Schiff bases and their metal complexes as urease inhibitors – A brief review

da Silva, 2011, Schiff bases: a short review of their antimicrobial activities, J Adv Res, 2, 1, 10.1016/j.jare.2010.05.004 Schiff, 1866, Eine neue reihe organischer diamine, Eur J Org Chem, 140, 92 Schiff, 1864, Mittheilungen aus dem Universitätslaboratorium in Pisa: Eine neue Reihe organischer Basen, Liebigs Ann Chem, 131, 118, 10.1002/jlac.18641310113 Dhar, 1982, Schiff-bases and their applications, J Sci Ind Res India, 41, 501 Abdel-Rahman, 2016, Some new nano-sized mononuclear Cu(II) Schiff base complexes: design, characterization, molecular modeling and catalytic potentials in benzyl alcohol oxidation, Catal Lett, 146, 1373, 10.1007/s10562-016-1755-0 Sztanke, 2013, An insight into synthetic Schiff bases revealing antiproliferative activities in vitro, Bioorgan Med Chem, 21, 3648, 10.1016/j.bmc.2013.04.037 Utreja, 2015, Schiff bases and their metal complexes as anti-cancer agents: a review, Curr Bioact Compd, 11, 215, 10.2174/1573407212666151214221219 Abdel-Rahman, 2013, Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA interaction of few high spin Fe(II) Schiff base amino acid complexes, Spectrochim Acta A, 111, 266, 10.1016/j.saa.2013.03.061 Abdel-Rahman, 2014, Metal based pharmacologically active agents: Synthesis, structural characterization, molecular modeling, CT-DNA binding studies and in vitro antimicrobial screening of iron(II) bromosalicylidene amino acid chelates, Spectrochim Acta A, 117, 366, 10.1016/j.saa.2013.07.056 Abdel-Rahman, 2016, Sonochemical synthesis, DNA binding, antimicrobial evaluation and in vitro anticancer activity of three new nano-sized Cu(II), Co(II) and Ni(II) chelates based on tri-dentate NOO imine ligands as precursors for metal oxides, J Photochem Photobiol B, 162, 298, 10.1016/j.jphotobiol.2016.06.052 Abdel-Rahman, 2017, DNA interaction, antimicrobial, anticancer activities and molecular docking study of some new VO(II), Cr(III), Mn(II) and Ni(II) mononuclear chelates encompassing quaridentate imine ligand, J Photochem Photobiol B, 170, 271, 10.1016/j.jphotobiol.2017.04.003 Kajal, 2013, Schiff bases: a versatile pharmacophore, J Catal, 2013 Bringmann, 2004, Ancistrotanzanine C and Related 5, 1 ‘-and 7, 3 ‘-Coupled Naphthylisoquinoline Alkaloids from Ancistrocladus tanzaniensis, J Nat Prod, 67, 743, 10.1021/np0340549 Souza, 2007, Antimycobacterial and cytotoxicity activity of synthetic and natural compounds, Quim Nova, 30, 1563, 10.1590/S0100-40422007000700012 Guo, 2007, Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan, Carbohyd Res, 342, 1329, 10.1016/j.carres.2007.04.006 da Silva, 2017, Studies on free radical scavenging, cancer cell antiproliferation, and calf thymus DNA interaction of Schiff bases, J Photochem Photobiol B, 172, 129, 10.1016/j.jphotobiol.2017.05.020 Martins, 2017, Copper (II) nitroaromatic schiff base complexes: synthesis, biological activity and their interaction with DNA and albumins, J Brazil Chem Soc, 28, 87 Krajewska, 2009, Functional, catalytic and kinetic properties: a review, J Mol Catal B-Enzym, 59, 9, 10.1016/j.molcatb.2009.01.003 Modolo, 2015, An overview on the potential of natural products as ureases inhibitors: a review, J Adv Res, 6, 35, 10.1016/j.jare.2014.09.001 Follmer, 2010, Ureases as a target for the treatment of gastric and urinary infections, J Clin Pathol, 63, 424, 10.1136/jcp.2009.072595 Maroney, 2014, Nonredox nickel enzymes, Chem Rev, 114, 4206, 10.1021/cr4004488 Boer, 2014, Nickel-dependent metalloenzymes, Arch Biochem Biophys, 544, 142, 10.1016/j.abb.2013.09.002 Amtul, 2002, Chemistry and mechanism of urease inhibition, Curr Med Chem, 9, 1323, 10.2174/0929867023369853 van Vliet, 2001, Nickel-responsive induction of urease expression in helicobacter pylori is mediated at the transcriptional level, Infect Immun, 69, 4891, 10.1128/IAI.69.8.4891-4897.2001 Mobley, 1989, Microbial ureases: significance, regulation, and molecular characterization, Microbiol Rev, 53, 85, 10.1128/MMBR.53.1.85-108.1989 Raz, 2005, Who are you—Staphylococcus saprophyticus?, Clin Infect Dis, 40, 896, 10.1086/428353 Nielubowicz, 2010, Host–pathogen interactions in urinary tract infection, Nat Rev Uro, 7, 430, 10.1038/nrurol.2010.101 Flores-Mireles, 2015, Urinary tract infections: epidemiology, mechanisms of infection and treatment options, Nat Rev Microbiol, 13, 269, 10.1038/nrmicro3432 Aslam, 2011, Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors, Eur J Med Chem, 46, 5473, 10.1016/j.ejmech.2011.09.009 Saeed, 2015, 2-(Hetero(aryl)methylene)hydrazine-1-carbothioamides as Potent Urease Inhibitors, Chem Biol Drug Des, 85, 225, 10.1111/cbdd.12379 Rafiq, 2017, Facile synthesis, biological evaluation and molecular docking studies of novel substituted azole derivatives, J Mol Struct, 1138, 177, 10.1016/j.molstruc.2017.03.013 Iftikhar, 2017, Design, synthesis, in vitro Evaluation and docking studies on dihydropyrimidine-based urease inhibitors, Bioorg Chem, 74, 53, 10.1016/j.bioorg.2017.07.003 Rahim, 2016, Synthesis and antiurease & antioxidant activities of Bis-Schiff bases of isophthalaldehyde, Asian J Chem, 28, 39, 10.14233/ajchem.2016.19168 Weser, 1979, Health effects, 197 Forstner, 1979 Flemming, 1989, Copper toxicity and chemistry in the environment: a review, Water, Air, Soil Pollut, 44, 143, 10.1007/BF00228784 Garribba, 2006, The determination of the geometry of Cu(II) complexes: an EPR spectroscopy experiment, J Chem Educ, 83, 1229, 10.1021/ed083p1229 Li, 2007, Transition metal complexes (M = Cu, Ni and Mn) of Schiff-base ligands: syntheses, crystal structures, and inhibitory bioactivities against urease and xanthine oxidase, Inorg Chim Acta, 360, 2881, 10.1016/j.ica.2007.02.019 Follmer, 2005, Effect of chemical modification of histidines on the copper-induced oligomerization of jack bean urease (EC 3.5.1.5), Arch Biochem Biophys, 435, 15, 10.1016/j.abb.2004.12.001 Cheng, 2007, New method for the synthesis of a mononucleating cyclic peptide ligand, crystal structures of its Ni, Zn, Cu, and Co complexes, and their inhibitory bioactivity against urease, Aust J Chem, 60, 375, 10.1071/CH06479 You, 2016, Inhibition studies of Helicobacter pylori urease with Schiff base copper(ii) complexes, RSC Adv, 6, 16679, 10.1039/C6RA00500D Pervez, 2016, Synthesis, cytotoxic and urease inhibitory activities of some novel isatin-derived bis-Schiff bases and their copper(ii) complexes, MedChemCommun, 5, 914, 10.1039/C5MD00529A Pan, 2016, Synthesis, structures and Helicobacter pylori urease inhibitory activity of copper(II) complexes with tridentate aroylhydrazone ligands, J Inorg Biochem, 159, 22, 10.1016/j.jinorgbio.2016.02.017 Chen, 2010, Synthesis, molecular docking and biological evaluation of Schiff base transition metal complexes as potential urease inhibitors, Eur J Med Chem, 45, 4473, 10.1016/j.ejmech.2010.07.007 Habala, 2016, Antimicrobial activity and urease inhibition of schiff bases derived from isoniazid and fluorinated benzaldehydes and of their copper(II) complexes, Molecules, 21, 1742, 10.3390/molecules21121742 Dong, 2011, Synthesis, crystal structure, and urease inhibition studies of copper(II) and cobalt(III) complexes with bi(2-fluorobenzylaminoethyl)amine, Transit Metal Chem, 36, 319, 10.1007/s11243-011-9472-4 Cui, 2011, Synthesis, molecular docking, and activity of Schiff-base copper(II) complex with N-n-butylsalicylaldiminate as Helicobacter pylori urease inhibitor, J Coord Chem, 64, 610, 10.1080/00958972.2011.552110 You, 2010, Synthesis, crystal structures and urease inhibitory activity of copper(II) complexes with Schiff bases, Inorg Chem Commun, 13, 996, 10.1016/j.inoche.2010.05.016 Berg, 1996, The galvanization of biology: a growing appreciation for the roles of zinc, Science, 271, 1081, 10.1126/science.271.5252.1081 Auld, 2004, Structural zinc sites, 403 Patel, 2007, Analysis of the structural consensus of the zinc coordination centers of metalloprotein structures, Bba-Proteins Proteom, 1774, 1247, 10.1016/j.bbapap.2007.07.010 Wang, 2009, Syntheses, crystal structures, and urease inhibitory properties of copper (II) and zinc (II) complexes with 2-bromo-4-chloro-6-[(2-dimethylaminoethylimino) methyl] phenol, J Coord Chem, 62, 2860, 10.1080/00958970902946702 Qiu, 2013, Syntheses, urease inhibition activities, and fluorescent properties of transition metal complexes, J Coord Chem, 66, 1616, 10.1080/00958972.2013.787144 Shi, 2010, Synthesis, characterization, and crystal structures of two Schiff base zinc (II) complexes with urease inhibitory activities, Russ J Coord Chem, 36, 535, 10.1134/S1070328410070109 Shi, 2013, Synthesis, crystal structures, and biological activity of zinc (II) complexes derived from 4-bromo-2-[(3-diethylaminopropylimino) methyl] phenol, Russ J Coord Chem, 39, 297, 10.1134/S1070328413030111 Shi, 2012, Synthesis, crystal structures, and biological activity of Schiff base zinc (II) complexes derived from (2-piperidin-1-ylethyl)-(1-pyridin-2-ylethylidene) amine, Synth React Inorg M, 42, 480, 10.1080/15533174.2011.613083 Wang, 2012, Synthesis, crystal structures, and urease inhibitory properties of two isostructural dinuclear zinc(II) complexes with schiff base 5-methoxy-2-[(2-methylaminoethylimino)methyl]phenol, Synth React Inorg M, 42, 1405, 10.1080/15533174.2012.680151 You, 2009, Influence of the steric effects of the Schiff bases and the hydrogen bonds on the bridging modes of the azide groups: Syntheses and crystal structures of three azide-bridged Schiff base zinc(II) complexes, Inorg Chem Commun, 12, 444, 10.1016/j.inoche.2009.03.009 Carlini, 2016, Ureases as multifunctional toxic proteins: a review, Toxicon, 110, 90, 10.1016/j.toxicon.2015.11.020 Carter, 2009, Interplay of metal ions and urease, Metallomics, 1, 207, 10.1039/b903311d Shi, 2007, Synthesis, crystal structure and urease inhibitory activities of Schiff base metal complexes, Inorg Chem Commun, 10, 404, 10.1016/j.inoche.2006.12.011 Dillard, 1982, The oxidation states of cobalt and selected metals in Pacific ferromanganese nodules, Geochim Cosmochim Acta, 46, 755, 10.1016/0016-7037(82)90027-8 Shamma, 2018, Synthesis, characterization and biological properties of mixed ligand complexes of cobalt(II/III) valproate with 2,9-dimethyl-1,10-phenanthroline and 1,10-phenanthroline, Appl Organomet Chem, 32, 3904, 10.1002/aoc.3904 Lv, 2006, Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived schiff bases, J Inorg Biochem, 100, 1888, 10.1016/j.jinorgbio.2006.07.014 Lu, 2012, Synthesis, structures, and urease inhibition of nickel(II), zinc(II), and cobalt(II) complexes with similar hydroxy-rich Schiff bases, J Coord Chem, 65, 339, 10.1080/00958972.2011.653785 Jing, 2016, Synthesis, structures and urease inhibitory activity of cobalt(III) complexes with Schiff bases, Bioorgan Med Chem, 24, 270, 10.1016/j.bmc.2015.12.013 Wang, 2010, Synthesis and crystal structures of cobalt(III) and zinc(II) complexes derived from 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol with urease inhibitory activity, Russ J Coord Chem, 36, 177, 10.1134/S1070328410030036 You, 2007, New method for the synthesis of bis-Schiff base trinuclear cobalt(II) complex with urease inhibitory activity, Inorg Chem Commun, 10, 1273, 10.1016/j.inoche.2007.08.007 Verma, 1998, Nutritional factors that can favorably influence the glucose/insulin system: vanadium, J Am Colloids Nutr, 17, 11, 10.1080/07315724.1998.10718730 Goc, 2006, Biological activity of vanadium compounds, Cent Eur J Biol, 1, 314 Ashiq, 2008, Synthesis, spectroscopy, and biological properties of vanadium(IV)–hydrazide complexes, Chem Biodivers, 5, 82, 10.1002/cbdv.200890016 Sanna, 2017, Speciation of potential anti-diabetic vanadium complexes in real serum samples, J Inorg Biochem, 173, 52, 10.1016/j.jinorgbio.2017.04.023 Kioseoglou, 2015, The chemistry and biology of vanadium compounds in cancer therapeutics, Coordin Chem Rev, 301–302, 87, 10.1016/j.ccr.2015.03.010 Leon, 2017, Vanadium, ruthenium and copper compounds: a new class of nonplatinum metallodrugs with anticancer activity, Curr Med Chem, 24, 112, 10.2174/0929867323666160824162546 Sinha, 2017, Induction of apoptosis in human colorectal cancer cell line, HCT-116 by a vanadium- Schiff base complex, Biomed Pharmacother, 92, 509, 10.1016/j.biopha.2017.05.108 Chohan, 2010, Metal based biologically active compounds: design, synthesis, and antibacterial/antifungal/cytotoxic properties of triazole-derived Schiff bases and their oxovanadium(IV) complexes, Eur J Med Chem, 45, 2739, 10.1016/j.ejmech.2010.02.053 Ebrahimipour, 2016, A novel oxido-vanadium(V) Schiff base complex: synthesis, spectral characterization, crystal structure, electrochemical evaluation, and biological activity, Res Chem Intermediat, 42, 611, 10.1007/s11164-015-2045-y Huo, 2014, Synthesis, characterization and urease inhibition of a novel acetylhydroxamate-coordinated oxovanadium(V) complex with hydrazone ligand, Inorg Chem Commun, 45, 131, 10.1016/j.inoche.2014.04.008 Sheng, 2014, Synthesis, crystal structure, and urease inhibition of [N′-(3,5-dibromo-2-hydroxybenzylidene)isonicotinohydrazido]-(benzohydroxamato)oxovanadium(V), Russ J Coord Chem, 40, 505, 10.1134/S1070328414070082 You, 2012, Synthesis, structures, and urease inhibitory activities of oxovanadium(V) complexes with Schiff bases, Irnoganica Chim Acta, 384, 54, 10.1016/j.ica.2011.11.039 Ren, 2014, Synthesis, structures and Helicobacter pylori urease inhibition of schiff base vanadium complexes containing acetohydroxamate ligands, Chin J Inorg Chem, 30, 640 You, 2011, Synthesis, characterization and urease inhibitory activity of oxovanadium(V) complexes with similar Schiff bases, Inorg Chem Commun, 14, 636, 10.1016/j.inoche.2011.01.038 Zhao, 2013, Synthesis, structures, and Helicobacter pylori urease inhibition of oxovanadium(V) complexes with hydrazones, Chin J Inorg Chem, 29, 867 You, 2012, Synthesis and structures of dioxovanadium(V) complexes with Schiff bases and their inhibition studies on Helicobacter pylori urease, Chin J Inorg Chem, 28, 1271 You, 2011, Preparation and structural characterization of oxovanadium(V) complexes with Schiff bases and their inhibition studies on Helicobacter pylori urease, J Coord Chem, 64, 3510, 10.1080/00958972.2011.625021 Zhang, 2017, Synthesis, characterization, and antimicrobial activity of two Schiff base silver(I) complexes derived from 4-carboxybenzaldehyde, J Coord Chem, 70, 1066, 10.1080/00958972.2017.1285399 Shi, 2012, Synthesis, crystal structures, and biological activity of Cu(II), Mn(III), and Fe(III) complexes derived from N,N′-bis(4-methoxysalicylidene)ethylenediamine, Synth React Inorg Met-Org Nano-Metal Chem, 42, 1177, 10.1080/15533174.2012.684236 Zhang, 2011, Unprecedented preparation of bis-Schiff bases and their manganese(III) complexes with urease inhibitory activity, Inorg Chem Commun, 14, 1636, 10.1016/j.inoche.2011.06.027 You, 2008, Synthesis, crystal structures, and urease inhibitory activities of three novel thiocyanato-bridged polynuclear Schiff base cadmium(II) complexes, Z Anorg Allg Chem, 634, 142, 10.1002/zaac.200700345 Shi, 2010, Synthesis, crystal structures, and urease inhibitory activities of two isostructural schiff base cadmium(II) complexes, Synth React Inorg Met-Org Nano-Metal Chem, 40, 359, 10.1080/15533174.2010.487057 Choudhary MI, Khan A, Khan KM, Ambreen N, Wahab A-t, Rahman A-u. InventorsSchiff bases of thiazoles: a new class of ureases inhibitors. Patent # US20150368214A1, United States, 2015. Hameed, 2017, Schiff bases in medicinal chemistry: a patent review (2010-2015), Expert Opin Ther Pat, 27, 63, 10.1080/13543776.2017.1252752 Modolo LV, de Fatima A, de Souza LT, Horta LP, da Silva CM, Barboa GM, et al. Urea pearls combine with almines, method for producing, same and use thereof in agriculture, and use of aldimines for the treatment of bacterial infections. Patent # WO2016174648A1, National Institute for Industrial Property (INPI), Brazil; 2016.