| 含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究 |
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| 引用本文： | 贺军,唐雪梅,周清,彭峰,刘婷婷,柳立伟,贺鸣,谢承卫,薛伟. 含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究[J]. 有机化学, 2021, 0(2): 708-718 |
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| 作者姓名： | 贺军 唐雪梅 周清 彭峰 刘婷婷 柳立伟 贺鸣 谢承卫 薛伟 |
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| 作者单位： | 贵州大学精细化工研究开发中心绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与生物工程重点实验室 |
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| 基金项目： | 国家自然科学基金(No.21867003);贵州省自然科学基金(Nos.20192452,20191105,20171028)资助项目. |
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| 摘 要： | 以杨梅苷为原料,通过活性拼接,设计并合成一系列含喹唑啉硫醚的杨梅素衍生物,其结构通过1H NMR、13CNMR、19F NMR和HRMS进行确证.生物活性测试结果表明,该类化合物对水稻白叶枯病菌(X.Oryzae)、柑橘溃疡病菌(X.Citri)和烟草青枯病菌(R.Solanacearum)表现出一定的抑制活性.其中,...
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| 关 键 词： | 杨梅素衍生物 喹唑啉硫醚 生物活性 活体实验 扫描电镜 |
Design,Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety |
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| He Jun,Tang Xuemei,Zhou Qing,Peng Feng,Liu Tingting,Liu Liwei,He Ming,Xie Chengwei,Xue Wei. Design,Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 0(2): 708-718 |
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| Authors: | He Jun Tang Xuemei Zhou Qing Peng Feng Liu Tingting Liu Liwei He Ming Xie Chengwei Xue Wei |
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| Affiliation: | (Key Laboratory of Green Pesticide and Bioengineering of Ministry of Education,State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering,Center for Research and Development of Fine Chemicals,Guizhou University,Guivang 550025) |
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| Abstract: | A series of myricetin derivatives containing quinazoline thioether moiety were designed and synthesized using myricetrin as the starting material through active splicing strategy. All target compounds were characterized by 1H NMR,13C NMR,19N MR and HRMS. Their biological activities were evaluated. The results of biological activities showed that these compounds exhibited certain inhibitory activities against X. oryzae, X. citri and R. solanacearum. Among them, 3-(3-((6-bromoquinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4 H-chromen-4-one(A15) displayed appreciable inhibitory effect against X. oryzae with a half maximal effective concentration(EC50) values of 13.9 μg/mL, which was better than those of the control drugs of bismerthiazol(88.9 μg/mL) and thiodiazole-copper(68.1 μg/mL). The EC50 values of 3-(4-((6-chloroquinazolin-4-yl)thio)butoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4 H-chromen-4-one(A3), 3-(3-((6-chloroquinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4 H-chromen-4-one(A14), 3-(3-((6-chloroquinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4 H-chromen-4-one(A15) and 3-(3-((6-fluoroquinazolin-4-yl)-thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4 H-chromen-4-one(A16) against Ralstonia solanacearum were 1.1, 14.0, 11.9 and 7.5 μg/mL, respectively, which were superior to the control drugs of bismerthiazol(38.5 μg/mL) and thiodiazole-copper(184.8 μg/mL). The results of in vivo experiments showed that compound A15 has good curative and protective activities against X. oryzae. The possible antibacterial mechanisms of target compound A3 against R. solanacearum and A15 against X. oryzae were preliminarily discussed base on scanning electron microscope analyses. |
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| Keywords: | myricetin derivative quinazoline thioether biological activity in vivo experiment scanning electron microscope |
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