Citation: Liu-Zhou Gao, Yu-Suo Xie, Tao Li, Wen-Long Huang, Guo-Qiang Hu. Synthesis and antibacterial activity of novel [1,2,4]triazolo [3,4-h][1,8]naphthyridine-7-carboxylic acid derivatives[J]. Chinese Chemical Letters, ;2015, 26(1): 149-151. doi: 10.1016/j.cclet.2014.09.017 shu

Synthesis and antibacterial activity of novel [1,2,4]triazolo [3,4-h][1,8]naphthyridine-7-carboxylic acid derivatives

1.
a Institute of Chemical Biology, Henan University, Kaifeng 475001, China;
2.
b Centre of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China

Corresponding author: Guo-Qiang Hu,
Received Date: 4 July 2014
Available Online: 2 September 2014
Fund Project:

Novel tricyclic fluoroquinolones, [1,2,4]triazolo[3,4-h][1,8]naphthyridine-8-one-7-carboxylic acid derivatives 4a-4h bearing carrying a functional Mannich-base moiety at the C-8 position, were synthesized and evaluated for their antimicrobial activity. The results showed that some compounds with a piperazine side chain exhibited comparable or better antibacterial activity than comparator cirprofloxacin. Furthermore, the targeted compounds also displayed a broad spectrum of activity against resistant strains including both Gram-negative and Gram-positive bacteria. In particular, compound 4h showed an MIC of 0.25 μg/mL in antibacterial assay against multiple drug-resistant Escherichia coli, which represents an about 30-fold increase of potency compared to ciprofloxacin. Thus, their excellent antibacterial activity against resistant strains suggests that triazole-fused fluoroquinolones warrant further optimization as novel anti-infective chemotherapies.
- Triazole,
- Tricyclic fluoroquinolone,
- Synthesis,
- Antibacterial activity
References
1. [1]
  [1] T. Tomašić, L.P. Mašič, Prospects for developing new antibacterials targeting bacterial type IIA topoisomerases, Curr. Top. Med. Chem. 14 (2014) 130-151.
2. [2]
  [2] X.D. Wang, W. Wei, P.F. Wang, et al., Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: design, synthesis and evaluation as antibacterial agent, Bioorg. Med. Chem. 22 (2014) 3620-3628.
3. [3]
  [3] K. Chauhan, P. Singh, V. Kumar, et al., Investigation of Ugi-4CC derived 1Htetrazol- 5-yl-(aryl) methyl piperazinyl-6-fluoro-4-oxo-1 4-dihydroquinoline-3- carboxylic acid: synthesis, biology and 3D-QSAR analysis, J. Eur. Med. Chem. 78 (2014) 442-454.
4. [4]
  [4] K.M. Hutchings, T.P. Tran, E.L. Ellsworth, et al., Synthesis and antibacterial activity of the C-7 side chain of 3-aminoquinazoline-diones, Bioorg. Med. Chem. Lett. 18 (2008) 5087-5090.
5. [5]
  [5] M.J. Nieto, A.B. Pierini, N. Singh, et al., SAR analysis of new dual targeting fluoroquinolones. Implications of the benzenesulfonyl group, Med. Chem. 8 (2012) 349-360.
6. [6]
  [6] H. Takiff, E. Guerrero, Current prospects for the fluoroquinolones as first-line tuberculosis therapy, Antimicrob. Agents Chemother. 55 (2011) 5421-5429.
7. [7]
  [7] C. Zhi, Z.Y. Long, A. Manikowski, et al., Hybrid antibacterials. DNA polymerase- topoisomerase inhibitors, J. Med. Chem. 49 (2006) 1455-1465.
8. [8]
  [8] Y. Jinbo, H. Kondo, M. Taguchi, et al., Synthesis and antibacterial activity of thiazolopyrazine-incorporated tetracyclic quinolone antibacterial agents. 2, J. Med. Chem. 37 (1994) 2791-2796.
9. [9]
  [9] Y.D. Li, W.T. Mao, Z.J. Fan, et al., Synthesis and biological evaluation of novel 1,2,4- triazole containing 1,2,3-thiadiazole derivatives, Chin. Chem. Lett. 24 (2013) 1134-1136.
10. [10]
  [10] M. Koparir, C. Orek, A.E. Parlak, et al., Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H- 1,2,4-triazole-3-thiones, J. Eur. Med. Chem. 63 (2013) 340-346.
11. [11]
  [11] G.Q. Hu, Z.Q. Zhang, W.L. Huang, H.B. Huang, S.T. Huang, Synthesis and antibacterial activity of new tetracyclic triazolothiadiazino fluoroquinolones, Chin. Chem. Lett. 15 (2004) 23-25.
1. [1]
  [1] T. Tomašić, L.P. Mašič, Prospects for developing new antibacterials targeting bacterial type IIA topoisomerases, Curr. Top. Med. Chem. 14 (2014) 130-151.
2. [2]
  [2] X.D. Wang, W. Wei, P.F. Wang, et al., Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: design, synthesis and evaluation as antibacterial agent, Bioorg. Med. Chem. 22 (2014) 3620-3628.
3. [3]
  [3] K. Chauhan, P. Singh, V. Kumar, et al., Investigation of Ugi-4CC derived 1Htetrazol- 5-yl-(aryl) methyl piperazinyl-6-fluoro-4-oxo-1 4-dihydroquinoline-3- carboxylic acid: synthesis, biology and 3D-QSAR analysis, J. Eur. Med. Chem. 78 (2014) 442-454.
4. [4]
  [4] K.M. Hutchings, T.P. Tran, E.L. Ellsworth, et al., Synthesis and antibacterial activity of the C-7 side chain of 3-aminoquinazoline-diones, Bioorg. Med. Chem. Lett. 18 (2008) 5087-5090.
5. [5]
  [5] M.J. Nieto, A.B. Pierini, N. Singh, et al., SAR analysis of new dual targeting fluoroquinolones. Implications of the benzenesulfonyl group, Med. Chem. 8 (2012) 349-360.
6. [6]
  [6] H. Takiff, E. Guerrero, Current prospects for the fluoroquinolones as first-line tuberculosis therapy, Antimicrob. Agents Chemother. 55 (2011) 5421-5429.
7. [7]
  [7] C. Zhi, Z.Y. Long, A. Manikowski, et al., Hybrid antibacterials. DNA polymerase- topoisomerase inhibitors, J. Med. Chem. 49 (2006) 1455-1465.
8. [8]
  [8] Y. Jinbo, H. Kondo, M. Taguchi, et al., Synthesis and antibacterial activity of thiazolopyrazine-incorporated tetracyclic quinolone antibacterial agents. 2, J. Med. Chem. 37 (1994) 2791-2796.
9. [9]
  [9] Y.D. Li, W.T. Mao, Z.J. Fan, et al., Synthesis and biological evaluation of novel 1,2,4- triazole containing 1,2,3-thiadiazole derivatives, Chin. Chem. Lett. 24 (2013) 1134-1136.
10. [10]
  [10] M. Koparir, C. Orek, A.E. Parlak, et al., Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H- 1,2,4-triazole-3-thiones, J. Eur. Med. Chem. 63 (2013) 340-346.
11. [11]
  [11] G.Q. Hu, Z.Q. Zhang, W.L. Huang, H.B. Huang, S.T. Huang, Synthesis and antibacterial activity of new tetracyclic triazolothiadiazino fluoroquinolones, Chin. Chem. Lett. 15 (2004) 23-25.
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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

Synthesis and antibacterial activity of novel [1,2,4]triazolo [3,4-h][1,8]naphthyridine-7-carboxylic acid derivatives

References

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通讯作者: 陈斌, bchen63@163.com