SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 05: 1015 - 1021

DOI: https://doi.org/10.6023/cjoc201210012

研究论文

含吡唑取代基的1,2,4-三唑[3,4-b]-1,3,4-噻二唑类衍生物的合成及生物活性

  • 姚明星 ,
  • 安悦 ,
  • 闫杰 ,
  • 田星 ,
  • 魏诗
展开
  • a 辽宁师范大学化学化工学院 大连 116029;
    b 辽宁师范大学分析测试中心 大连 116029;
    c 辽宁师范大学化学生命科学 大连 116029

收稿日期: 2012-10-11

  修回日期: 2013-01-17

  网络出版日期: 2013-01-21

基金资助

辽宁省教育厅基金(No. 2008349)资助项目.

收起

Synthesis and Biological Activities of Novel Substituted-pyrazole 1,2,4-Triazolo[3,4-b]benzothiazole

  • Yao Mingxing ,
  • An Yue ,
  • Yan Jie ,
  • Tian Xing ,
  • Wei Shi
Expand
  • a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b Analysis and Inspection Center, Liaoning Normal University, Dalian 116029;
    c School of Life Sciences, Liaoning Normal University, Dalian 116029

Received date: 2012-10-11

  Revised date: 2013-01-17

  Online published: 2013-01-21

Supported by

Project supported by the Fund of Liaoning Provincial Department of Education (No. 2008349).

Fold

摘要

以4-氨基-5-巯基-1,2,4-均三唑的衍生物和5-吡唑甲酸及其衍生物为原料, 设计合成21个未见报道的新的3-取 代-6-吡唑基-1,2,4-三唑[3,4-b]-1,3,4-噻二唑类化合物. 通过IR和1H NMR及元素分析对化合物结构进行表征. 小麦芽鞘法对目标化合物生长活性测试结果表明, 所合成的化合物均表现出不同程度的生长活性; 抑菌活性测试结果表明部分化合物表现出较好的抑菌活性. 其中化合物3g和3h的活性最好, 与氯霉素相似. 对大肠杆菌和金黄色葡萄球菌的抗菌药物最低抑菌浓度(MIC值)3g达到6.25和3.13 mg/L, 3h达到12.5和6.25 mg/L.

关键词： 1,2,4-三唑[3,4-b]-1,3,4-噻二唑; 合成; 生物活性

本文引用格式

姚明星 , 安悦 , 闫杰 , 田星 , 魏诗 . 含吡唑取代基的1,2,4-三唑[3,4-b]-1,3,4-噻二唑类衍生物的合成及生物活性[J]. 有机化学, 2013 , 33(05) : 1015 -1021 . DOI: 10.6023/cjoc201210012

Abstract

Twenty-one new derivatives have been synthesized using 3-substituted-4-amino-5-mercapto-1,2,4-triazale and pyrazole carboxylic acid as the staring materials. The structures of the title compounds were characterized by IR, 1H NMR and elemental analyses. The wheat gemma method preliminary bioassay results indicated that some compounds display herbicidal activity to some extent, and bacteriostatic activity test results show that the part of compounds show excellent fungicidal activity, particularly compounds 3g and 3h exhibit higher than the others, and were similar with chloramphenicol. The minimum inhibitory concentrations (MIC) of 3g and 3h with Escherichia coli and Staphylococcus aureus is 6.25 and 3.13 mg/L, and 12.5 and 6.25 mg/L, respectively.

Key words： 1,2,4-triazolo[3,4-b]benzothiazole; synthesis; biological activity

参考文献

[1] Alexander, F. P.; Anatoly, T. S.; Alan, R. K. Heterocycles in Life and Society, Wiley, New York, 2011, pp. 209～246.
[2] Wang, Y.-G.; Wang, Z.-Y.; Zhao, X.-J.; Song, X.-J. Chin. J. Org. Chem. 2004, 24, 1606 (in Chinese).
(汪炎钢, 王子云, 赵新筠, 宋建新, 有机化学, 2004, 24, 1606.)
[3] Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myer, B. J.; Gilles, S.; Simth, B. K.; Lindsey, F.; Clark, C. E.; Daniel, C. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[4] Shivarama Holla, B.; Narayana Poojary, K.; Sooryanarayana Rao, B.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511.
[5] Hirpara, H. M.; Sodha, V. A.; Trivedi, A. M.; Khatri, B. L.; Parikh, A. R. Indian J. Chem. 2003, 42, 1756.
[6] Sadaf, J. G.; Suroor, A. K.; Nadeem, S. Bioorg. Med. Chem. Lett. 2012, 20, 4762.
[7] Holla, B. S.; Poojary, K. N.; Rao, B. S.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511.
[8] Kolavi, G.; Hegde, V.; Khan, I.; Gadad, P. Bioorg. Med. Chem. 2006, 14, 3069.
[9] Prasad, D. J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2009, 44, 551.
[10] Fan, Z.-J; Yang, Z.-K.; Zhang, H.-K.; Mi, N.; Wang, H.; Cai, F.; Zou, X.; Zheng, Q.-X.; Song, H. J. Agric. Food Chem. 2010, 58, 2630.
[11] Song, X.-J.; Wang, S.; Tan, X.-H.; Wang, Z.-Y.; Wang, Y.-G. Chin. J. Org. Chem. 2007, 27, 72 (in Chinese).
(宋新建, 王胜, 谭小红, 王子云, 汪炎钢, 有机化学, 2007, 27, 72.)
[12] Deng, X.-Q.; Song, M.-X.; Wei, C.-X.; Li, F.-N.; Quan, Z. S. Med. Chem. 2010, 6, 313.
[13] Kenneth, A. R.; Matsuura, N.; Tabuchi, F. EP 0213814, 1987 [Chem. Abstr. 1987, 107, 178600].
[14] An, Y.; Zhou, G.-H.; Xing, Y.-H.; Mu, P.-P.; Hu, J.-H. Chin. J. Org. Chem. 2008, 25, 539 (in Chinese).
(安悦, 周光华, 邢永恒, 牟萍萍, 胡皆汗, 有机化学, 2008, 25, 539.)
[15] Zhou, G.-H. M. S. Thesis, Liaoning Normal University, Dalian, 2008 (in Chinese).
(周光华, 硕士论文, 辽宁师范大学, 大连, 2008.)
[16] An, Y.; Zhang, T.; Jiang, H.; Zhang, L.; Han, J.; Yao, M.-X. Chin. J. Org. Chem. 2012, 32, 1308 (in Chinese).
(安悦, 张婷, 姜华, 张琳, 韩杰, 姚明星, 有机化学, 2012, 32, 1308.)
[17] Zhang, Z.-Y.; Li, M.; Zhao, L.; Li, M.-Z.; Liao, R.-A. Chin. J. Org. Chem. 1993, 13, 397 (in Chinese).
(张自义, 李明, 赵岚, 李正名, 廖仁安, 有机化学, 1993, 13, 397.)
[18] Gabriela, L. A.; Barbuceanu, S. F.; Gabriela, B.; Ioana, S; Gabriel, S.; Constantin, D. Eur. J. Med. Chem. 2010, 45, 6139.
[19] Kumar, S. G. V.; Prasa, R. Y.; Mallikarjuna, B. P.; Chandrashekar, S. M. Eur. J. Med. Chem. 2010, 45, 5120.
Options
文章导航

/

〈 〉