Synthesis and investigation of antimicrobial activities of nitrofurazone analogues containing hydrazide-hydrazone moiety

Saudi Pharmaceutical Journal - Tập 25 Số 7 - Trang 1097-1102 - 2017
Łukasz Popiołek1, Anna Biernasiuk2
1Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland
2Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Medical University of Lublin, 1 Chodźki Street, 20-093, Lublin, Poland

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Backes, 2014, Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides, Bioorg. Med. Chem., 22, 4629, 10.1016/j.bmc.2014.07.022

Bala, 2013, Hydrazones as promising lead with diversity in bioactivity-therapeutic potential in present scenario, Int. J. Pharm. Sci. Rev. Res., 18, 65

Clinical and Laboratory Standards Institute, 2012. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. M27-S4. Wayne, PA, USA.

Coates, 2002, The future challenges facing the development of new antimicrobial drugs, Nat. Rev. Drug. Discov., 1, 895, 10.1038/nrd940

Cukurovali, 2014, Synthesis, characterization, investigation of biological activity and theoretical studies of hydrazone compounds containing choloroacetyl group, J. Mol. Struct., 1075, 566, 10.1016/j.molstruc.2014.06.070

Çıkla, 2013, Synthesis, cytotoxicity and pro-apoptosis of etodolac hydrazide derivatives as anticancer agents, Arch. Pharm. Chem. Life Sci., 346, 367, 10.1002/ardp.201200449

Deep, 2010, Design and biological evaluation of biphenyl-4-carboxylic acid hydrazide-hydrazone for antimicrobial activity, Acta Pol. Pharm., 67, 255

European Committee for Antimicrobial Susceptibility Testing (EUCAST), 2003, Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by broth dilution. EUCAST discussion document E. Dis 5.1, Clin. Microbiol. Infect., 9, 1

He, 2016, Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety, Bioorg. Med. Chem. Lett., 26, 3263, 10.1016/j.bmcl.2016.05.059

Koçyiğit-Kaymakçıoğlu, 2006, Synthesis and characterization of novel hydrazide–hydrazones and the study of their structure–antituberculosis activity, Eur. J. Med. Chem., 41, 1253, 10.1016/j.ejmech.2006.06.009

Koçyiğit-Kaymakçıoğlu, 2009, Antituberculosis activity of hydrazones derived from 4-fluorobenzoic acid hydrazide, Med. Chem. Res., 18, 277, 10.1007/s00044-008-9126-z

Kumar, 2011, Synthesis, antimicrobial evaluation and QSAR studies of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides, Chin. Chem. Lett., 22, 1293, 10.1016/j.cclet.2011.06.014

Kumar, 2012, Novel bis(indolyl)hydrazide–hydrazones as potent cytotoxic agents, Bioorg. Med. Che. Lett., 22, 212, 10.1016/j.bmcl.2011.11.031

Küçükgüzel, 2002, Synthesis, characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds, Eur. J. Med. Chem., 37, 197, 10.1016/S0223-5234(01)01326-5

Küçükgüzel, 2003, Synthesis and biological activities of diflunisal hydrazide-hydrazones, Eur. J. Med. Chem., 38, 1005, 10.1016/j.ejmech.2003.08.004

Küçükgüzel, 2015, Synthesis of tolmetin hydrazide-hydrazones and discovery of a potent inducer in colon cancer cells, Arch. Pharm. Chem. Life Sci., 348, 730, 10.1002/ardp.201500178

Loncle, 2004, Synthesis and antifungal activity of cholesterol-hydrazone derivatives, Eur. J. Med. Chem., 39, 1067, 10.1016/j.ejmech.2004.07.005

McCalla, 1970, Mode of action of nitrofurazone, J. Bacteriol., 1126, 10.1128/JB.104.3.1126-1134.1970

Moellering, 2011, Discovering new antimicrobial agents, Int. J. Antimicrob. Agents, 37, 2, 10.1016/j.ijantimicag.2010.08.018

Mohareb, 2010, Synthesis of hydrazide-hydrazone derivatives and their evaluation of antidepressant, sedative and analgesic agents, J. Pharm. Sci. Res., 2, 185

Moldovan, 2011, Synthesis and anti-inflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole, Eur. J. Med. Chem., 46, 526, 10.1016/j.ejmech.2010.11.032

Morjan, 2014, Antibacterial activities of novel nicotinic acid hydrazides and their conversion into N-acetyl-1,3,4-oxadiazoles, Bioorg. Med. Chem. Lett., 24, 5796, 10.1016/j.bmcl.2014.10.029

Mukherjee, 2016, Development of novel bis(indolyl)-hydrazide−hydrazone derivatives as potent microtubule-targeting cytotoxic agents against A549 lung cancer cells, Biochemistry, 55, 3020, 10.1021/acs.biochem.5b01127

Nasr, 2014, Anticancer activity of new coumarin substituted hydrazide-hydrazone derivatives, Eur. J. Med. Chem., 76, 539, 10.1016/j.ejmech.2014.02.026

Özkay, 2010, Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem., 45, 3293, 10.1016/j.ejmech.2010.04.012

Pavan, 2010, Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/hydrazones: anti – mycobacterium tuberculosis activity and cytotoxicity, Eur. J. Med. Chem., 45, 1898, 10.1016/j.ejmech.2010.01.028

Pieczonka, 2013, Synthesis and evaluation of antimicrobial activity of hydrazones derived from 3-oxido-1H-imidazole-4-carbohydrazides, Eur. J. Med. Chem., 64, 389, 10.1016/j.ejmech.2013.04.023

Popiołek, 2016, Hydrazide-hydrazones of 3-methoxybenzoic acid and 4-tert-butylbenzoic acid with promising antibacterial activity against Bacillus spp., J. Enz. Inh. Med. Chem., 31, 62, 10.3109/14756366.2016.1170012

Popiołek, 2016, Design, synthesis and in vitro antimicrobial activity of hydrazide-hydrazones of 2-substituted acetic acid, Chem. Biol. Drug Des., 88, 873, 10.1111/cbdd.12820

Popiołek, 2014, Synthesis and antimicrobial evaluation of new Schiff base hydrazones bearing 1,2,4-triazole moiety, Phosphorus, Sulfur Silicon Relat. Elem., 189, 1611, 10.1080/10426507.2013.789878

Popiołek, 2016, Synthesis and in vitro antimicrobial activity of nalidixic acid hydrazones, J. Het. Chem., 53, 1589, 10.1002/jhet.2468

Popiołek, 2016, Synthesis, dissociation constants, and antimicrobial activity of novel 2,3-disubstituted-1,3- thiazolidin-4-one derivatives, J. Het. Chem., 53, 393, 10.1002/jhet.2418

Rambabu, 2015, Synthesis, characterization and antimicrobial activity of some novel hydrazone derivatives of anacardic acid, Der Pharm. Chem., 7, 90

Rasras, 2010, Synthesis and antimicrobial activity of cholic acid hydrazone analogues, Eur. J. Med. Chem., 45, 2307, 10.1016/j.ejmech.2010.02.006

Rollas, 2007, Biological activities of hydrazone derivatives, Molecules, 12, 1910, 10.3390/12081910

Rutkauskas, 2013, Synthesis and antimicrobial activity of 1,3-disubstituted pyrrolidinones with hydrazone and naphthoquinone moieties, Chemija, 4, 74

Satyanarayana, 2014, Synthesis and antimicrobial activity of novel hydrazone derivatives of 4-(4-chlorophenyl)cyclohexanecarboxylic acid, J. Appl. Chem., 3, 1232

Şenkardes, 2016, Synthesis of novel diflunisal hydrazide-hydrazones as anti-hepatitis C virus agents and hepatocellular carcinoma inhibitors, Eur. J. Med. Chem., 108, 301, 10.1016/j.ejmech.2015.10.041

Velezheva, 2016, Synthesis and antituberculosis activity of indole–pyridine derived hydrazides, hydrazide–hydrazones, and thiosemicarbazones, Bioorg. Med. Chem. Lett., 26, 978, 10.1016/j.bmcl.2015.12.049

Wardakhan, 2013, Synthesis and anti-tumor evaluation of novel hydrazide and hydrazide-hydrazone derivatives, Acta Pharm., 63, 45, 10.2478/acph-2013-0004

Wiegand, 2008, Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances, Nat. Protoc., 3, 163, 10.1038/nprot.2007.521