Citation: Yu Haihong, Zhou Shengchao, Guo Tingting, Liang Zhuo, Chen Huabin, Dai Weikai, Song Mingxia. Synthesis and Antimicrobial Activity Evaluation of Aminoguanidine Derivatives Containing a Biphenyl Moiety[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1497-1502. doi: 10.6023/cjoc201811012 shu

Synthesis and Antimicrobial Activity Evaluation of Aminoguanidine Derivatives Containing a Biphenyl Moiety

Basic Medical and Pharmacy College, School of Medicine, Jinggangshan University, Ji'an 343009

Corresponding author: Song Mingxia, freexiaoxiao83@aliyun.com
Received Date: 6 November 2018
Revised Date: 18 December 2018
Available Online: 9 May 2019
Fund Project: the Doctoral Foundation of Jinggangshan University JZB1317the National Natural Science Foundation of China 81560561Project supported by the National Natural Science Foundation of China (No. 81560561), and the Doctoral Foundation of Jinggangshan University (No. JZB1317)

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A series of aminoguanidine derivatives containing a biphenyl moiety were designed, synthesized, and characterized by spectra methods using chalcone-aminoguanidine derivative as the lead compound. The antibacterial activity of the target compounds was evaluated. The results indicated that most of the target compounds showed potent inhibitory activity with the minimum inhibitory concentration values (MICs) in range of 0.5~8 μg/mL. Among of which, 2-((4'-bromo-[1, 1'-biphenyl]-4-yl)methylene)hydrazine-1-carboximidamide (3j) exhibited broad-spectrum antibacterial activity, effective to all the chosen strains including two multidrug-resistant gram-positive strains, showed the most potent inhibitory against S. aureus CMCC(B) 26003, E. faecalis CMCC 29212 and multidrug-resistant S. aureus ATCC 33591 with a MIC value of 0.5 μg/mL. Moreover, low cytotoxicity of compound 3j (HEK 293T, IC₅₀=60.90 µmol/L) was found. These results suggested that the Compound 3j, with high safety, was potential and valuable in the research of novel antibacterial drugs.
- aminoguanidine,
- biphenyl,
- antimicrobial activity
1. [1]
  Bi, Y.; Liu, X. X.; Zhang, H. Y.; Yang, X.; Liu, Z. Y.; Lu, J.; Lewis, P. J.; Wang, C. Z.; Xu, J. Y.; Meng, Q. G.; Ma, C.; Yuan, C. S. Molecules 2017, 22, 590. doi: 10.3390/molecules22040590
2. [2]
  Carrel, M.; Perencevich, E. N.; David, M. Z. Emerging Infect. Dis. 2015, 21, 1973. doi: 10.3201/eid2111.150452
3. [3]
  Hvistendahl, M. Science 2012, 336, 795. doi: 10.1126/science.336.6083.795
4. [4]
  Yezli, S.; Li, H. Int. J. Antimicrob. Agents 2012, 40, 389. doi: 10.1016/j.ijantimicag.2012.07.009
5. [5]
  Azeredo da Silveira, S.; Perez, A. Expert Rev. Anti-Infect. Ther. 2015, 13, 531. doi: 10.1586/14787210.2015.1028367
6. [6]
  Kang, Y.; Zhao, M.; Zhang, J. Chin. J. Antibiot. 2017, 42, 169(in Chinese). doi: 10.3969/j.issn.1001-8689.2017.03.002
7. [7]
  Ward, R. S. Nat. Prod. Rep. 1999, 16, 75. doi: 10.1039/a705992b
8. [8]
  Whiting, D. A. Nat. Prod. Rep. 2001, 18, 583. doi: 10.1039/b003686m
9. [9]
  Chang, J. B.; Reiner, J.; Xie, J. X. Chem. Rev. 2005, 105, 4581. doi: 10.1021/cr050531b
10. [10]
  Chen, D. F.; Zhang S. X.; Lan, X. Bioorg. Med. Chem. 1997, 5, 715. doi: 10.1016/S0968-0896(97)00014-X
11. [11]
  Raffa, D.; Plescia, F.; Maggio, B.; Raimondi, M. V.; D'Anneo, A.; Lauricella, M.; Daidone, G. Eur. J. Med. Chem. 2017, 132, 262. doi: 10.1016/j.ejmech.2017.03.051
12. [12]
  Chen, Y.; Du, Y. J.; Suo, F. X. J. Henan Normal Univ. (Nat. Sci.) 2001, 29, 43(in Chinese).
13. [13]
  Wei, Z. Y.; Chi, K. Q.; Yu, Z. K.; Liu, H. Y.; Sun, L. P.; Zheng, C. J.; Piao, H. R. Bioorg. Med. Chem. Lett. 2016, 26, 5920. doi: 10.1016/j.bmcl.2016.11.001
14. [14]
  Sidoryk, K.; Świtalska, M.; Rózga, P.; Wietrzyk, J.; Bujak, I.; Żerek, B.; Kaczmarek, Ł.; Cybulski, M. Med. Chem. Res. 2017, 26, 3354. doi: 10.1007/s00044-017-2028-1
15. [15]
  Gao, Z. M.; Wang, T. T.; Li, S. Z.; Wan, H. Q.; Wang, G.; Wu, Y. B.; Deng, X. Q.; Song, M. X. Chin. J. Org. Chem. 2016, 36, 2484(in Chinese).
16. [16]
  Li, Y. R.; Li, C.; Liu, J. C.; Guo, M.; Zhang, T. Y.; Sun, L. P.; Zheng, C. J.; Piao, H. R. Bioorg. Med. Chem. Lett. 2015, 25, 5052. doi: 10.1016/j.bmcl.2015.10.028
17. [17]
  Xu, H.; Wang, Y. Y. Bioorg. Med. Chem. Lett. 2010, 20, 7274 doi: 10.1016/j.bmcl.2010.10.084
18. [18]
  Mourer, M.; Dibama, H. M.; Fontanay, S.; Grare, M.; Duval, R. E.; Finance, C.; Vains, J. B. R. Bioorg. Med. Chem. 2009, 17, 5496. doi: 10.1016/j.bmc.2009.06.040
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