Citation: ZHANG Chenglu, CHENG Anqi, TANG Jie, GUO Yang, SUN Lijie, XI Huan. Synthesis and Biological Activity of the Novel Mannich Bases of 5-Alkyl-1,2,4-triazole[J]. Chinese Journal of Applied Chemistry, ;2016, 33(5): 554-564. doi: 10.11944/j.issn.1000-0518.2016.05.150267 shu

Synthesis and Biological Activity of the Novel Mannich Bases of 5-Alkyl-1,2,4-triazole

1.
College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: ZHANG Chenglu,
Received Date: 28 July 2015
Available Online: 7 December 2015
Fund Project:

Twenty-two novel Mannich bases of 5-alkyl-1,2,4-triazole were designed and synthesized to evaluate their biological activities. The plant growth regulating activity, herbicidal activity and the inhibitory activity on cell division cycle protein 25B(CDC25B) of those molecules were screened. Most of the molecules exhibit good cytokinin activity and herbicidal activity, indicating their potential as novel pesticide. One of these molecules performs good inhibitory activity against CDC25B, and is a potential leading compound for anti-concer drug design.
- alkyl-triazole,
- Mannich base,
- plant growth regulator,
- herbicidal activity,
- inhibitors against CDC25B
1. [1]
  [1] Bandara P M S,Tanino K K. Paclobutrazol Enhances Minituber Production in Norland Potatones[J]. J Plant Growth Regul,1995,14:151-155.
2. [2]
  [2] Nishikawa S,Kurono M,Shibayama K. Synthesis and Cytokinin Activity of Fluorescent 7-Phenylethynylimidazo[4,5-b]pyridine and Its Riboside[J]. J Agric Food Chem,2000,48(6):2559-2564.
3. [3]
  [3] Zeffari G R,Peres L E P,Kerbauy G B. Endogenous Levels of Cytokinins, Indoleacetic Acid, Abscisic Acid, and Pigments in Variegated Somaclones of Micropropagated Banana Levels[J]. J Plant Growth Regul,1998,17(2):59-61.
4. [4]
  [4] Hicks K A,Sundas A,Meeks-Wagner D R. Arabidopsis Early Flowering Mutants Reveal Multiple Levels of Regulation in the Vegetative-to-Floral Transition[J]. Semin Cell Dev Biol,1999,35(3):177-184.
5. [5]
  [5] Holla B S,Rao B S,Shridhara K,et al. Synthesis, Characterisation and Biological Studies on Some Mannich Bases Carrying 2,4-Dichlorophenylfurfural Moiety[J]. II Farmaco,2000,55(5):338-344.
6. [6]
  [6] 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(9):5515-5522.
7. [7]
  [7] ZHANG Chenglu,ZHU Chang'an,WU Feiyu,et al. Synthesis, Biological Activity and Electrochemical Properties of Ferrocenyl 1,3,4-Triazoles Derivatives[J]. Chinese J Appl Chem,2014,31(4):455-461(in Chinese).张成路,朱长安,武飞宇,等. 二茂铁基1,3,4-三唑席夫碱衍生物合成及生物活性和电化学性质[J]. 应用化学,2014,31(4):455-461.
8. [8]
  [8] Szatmari I,Fulop F. Syntheses, Transformations and Applications of Aminonaphthol Derivatives Prepared via Modified Mannich Reactions[J]. Tetrahedron,2013,69(4):1255-1278.
9. [9]
  [9] Plech T,Wujec M,Siwek A,et al. Synthesis and Antimicrobial Activity of Thiosemicarbazides, S-triazoles and Their Mannich Bases Bearing 3-Chlorophenyl Moiety[J]. Eur J Med Chem,2011,46(8):241-248.
10. [10]
  [10] SHEN Shengqiang,SUN Xiaohong,LIU Yuanfa,et al.Synthesis and Biological Activity of 1,3,4-Oxadiazole Mannich Bases Containing Pyrimidine Rings[J]. Chem J Chinese Univ,2014,7(35)1527-1532(in Chinese).沈生强,孙晓红,刘源发,等. 含嘧啶环的1,3,4-噁二唑Mannich碱的合成及生物活性[J]. 高等学校化学学报,2014,7(35):1527-1532.
11. [11]
  [11] ZHENG Yuguo,WEI Quanxian,LU Yin,et al. Synthesis of a Novel Mannich Base Containing 1,2,4-Triazole Schiff Base and Pyrazole Unit[J]. Chinese J Synth Chem,2015,23(1):55-58(in Chinese).郑玉国,魏全鲜,陆寅,等. 新型含均三氮唑Schiff碱吡唑基Mannich碱的合成[J]. 合成化学,2015,23(1):55-58.
12. [12]
  [12] Ayako T,Go H,Yusuke K,et al. Dual-Specificity Phosphatase CDC25A/B Inhibitor Identified from a Focused Library with Nonelectrophilic Core Structure[J]. ACS Med Chem Lett,2012,3(4):294-298.
13. [13]
  [13] George L,Sergii D,Dmitry B,et al. Inhibition of CDC25B Phosphatase Through Disruption of Protein-Protein Interaction[J]. ACS Chem Biol,2015,10(2):390-394.
14. [14]
  [14] ZHANG Chenglu,GUO Yang,WU Yifei,et al.Synthesis and Biological Activities of 3-Aliphatic-1,2,4-Triazole [3,4-b]-1,3,4-Thiatriazole Derivatives Containing Pyridine Unit[J]. Chinese J Appl Chem,2014,31(12):1419-1427(in Chinese).张成路,国阳,吴一非,等. 含吡啶组块3-脂肪基-1,2,4-三唑并[3,4-b]-1,3,4噻二唑衍生物的合成及生物活性[J]. 应用化学,2014,31(12):1419-1427.
15. [15]
  [15] George T,Mehta D V,Tahilramani R,et al. Synthesis of Some s-Triazoles with Potential Analgetic and Antiinflammatory Activities[J]. J Med Chem,1971,14(4):335-338.
16. [16]
  [16] JIN Zhong,LIU Wei,HUO Aihong,et al. Selective Reduction, Characterization and Biological Activity of 3-Aryl-1-Ferrocynyl-2-(1H-1,2,4-Triazol-1-yl)-2-Propen-1-One Derivatives[J]. Chem J Chinese Univ,2005,26(9):1640-1644(in Chinese).金钟,刘伟,霍爱红,等. 3-芳基-1-二茂铁基-2-(1H-1,2,4-三唑-1-基)-2-丙烯酮类衍生物的选择性还原、产物结构表征及其生物活性研究[J]. 高等学校化学学报,2005,26(9):1640-1644.
17. [17]
  [17] Li R,Chen J,Yuan D Y,et al. Indication of the Expression of Transgene in Rice Plant Based on Hyperspectral Remote Sensing TechniqueⅡ-Growth Monitoring of Samples in the Contrast Experiment[J]. Spectrosc Spectr Anal,2011,6(31):1621-1626.
18. [18]
  [18] Huang W G,Jiang Y Y,Li Q,et al. Synthesis and Biological Evaluation of(±)-Cryptotanshinone and Its Simplified Analogues as Potent CDC25 Inhibitors[J]. Tetrahedron,2005,61(7):1863-1870.
19. [19]
  [19] ZHANG Chenglu,SUN Lijie,WU Feiyu,et al. Synthesis and Bioactivity of 14-Bis[3-aliphatic/aryl-1,2,4-triazole [3,4-b]-1,3,4-thiatriazole-6-yl]Aryl Derivatives[J]. Chem J Chinese Univ,2014,35(7):1445-1450(in Chinese).张成路,孙丽杰,武飞宇,等. 1,4-双[3-脂肪基/苯基-1,2,4-三唑并[3,4-b]-1,3,4-噻二唑-6-基]芳基衍生物的合成与生物活性[J]. 高等学校化学学报,2014,35(7):1445-1450.
20. [20]
  [20] Lindqvist A,Källström H,Lundgren A,et al. Cdc25B Cooperates with Cdc25A to Induce Mitosis but Has a Unique Role in Activating Cyclin B1 Cdk1 at the Centrosome[J]. J Cell Biol,2005,171(1):35-45.
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沈阳化工大学材料科学与工程学院沈阳 110142