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]
  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
3. [3]
  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
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]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
11. [11]
  Shipeng WANG , Shangyu XIE , Luxian LIANG , Xuehong WANG , Jie WEI , Deqiang WANG . Piezoelectric effect of Mn, Bi co-doped sodium niobate for promoting cell proliferation and bacteriostasis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1919-1931. doi: 10.11862/CJIC.20240094
12. [12]
  Dong-Bing Cheng , Junxin Duan , Haiyu Gao . Experimental Teaching Design on Chitosan Extraction and Preparation of Antibacterial Gel. University Chemistry, 2024, 39(2): 330-339. doi: 10.3866/PKU.DXHX202308053
13. [13]
  Yu Wang , Haiyang Shi , Zihan Chen , Feng Chen , Ping Wang , Xuefei Wang . 具有富电子Pt^δ^-壳层的空心AgPt@Pt核壳催化剂：提升光催化H₂O₂生成选择性与活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-. doi: 10.1016/j.actphy.2025.100081
14. [14]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
15. [15]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
16. [16]
  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
17. [17]
  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
18. [18]
  Yue Li , Minghao Fan , Conghui Wang , Yanxun Li , Xiang Yu , Jun Ding , Lei Yan , Lele Qiu , Yongcai Zhang , Longlu Wang . 3D layer-by-layer amorphous MoS_x assembled from [Mo₃S₁₃]^2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764
19. [19]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
20. [20]
  Jingjie Tang , Luying Xie , Jiayu Liu , Shangyu Shi , Xinyu Sun , Jiayang Lin , Qikun Yang , Chuan'ang Yu , Zecheng Wang , Yingying Wang , Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1088)
HTML views(116)

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