2-dimethylbenzamide（4AFd） exhibit comparable fungicidal activity against cucumber powdery mildew to the reference metrafenone.