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
-
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.
-
-
-
[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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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.
-
[1]
-
-
-
[1]
Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
-
[2]
Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
-
[3]
Nian LIU , Biao ZHENG , Kun WANG , Chunbao ZHENG , Qingyan HAN , Enjie HE , Saidong XUE . Synthesis and spectroscopic performance of double perovskite Li0.5La0.5MgSrWO6∶Mn4+ phosphors for plant growth lighting. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 129-140. doi: 10.11862/CJIC.20250069
-
[4]
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
-
[5]
Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
-
[6]
Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
-
[7]
Wei Li , Han Xu , Chuancan Gu , Ziyan Liu , Yan'an Li , Yan Geng . Digital Experiment on Nano-COF Materials Modulating Intracellular Ca²⁺ Concentration to Enhance Photodynamic Therapy. University Chemistry, 2026, 41(1): 354-362. doi: 10.12461/PKU.DXHX202506001
-
[8]
Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
-
[9]
Aoyun Meng , Zhenhua Li , Guoyuan Xiong , Zhen Li , Jinfeng Zhang . S-scheme heterojunction Al6Si2O13/BiOBr with enhanced charge transfer effect for efficient and stable photocatalytic degradation of triazophos and dichlorvos pesticides. Acta Physico-Chimica Sinica, 2026, 42(5): 100186-0. doi: 10.1016/j.actphy.2025.100186
-
[10]
Yajie Li , Bin Chen , Yiping Wang , Hui Xing , Wei Zhao , Geng Zhang , Siqi Shi . Inhibiting Dendrite Growth by Customizing Electrolyte or Separator to Achieve Anisotropic Lithium-Ion Transport: A Phase-Field Study. Acta Physico-Chimica Sinica, 2024, 40(3): 2305053-0. doi: 10.3866/PKU.WHXB202305053
-
[11]
Chunyang Zheng , Shiyu Liu , Nuo Yi , Hong Shang . The Adventures in the Kingdom of Plant Pigments. University Chemistry, 2024, 39(9): 170-176. doi: 10.3866/PKU.DXHX202308085
-
[12]
Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
-
[13]
Wenjuan SHI , Yuxuan LEI , Lei HOU , Yaoyu WANG . Synthesis, structure, and luminescence properties of trinucluear Cu(Ⅰ)-pyrazole complexes containing different substituent groups. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 543-550. doi: 10.11862/CJIC.20250270
-
[14]
Zimo Shen , Tongwei Zhang , Zhiyi Zhu , Zonghao Gong , Qing Feng , Jinyi Yang , Zhen Li , Min Liu , Wei Qi . From Alkaloid to Anticancer Agent: The Transformative Journey of Camptothecin. University Chemistry, 2025, 40(10): 161-165. doi: 10.12461/PKU.DXHX202411027
-
[15]
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
-
[16]
Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
-
[17]
Dongqi Cai , Fuping Tian , Zerui Zhao , Yanjuan Zhang , Yue Dai , Feifei Huang , Yu Wang . Exploration of Factors Influencing the Determination of Ion Migration Number by Hittorf Method. University Chemistry, 2024, 39(4): 94-99. doi: 10.3866/PKU.DXHX202310031
-
[18]
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
-
[19]
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
-
[20]
Zhengqi SHEN , Hanxue LIU , Lin HOU , Meng REN , Xiangyu DAI , Yating ZHANG , Zhi SU , Chao GE , Xuling XUE , Hongke LIU . A dual-pathway synergistic inhibition strategy based on ruthenium/iridium metal complexes targeting GPX4 and DHODH: Mechanism of directly activating ferroptosis in leukemia cells. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 271-283. doi: 10.11862/CJIC.20250230
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(733)
- HTML views(71)
Login In
DownLoad: