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

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

目的设计合成3-取代苯甲酰基-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-取代苯甲酰基-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。

Aim To design and synthesize some 3-substituted benzoyl-4H-chromen-4-ones and to evaluate their antimycobacterial activity.Methods The target compounds were synthesized from 1,2,3-benzene triol 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.