6,453
Views
28
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis, characterization and antibacterial activity of Cu (II) and Zn (II) complexes of 5-aminobenzofuran-2-carboxylate Schiff base ligands

ORCID Icon, ORCID Icon & ORCID Icon
Pages 440-449 | Received 18 Apr 2018, Accepted 04 Mar 2019, Published online: 19 Mar 2019

References

  • Moellering R Jr. Discovering new antimicrobial agents. Int J Antimicrob Agents. 2011;37:2–9. doi: 10.1016/j.ijantimicag.2010.08.018
  • Schiff H. Mittheilungen aus dem Universitatslaboratorium in Pisa: eine neue Reihe organischer Basen. Justus Liebigs Annalen Der Chemie. 1864;131:118–119. doi: 10.1002/jlac.18641310113
  • Dhar D, Taploo C. Schiff bases and their applications. J Sci Ind Res. 1982;41:501–506.
  • Przybylski P, Huczynski A, Pyta K, et al. Biological properties of Schiff bases and Azo derivatives of phenols. Curr Org Chem. 2009;13:124–148. doi: 10.2174/138527209787193774
  • Bringmann G, Dreyer M, Faber J, et al. Ancistrotanzanine C and related 5,1- and 7,3-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. J Nat Prod. 2004;67:743–748. doi: 10.1021/np0340549
  • Dawood K. Benzofuran derivatives: a patent review. Expert Opin Ther Pat. 2013;23:1133–1156. doi: 10.1517/13543776.2013.801455
  • Habtemariam S. Antiinflammatory activity of the antirheumatic herbal drug, gravel root (Eupatorium purpureum): further biological activities and constituents. Phytother Res. 2001;15:687–690. doi: 10.1002/ptr.887
  • Pauletti P, Araujo A, Young M, et al. Nor-Lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity. Phytochemistry. 2000;55:597–601. doi: 10.1016/S0031-9422(00)00225-9
  • Masubuchi M, Kawasaki K, Ebiike H, et al. Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1. Bioorg Med Chem Lett. 2001;11:1833–1837. doi: 10.1016/S0960-894X(01)00319-5
  • Wrobel J, Dietrich A, Antane M. Benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia. US Patent. 2001;6, 251, 936:1–57.
  • Kayser O, Chen M, Kharazmi A, et al. Aurones interfere with Leishmania major mitochondrial fumarate reductase. Z Naturforsch C. 2002;57:717–720. doi: 10.1515/znc-2002-7-828
  • Hayakawa I, Shioya R, Agatsuma T, et al. 4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents. Bioorg Med Chem Lett. 2004;14:455–458. doi: 10.1016/j.bmcl.2003.10.039
  • Proksch P, Rodriguez E. Chromenes and benzofurans of the asteraceae, their chemistry and biological significance. Phytochemistry. 1983;22:2335–2348. doi: 10.1016/0031-9422(83)80118-6
  • Oter O, Ertekin K, Kirilmis C, et al. Characterization of a newly synthesized fluorescent benzofuran derivative and usage as a selective fiber optic sensor for Fe(III). Sens Actuators B Chem. 2007;122:450–456. doi: 10.1016/j.snb.2006.06.010
  • Karatas F, Koca M, Kara H, et al. Synthesis and oxidant properties of novel (5-bromobenzofuran-2-yl)(3-methyl-3-mesitylcyclobutyl)ketonethiosemicarbazone. Eur J Med Chem. 2006;41:664–669. doi: 10.1016/j.ejmech.2006.01.003
  • Habermann J, Ley S, Smits R. Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents. J Chem Soc Perkin Trans. 1999;1:2421–2423. doi: 10.1039/a904384e
  • Chohan Z, Farooq M. Mixed ligand biologically active complexes cobalt (II), copper (II), nickel (II) and zinc (II) with triazine-derived NO and NS donor systems. Pak J Pharm Sci. 1995;17:14–18.
  • Eswaran S, Adhikari A, Pal N, et al. Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents. Bioorg Med Chem Lett. 2010;20:1040–1044. doi: 10.1016/j.bmcl.2009.12.045
  • Thomas K, Adhikari A, Telkar S, et al. Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents. Eur J Med Chem. 2011;46:5283–5292. doi: 10.1016/j.ejmech.2011.07.033
  • Vavríkova E, Polanc S, Kocevar M, et al. New fluorine-containing hydrazones active against MDR-tuberculosis. Eur J Med Chem. 2011;46:4937–4945. doi: 10.1016/j.ejmech.2011.07.052
  • Renuka J, Reddy K, Srihari K, et al. Design, synthesis, biological evaluation of substituted benzofurans as DNA gyraseB inhibitors of mycobacterium tuberculosis. Bioorg Med Chem. 2014;22:4924–4934. doi: 10.1016/j.bmc.2014.06.041
  • Mandewale M, Kokate S, Thorat B, et al. Zinc complexes of hydrazone derivatives bearing 3,4-dihydroquinolin-2(1H)-one nucleus as new anti-tubercular agents. Arab J Chem. 2016. doi: 10.1016/j.arabjc.2016.07.016
  • Mandewale M, Thorat B, Nivid Y, et al. Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn (II) complexes. J Saudi Chem Soc. 22(2):218–228. doi: 10.1016/j.jscs.2016.04.003
  • Mandewale M, Thorat B, Shelke D, et al. Synthesis and biological evaluation of new hydrazone derivatives of quinoline and their Cu (II) and Zn (II) complexes against mycobacterium tuberculosis. Bioinorg Chem Appl. 2015. doi: 10.1155/2015/153015
  • Mandewale M, Thorat B, Yamgar R. Synthesis and anti-mycobacterium study of some fluorine containing Schiff bases of quinoline and their metal complexes. Der Pharma Chemica. 2015;7:207–215.
  • Yamgar R, Nivid Y, Nalawade S, et al. Novel zinc (II) complexes of heterocyclic ligands as antimicrobial agents: synthesis, characterisation, and antimicrobial studies. Bioinorg Chem Appl. 2014. doi: 10.1155/2014/276598
  • Mohamed G, Omar M, Hindy A. Metal complexes of schiff bases: preparation characterization and biological activity. Turk J Chem. 2006;30:361–382.
  • Babu V, Ramesh A, Raghuram P, et al. Electron spin resonance studies on complexes of copper (II) with o-phenolic oximes. Polyhedron. 1982;1:607–610. doi: 10.1016/S0277-5387(00)80854-2
  • Agharia E. ESR spectral studies of some copper (II) complexes of 1-(1-hydroxy-2-naphthyl)-3-(phenyl or substituted phenyl)-prop-2-en-1-ones. J Applicable Chem. 2014;3:2514–2525.
  • Lourenco M, DeSouza M, Pinheiro A, et al. Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues. ARKIVOC. 2007;15:181–191.
  • Kiehlbauch J, Hannett G, Salfinger M, et al. Use of the national committee for clinical laboratory standards guidelines for disk diffusion susceptibility testing in New York state laboratories. J Clin Microbiol. 2000;38:3341–3348.
  • Tweedy B. Possible mechanism for reduction of elemental sulfur by monilinia fructicola. Phytopathology. 1964;55:910–914.
  • Kralova A, Kissova K, Svajlenova O, et al. Biological activity of copper (II) N-salicylideneaminoacidato complexes. Reduction of chlorophyll content in freshwater alga Chlorella vulgaris and inhibition of photosynthetic electron transport in spinach chloroplasts. Chem Pap. 2004;58:357–361.
  • Parekh J, Inamdhar P, Nair R, et al. Synthesis and antibacterial activity of some Schiff bases derived from 4-aminobenzoic acid. J Serb Chem Soc. 2005;70:1155–1162. doi: 10.2298/JSC0510155P
  • Vaghasia Y, Nair R, Soni M, et al. Synthesis, structural determination and antibacterial activity of compounds derived from vanillin and 4-aminoantipyrine. J Serb Chem Soc. 2004;69:991–998. doi: 10.2298/JSC0412991V
  • Galm U, Heller S, Shapiro S, et al. Antimicrobial and DNA gyrase-inhibitory activities of novel clorobiocin derivatives produced by mutasynthesis. Antimicrob Agents Chemother. 2004;48:1307–1312. doi: 10.1128/AAC.48.4.1307-1312.2004
  • Alvarez E, Vartanian V, Brodbelt J. Metal complexation reactions of quinolone antibiotics in a quadrupole ion trap. Anal Chem. 1997;69:1147–1155. doi: 10.1021/ac9609081
  • Selimović E, Jeremić S, Ličina B, et al. Kinetics, DFT study and antibacterial activity of zinc(II) and copper(II) terpyridine complexes. J Mex Chem Soc. 2018;62(1):1–18. doi: 10.29356/jmcs.v62i1.576