Synthesis and Biological Activity of Novel 1,2,4-Triazolothiadiazine Derivatives Containing Pyrazole Unit

doi:10.11944/j.issn.1000-0518.2015.02.140163

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (2): 151-157.DOI: 10.11944/j.issn.1000-0518.2015.02.140163

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Synthesis and Biological Activity of Novel 1,2,4-Triazolothiadiazine Derivatives Containing Pyrazole Unit

ZHENG Yuguo^*, GUO Qingqing, ZHOU Li, LI Shijie, YU Zhonglin, LIU Cuiju, XIONG Xiang

Institute of Green Chemistry-Synthesis Technology,Key Laboratory of Research and Development of Ethnomedicinal Biological Resources,Xingyi Normal University for Nationalities,Xingyi,Guizhou 562400,China

Received:2014-05-06 Revised:2014-07-21 Published:2015-02-10 Online:2015-02-10
Contact: Corresponding author:ZHENG Yuguo, associate professor; Tel:0859-3222483; E-mail:yuguobaolong@163.com; Research interests:design and research of novel pesticide
Supported by:
Supported by Natural Science Foundation of Guizhou Province(No.2010090), the Promotion Project of Higher Education of Guizhou Province(No.[2011]278), Higher Educational Quality and Reform Project of Guizhou Province(No.[2011]281, No.[2012]426, No.[2013]446), the Natural Science Foundation of Xingyi Normal University for Nationnality(No.llxyy202)

Abstract

Abstract:

A series of 4-(1-phenyl-3-methyl-5-chloro-1H-pyrazolelideneamino)-5-(substituted aryl)-2H-1,2,4-triazole-3(4H)-thiones was synthesized by the condensation reaction of 5-chloro-1-phenyl-3-methyl-1H-pyrazole-4-aldehyde with 4-amino-5-(substituted phenyl-2H-1,2,4-triazole-3(4H)-thione. Alkylation of compound 6 with ethyl-2-chloroacetate or 1-(chloromethyl)-4-nitrobenzene afforded 5,6-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine derivatives containing pyrazole unit. Their structures were confirmed by ¹H NMR, IR and elemental analyses. Preliminary bioassay indicates that the anti-fungicidal activity of compound 8a(3-(2-methyphenyl)-6-(5-chloro-2-methyl-4-phenylpyrazole)-7-(4-nitrophenyl)-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine) to Colletotrichum lagenarium at the concentration of 100 mg/L is 90%.

Key words: pyrazo, triazolo[3, 4-b][1, 3, 4]thiadiazine, synthesis, bioactivity

CLC Number:

O626.2

ZHENG Yuguo ,GUO Qingqing,ZHOU Li,LI Shijie,YU Zhonglin,LIU Cuiju,XIONG Xiang. Synthesis and Biological Activity of Novel 1,2,4-Triazolothiadiazine Derivatives Containing Pyrazole Unit[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 151-157.

References

[1] ZHOU Baohan,CAO Hong,WANG Hongqing, et al . Synthesis and Biological Activity of N -Acylpyrazole Derivatives[J]. Chinese J Appl Chem ,2005,22(4):391-394 (in Chinese). 周宝晗,曹宏,王宏青,等. N -酰基吡唑衍生物的合成与生物活性[J]. 应用化学,2005,22(4):391-394.
[2] ZHANG Xiuli,LV Xianhai,JIANG Wanquan. Synthesis and Fungicidal Activity of New Pyrazole-Acyl Fluoro-Substituted Aromatic Thiourea Derivatives[J]. Chinese J Appl Chem ,2008,25(4):459-463(in Chinese). 张袖丽,吕献海,江万权. 新型吡唑甲酰基含氟芳基硫脲的合成及其杀菌活性[J]. 应用化学,2008,25(4):459-463.
[3] LIU Xinhua,WANG Shifan,SONG Baoan, et al . Synthesis and Bactericidal Activities of Novel Pyrazole-1-carbothioamide Derivatives[J]. Chinese J Appl Chem ,2006,23(12):1355-1358(in Chinese). 刘新华,王世范,宋宝安,等. 新型吡唑N-硫代酰胺类衍生物的合成与杀菌活性[J]. 应用化学,2006,23(12):1355-1358.
[4] Fustero S,Roman R,Fu J, et al . Synthesis of New Fluorinated Tebufenpyrad Analogs with Acaricidal Activity Through Regioselective Pyrazole Formation[J]. J Org Chem ,2008,73(21):8545-8552.
[5] Hall A,Billinton A,Bristow A K, et al . Discovery of Brain Penetrant, Soluble, Pyrazole Amide EP 1 Receptor Antagonists[J]. Bioorg Med Chem Lett ,2008,18(14):4027-4032.
[6] Vicentini C B,Romagnoli C,Andreotti E, et al . Synthetic Pyrazole Derivatives as Growth Inhibitors of Some Phytopathogenic Fungi[J]. J Agric Food Chem ,2007,55(25):10331-10338.
[7] Varnes J G,Wacker D A,Jacobson I C, et al . Design, Structure-activity Relationship, and Pharmacokinetic Profile of Pyrazole-based Indoline Factor Xa Inhibitors[J]. Bioorg Med Chem Lett ,2007,17(23):6481-6488.
[8] CHEN Wenbin,JIN Guiyu. Syntheses and Biological Activities of α- [(1 H -1,2,4-Triazol-1-yl)methyl]- β -aryl- β -arylthio Substituted Phenylpropanol[J]. Chinese J Appl Chem ,2002,19(6):527-530(in Chinese). 陈文彬,金桂玉. α -[(1 H -1,2,4-三唑-1-基)甲基]- β- 芳基 -β -芳硫基取代苯丙醇的合成及生物活性研究[J]. 应用化学,2002,19(6):527-530.
[9] ZHENG Yuguo,WEI Xue,GUO Qingqing, et al . Synthesis and Biological Activities of Novel Bistriazolyl-3(2 H )-pyridazinones[J]. Chinese J Appl Chem ,2011,28(9):1028-1034(in Chinese). 郑玉国,魏学,郭晴晴,等. 双三唑席夫碱哒嗪酮衍生物合成及其生物活性[J]. 应用化学,2011,28(9):1028-1034.
[10] ZHENG Yuguo,XUE Wei,WEI Xue. Ultrasonic Radiative Synthesis and Biological Activities of Morpholinomethylamino Containing 1,2,4-Triazole-5-thiones[J]. Chinese J Appl Chem ,2010,27(10):1165-1171(in Chinese). 郑玉国,薛伟,魏学. 三唑硫酮氨席夫碱吗啡亚甲胺的超声辐射合成及其生物活性[J]. 应用化学,2010,27(10):1165-1171.
[11] Almajan G L,Barbuceanu S F,Almajan E R, et al . Synthesis, Characterization and Antibacterial Activity of Some Triazole Mannich Bases Carrying Diphenylsulfone Moieties[J]. Eur J Med Chem ,2009,44(7):3083-3089.
[12] Li F L,Dai B,Song H B, et al . Synthesis, Structure, and Fungicidal Activity of Triorganotin (4 H -1,2,4-triazol-4-yl)benzoates[J]. Heteroat Chem ,2009,20(7):411-417.
[13] Wang B L,Shi Y X,Ma Y, 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]. J Agric Food Chem ,2010,58(23):5515-5522.
[14] Wang M H,Zhu R Z,Fan Z J, et al . Bitriazolyl Acyclonucleosides Synthesized via Huisgen Reaction Using Internal Alkynes Show Antiviral Activity Against Tobacco Mosaic Virus[J]. Bioorg Med Chem Lett ,2011,21(1):354-357.
[15] HUI Xinping,ZHANG Yan,XU Pengfei, et al . Synthesis and Antibacterial Activities of Novel 4-Substituted-6-(4-chlorophenyl)-7-(1 H -1,2,4-triazol-1-yl)-1',2',4'-triazolo[3,4-b]-1″,3″,4″-thiadiazines[J]. Chinese J Org Chem ,2005,25(6):700-704(in Chinese). 惠新平,张艳,许鹏飞,等. 新型3-取代-6-(4-氯苯基)-7-(1 H -1,2,4-三唑-1-基)-1',2',4'-三唑[3,4-b]-1″,3″,4″-噻二嗪衍生物的合成及抗菌活性[J]. 有机化学,2005,25(6):700-704.
[16] Holla B S,Rao S B,Sarojini B K, et al . Synthesis and Studies on Some New Fluorine Containing Triazolothiadiazines as Possible Antibacterial, Antifungal and Anticancer Agents[J]. Eur J Med Chem ,2006,41(5):657-663.
[17] Zafer A K,Gulhan Z,Ahmet O, et al . New Triazole and Triazolothiadiazine Derivatives as Possible Antimicrobial Agents[J]. Eur J Med Chem ,2008,43(1):155-159.
[18] Karegoudar P,Prasad D J,Ashok M, et al . Synthesis, Antimicrobial and Anti-inflammatory Activities of Some 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazines Bearing Trichlorophenyl Moiety[J]. Eur J Med Chem ,2008,43(4):808-815.
[19] ZHENG Yuguo,XUE Wei,LU Ping, et al . Synthesis and Antitumor Activity of 5,6-2 H -[1,2,4]-Triazolo [3,4-b][1,3,4]thiadiazine Derivatives[J]. Chinese J Org Chem ,2011,31(6):912-916(in Chinese). 郑玉国,薛伟,卢平,等. 5,6-2 H -1,2,4-三[3,4-b][1,3,4]噻二嗪衍生物的合成及抗癌活性[J]. 有机化学,2011,31(6):912-916.
[20] LI Zaiguo. Preparation of Organic Intermediaters[M]. Beijing:Chemistry Industry Press,2001:150(in Chinese). 李在国. 有机中间体制备[M]. 北京:化学工业出版社,2001:150.
[21] Liu C L,Li L,Li Z M. Desigan, Synthesis, and Biological Activity of Novel 4-(3,4-Dimethoxyphenyl)-2-methylthiazole-5-carboxylic Acid Derivatives[J]. Bioorg Med Chem ,2004,14(12):2825-2830.

Synthesis and Biological Activity of Novel 1,2,4-Triazolothiadiazine Derivatives Containing Pyrazole Unit

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