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Anti-Infective Agents

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ISSN (Print): 2211-3525
ISSN (Online): 2211-3533

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Research Article

Synthesis and Biological Evaluation, Structural Elucidation, Thermogravimetric Analysis, X-Ray Diffraction Studies of a Schiff Base Derived from 3-formylchromone and 3-aminoquinoline and their Cu(II) and Co(II) Complexes

Author(s): Sushil K. Ghumbre*, Amol V. Patil, Atul S. Renge, Satish A. Dake and Bhimrao C. Khade*

Volume 20, Issue 4, 2022

Published on: 07 July, 2022

Article ID: e080422203270 Pages: 16

DOI: 10.2174/2211352520666220408092913

Price: $65

Abstract

Introduction: The study of novel Schiff bases and their metal complexes has achieved enormous attention of inorganic as well as medicinal chemists.

Objective: The objective of this study is to study the structural elucidation and antimicrobial screening of 3-formylchromone and 3-aminoquinoline-based Schiff base and their metal complexes.

Methods: Cu(II) and Co(II) complexes of 3-((quinolino-3-ylimino) methyl)-4H-chromen-4- one ligand were synthesized and characterized by elemental analysis, molar conductivity measurement, infrared, UV-Visible, 1H NMR spectral studies, thermogravimetric analysis, and powder X-ray diffraction studies.

Results: Antibacterial activity of synthesized compounds were screened against Klebsiella pneumoniae, Staphylococcus aureus, and Proteus vulgaris, and antifungal activity was screened against fungi Candida albicans and Aspergillus niger. Schiff base ligand and their Cu(II) and Co(II) complexes revealed significant antibacterial and antifungal activity against tested strains. Octahedral geometry of metal complexes was proven by analytical, physical, and spectral data.

Conclusion: In this present work, novel Schiff base 3-((quinolino-3-ylimino) methyl)-4Hchromen- 4-one and its Cu(II) and Co(II) complexes revealed promising antibacterial and antifungal activities.

Keywords: Antibacterial activity, Antifungal Activity, 3-aminoquinoline, 3-formylchromone, Powder X-ray Diffraction, Thermogravimetric studies.

Graphical Abstract

[1]
Roviello, G.; Musumeci, D.; Castiglione, M.; Bucci, E.M.; Pedone, C.; Benedetti, E. Solid phase synthesis and RNA-binding studies of a serum-resistant nucleo-ε-peptide. J. Pept. Sci., 2009, 15(3), 155-160.
[http://dx.doi.org/10.1002/psc.1072] [PMID: 18985708]
[2]
Roviello, G.N.; Moccia, M.; Sapio, R.; Valente, M.; Bucci, E.M.; Castiglione, M.; Pedone, C.; Perretta, G.; Benedetti, E.; Musumeci, D. Synthesis, characterization and hybridization studies of new nucleo-γ-peptides based on diaminobutyric acid. J. Pept. Sci., 2006, 12(12), 829-835.
[http://dx.doi.org/10.1002/psc.819] [PMID: 17131297]
[3]
Roviello, G.N.; Roviello, V.; Autiero, I.; Saviano, M. Solid phase synthesis of TyrT, a thymine-tyrosine conjugate with poly(A) RNA-binding ability. RSC Advances, 2016, 6(33), 27607-27613.
[http://dx.doi.org/10.1039/C6RA00294C] [PMID: 29057072]
[4]
Musumeci, D.; Ullah, A.; Ikram, A.; Roviello, G.N. Novel insights on nucleopeptide binding: A spectroscopic and in silico investigation on the interaction of a thymine-bearing tetrapeptide with homoadenine DNA. J. Mol. Liq., In press
[http://dx.doi.org/10.1016/j.molliq.2021.117975]
[5]
Nicolas, P.E.; Sadler, P.J. 100 years of metal coordination chemistry: From Alfred Werner to anticancer metallodrugs. Pure Appl. Chem., 2014, 86(12), 1897-1910.
[http://dx.doi.org/10.1515/pac-2014-0504]
[6]
Fik-Jaskółka, M.A.; Pospieszna-Markiewicz, I.; Roviello, G.N.; Kubicki, M.; Radecka-Paryzek, W.; Patroniak, V. Synthesis and spectroscopic investigation of a hexaaza lanthanum(iii) macrocycle with a hybrid-type G4 DNA stabilizing effect. Inorg. Chem., 2021, 60(4), 2122-2126.
[http://dx.doi.org/10.1021/acs.inorgchem.0c03260] [PMID: 33528248]
[7]
El-Gammal, O.A.; Mohamed, F.S.; Rezk, G.N.; El-Bindary, A.A. Structural characterization and biological activity of a new metal complexes based of Schiff base. J. Mol. Liq., 2021, 330, 115522.
[http://dx.doi.org/10.1016/j.molliq.2021.115522]
[8]
Sonnekar, V.S.; Jadhav, W.N.; Dake, S.A.; Dhole, S.G.; Narwade, S.S.; Pawar, R.P. Synthesis and anti-microbial activities of some thiourea based meatl complexes. Eur. Chem. Bull., 2014, 3(8), 792-797.
[9]
Prabhakaran, R.; Huang, R.; Natarajan, K. X-ray crystallographic investigation and biological activities of Ru(III) complexes containing Schiff base and triphenyl phosphine arsine. Inorg. Chim. Acta, 2006, 359, 3359-3362.
[http://dx.doi.org/10.1016/j.ica.2006.03.032]
[10]
Kannan, S.; Naresh, Kumar.K.; Ramesh, R. Ruthenium (III) complexes of amine-bis(phenolate) ligands as catalysts for transfer hydrogenation of ketones. Polyhedron, 2008, 27, 701-708.
[http://dx.doi.org/10.1016/j.poly.2007.10.024]
[11]
Wang, B.D.; Yang, Z.Y.; Crewdson, P.; Wang, D.Q. Synthesis, crystal structure and DNA-binding studies of the Ln(III) complex with 6-hydroxychromone-3-carbaldehyde benzoyl hydrazone. J. Inorg. Biochem., 2007, 101(10), 1492-1504.
[http://dx.doi.org/10.1016/j.jinorgbio.2007.04.007] [PMID: 17692381]
[12]
Piao, L.Z.; Park, H.R.; Park, Y.K.; Lee, S.K.; Park, J.H.; Park, M.K. Mushroom tyrosinase inhibition activity of some chromones. Chem. Pharm. Bull. (Tokyo), 2002, 50(3), 309-311.
[http://dx.doi.org/10.1248/cpb.50.309] [PMID: 11911191]
[13]
Khan, K.M.; Ambreen, N.; Hussain, S.; Perveen, S.; Choudhary, M.I. Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors. Bioorg. Med. Chem., 2009, 17(8), 2983-2988.
[http://dx.doi.org/10.1016/j.bmc.2009.03.020] [PMID: 19329330]
[14]
Shim, Y.S.; Kim, K.C.; Chi, D.Y.; Lee, K.H.; Cho, H. Formylchromone derivatives as a novel class of protein tyrosine phosphatase 1B inhibitors. Bioorg. Med. Chem. Lett., 2003, 13(15), 2561-2563.
[http://dx.doi.org/10.1016/S0960-894X(03)00479-7] [PMID: 12852966]
[15]
Martens, S.; Mithöfer, A. Flavones and flavone synthases. Phytochemistry, 2005, 66(20), 2399-2407.
[http://dx.doi.org/10.1016/j.phytochem.2005.07.013] [PMID: 16137727]
[16]
Di Braccio, M.; Grossi, G.; Roma, G.; Marzano, C.; Baccichetti, F.; Simonato, M.; Bordin, F. Pyran derivatives. Part XXI. Antiproliferative and cytotoxic properties of novel N-substituted 4-aminocoumarins, their benzo-fused derivatives, and some related 2-aminochromones. Farmaco, 2003, 58(11), 1083-1097.
[http://dx.doi.org/10.1016/S0014-827X(03)00160-5] [PMID: 14572859]
[17]
Middleton, E., Jr; Kandaswami, C.; Theoharides, T.C. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol. Rev., 2000, 52(4), 673-751.
[PMID: 11121513]
[18]
Teimouri, M.B. Serendipitous stereoselective synthesis of brand-new fluorescent dyes:(1Z)-(alkylimino)[(chromone-3-yl) methylene]-1,3-dihydro-9H-furo[3,4-b]-chromen-9-one-type fluorophores with blue fluorescence emission properties. Tetrahedron, 2011, 67, 1837-1843.
[http://dx.doi.org/10.1016/j.tet.2011.01.033]
[19]
Wang, B.; Yang, Z.Y.; Lu, M.H.; Hai, J.; Wang, Q.; Chen, Z.N. Synthesis, characterization, cytotoxic activity and DNA binding Ni(II) complex with the 6-hydroxy chromone-3-carbaldehyde thiosemicarbazone. J. Organomet. Chem., 2009, 694, 4069-4075.
[http://dx.doi.org/10.1016/j.jorganchem.2009.08.024]
[20]
Hoult, J.R.S.; Payá, M. Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol., 1996, 27(4), 713-722.
[http://dx.doi.org/10.1016/0306-3623(95)02112-4] [PMID: 8853310]
[21]
Langer, P.; Appel, B. Domino ‘Michael-retro-Michael-aldol’ reactions of 1,3-bis-silyl enol ethers with 3-formylchromones. Tetrahedron Lett., 2003, 44, 7921-7923.
[http://dx.doi.org/10.1016/j.tetlet.2003.09.008]
[22]
Sandulache, A.; Silva, A.M.S.; Cavaleiro, J.A.S. Diels-Alder reaction of 3-carboxaldehyde with ortho-Benzoquinodimethane. New synthesis of Benzo[b]xanthones. Tetrahedron, 2002, 58, 105-114.
[http://dx.doi.org/10.1016/S0040-4020(01)01131-0]
[23]
Nayak, S.; Gamez, P.; Kozievcar, B.; Pevec, A.; Roubeau, O.; Dehnen, S.; Reedijk, J. Coordination compounds from the planar tridentate Schiff-base ligand 2-methoxy-6-((quinolin-8-ylimino)methyl)phenol (mqmpH) with several transition metal ions: Use of [FeIII(mqmp)(CH3OH)Cl2] in the catalytic oxidation of alkanes and alkenes. Polyhedron, 2010, 29, 2291-2296.
[http://dx.doi.org/10.1016/j.poly.2010.04.035]
[24]
Ikram, M.; Rehman, S.; Ali, M. Faridoon; Schulzke, C.; Blake, R. J.; Blake, A. J.; K.; Malook, Wong, H.; Rehman, S.U. Urease and α-chymotrypsin inhibitory activities of transition metal complexes of new Schiff base ligand: Kinetic and thermodynamic studies of the synthesized complexes using TG–DTA pyrolysis. Thermochim. Acta, 2013, 562, 22-28.
[http://dx.doi.org/10.1016/j.tca.2013.03.026]
[25]
Ghumbre, S.K.; Ujgare, S.R.; Borude, K.R.; Khade, B.C. Synthesis, characterization and antimicrobial screening studies of some metal complexes of novel schiff base of 3-formyl-6-methylchromone and 3-aminoquinoline. Int. Res. J. Pharm., 2018, 9(7), 202-206.
[http://dx.doi.org/10.7897/2230-8407.097149]
[26]
Ghumbre, S.K.; Sagar, S.S.; Renge, A.S.; Khade, B.C. A novel Schiff base of 3-formyl-6-methylchromone and 3-aminoquinoline and its Cu(II) and Co(II) complexes: Synthesis, characterization and Antimicrobial screening studies. Curr. Pharm. Res., 2019, 401, 9-17.
[27]
Youssef, T.A. Reactions of chromium and molybdenum carbonyls with bis-(salicylaldehyde)-1,3-propylenediimine Schiff base. J. Coord. Chem., 2008, 61, 816-819.
[http://dx.doi.org/10.1080/00958970701436699]
[28]
Kavitha, P.; Laxma, R.K. Synthesis, spectral characterization, morphology, biological activity and DNA cleavage studies of metal complexes with chromone Schiff base. Arab. J. Chem., 2016, 9, 596-605.
[http://dx.doi.org/10.1016/j.arabjc.2012.09.001]
[29]
Anitha, C.; Sheela, C.D.; Tharmaraj, P.; Johnson, R.S. Synthesis and characterization of VO(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes of chromone based azo-linked Schiff base ligand. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2012, 98, 35-42.
[http://dx.doi.org/10.1016/j.saa.2012.08.022] [PMID: 22982386]
[30]
Kavitha, P.; Laxma, R.K. Pd(II) complexes bearing chromone based Schiff bases: Synthesis, characterization and biological activity studies. Arab. J. Chem., 2016, 9, 640-648.
[http://dx.doi.org/10.1016/j.arabjc.2013.06.018]
[31]
Kavitha, P.; Saritha, M.; Laxma, R.K. Synthesis, structural characterization, fluorescence, antimicrobial, antioxidant and DNA cleavage studies of Cu(II) complexes of formyl chromone Schiff bases. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2013, 102, 159-168.
[http://dx.doi.org/10.1016/j.saa.2012.10.037] [PMID: 23220531]
[32]
Wang, B.; Yang, Z.; Qin, D.; Chen, Z. Synthesis, characterization, cytotoxic activity and DNA-binding of the Ln(III) complexes with ethylenediiminobi(6-hydroxychromone-3-carbaldehyde) Schiff base. J. Photochem. Photobiol. Chem., 2008, 194, 49-58.
[http://dx.doi.org/10.1016/j.jphotochem.2007.07.024]
[33]
Aazam, E.S.; Husseiny, E.L. Synthesis and photoluminescent properties of a Schiff-base ligand and its mononuclear Zn(II), Cd(II), Cu(II), Ni(II) and Pd(II) metal complexes. Arab. J. Chem., 2012, 5, 45-53.
[http://dx.doi.org/10.1016/j.arabjc.2010.07.022]
[34]
Li, Y.; Yang, Z.Y.; Wu, J.C. Synthesis, crystal structures, biological activities and fluorescence studies of transition metal complexes with 3-carbaldehyde chromone thiosemicarbazone. Eur. J. Med. Chem., 2010, 45(12), 5692-5701.
[http://dx.doi.org/10.1016/j.ejmech.2010.09.025] [PMID: 20884087]
[35]
Rosu, T.; Pahontu, E.; Maxim, C.; Georgescu, R.; Stanica, N.; Almajan, G.L.; Gulea, A. Synthesis, characterization and antibacterial activity of some new complexes of Cu(II), Ni(II), VO(II), Mn(II) with Schiff base derived from 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one. Polyhedron, 2010, 29, 757-766.
[http://dx.doi.org/10.1016/j.poly.2009.10.017]
[36]
Maurya, R.C.; Mishra, D.D.; Mukherjee, S.; Trivedi, P.K. Novel mixed-ligand derivatives ofbis(acetylacetonato)-bis(methylaceto-acetato) and bis(ethylacetoacetate)-nickel(II) with some potentially mono-, bi- and tri-dentate 2/3-pyrazoline-5-ones. Trans. Met. Chem. , 1991, 16, 524-527.
[http://dx.doi.org/10.1007/BF01024323]
[37]
Khalil, S.M.E.; Selleem, H.S.; El-Shetary, B.A.; Shebl, M. Mono- and Bi-Nuclear Metal Complexes of Schiff-Base Hydrazone (ONN) Derived from o-Hydroxyacetophenone and 2-Amino-4-Hydrazino-6-Methyl Pyrimidine. J. Coord. Chem., 2002, 55, 883-899.
[http://dx.doi.org/10.1080/0095897022000002213]
[38]
Ibrahim, M.A. EI-Mahdhy, K.M. Synthesis, and antimicrobial activity of some new heterocyclic schiff bases derived from 2-amino-3-formylchromone. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184, 2945-2958.
[http://dx.doi.org/10.1080/10426500802625594]
[39]
Philip, J.E.; Antony, S.A.; Eeettinilkunnathil, S.J. PrathapachandraKurup, M. R.; Velayudhan, M. P. Design, synthesis, antimicrobial and antioxidant activity of 3-formylchromone hydrazoneand their metal (II) complexes. Inorg. Chim. Acta, 2018, 469, 87-97.
[http://dx.doi.org/10.1016/j.ica.2017.09.006]
[40]
Ikram, M.; Rehman, S.U.; Rehman, S.; Baker, R.J.; Schulzke, C. Synthesis, characterization and distinct butyrylcholinesterase activities of transition metal complexes of 2-[(E)-(quinolin-3-ylimino)methyl]phenol. Inorg. Chim. Acta, 2012, 390, 210-216.
[http://dx.doi.org/10.1016/j.ica.2012.04.036]
[41]
Shelke, V.A.; Jadhav, S.M.; Patharkar, V.R.; Shankarwar, S.G.; Munde, A.S.; Chondhekar, T.K. Synthesis, spectroscopic characterization and thermal studies of some rare earth metal complexes of unsymmetrical tetradentate Schiff base ligand. Arab. J. Chem., 2012, 5, 501-507.
[http://dx.doi.org/10.1016/j.arabjc.2010.09.018]
[42]
Swathy, S.S.; Joseyphus, R.S.; Nisha, V.P.; Subhadrambika, N.; Mohanan, K. Synthesis, spectroscopic investigation and antimicrobial activities of some transition metal complexes of a [(2-hydroxyacetophenone)-3-isatin]-bishydrazone. Arab. J. Chem., 2016, 9, S1847-S1857.
[http://dx.doi.org/10.1016/j.arabjc.2012.05.004]
[43]
Erer, H.; Yesilel, O.Z.; Darcan, C.; Buyukgungor, O. Synthesis, spectroscopic, thermal Studies, antimicrobial activities and crystal structures of Co(II), Ni(II), Cu(II) and Zn(II)-orotate complexes with 2-methylimidazole. Polyhedron, 2009, 28, 3087-3093.
[http://dx.doi.org/10.1016/j.poly.2009.06.052]
[44]
Bharty, M.K.; Dani, R.K.; Kushawaha, S.K.; Singh, N.K.; Kharwar, R.N.; Butcher, R.J. Mn(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and Co(II) complexes of 1-phenyl-1H-tetrazole-5-thiol: Synthesis, spectral, structural characterization and thermal studies. Polyhedron, 2015, 88, 208-221.
[http://dx.doi.org/10.1016/j.poly.2014.12.013]
[45]
Kolhe, N.; Jadhav, S. Synthesis, characterization and biological screening of Cu(II)-3-Formylchromone derivative complex. Res. Chem. Intermed., 2019, 45(3), 973-996.
[http://dx.doi.org/10.1007/s11164-018-3656-x]
[46]
Kadam, M.S.; Khiste, A.S.; Dake, S.A.; Khade, B.C. Studies on X-ray diffraction, thermogravimetric stability, antibacterial-antifungal activity of Fe(II), Ni(II), Cu(II) metal chloroquine complexes against bacterial strains and fungal spore. Antiinfect. Agents, 2020, 18, 339-351.
[http://dx.doi.org/10.2174/2211352517666191021090630]

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