Citation: Zhang Chenglu, Tang Jie, Yin Liying, Xi Huan, Guo Yang, Sun Lijie. One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 358-362. doi: 10.6023/cjoc201507029 shu

One Pot Synthesis of 3-Substituted-1-morpholino-1,2,4-triazole Mannich Bases and Their Activity Evaluation

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

Corresponding author: Zhang Chenglu,
Received Date: 24 July 2015
Available Online: 8 October 2015
Fund Project: 辽宁省教育厅科学技术研究(No. 2009A426)资助项目 (No. 2009A426)

15 Schiff bases were synthesized by the reactions of 3-p-chlorophenyl, 3-p-methoxyphenyl and 3-n-pentyl-1,2,4-triazole with five different aromatic aldehydes, respectively. Then 14 novel Mannich bases (PCTABM, PMTABM and PETABM) were first afforded by the reactions of Schiff bases with formaldehyde and morpholine through multi-component one-pot reaction. In order to explore the effect of different 3-substituted groups on biological activities, four Mannich bases FcTABM of 3-ferrocenyl-1,2,4-triazole were also synthesized starting from 3-ferrocenyl-1,2,4-triazole by the similar method. IR, ¹H NMR and HRMS were used to characterize the structure of the target molecules. The biological activities of the target molecules were evaluated. As a result, the target compounds exhibited excellent activities in plant growth regulators and herbicidal activity. There are 14 target compounds exhibited excellent inhibitory activity against Cdc25B, in which the IC₅₀ values of 7c, 8e, 9e, 10b～10e IC₅₀ were all smaller than the reference Na₃VO₄, which were expected to be Cdc25B inhibitors.
- Mannich base,
- Cdc25B inhibitor,
- plant growth regulator,
- herbicidal activity
1. [1]
  [1] Ashok, M.; Holla, B. S.; Poojary, B. Eur. J. Med. Chem. 2007, 42, 1095.
2. [2]
  [2] Roman, G. Eur. J. Med. Chem. 2015, 89, 743.
3. [3]
  [3] Li, G. H.; Yang, H. Chin. J. Org. Chem. 2008, 28, 1918 (in Chinese). (李国华, 杨红, 有机化学, 2008, 28, 1918.)
4. [4]
  [4] Navidpour, L.; Shafaroodi, H.; Abdi, K.; Amini, M.; Ghahremani, H. M.; Dehpour, A. R.; Shafiee, A. Bioorg. Med. Chem. 2006, 14, 2507.
5. [5]
  [5] Holla, B. S.; Veerendra, B.; Shivananda, M. K.; Poojary, B. Eur. J. Med. Chem. 2003, 38, 759.
6. [6]
  [6] Wang, B. L.; Shi, Y. X.; Ma, Y.; Liu, X. H.; Li, Y. H.; Song, H. B.; Li, B. J.; Li, Z. M. J Agric Food Chem. 2010, 58, 5515.
7. [7]
  [7] Deng, X. M.; Wang, J. H.; Zhang, J. M.; Sim, T.; Kim, N. D.; Sasaki, T.; Luther, W.; George, R. E.; Janne, P. A.; Gray, N. S. Med. Chem. Lett. 2011, 2, 379.
8. [8]
  [8] Kunj, B. M.; Vinod, K. T. J. Org. Chem. 2014, 79, 5752.
9. [9]
  [9] Burbuliene, M. M.; Jakubkiene, V.; Mekuskiene, G.; Udrenaitea, E.; Smiciusa, R.; Vainilaviciusa, P. Farmaco 2004, 59, 767.
10. [10]
  [10] Koparir, M.; Orek, C.; Parlak, A. E.; Söylemez, A.; Koparir, P.; Karatepe, M.; Dastan, S. D. Eur. J. Med. Chem. 2013, 63, 340.
11. [11]
  [11] Jakubkiene, V.; Burbuliene, M. M.; Mekuskiene, G.; Emilija, U.; Gaidelis, P.; Vainilavičius, P. Farmaco 2003, 58, 323.
12. [12]
  [12] Ashok, M.; Holla, B. S.; Poojary, B. Eur. J. Med. Chem. 2007, 42, 1095.
13. [13]
  [13] Holla, B. S.; Rao, B. S.; Shridhara, K.; Akberali, P. M. Farmaco 2000, 55, 338.
14. [14]
  [14] Hu, G. Q.; Wang, G. Q.; Duan, N. N.; Wen, X. Y.; Cao, T.Y.; Xie, S. Q.; Huang, W. L. Acta Pharm. Sin. B 2012, 2, 312.
15. [15]
  [15] Kaminski, K.; Obniska, J.; Chlebek, I.; Wiklik, B.; Rzepka, S. Bioorg. Med. Chem. 2013, 21, 6821.
16. [16]
  [16] Arafa, W. A. A; Mohamed, A. S. Chin. J. Chem. 2011, 29, 1661.
17. [17]
  [17] Mohamed, R. A. Molecules 2014, 19, 18897.
18. [18]
  [18] Mostafa, A. H.; Refaat, M. S.; Mohammed, A. A.; Mohammed, F. M. Arch. Pharm. Res. 2011, 34, 1239.
19. [19]
  [19] Tsuchiya, A.; Hirai, G.; Koyama, Y.; Oonuma, K.; Otani, Y.; Osada, H.; Sodeoka, M. Med. Chem. Lett. 2012, 3, 294.
20. [20]
  [20] Li, Q. H.; Wang, M. M. Chem. Res. Appl. 2010, 22, 186 (in Chinese). (李清寒, 王苗苗, 化学研究与应用, 2010, 22, 186.)
21. [21]
  [21] Zhu, C. A.; Wu, F. Y.; Wang, X.; Gao, L. N.; Weng, Q. F.; Shi, L.; Zhang, C. L. Chin. J. Appl. Chem. 2014, 31, 455 (in Chinese). (朱长安, 武飞宇, 王雪, 高丽娜, 翁前锋, 石丽, 张成路, 应用化学, 2014, 31, 455.)
22. [22]
  [22] Lavecchia, A.; Giovanni, C. D.; Pesapane, A.; Montuori, N.; Ragno, P.; Martucci, N. M.; Masullo, M.; Vendittis, E. D. J. Med. Chem. 2012, 55, 4142.
23. [23]
  [23] Sahoo, P. K.; Sharma, R.; Pattanayak, P. Med. Chem. Res. 2010, 19, 127.
24. [24]
  [24] George, T.; Mehta, D. V.; Tahilramani, R.; David, J.; Talwalker, P. K. J. Med. Chem. 1971, 14, 335.
25. [25]
  [25] Zhang, C. L.; Wang, X.; Guo, Y. Wu, Y. F.; Gao, L. N.; Sun, L. J.; Chai, J. H.; Zhu, C. A. Chin. J. Org. Chem. 2014, 34, 2331 (in Chinese). (张成路, 王雪, 国阳, 吴一非, 高丽娜, 孙丽杰, 柴金华, 朱长安, 有机化学, 2014, 34, 2331.)
26. [26]
  [26] Gupta, A, K.; Prachand, S.; Patel, A.; Jain, S. Int. J. Pharm. Life Sci. 2012, 3, 1848.
1. [1]
  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
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
3. [3]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
4. [4]
  Xueqi Yang , Juntao Zhao , Jiawei Ye , Desen Zhou , Tingmin Di , Jun Zhang . 调节NNU-55(Fe)的d带中心以增强CO₂吸附和光催化活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100074-. doi: 10.1016/j.actphy.2025.100074
5. [5]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-. doi: 10.1016/j.actphy.2025.100052
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
10. [10]
  Limei CHEN , Mengfei ZHAO , Lin CHEN , Ding LI , Wei LI , Weiye HAN , Hongbin WANG . Preparation and performance of paraffin/alkali modified diatomite/expanded graphite composite phase change thermal storage material. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 533-543. doi: 10.11862/CJIC.20230312
11. [11]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
12. [12]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
13. [13]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
14. [14]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
15. [15]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
16. [16]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
17. [17]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
18. [18]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
19. [19]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
20. [20]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(975)
HTML views(102)

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