Citation: Li-Yuan Zhang, Bao-Lei Wang, Yi-Zhou Zhan, Yan Zhang, Xiao Zhang, Zheng-Ming Li. Synthesis and biological activities of some fluorine-and piperazine-containing 1,2,4-triazole thione derivatives[J]. Chinese Chemical Letters, ;2016, 27(01): 163-167. doi: 10.1016/j.cclet.2015.09.015 shu

Synthesis and biological activities of some fluorine-and piperazine-containing 1,2,4-triazole thione derivatives

  • Corresponding author: Bao-Lei Wang,  Zheng-Ming Li, 
  • Received Date: 22 April 2015
    Available Online: 10 July 2015

    Fund Project: This work was supported by the National Natural Science Foundation of China(No. 21372133) (No. 21372133)"111" Project of Ministry of Education of China(No. B06005). (No. B06005)

  • A series of fluorine-and piperazine-containing 1,2,4-triazole thione derivatives were synthesized by the Mannich reaction of triazole intermediates with various substituted piperazines and formaldehyde in high yields. Structures of title compounds were confirmed by melting points, IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays for 17 novel title compounds showed that several compounds have significant fungicidal activity against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cerealis at 50μg/mL.
  • 加载中
    1. [1]

      [1] J. Zhang, G.M. Xiao, Study progress in nitrogenous heterocyclic compounds, Petrochem. Technol. 40(2011) 579-584.

    2. [2]

      [2] J.Y. Xu, Y. Zeng, B. Jiang, et al., Synthesis, anti-inflammatory activities and SAR studies of 1,5-diaryl substituted-1,2,4-triazoles, Chin. J. Med. Chem. 18(2008) 321-328.

    3. [3]

      [3] Q.H. Li, G. Zhang, Y. Ding, et al., Synthesis and anti-tumor activities of novel triazole Schiff-base derivatives, J. Southwest Univ. Natl:Natl. Sci. Ed. 40(2014) 826-832.

    4. [4]

      [4] Y.G. Zheng, W. Xue, Q.Q. Guo, et al., Synthesis and antitumor activity of 5,6-2H-[1,2,4]-triazolo[3,4-b][1,3,4] thiadiazine derivatives, Chin. J. Org. Chem. 31(2011) 912-916.

    5. [5]

      [5] Z.X. Feng, W.N. Zhang, Y.J. Zhou, et al., Synthesis and antifungal activities of 1-[2-(N-methyl-N-substituted-benzyl)amino-2-(4-tert-butylphenyl)ethyl]-1H-1,2,4-triazoles, Chem. J. Chin. Univ. 21(2000) 1221-1226.

    6. [6]

      [6] K. Yin, L.H. Jiang, H.X. Zhou, Y. Huang, J.N. Xiang, Synthesis and insecticidal activity of 2-perfluoroalkyl-substituted or glucopyranosyl-substituted 2,4-dihydro-1,2,4-triazole-3-thione Schiff base, Chin. J. Org. Chem. 28(2008) 1016-1023.

    7. [7]

      [7] X.Y. Zhao, Y.X. Gong, Z.W. Zhang, et al., Synthesis and plant growth regulating activity of N-5-(3-carboxy-1,2,4-triazolyl)-N'-aroyl urea, Chin. J. Appl. Chem. 20(2003) 594-596.

    8. [8]

      [8] Q. Wu, Z.C. Wang, X. Wei, W. Xue, Synthesis and antibacterial activities of 1-substituted-4-[5-(4-substitutedphenyl)-1,3,4-thiadiazol-2-sulfonyl]piperazine derivatives, Chin. J. Synth. Chem. 22(2014) 429-434.

    9. [9]

      [9] D.H. Jiang, M. Huang, Design and synthesis of thieno[3,2-d]pyrimidine derivatives containing a piperazine unit as anticancer agents, Chem. Reag. 34(2012) 797-799.

    10. [10]

      [10] G.Y. Li, S.G. Yan, S. Jiang, et al., Synthesis of piperazine derivatives containing pyridinemethyl/thiazolemethyl and their biological activities, Chin. J. Org. Chem. 28(2008) 2001-2006.

    11. [11]

      [11] S. Liang, C.M. Liu, Y.S. Jin, et al., Synthesis and the antifungal activity of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[(4-substituted)-piperazine-1-yl]-2-propanols, Chin. J. Med. Chem. 14(2004) 71-75.

    12. [12]

      [12] G.M. Ye, Q.Y. Sun, Y.Y. Jiang, et al., Synthesis and antifungal activity of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-[(4-substituted-piperazine)-1-yl]-2-propanols, Acad. J. Sec. Mil. Med. Univ. 26(2005) 1161-1164.

    13. [13]

      [13] H. Foks, M. Janowiec, Z. Zwolska, E. Augustynowicz-Kopeć, Synthesis and tuberculostatic activity of some 2-piperazinmethylene derivatives 1,2,4-triazole-3-thiones, Phosphorus Sulfur Silicon Relat. Elem. 180(2005) 537-543.

    14. [14]

      [14] B.L. Wang, Y.X. Shi, Y. Ma, et al., Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-triazole) Mannich bases containing piperazine rings, J. Agric. Food Chem. 58(2010) 5515-5522.

    15. [15]

      [15] B.L. Wang, X.H. Liu, X.L. Zhang, et al., Synthesis, structure and biological activity of novel 1,2,4-triazole Mannich bases containing a substituted benzylpiperazine moiety, Chem. Biol. Drug Des. 78(2011) 42-49.

    16. [16]

      [16] A. Demirbas, D. Sahin, N. Demirbas, S.A. Karaoglu, Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities, Eur. J. Med. Chem. 44(2009) 2896-2903.

    17. [17]

      [17] B.S. Holla, B.S. Rao, K. Shridhara, P.M. Akberali, Studies on arylfuran derivatives:Part XI. Synthesis, characterisation and biological studies on some Mannich bases carrying 2,4-dichlorophenylfurfural moiety, Il Farmaco 55(2000) 338-344.

    18. [18]

      [18] K.V. Sujith, J.N. Rao, P. Shetty, B. Kalluraya, Regioselective reaction:synthesis and pharmacological study of Mannich bases containing ibuprofen moiety, Eur. J. Med. Chem. 44(2009) 3697-3702.

    19. [19]

      [19] P. Zlatoidský, T. Maliar, Synthesis of 1-(4-acyloxybenzoyloxyacetyl)-4-alkylpiperazines and 1-(4-acyloxybenzoyl)-4-alkylpiperazines as inhibitors of chymotrypsin, Eur. J. Med. Chem. 31(1996) 669-674.

    20. [20]

      [20] R.R. Adams, F.C. Whitmore, Heterocyclic basic compounds. IV. 2-aminoalkylamino-pyrimidines, J. Am. Chem. Soc. 67(1945) 735-738.

    21. [21]

      [21] J.Y. Tong, Y.X. Shi, X.H. Liu, N.B. Sun, B.J. Li, Synthesis and fungicidal activity of 1,2,4-triazole derivatives containing 2-fluorophenyl moiety, Chin. J. Org. Chem. 32(2012) 2373-2377.

    22. [22]

      [22] C.Y. Liu, Q.Q. Zhao, J. Li, Synthesis study of new Schiff base containing thiocabamide group derivatives of 3-argl-4-amino-5-mercapto-1,2,4-triazoles, Chem. Reag. 23(2001) 344-345.

    23. [23]

      [23] S.J. Xue, C.S. Xiang, S.R. Yu, et al., Synthesis and crystal structure of 5-(p-tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-triazole-3-thione ethyl acetate solvate, Chin. J. Struct. Chem. 27(2008) 389-393.

    24. [24]

      [24] B.L. Wang, R.G. Duggleby, Z.M. Li, et al., Synthesis, crystal structure and herbicidal activity of mimics of intermediates of the KARI reaction, Pest Manag. Sci. 61(2005) 407-412.

    25. [25]

      [25] H. Bayrak, A. Demirbas, S.A. Karaoglu, N. Demirbas, Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities, Eur. J. Med. Chem. 44(2009) 1057-1066.

    26. [26]

      [26] S. Ceylan, H. Bektas, H. Bayrak, et al., Syntheses and biological activities of new hybrid molecules containing different heterocyclic moieties, Arch. Pharm. 346(2013) 743-756.

    27. [27]

      [27] F. Micheli, G. Bonanomi, F.E. Blaney, et al., 1,2,4-Triazol-3-yl-thiopropyl-tetrahydrobenzazepines:a series of potent and selective dopamine D3 receptor antagonists, J. Med. Chem. 50(2007) 5076-5089.

    28. [28]

      [28] P. Polucci, P. Magnaghi, M. Angiolini, et al., Alkylsulfanyl-1,2,4-triazoles, a new class of allosteric valosine containing protein inhibitors. Synthesis and structureactivity relationships, J. Med. Chem. 56(2013) 437-450.

  • 加载中
    1. [1]

      Tao YuVadim A. SoloshonokZhekai XiaoHong LiuJiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901

    2. [2]

      Jia-Ru LiNing LiLi-Ling HeJun He . Fluorine-functionalized zirconium-organic cages for efficient photocatalytic oxidation of thioanisole. Chinese Chemical Letters, 2025, 36(1): 109934-. doi: 10.1016/j.cclet.2024.109934

    3. [3]

      Ping SunYuanqin HuangShunhong ChenXining MaZhaokai YangJian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005

    4. [4]

      Wei SunAnjing LiaoLi LeiXu TangYa WangJian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855

    5. [5]

      Anjing LiaoWei SunYaming LiuHan YanZhi XiaJian Wu . Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides. Chinese Chemical Letters, 2025, 36(3): 110094-. doi: 10.1016/j.cclet.2024.110094

    6. [6]

      Ali DaiZhiguo ZhengLiusheng DuanJian WuWeiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462

    7. [7]

      Jian SongShenghui WangQiuge LiuXiao WangShuo YuanHongmin LiuSaiyang ZhangN-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678

    8. [8]

      Wenyi MeiLijuan XieXiaodong ZhangCunjian ShiFengzhi WangQiqi FuZhenjiang ZhaoHonglin LiYufang XuZhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825

    9. [9]

      Qian WangYeping BianGagan DhawanWei ZhangAlexander E. SorochinskyAta MakaremVadim A. SoloshonokJianlin Han . FDA approved fluorine-containing drugs in 2023. Chinese Chemical Letters, 2024, 35(11): 109780-. doi: 10.1016/j.cclet.2024.109780

    10. [10]

      Jia JIZhaoyang GUOWenni LEIJiawei ZHENGHaorong QINJiahong YANYinling HOUXiaoyan XINWenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344

    11. [11]

      Maitri BhattacharjeeRekha Boruah SmritiR. N. Dutta PurkayasthaWaldemar ManiukiewiczShubhamoy ChowdhuryDebasish MaitiTamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007

    12. [12]

      Bairu MengZongji ZhuoHan YuSining TaoZixuan ChenErik De ClercqChristophe PannecouqueDongwei KangPeng ZhanXinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827

    13. [13]

      Junjun HuangRan ChenYajian HuangHang ZhangAnran ZhengQing XiaoDan WuRuxia DuanZhi ZhouFei HeWei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594

    14. [14]

      Boran ChengLei CaoChen LiFang-Yi HuoQian-Fang MengGanglin TongXuan WuLin-Lin BuLang RaoShubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969

    15. [15]

      Yu-Yu TanLin-Heng HeWei-Min He . Copper-mediated assembly of SO2F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986

    16. [16]

      Zhuangzhuang ZhangYaru QiaoJun ZhaoDai-Huo LiuMengmin JiaHongwei TangLiang WangDongmei DaiBao Li . Fluorine-doped K0.39Mn0.77Ni0.23O1.9F0.1 microspheres with highly reversible oxygen redox reaction for potassium-ion battery cathode. Chinese Chemical Letters, 2025, 36(3): 109907-. doi: 10.1016/j.cclet.2024.109907

    17. [17]

      Jialiang XUJiabin CUI . Recent biological applications of corroles: From diagnosis to therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2303-2317. doi: 10.11862/CJIC.20240245

    18. [18]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    19. [19]

      Zikang HuHengjie ZhangZhengqiu LiTianbao ZhaoZhipeng GuQijuan YuanBaoshu Chen . Multifunctional photothermal hydrogels: Design principles, various functions, and promising biological applications. Chinese Chemical Letters, 2024, 35(10): 109527-. doi: 10.1016/j.cclet.2024.109527

    20. [20]

      Yanye FanJingjing ChenBichun ChenJinyu BaiBowen YangFeng LiangLijing Fang . Design, synthesis and biological evaluation of Leu10-teixobactin analogues. Chinese Chemical Letters, 2025, 36(4): 110075-. doi: 10.1016/j.cclet.2024.110075

Metrics
  • PDF Downloads(0)
  • Abstract views(760)
  • HTML views(7)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return