Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents

被引:75
作者
Kant, Rama [1 ]
Singh, Vishal [1 ]
Nath, Gopai [2 ]
Awasthi, Satish Kumar [3 ]
Agarwal, Alka [1 ]
机构
[1] Banaras Hindu Univ, Inst Med Sci, Dept Med Chem, Varanasi 221005, Uttar Pradesh, India
[2] Banaras Hindu Univ, Inst Med Sci, Dept Microbiol, Varanasi 221005, Uttar Pradesh, India
[3] Univ Delhi, Dept Chem, Chem Biol Res Lab, Delhi 110007, India
关键词
1,2,3-Triazole conjugates; Ciprofloxacin; Antibacterial activity; Hemotoxicity; CLICK CHEMISTRY; 1,2,4-TRIAZOLE-CIPROFLOXACIN HYBRIDS; PIPERAZINYL QUINOLONES; MOLECULAR DOCKING; TRIAZOLE HYBRIDS; DERIVATIVES; ANALOGS; ANTIBIOTICS; 1,2,3-TRIAZOLES; RESISTANCE;
D O I
10.1016/j.ejmech.2016.08.031
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of new bis-1,2,3-triazole linked ciprofloxacin conjugates was designed, synthesized and evaluated in vitro antibacterial activity against a panel of clinically relevant bacteria. A significant part of the compounds displayed enhanced activity against both Gram-positive and Gram-negative species of bacteria as compared to the parent drug. Additionally, negligible toxicity profile of compounds indicates that they may act a good antibiotic in future. Despite relatively small number of synthesized conjugates, it was possible to observe important dependences between their structure and activity. (C) 2016 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:218 / 228
页数:11
相关论文
共 66 条
[1]   Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].
Agalave, Sandip G. ;
Maujan, Suleman R. ;
Pore, Vandana S. .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718
[2]   A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents [J].
Anand, Ashish ;
Naik, Reshma J. ;
Revankar, Hrishikesh M. ;
Kulkarni, Manohar V. ;
Dixit, Sheshagiri R. ;
Joshi, Shrinivas D. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 105 :194-207
[3]   Peptide Triazole Inactivators of HIV-1 Utilize a Conserved Two-Cavity Binding Site at the Junction of the Inner and Outer Domains of Env gp120 [J].
Aneja, Rachna ;
Rashad, Adel A. ;
Li, Huiyuan ;
Sundaram, Ramalingam Venkat Kalyana ;
Duffy, Caitlin ;
Bailey, Lauren D. ;
Chaiken, Irwin .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (09) :3843-3858
[4]  
[Anonymous], 2009, OXF DIFFR
[5]  
ATARASHI S, 1987, CHEM PHARM BULL, V35, P1896
[6]   Synthesis of lipophilic dimeric C-7/C-7-linked ciprofloxacin and C-6/C-6-linked levofloxacin derivatives. Versatile in vitro biological evaluations of monomeric and dimeric fluoroquinolone derivatives as potential antitumor, antibacterial or antimycobacterial agents [J].
Azema, Joelle ;
Guidetti, Brigitte ;
Korolyov, Alexander ;
Kiss, Robert ;
Roques, Christine ;
Constant, Patricia ;
Daffe, Mamadou ;
Malet-Martino, Myriam .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :6025-6038
[7]  
Bezouska K., 2002, REV MOL BIOTECHNOLOG, P269, DOI DOI 10.1016/S1389-0352(01)00064-2
[8]   Medicinal potential of ciprofloxacin and its derivatives [J].
Castro, William ;
Navarro, Maribel ;
Biot, Christophe .
FUTURE MEDICINAL CHEMISTRY, 2013, 5 (01) :81-96
[9]   Chemometric studies on the bactericidal activity of quinolones via an extended VolSurf approach [J].
Cianchetta, G ;
Mannhold, R ;
Cruciani, G ;
Baroni, M ;
Cecchetti, V .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3193-3201
[10]  
Cooke Fiona J, 2004, Travel Med Infect Dis, V2, P67, DOI 10.1016/j.tmaid.2004.04.005