SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 7: 1975 - 1982

DOI: https://doi.org/10.6023/cjoc202003013

研究论文

含腙结构单元的喹唑啉酮衍生物的设计、合成与生物活性研究

  • 邵利辉 ,
  • 甘宜远 ,
  • 侯迷 ,
  • 陶世林 ,
  • 张丽琼 ,
  • 王贞超 ,
  • 欧阳贵平
展开
  • a 贵州大学药学院 贵阳 550025;
    b 贵州医科大学药用植物功效与利用国家重点实验室 贵阳 550014;
    c 贵州大学精细化工研究开发中心 贵阳 550025;
    d 贵州省合成药物工程实验室 贵阳 550025

收稿日期: 2020-03-05

  修回日期: 2020-04-10

  网络出版日期: 2020-05-08

基金资助

国家自然科学基金（No.20161055）、药用植物功效与利用国家重点实验室（No.FAMP201707K）和贵州省科技计划（No.20185781）资助项目.

收起

Design, Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units

  • Shao Lihui ,
  • Gan Yiyuan ,
  • Hou Mi ,
  • Tao Shilin ,
  • Zhang Liqiong ,
  • Wang Zhenchao ,
  • Ouyang Guiping
Expand
  • a College of Pharmacy, Guizhou University, Guiyang 550025;
    b State Key Laboratory of Functions and Application of Medicinal Plants, Guizhou Medicinal University, Guiyang 550014;
    c Center for Research of Fine Chemicals, Guizhou University, Guiyang 550025;
    d Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang 550025

Received date: 2020-03-05

  Revised date: 2020-04-10

  Online published: 2020-05-08

Supported by

Project supported by the National Natural Science Foundation of China (No. 21867004), the State Key Laboratory of Functions and Applications of Medicinal Plants (No. FAMP201707K) and the Guizhou Provincial Science Technology Program for Platform and Talents (No. 20185781).

Fold

摘要

以靛红酸酐为起始原料，设计并合成了一系列新颖的含腙结构单元的喹唑啉酮类衍生物.所有目标化合物经1H NMR、13C NMR和高分辨质谱（HRMS）表征确证其结构.初步抗菌活性结果显示，该类化合物对水稻白叶枯病菌（Xanthomonas oryzae pv. Oryzae，Xoo）、猕猴桃溃疡病菌（Pseudomonassyringae pv. actinidae，Psa）和柑橘溃疡病菌（Xanthomonas axonopodis pv. Citri，Xac）均表现出一定的抑制活性.其中3-甲基-2-（（（4-（（2-（4-甲基苯磺酰基）肼基）甲基）苯氧基）甲基）喹唑啉-4（3H）-酮（G18）、3-甲基-2-（（（4-（（2-（2，6-二氯苯基）肼基）甲基）苯氧基）甲基）喹唑啉-4（3H）-酮（G12）和3-甲基-2-（（（4-（（2-（苯磺酰基）肼基）甲基）苯氧基）甲基）喹唑啉-4（3H）-酮（G16）对Xoo、Psa和Xac三种细菌的抑制活性分别优于对照药叶枯唑和噻菌铜.另外，3-甲基-2-（（（4-（（2-（3，5-二氯苯基）肼基）甲基）苯氧基）甲基）喹唑啉-4（3H）-酮（G5）对Xoo、Psa和Xac三种细菌均表现出良好的广谱抗菌活性.

关键词： 喹唑啉酮衍生物; 腙; 抑菌活性; 构效关系

本文引用格式

邵利辉 , 甘宜远 , 侯迷 , 陶世林 , 张丽琼 , 王贞超 , 欧阳贵平 . 含腙结构单元的喹唑啉酮衍生物的设计、合成与生物活性研究[J]. 有机化学, 2020 , 40(7) : 1975 -1982 . DOI: 10.6023/cjoc202003013

Abstract

A series of novel quinazolinone derivatives containing hydrazone structural units were designed and synthesized with isatoic anhydride as the starting material. All target compounds were characterized by 1H NMR, 13C NMR and HRMS. The preliminary antibacterial activity results showed that the compounds exhibited a certain inhibitory activity against Xanthomonas oryzae pv. oryzae (Xoo), Pseudomonas syringae pv. actinidiae (Psa) and Xanthomonas axonopodis pv. citri (Xac). Among them, (E)-4-methyl-N'-(4-((3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methoxy)benzylidene)benzenesulfonohydrazi-de (G18), (E)-2-((4-((2-(2,6-dichlorophenyl)hydrazono)methyl)phenoxy)methyl)-3-methylquinazolin-4(3H)-one (G12) and (E)-N'-(4-((3-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)methoxy)benzylidene)benzenesulfonohydrazide (G16) displayed better antibacterial activity against Xoo, Xac and Psa than the control drugs of bismerthiazol and thiediazole-copper, respectively. Notably, (E)-2-((4-((2-(3,5-dichlorophenyl)hydrazono)methyl)phenoxy)methyl)-3-methylquinazolin-4(3H)-one (G5) displayed fine broad-spectrum antimicrobial activity against Xoo, Xac and Psa.

Key words： quinazolinone derivative; hydrazone; antibacterial activity; structure-activity relationship

参考文献

[1] Fan, Z. J.; Shi, J.; Luo, N.; Ding, M. H.; Bao, X. P. J. Agric. Food Chem. 2019, DOI:10.1021/acs.jafc.9b04733.
[2] Shao, L. H.; Gan, Y. Y.; Zhang, L. Q.; Wang, Z. C.; Ouyang, G. P. Chem. Bull. 2019, 82, 779(in Chinese). (邵利辉, 甘宜远, 张丽琼, 王贞超, 欧阳贵平, 化学通报, 2019, 82, 779.)
[3] Vande, A. P.; Elliott, V. L.; Chang, S.; Lpoez-ruiz, F. J.; Marcroft, S. J.; Idnurm, A. PloS One 2017, 12, e0188106.
[4] Zhao, X. Q.; Li, F.; Zhuang, W. P.; Xue, X. W.; Lian, Y. Y.; Fan, J. H.; Fang, D. S. Org. Process Res. Dev. 2010, 14, 346.
[5] Hao, M. C.; Yin, X. Z.; Wang, H.; Xu, L. Y.; Dong, J. H. Chin. J. Med. Chem. 2007, 17, 368(in Chinese). (郝明春, 殷学治, 王辉, 徐莉英, 董金华, 中国药物化学杂志, 2007, 17, 368.)
[6] Xu, P. Y.; Chen, Z. W. Chin. J. Synth. Chem. 2016, 24, 824(in Chinese). (徐盼云, 陈志卫, 合成化学, 2016, 24, 824.)
[7] Peng, J. B.; Geng, H. Q.; Wang, W.; Qi, X. X.; Ying, J.; Wu, X. F. J. Catal. 2018, 365, 10.
[8] Sojitra, N. A.; Dixit, R. B.; Patel, R. K.; Patel, J. P.; Dixit, B. C. J. Saudi Chem. Soc. 2016, 20, S29.
[9] Li, X. Q.; Gan, Y. Y.; Meng, J.; Li, W.; Qi, Y. Y.; Tian, K.; Ouyang, G. P.; Wang, Z. C. J. Heterocycl. Chem. 2018, 55, 1382.
[10] Kandile, N. G.; Mohamed, M. I.; Zaky, H.; Mohamed, H. M. Eur. J. Med. Chem. 2009, 44, 1989.
[11] Mughal, E. U.; Ayaz, M.; Hussain, Z.; Hasan, A.; Sadiq, A.; Riaz, M.; Malik, A.; Hussain, S.; Choudhary, M. Bioorg. Med. Chem. 2006, 14, 4704.
[12] Pang, F. H.; Dong, H. F.; Wang, X.; Li, F. Y.; Huang, L.; Lin, J. X.; Chem. Res. Appl. 2016, 26, 164.
[13] Le, Y.; Gan, Y. Y.; Fu, Y. H.; Liu, J. M.; Li, W.; Zou, X.; Zhou, Z. X.; Wang, Z. C.; Ouyang, G. P.; Yan, L. J. J. Enzyme Inhib. Med. Chem. 2019, 35, 555.
[14] Dey, R.; Kumar, P.; Jee, P. B. J. Org. Chem. 2018, 83, 5438.
[15] Hanusek, J.; Drabina, P.; Sedlák, M. S.; Rosa, P. J. Heterocycl. Chem. 2006, 43, 1281.
[16] Kabri, Y.; Gellis, A.; Vanelle, P. Green Chem. 2009, 11, 201.
[17] Chen, Y.; Li, P.; Chen, M.; Su, S. J.; He, J.; Zhang, M.; Liu, L. W.; Chen, M. Chin. J. Org. Chem. 2019, 39, 2813(in Chinese). (陈英, 李普, 陈梅, 苏时军, 贺军, 张敏, 柳立伟, 薛伟, 有机化学, 2019, 39, 2813.)
Options
文章导航

/

〈 〉