Citation: Zhang Junhui, Liu Si, Shi Yanhua, Jiang Lin. Syntheses and Antifungal Activities of 2-[(Pyridin-3-yl)methylamino]-1H-imidazol-4(5H)-one Derivatives[J]. Chemistry, ;2018, 81(3): 248-252. shu

Syntheses and Antifungal Activities of 2-[(Pyridin-3-yl)methylamino]-1H-imidazol-4(5H)-one Derivatives

College of Chemistry and Material Science, Shandong Agricultural University, Tai'an 271018

Corresponding author: Jiang Lin, jiangl@sdau.edu.cn
Received Date: 25 October 2017
Accepted Date: 5 January 2018

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Starting from 2-thiohydantoin, substituted benzaldehydes, methyl iodide and pyridin-3-ylmethyl amine, a series of 5-substituted benzylidene-2-[(pyridine-3-yl)methylamino]-1H-imidazol-4(5H)-ones (3a~3i) were synthesized by Knoevenagel condensation, methylation and substitution reactions. The structures of the target compounds were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. The preliminary antifungal activity results indicated that all target compounds display moderate inhibitory activities against B. cinerea at the concerntration of 100μg/mL, with inhibition rates in the range of 69.5%~83.2%. Most of the target compounds exhibited notable activities against S. sclerotiorum at the same dosage, with inhibition rates in the range of 87.9%~100%, which were higher than that of the control fungicides, triazolone and chlorothalonil.
- Pyridine,
- Imidazolone,
- Synthesis,
- Antifungal activity
1. [1]
  P Picconia, P Prabaharan, J L Auer et al. Bioorg. Med. Chem., 2017, 25(15):3971~3979.
2. [2]
3. [3]
  J F Renard, F Lecomte, P Hubert et al. Eur. J. Med. Chem. 2014, 74(1):12~22.
4. [4]
5. [5]
  T X Li, J Zhang, J K Pan et al. Eur. J. Med. Chem., 2017, 125(1):657~662.
6. [6]
  B L Wang, H W Zhu, Y Ma et al. J. Agr. Food Chem., 2013, 61(23):5483~5493.
7. [7]
8. [8]
  A Y Guan, C L Liu, X F Sun et al. Bioorg. Med. Chem., 2016, 24(3) 342~353.
9. [9]
10. [10]
  F R Wu, H Jiang, B S Zheng et al. J. Med. Chem., 2015, 58(17):6899~6908.
11. [11]
  W K Liao, G Hu, Z Guo et al. Bioorg. Med. Chem., 2015, 23(15):4410~4422.
12. [12]
  K Lewellyn, D Bialonska, N D Chaurasiya et al. Bioorg. Med. Chem. Lett., 2012, 22(15):4926~4929.
13. [13]
14. [14]
15. [15]
  S M Gomha, H M E Hassaneen. Molecules, 2011, 16(8):6549~6560.
16. [16]
17. [17]
18. [18]
19. [19]
20. [20]
  A I Khodair, H I El-Subbagh, A M Al-Obaid. Phosphorus Sulfur, 1998, 140(1):159~181.
21. [21]
  D ŁaŻewska, P Maludziński, E Szymańska et al. Biomed. Chromatogr., 2007, 21(3):291~298.
22. [22]
  I Subtel'na, D Atamanyuk, E Szymanska et al. Bioorg. Med. Chem., 2010, 18(14):5090~5102.
23. [23]
  K KieC'-Kononowicz, J Karolak-Wojciechowska, J Handzlik. Acta Poloniae Pharm. Drug Res., 1998, 55(5):381~388.
24. [24]
25. [25]
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
3. [3]
  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
4. [4]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
7. [7]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
10. [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. [11]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
12. [12]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
13. [13]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
14. [14]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
15. [15]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
16. [16]
  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
17. [17]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
18. [18]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
19. [19]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
20. [20]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

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沈阳化工大学材料科学与工程学院沈阳 110142