有机化学 ›› 2016, Vol. 36 ›› Issue (1): 207-212.DOI: 10.6023/cjoc201506026 上一篇    下一篇

研究简报

新型含4-苯基-5-硫亚基-1,2,4-三唑曼尼希碱的喹唑啉酮类衍生物的设计合成及其生物活性研究 2017-2018 Awarded

闫柏任, 吕新阳, 杜欢, 鲍小平   

  1. 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农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2015-06-24 修回日期:2015-08-18 出版日期:2016-01-25 发布日期:2015-09-15
  • 通讯作者: 鲍小平 E-mail:baoxp_1980@aliyun.com
  • 基金资助:

    国家自然科学基金(No. 21362003)资助项目.

Design, Synthesis and Biological Activities of Novel Quinazolinone Derivatives Bearing 4-Phenyl-5-thioxo-1,2,4-triazole Mannich Bases

Yan Boren, Lü Xinyang, Du Huan, Bao Xiaoping   

  1. State Key Laboratory Breeding Base of Green Pesticide andAgricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2015-06-24 Revised:2015-08-18 Online:2016-01-25 Published:2015-09-15
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21362003).

以喹唑啉-4-酮为起始原料, 经五步反应合成了9个新型的含4-苯基-5-硫亚基-1,2,4-三唑曼尼希碱的喹唑啉酮类衍生物6a6i, 通过1H NMR、13C NMR、IR和元素分析对它们的结构进行了表征, 并用X射线单晶衍射法测定了3-[(1-吗啉甲基-4-苯基-5-硫亚基-4,5-二氢-1H-1,2,4-三唑-3-基)甲基]喹唑啉-4(3H)-酮(6e)的晶体结构. 初步生物活性测试结果表明, 绝大部分该类化合物在200 μg/mL浓度下对水稻白叶枯病菌和柑橘溃疡病菌都表现出了优良的抑制活性; 在50 μg/mL浓度下该类化合物对所测六种真菌都具有一定的抑制活性.

关键词: 喹唑啉酮, 1,2,4-三唑, 曼尼希碱, 抗菌活性

Using quinazolin-4-one as the starting compound, nine novel quinazolinone derivatives 6a6i bearing the 4-phenyl-5- thioxo-1,2,4-triazole Mannich base unit were prepared through a five-step synthetic procedure. The structures of target compounds were characterized by 1H NMR, 13C NMR, IR and elemental analysis. 3-((1-Morpholinomethyl-4-phenyl- 5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)quinazolin-4(3H)-one was further confirmed by X-ray single crystal diffraction method. The preliminary biological test indicated that almost all of the title compounds had excellent antibacterial activities against Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri at the concentration of 200 μg/mL. Moreover, compounds 6a6i displayed a certain inhibitory effect against six kinds of tested fungi at the concentration of 50 μg/mL.

Key words: quinazolinone, 1,2,4-triazole, Mannich base, antibacterial/antifungal activity