3-取代苯甲酰基-4H-色烯-4-酮的合成及其抗快速增殖分枝杆菌活性研究

目的 设计合成3-苯甲酰基-4H-色烯-4-酮类化合物，并测定其体外抗快速增殖分枝杆菌活性。 方法 以焦性没食子酸和取代苯甲酸为原料，经Friedel-Crafts酰基化、Baker-Venkataraman重排等反应合成目标化合物，初步测定了目标化合物的抗快速增殖分枝杆菌活性。结果 共合成8个3-苯甲酰基-4H-色烯-4-酮类化合物，其结构经核磁共振氢谱和质谱确证。化合物2a、2e呈现边缘抗快速增殖分枝杆菌活性。结论 在具有抗快速增殖分枝杆菌活性的天然产物(S)-3-(4-甲氧苄基)-7,8-亚甲二氧基二氢高异黄酮的2,3-位引入双键、7，8-位更换为甲氧基以及9位以羰基替代亚甲基均会导致抗快速增殖分枝杆菌活性的大幅降低。

Synthesis and antimycobacterial activity of substituted 3-benzoyl-4H-chromen-4-ones

Aim To design and synthesize some 3-benzoyl-4H-chromen-4-ones and to evaluate their antimycobacterial activity. Methods The target compounds were synthesized from 1,2,3-benzenetriol and substituted benzoic acid via Friedel-Crafts acylation and Baker-Venkataraman rearrangement, etc. Their MICs of in vitro antimycobacterial activity were determined. Results Eight compounds not reported were synthesized and their structures were confirmed by ¹H-NMR and MS. Compounds 2a and 2e had weak antimycobacterial activity. Conclusion The introduction of carbon-carbon double bond in position 2, methoxy groups in position 7,8 and carbonyl group in position 9 in the natural product 3-(4-methoxybenzyl)-7,8-methylenedioxy-chroman-4-one would lead the decrease of antimycobacterial activity.