Citation: Gao Zhimin, Wang Tiantian, Li Shenzhen, Wan Huiqi, Wang Gang, Wu Yinbin, Deng Xianqing, Song Mingxia. Synthesis and Antibacterial Activity Evaluation of (2-Chloroquinolin- 3-yl)methyleneamino Guanidine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2484-2488. doi: 10.6023/cjoc201604041 shu

Synthesis and Antibacterial Activity Evaluation of (2-Chloroquinolin- 3-yl)methyleneamino Guanidine Derivatives

1.
Basic Medical and Pharmacy College, Jinggangshan University, Ji'an 343009

Corresponding author: Song Mingxia, freexiaoxiao83@aliyun.com
Received Date: 19 April 2016
Revised Date: 31 May 2016

Fund Project: National Natural Science Foundation of China 81560561Doctoral Foundation of Jinggangshan University JZB1317

Figures(1)

In order to find new antibacterial agent with wide spectra and high activities, 8 new (2-chloroquinolin-3-yl)meth- yleneamino guanidine derivatives were synthesized based on combination principles, whose structures were then identified by spectral methods. All of the compounds provided exhibited good inhibitory activities against the strains chosen, except Salmonella typhimurium 2421 and Pseudomonas aeruginosa 2742, of which MICs were mostly in the range of 2.0~16 μg/mL. The compound 4h showed the best broad-spectrum antibacterial activities, whose MIC value was 2.0 μg/mL against six strains. The inhibitory activities of 4h, against Staphylococcus aureus KCTC 503 and two drug-resistance bacterias (Methicillin-resistant Staphylococcus aureus CCARM 3167 and Quinolone-resistant Staphylococcus aureus CCARM 3505), were superior or equal to positive controls gatifloxacin, moxifloxacin, norfloxacin and oxacillin.
- alkylene aminoguanidine,
- 2-chloroquinoline,
- antibacterial activity,
- drug-resistance bacteria
1. [1]
  Livermore, D. M. J. Antimicrob. Chemother. 2009, 64(Suppl. 1), i29.
2. [2]
  Azeredo da Silveira, S.; Perez, A. Expert Rev. Anti-Infect. Ther. 2015, 13, 531.
3. [3]
  Hvistendahl, M. Science 2012, 336, 795.
4. [4]
  Yezli, S.; Li, H. Int. J. Antimicrob. Agents 2012, 40, 389.
5. [5]
6. [6]
  Kofteridis, D. P.; Alexopoulou, C.; Valachis, A.; Maraki, S.; Dimopoulou, D.; Georgopoulos, D.; Samonis, G. Clin. Infect. Dis. 2010, 51, 1238.
7. [7]
  Velkov, T.; Thompson, P. E.; Nation, R. L.; Li, J. J. Med. Chem. 2010, 53, 1898.
8. [8]
  Thomas K. D.; Adhikari, A. V.; Telkar, S.; Chowdhury, I. H.; Mahmood, R.; Pal, N. K.; Row, G.; Sumesh, E. Eur. J. Med. Chem. 2011, 46, 5283.
9. [9]
  Eswaran, S.; Adhikari, A. V.; Shetty, N. S. Eur. J. Med. Chem. 2009, 44, 4637.
10. [10]
  Kategaonkar, A. H.; Shinde, P. V.; Kategaonkar, A. H.; Pasale, S. K.; Shingate, B. B.; Shangare, M. S. Eur. J. Med. Chem. 2010, 45, 3142.
11. [11]
  Lilienkampf, A.; Mao, J.; Wan, B.; Wang, Y.; Franzblau, S. G.; Kozikowski, A. P. J. Med. Chem. 2009, 52, 2109.
12. [12]
  Denny, W. A.; Wilson, W. R.; Ware, D. C.; Atwell, G. J.; Milbank, J. B.; Stevenson, R. J. WO 2002059122, 2002[Chem. Abstr. 2002, 137, 149339].
13. [13]
  Strekowski, L.; Mokrosz, J. L.; Honkan, V. A.; Czarny, A.; Cegla, M. T.; Patterson, S. E.; Wydra, R. L.; Schinazi, R. F. J. Med. Chem. 1991, 34, 1739.
14. [14]
  Nasveld, P.; Kitchener, S. Trans. R. Soc. Trop. Med. Hyg. 2005, 99, 2.
15. [15]
  Ferreira, E. G.; Wilke, D. V.; Jimenez, P. C.; de Oliveira, J. R.; Pessoa O. D.; Silveira, E. R.; Viana, F. A.; Pessoa, C.; de Moraes, M. O.; Hajdu, E.; Costa-Lotufo L. V. Chem. Biodiversity 2011, 8, 1433.
16. [16]
  Ren, S.; Wang, R.; Komatsu, K.; Bonaz-Krause, P.; Zyrianov, Y.; McKenna C. E.; Csipke C.; Tokes Z. A.; Lien E. J. J. Med. Chem. 2002, 45, 410.
17. [17]
  Mourer, M.; Dibama, H. M.; Fontanay, S.; Grare, M.; Duval, R. E.; Finance, C.; Regnouf-de-Vains, J. B. Bioorg. Med. Chem. 2009, 17, 5496.
18. [18]
  Guo, M.; Zheng, C.J.; Song, M.X.; Wu, Y.; Sun, L.P.; Li, Y.J.; Liu, Y.; Piao, H.R. Bioorg. Med. Chem. Lett. 2013, 23, 4358.
1. [1]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
2. [2]
  Jing FENG , Renshu WANG , Hu WANG , Hailong LIU . Co(Ⅱ) and Ni(Ⅱ) complexes of 3,3-diphenylpropionic acid and 2,2′-dipyridylamine: Structures and biological activities. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 617-631. doi: 10.11862/CJIC.20250265
3. [3]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
4. [4]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
5. [5]
  Yuanyuan Zeng , Xiaoti Chang , Jingru Li , Qilin Wang . 骨架编辑策略：异喹啉到2-氨基-1-萘甲醛的转化. University Chemistry, 2026, 41(10): 309-315. doi: 10.12461/PKU.DXHX202510028
6. [6]
  Chengyu JIANG , Xufeng LIU . Synthesis, structural characterization, electrocatalytic proton reduction, and fungicidal activity of thiazole-containing di-iron complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 355-364. doi: 10.11862/CJIC.20250253
7. [7]
  Xinzhe ZHANG , Jiarong XU , Mochou GAO , Yage LIU , Yanbao ZHAO , Jingzeng CUI , Xueyan ZOU . Silver chloride/chitosan-based chloramine nanohybrid with excellent antibacterial activity: Design and structure characterization as well as Ag⁺-Cl^- synergistic antibacterial effect. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 428-438. doi: 10.11862/CJIC.20250123
8. [8]
  Jia JI , Tengqi YAO , Wenqian DENG , Wenjing SHI , Xuan LÜ , Lin TIAN , Xiaoyan XIN , Yinling HOU . Structures, antibacterial activities, and interactions with DNA of two nickel complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 78-86. doi: 10.11862/CJIC.20250141
9. [9]
  Huilin ZHENG , Tao WANG , Ruilin GAO , Mengke ZHOU , Xinyue LI , Hui WANG , Xiaoxia GU . Antitumor and antibacterial activities of transition metal complexes incorporating pyridyl salicylaldehyde Schiff base. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 897-905. doi: 10.11862/CJIC.20250358
10. [10]
  Mengyun Wu , Yuxin Deng , Wenhui Wang , Dongdong Xu , Langui Xie , Peipei Sun . 电化学合成4-氯-2-三异丙基硅基喹啉. University Chemistry, 2026, 41(5): 222-229. doi: 10.12461/PKU.DXHX202511044
11. [11]
  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
12. [12]
  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
13. [13]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
14. [14]
  Congqi Zhu , Bo Liu , Ruchun Li . Dual active sites enhancing alkaline H₂-production performance. Acta Physico-Chimica Sinica, 2025, 41(11): 100146-0. doi: 10.1016/j.actphy.2025.100146
15. [15]
  Di WU , Ruimeng SHI , Zhaoyang WANG , Yuehua SHI , Fan YANG , Leyong ZENG . Construction of pH/photothermal dual-responsive delivery nanosystem for combination therapy of drug-resistant bladder cancer cell. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1679-1688. doi: 10.11862/CJIC.20240135
16. [16]
  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): 100074-0. doi: 10.1016/j.actphy.2025.100074
17. [17]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
18. [18]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
19. [19]
  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
20. [20]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2502)
HTML views(382)

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