新型螺嘧啶三酮类化合物的合成及其抗菌活性 |
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引用本文: | 张银勇,石程辉,周先礼. 新型螺嘧啶三酮类化合物的合成及其抗菌活性[J]. 合成化学, 2016, 24(8): 653-662. DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.08.16026 |
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作者姓名: | 张银勇 石程辉 周先礼 |
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作者单位: | 1. 西南交通大学 生命科学与工程学院,四川 成都 610031; 2. 中国科学院 上海药物研究所,上海 201203 |
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摘 要: | 根据生物电子等排原理,以2,3,4-三氟苯甲酸为原料,经硝化、还原、氧化和亲核取代反应制得中间体2-(2,3,4-三氟-5-硝基苯)-1,3-二氧戊环(4); 4分别经7步反应合成了12个新型的苯并噁唑酮或苯并咪唑酮螺嘧啶三酮类化合物(12a~12f, 19a~19f),其结构经1H NMR, 13C NMR和ESI-MS表征。采用CLSI标准研究了12和19对甲氧西林耐药金黄色葡萄球菌(A)、甲氧西林耐药表皮葡萄球菌(B)、青霉素耐药肺炎链球菌(C)和化脓性链球菌(D)的体外抗菌活性。结果表明:12的抗菌活性优于19,其中12a的抗菌活性最好,对A~D的MIC值分别为8~16 μg·mL-1。
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关 键 词: | 螺嘧啶三酮 苯并噁唑酮 苯并咪唑酮 II型拓扑异构酶抑制剂 合成 抗菌活性 |
收稿时间: | 2016-01-21 |
Synthesis and Antibacterial Activities of Novel Spiropyrimidinetrione Compounds |
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Abstract: | According to the principle of bioisosteric, an intermediate[2-(2,3,4-trifluoro-5-nitroben-zene)-1,3-dioxolame(4)] was prepared by the reaction of nitration, reduction, oxidation and nucleo-philic substitution from 2,3,4-trifluorobenzoic acid.Twelve novel spiropyrimidinetrione compounds containing benzoxazolinone or benzimidazolone(12a~12f, 19a~19f) were synthesized by a seven-step reaction from 4.The structures were characterized by 1 H NMR, 13 C NMR and ESI-MS.The anti-bacterial activities of 12 and 19 against methicillin-resistant Ataphylococcus aureus( A) , methicillin-re-sistant Staphylococcus epidermidis( B) , penicillin-resistant Streptococcus pneumonia( C) and Streptococ-cus pyogenes( D) were investigated by CLSI standard.The results indicated that the antibacterial activi-ties of 12 were better than 19.12a exhibited best activities with MIC of 8~16 μg· mL-1 . |
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Keywords: | spiropyrimidinetrione benzoxazolinone benzimidazolone type II topoisomerase inhibitor synthesis antibacterial activity |
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