研究简报

含苯并噻唑的硫脲嘧啶衍生物的合成及抗菌活性评价

  • 崔朋雷 ,
  • 刘娜 ,
  • 陈华 ,
  • 李小六
展开
  • a 河北大学化学与环境科学学院 河北省化学生物学重点实验室 保定 071002;
    b 河北农业大学理学院 保定 071001

收稿日期: 2018-01-27

  修回日期: 2018-03-19

  网络出版日期: 2018-06-01

基金资助

河北农业大学理工基金(No.LG20150503)资助项目.

Synthesis and Antibacterial Activity Evaluation of the Thiouracil Derivatives Containing Benzothiazole

  • Cui Penglei ,
  • Liu Na ,
  • Chen Hua ,
  • Li Xiaoliu
Expand
  • a Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002;
    b College of Science, Agricultural University of Hebei, Baoding 071001

Received date: 2018-01-27

  Revised date: 2018-03-19

  Online published: 2018-06-01

Supported by

Project supported by the Science and Technology Fund of Agricultural University of Hebei (No. LG20150503)

摘要

2-氨基苯并噻唑衍生物和对氯甲基苯甲酰氯反应合成中间体N-(苯并[d]噻唑-2-基)-4-(氯甲基)苯甲酰胺(5),进一步与4-氧代-6-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-腈(6)反应,合成了一系列未见报道的含苯并噻唑的硫脲嘧啶类化合物7.通过红外光谱、质谱、核磁共振谱和元素分析等方法对化合物进行了结构表征.测试了化合物7对解淀粉芽孢杆菌、金黄色葡萄球菌、枯草芽孢杆菌的抑菌活性.24 h抑菌试验结果显示,部分化合物对供试的菌株具有较强的抑制活性.

本文引用格式

崔朋雷 , 刘娜 , 陈华 , 李小六 . 含苯并噻唑的硫脲嘧啶衍生物的合成及抗菌活性评价[J]. 有机化学, 2018 , 38(10) : 2784 -2790 . DOI: 10.6023/cjoc201801040

Abstract

A series of unreported thiouracil derivatives 7 containing a benzothiazole moiety were synthesized by the reaction of 4-oxo-6-phenyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitrile (6) with N-(benzo[d]thiazol-2-yl)-4-(chloromethyl)-benzamide (5), which was prepared from the amidation of 2-aminobenzothiazole and 4-(chloromethyl)benzoyl chloride. The newly synthesized compounds 7 were characterized by IR, MS, NMR, and element analysis. All the compounds were evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. The results of the 24-hour antibacterial test showed that some compounds had good inhibitory activities against the three tested strains.

参考文献

[1] Davies, J.; Davies, D. Microbiol. Mol. Biol. Rev. 2010, 74, 417.
[2] Kumarasamy, K. K.; Toleman, M. A.; Walsh, T. R. Lancet Infect. Dis. 2010, 10, 597.
[3] Guillemot, D. Curr. Opin. Microbiol. 1999, 2, 494.
[4] Li, M. Y.; Huang, Y. J.; Tai, P. C.; Wang, B. H. Biochem. Biophys. Res. Commun. 2008, 368, 839.
[5] Chen, W. X.; Huang, Y. J.; Gundala, S. R.; Yang, H.; Li, M. Y.; Tai, P. C.; Wang, B. H. Bioorg. Med. Chem. 2010, 18, 1617.
[6] Chaudhary, A. S.; Jin, J. S.; Chen, W. X.; Tai, P. C.; Wang, B. H. Bioorg. Med. Chem. 2015, 23, 105.
[7] Cui, J. M.; Jin, J. S.; Chaudhary, A. S.; Hsieh, Y. Zhang, H.; Dai, C. F.; Damera, K.; Chen, W. X.; Tai, P. C.; Wang, B. H. ChemMed-Chem 2016, 11, 43.
[8] Cui, P. L.; Li, X. L.; Zhu, M. Y.; Wang, B. H.; Liu, J.; Chen, H. Bioorg. Med. Chem. Lett. 2017, 27, 2234.
[9] Cui, P. L.; Li, X. L.; Zhu, M. Y.; Wang, B. H.; Liu, J.; Chen, H. Eur. J. Med. Chem. 2017, 127, 159.
[10] Jiang, K.; Cao, L.; Hao, Z. F.; Chen, M. Y.; Chen, J. L.; Li, X.; Xiao, P.; Chen, L.; Wang, C. Y. Chin. J. Org. Chem. 2017, 37, 2221(in Chinese). (蒋凯, 曹梁, 郝志峰, 陈美燕, 程洁銮, 李晓, 肖萍, 陈亮, 汪朝阳, 有机化学, 2017, 37, 2221.)
[11] Zhang, Z. Y.; Li, W. J.; Ye, K. Q.; Zhang, H. Y. Acta Chim. Sinica 2016, 74, 179(in Chinese). (张振宇, 李婉君, 叶开其, 张红雨, 化学学报, 2016, 74, 179.)
[12] Moustafa, T. G.; Nadia, S. E. G.; Eman, R. E. B.; Mohamed, M. E. K.; Nanting, N. Chin. Chem. Lett. 2016, 27, 380.
[13] Abdou, W. M.; Barghash, R. F.; Sediek, A. A. Eur. J. Med. Chem. 2012, 57, 362.
[14] Yang, L. O.; Huang, Y. H.; Zhao, Y. W.; He, G.; Xie, Y. M.; Liu, J.; He, J.; Liu, B.; Wei, Y. Q. Bioorg. Med. Chem. Lett. 2012, 22, 3044.
[15] Suresh, M.; Sridevi, G.; Nuthangi, S.; Palakondu, L.; Sreekanth, B. J. Arabian J. Chem. 2016, 9, 681.
[16] Alessandro, S.; Kenneth, S.; Steven, D. J.; Bart, V.; Jef, R.; Jozef, A.; Piet, H. Chem. Biodiversity 2011, 8, 253.
[17] Mitra, R.; Mehdi, P.; Abolghasem, D.; Sattar, S. Chem. Heterocycl. Comd. 2015, 51, 918.
[18] Priya, R. M.; Chhaganbhai, N. P. Org. Med. Chem. Lett. 2012, 2, 29.

文章导航

/