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
-
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.
-
-
-
[1]
[1] J. Zhang, G.M. Xiao, Study progress in nitrogenous heterocyclic compounds, Petrochem. Technol. 40(2011) 579-584.
-
[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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] R.R. Adams, F.C. Whitmore, Heterocyclic basic compounds. IV. 2-aminoalkylamino-pyrimidines, J. Am. Chem. Soc. 67(1945) 735-738.
-
[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] 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] 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] 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] 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] 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] 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] 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.
-
[1]
-
-
-
[1]
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang 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]
Jia-Ru Li , Ning Li , Li-Ling He , Jun 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]
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
-
[4]
Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
-
[5]
Anjing Liao , Wei Sun , Yaming Liu , Han Yan , Zhi Xia , Jian 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]
Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming 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]
Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-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]
Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo 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]
Qian Wang , Yeping Bian , Gagan Dhawan , Wei Zhang , Alexander E. Sorochinsky , Ata Makarem , Vadim A. Soloshonok , Jianlin Han . FDA approved fluorine-containing drugs in 2023. Chinese Chemical Letters, 2024, 35(11): 109780-. doi: 10.1016/j.cclet.2024.109780
-
[10]
Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin 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]
Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna 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]
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong 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]
Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei 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]
Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin 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]
Yu-Yu Tan , Lin-Heng He , Wei-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]
Zhuangzhuang Zhang , Yaru Qiao , Jun Zhao , Dai-Huo Liu , Mengmin Jia , Hongwei Tang , Liang Wang , Dongmei Dai , Bao 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]
Jialiang XU , Jiabin 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]
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min 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]
Zikang Hu , Hengjie Zhang , Zhengqiu Li , Tianbao Zhao , Zhipeng Gu , Qijuan Yuan , Baoshu 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]
Yanye Fan , Jingjing Chen , Bichun Chen , Jinyu Bai , Bowen Yang , Feng Liang , Lijing Fang . Design, synthesis and biological evaluation of Leu10-teixobactin analogues. Chinese Chemical Letters, 2025, 36(4): 110075-. doi: 10.1016/j.cclet.2024.110075
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(760)
- HTML views(7)