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Microwave-assisted synthesis, spectral characterization and DFT studies of Zn(II) complexes based on N-acylhydrazone ligands: stability and antioxidant activity

Daniela Corrêa Santos, Ruan Roberto Henriques, Marcos Antonio Abreu Lopes Jr, Paulo José Sousa Maia, Andreza Miranda Barata Silva, Diego Fernando Silva Paschoal, Andréa Luzia Ferreira Souza

Abstract


This article reports the synthesis of seven Zn(II) complexes containing N-acylhydrazone ligands (L1 to L7) and the assessment of their antioxidant. Microwave assisted-synthesis of ligands with ZnCl2 in MeOH yielded tetrahedral Zn(II) complexes with a 1:2 metal: ligand ratio, characterized by HRMS, FTIR, and UV-Vis spectroscopy, thermal and electrochemical analyses, and DFT calculations. The (L3)2Zn complex exhibited the lowest thermal stability, and (L6)2Zn and (L7)2Zn were the most stable. XRD powder showed that all complexes have good crystallinity with crystalline dimensions ranging from 32 to 86 nm. Cyclic voltammetry of Zn(II) complexes indicated a reversible redox process for (L4)2Zn and an irreversible process for the remaining six complexes: (L1)2Zn to (L3)2Zn and (L5)2Zn to (L7)2Zn. Antioxidant activity of ligands and complexes was assessed by the DPPH method; the L7 ligand and corresponding (L7)2Zn complex exhibited good activity, IC50 = 65.30 μmol.l-1 and 78.70 μmol.l-1, respectively, when compared with standard ascorbic acid. 


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- D. G. Guimarães, L. A. Rolim, A. de A. Gonsalves, C. R. M. Araújo, Investigação do Potencial Bilógic de Hidrazonas Obtidas Sinteticamente na Última Década (2006-2016): Uma Revisão Sistemática, Revista Virtual de Química, 2017, 9, 2551–2592.

- A. Kajal, S. Bala, N. Sharma, S. Kamboj, V. Saini, Therapeutic Potential of Hydrazones as Anti-Inflammatory Agents, Int J Med Chem, 2014, 2014, 1–11.

- P. G. Cozzi, Metal-Salen Schiff base complexes in catalysis: Practical aspects, Chem Soc Rev, 2004, 33, 410–421.

- R. Manikandan, P. Viswanathamurthi, M. Muthukumar, Ruthenium(II) hydrazone Schiff base complexes: Synthesis, spectral study and catalytic applications, Spectrochim Acta A Mol Biomol Spectrosc, 2011, 83, 297–303.

- E. M. Barbosa, K. S. Souza, P. H. S. de Oliveira, Í. S. Costa, I. V. de França, L. dos Santos Mello, E. R. Dockal, J. da Cruz, E. A. Souza, P. J. S. Maia, Uranyl Salen-Type Complex as Co-catalyst for Electrocatalytic Oxidation of Ethanol, Electrocatalysis, 2021 doi:10.1007/s12678-021-00697-0.

- R. D. dos Santos, S. de Fatima Freire dos Santos, F. da Silva Moura, P. J. S. Maia, B. T. da Fonseca, R. H. de Almeida Santos, M. E. Medeiros, F. M. dos Santos Garrido, A. Casellato, A nickel(II) coordination polymer derived from a tridentate Schiff base ligand with N, O-donor groups: synthesis, crystal structure, spectroscopy, electrochemical behavior and electrocatalytic activity for H2O2 electroreduction in alkaline medium, Transition Metal Chemistry, 2017, 42, 301–310.

- H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, M. Ashfaq, M. N. Tahir, Synthesis, spectral characterization, SC-XRD, HSA, DFT and catalytic activity of a dioxidomolybdenum complex with aminosalicyl-hydrazone Schiff base ligand: An experimental and theoretical approach, Polyhedron, 2021, 208 doi:10.1016/j.poly.2021.115428.

- H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, M. Ashfaq, M. N. Tahir, Synthesis, spectral characterization, SC-XRD, HSA, DFT and catalytic activity of novel dioxovanadium(V) complex with aminobenzohydrazone Schiff base ligand: An experimental and theoretical approach, Inorganica Chim Acta, 2021, 526 doi:10.1016/j.ica.2021.120535.

- H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, M. Ashfaq, M. N. Tahir, Diverse coordination of isoniazid hydrazone Schiff base ligand towards iron(III): Synthesis, characterization, SC-XRD, HSA, QTAIM, MEP, NCI, NBO and DFT study, J Mol Struct, 2022, 1250 doi:10.1016/j.molstruc.2021.131691.

- H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, M. Ashfaq, M. N. Tahir, Titanium(IV) complex containing ONO-tridentate Schiff base ligand: Synthesis, crystal structure determination, Hirshfeld surface analysis, spectral characterization, theoretical and computational studies, J Mol Struct, 2021, 1241 doi:10.1016/j.molstruc.2021.130653.

- H. Kargar, M. Nateghi-Jahromi, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, S. Ali, M. Ashfaq, M. N. Tahir, Synthesis, spectral characterization, crystal structure and catalytic activity of a novel dioxomolybdenum Schiff base complex containing 4-aminobenzhydrazone ligand: A combined experimental and theoretical study, J Mol Struct, 2022, 1249 doi:10.1016/j.molstruc.2021.131645.

- H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, K. S. Munawar, Synthesis, spectra (FT-IR, NMR) investigations, DFT, FMO, MEP, NBO analysis and catalytic activity of MoO2(VI) complex with ONO tridentate hydrazone Schiff base ligand, J Mol Struct, 2021, 1245 doi:10.1016/j.molstruc.2021.131259.

- E. S. Aazam, M. M. Ghoneim, M. A. El-Attar, Synthesis, characterization, electrochemical behavior, and biological activity of bis azomethine dye derived from 2,3-diaminomaleonitrile and 2-hydroxy-1-naphthaldehyde and its zinc complex, J Coord Chem, 2011, 64, 2506–2520.

- D. C. Santos, P. J. S. Maia, M. A. de Abreu Lopes, J. S. B. Forero, A. L. F. de Souza, A Simple Isoniazid-Based N-Acylhydrazone Derivative as Potential Fluorogenic Probe for Zn2+ Ions, J Fluoresc, 2021, 31, 175–184.

- Â. de Fátima, C. de P. Pereira, C. R. S. D. G. Olímpio, B. G. de Freitas Oliveira, L. L. Franco, P. H. C. da Silva, Schiff bases and their metal complexes as urease inhibitors – A brief review, J Adv Res, 2018, 13, 113–126.

- J. A. Duce, A. I. Bush, Biological metals and Alzheimer’s disease: Implications for therapeutics and diagnostics, Prog Neurobiol, 2010, 92, 1–18.

- A. De Falco, D. S. Cukierman, R. A. Hauser-Davis, N. A. Rey, Doença de Alzheimer: Hipóteses etiológicas e perspectivas de tratamento, Quim Nova, 2016, 39, 63–80.

- D. C. Santos, R. R. Henriques, M. A. de A. L. Junior, A. B. Farias, T. L. do C. Nogueira, J. V. F. Quimas, N. C. Romeiro, L. L. da Silva, A. L. F. de Souza, Acylhydrazones as isoniazid derivatives with multi-target profiles for the treatment of Alzheimer’s disease: Radical scavenging, myeloperoxidase/acetylcholinesterase inhibition and biometal chelation, Bioorg Med Chem, 2020, 28 doi:10.1016/j.bmc.2020.115470.

- L. L. Tevez, M. S. Islas, M. J. J. Medina, M. Diez, O. E. Piros, E. C. Eduardo, E. G. Ferrer, P. A. M. Williams, Structural, spectral and potentiometric characterization, and antimicrobial activity studies of [Zn(phen)2(change)(H2O)](NO3)2.H2O, J Coord Chem, 2012, 65, 2304–2318.

- M. Almáši, Z. Vargová, D. Sabolová, J. Kudláčová, D. Hudecová, J. Kuchár, K. Györyová, Z. Vargová, D. Sabolová, J. Kudláčová, D. Hudecová, Ag ( I ) and Zn ( II ) isonicotinate complexes : design, characterization, antimicrobial effect, and CT-DNA binding studies, J Coord Chem, 2015, 68, 4423–4443.

- M. Poyraz, M. Sari, A. Guney, F. Demircis, S. Demirayak, E. Sahin, Synthesis, characterization and antimicrobial activity of a Zn ( II ) complex with 1- ( 1H- benzoimidazol-2-yl )-ethanone thiosemicarbazone, J Coord Chem, 2008, 61, 3276–3283.

- M. Amirnasr, R. S. Erami, K. Mereiter, K. S. Joß, S. Meghdadi, S. Abbasi, Syntheses, characterizations, X-ray crystal structures, and antibacterial activities of Co ( II ), Ni ( II ), and Zn ( II ) complexes of the Schiff base derived from 5-nitro-2-hydroxybenzaldehyde and benzylamine, J Coord Chem, 2015, 68, 616–631.

- I. C. R. L. Leal, K. R. N. Dos Santos, I. I. Júnior, O. A. C. Antunes, A. Porzel, L. Wessjohann, R. M. Kuster, Ceanothane and Lupane Type Triterpenes from Zizyphus joazeiro – An Anti-Staphylococcal Evaluation *, Planta Med, 2010, 76, 47–52.

- S. N. L. Aniele da, I. R. Guesdon, G. M. Corrêa, L. S. Silva, J. M. Mar, E. A. Sanches, A. B. Jaqueline de, D. F. de Moura do Carmo, Chemical composition and biological activities of the essential oil of peumus boldus molina (Monimiaceae), Revista Virtual de Quimica, 2020, 12, 433–446.

- A. T. Barbosa, V. H. N. da Silva, B. Y. K. da Silva, A. da S. N. Lopes, I. R. Guesdon, P. J. S. Maia, M. A. Abegg, G. M. Corrêa, D. F. de M. do Carmo, Chemical Composition and Biological Activities of Essential Oils from Fresh Vismia guianensis (Aubl.) Choisy and Vismia cayennensis (Jacq.) Pers. Leaves, Research, Society and Development, 2021, 10, e37410817440.

- A. Mermer, H. Boulebd, An eco-friendly method for the synthesis of 1,2,4-triazole-Schiff base derivatives in aqueous medium and DFT calculations, J Mol Struct, 2023, 1271 doi:10.1016/j.molstruc.2022.134102.

- Z. Yin, S. Li, X. Li, W. Shi, W. Liu, Z. Gao, M. Tao, C. Ma, Y. Liu, A review on the synthesis of metal oxide nanomaterials by microwave-induced solution combustion, RSC Adv, 2023, 13, 3265–3277.

- T. N. Moeketse, P. G. Baker, A. C. Farao, E. I. Iwuoha, Microwave-Assisted Synthesis of Schiff Base Metal–Ligand Complexes with Copper and Nickel Centres for Electrochemical In Vitro Sensing of Nitric Oxide in an Aqueous Solution, Chemosensors, 2022, 10 doi:10.3390/chemosensors10050175.

- P. T. Phan, J. Hong, N. Tran, T. H. Le, The Properties of Microwave-Assisted Synthesis of Metal–Organic Frameworks and Their Applications, Nanomaterials, 2023, 13, 352.

- A. Jain, S. De, P. Barman, Microwave-assisted synthesis and notable applications of Schiff-base and metal complexes: a comparative study, Research on Chemical Intermediates. , 2022, 48, 2199–2251.

- N. Otani, T. Furuya, N. Katsuumi, T. Haraguchi, T. Akitsu, Synthesis of amino acid derivative Schiff base copper(II) complexes by microwave and wet mechanochemical methods, Journal of the Indian Chemical Society, 2021, 98 doi:10.1016/j.jics.2021.100004.

- L. Findoráková, K. Győryová, M. Melník, M. Koman, F. A. N. El-dien, K. Győryová, M. Melník, M. Koman, F. A. N. El-, Preparation, thermal decomposition, and crystal structure of Zn ( II ) 2-chlorobenzoate complex with nicotinamide, 2010, 63, 3348–3355.

- J. Zhang, L. Tan, W. Jiang, W. Hu, Z. Wang, N-Alkyl substituted di(perylene bisimides) as air-stable electron transport materials for solution-processible thin-film transistors with enhanced performance, J Mater Chem C Mater, 2013, 1, 3200.

- M. Ismael, A.-M. M. Abdel-Mawgoud, M. K. Rabia, A. Abdou, Design and synthesis of three Fe(III) mixed-ligand complexes: Exploration of their biological and phenoxazinone synthase-like activities, Inorganica Chim Acta, 2020, 505, 119443.

- U. Holzwarth, N. Gibson, The Scherrer equation versus the ‘ Debye – Scherrer equation ’, Nat Nanotechnol, 2011, 6.

- A. Abdou, Synthesis, Structural, Molecular Docking, DFT, Vibrational Spectroscopy, HOMO-LUMO, MEP Exploration, antibacterial and antifungal activity of new Fe(III), Co(II) and Ni(II) hetero-ligand complexes, J Mol Struct, 2022, 1262, 132911.

- A. Abdou, O. A. Omran, A. Nafady, I. S. Antipin, Structural, spectroscopic, FMOs, and non-linear optical properties exploration of three thiacaix(4)arenes derivatives, Arabian Journal of Chemistry, 2022, 15, 103656.

- A. M. Abu-Dief, N. H. Alotaibi, E. S.Al-Farraj, H. A. Qasem, S. Alzahrani, M. K. Mahfouz, A. Abdou, Fabrication, structural elucidation, theoretical, TD-DFT, vibrational calculation and molecular docking studies of some novel adenine imine chelates for biomedical applications, J Mol Liq, 2022, 365, 119961.

- N. A. A. Elkanzi, A. M. Ali, M. Albqmi, A. Abdou, New Benzimidazole‐Based Fe (III) and Cr (III) Complexes: Characterization, Bioactivity Screening, and Theoretical Implementations Using DFT and Molecular Docking Analysis, Appl Organomet Chem, 2022, 36 doi:10.1002/aoc.6868.

- A. S. El-tabl, F. A. Aly, M. M. E. Shakdofa, M. E. Adel, Synthesis, characterization, and biological activity of metal complexes of azo hydrazone ligand, J Coord Chem, 2010, 63, 700–712.

- C. J. Dhanaraj, J. Johnson, DNA interaction, antioxidant and in vitro cytotoxic activities of some mononuclear metal ( II ) complexes of a bishydrazone ligand, Materials Science & Engineering C, 2017, 78, 1006–1015.

- B. Singh, P. Srivastava, Studies on 2, 6-diacetylpyridine bis(2-furoylhydrazone) complexes of bivalent 3d-metal ions Bachcha, Transition Metal Chemistry, 1987, 12, 475–477.

- K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds: Part A: Theory and Applications in Inorganic Chemistry: Sixth Edition, Infrared and Raman Spectra of Inorganic and Coordination Compounds: Part A: Theory and Applications in Inorganic Chemistry: Sixth Edition, 2008, 1–419.

- J. Xie, J. Qiao, L. Wang, J. Xie, Y. Qiu, An azomethine-zinc complex for organic electroluminescence : Crystal structure, thermal stability, and optoelectronic properties, Inorganica Chim Acta, 2005, 358, 4451–4458.

- J. Hu, J. Li, J. Qi, Y. Sun, Sensors and Actuators B: Chemical Acylhydrazone based fluorescent chemosensor for zinc in aqueous solution with high selectivity and sensitivity, Sens Actuators B Chem, 2015, 208, 581–587.

- K. Ouari, S. Bendia, J. Weiss, C. Bailly, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy Spectroscopic, crystal structural and electrochemical studies of zinc ( II ) -Schiff base complex obtained from 2, 3-diaminobenzene and 2-hydroxy naphthaldehyde, Spectrochim Acta A Mol Biomol Spectrosc, 2015, 135, 624–631.

- D. Meng, F. Liu, Y. Li, Z. Yang, G. Li, D. Guo, Synthesis, characterization and properties of salicylhydrazide-salicylacylhydrazone derivatives and their terbium complexes, Luminescence, 2016, 31, 507–514.

- S. Meghdadi, M. Amirnasr, Z. Azarkamanzad, K. S. Joß, F. Fadaee, A. Amiri, S. Abbasi, Benign synthesis of the unsymmetrical ligand activity, and crystal structures of Cu ( II ) and Zn ( II ) complexes, J Coord Chem, 2013, 66, 4330–4343.

- P. José, S. Maia, E. Medeiros, B. Maria, L. Vega, H. Nunes, Synthesis and characterization of a perylene derivative and its application as catalyst for ethanol electro-oxidation, Chemical Papers, 2018, 72, 1021–1030.

- E. M. Barbosa, I. S. Costa, P. H. S. de Oliveira, E. B. dos Santos, A. M. B. Silva, P. J. S. Maia, E. A. Souza, Perylene Derivative Complexes as Cocatalyst for Electrocatalytic Oxidation of Ethanol, Revista Virtual de Quimica, 2020, 12, 1653–1661.

- P. José, S. Maia, E. Medeiros, B. Maria, L. Vega, H. Nunes, Synthesis and characterization of a perylene derivative and its application as catalyst for ethanol electro-oxidation, Chemical Papers, 2018, 72, 1021–1030.

- P. José, S. Maia, J. Ferreira, C. Flávio, A. De Freitas, Photophysical properties of a perylene derivative for use as a catalyst in ethanol eletrooxidation, Research on Chemical Intermediates, 2019, 45, 5451–5472.

- S. P. Mohammed, B. Namsheer, Dr. J. Harindran, B. Thomas, M. K. Sebastian, Evaluation of Analgesic And Anti Oxidant Activities of Schiff Bases, European Journal of Pharmaceutical and Medicinal Research, 2016, 3, 418–424.

- M. Hanif, M. Hassan, M. Rafiq, Q. Abbas, A. Ishaq, S. Shahzadi, S. Seo, M. Saleem, Microwave-Assisted Synthesis, In Vivo Anti-Inflammatory And In Vitro Antioxidant Activities, And Molecular Docking Study Of New Substituted Schiff Base Derivatives, Pharm Chem J, 2018, 52, 424–437.

- S. P. Mohammed, B. Namsheer, Dr. J. Harindran, B. Thomas, M. K. Sebastian, Evaluation Of Analgesic And Anti Oxidant Activities Of Schiff Bases, European Journal of Pharmaceutical and Medicinal Research, 2016, 3, 418–424.

- R. S. Shivhare, D. K. Mahapatra, R. R. Nair,

S. N. Deshmukh, Schiff’s base derivatives of murrayanine demonstrated enhanced antioxidant activity than its parent moiety, Indian Journal of Pharmaceutical Education and Research, 2016, 50, 598–604.

- V. Gorantla, R. Gundla, S. S. Jadav, S. R. Anugu, J. Chimakurthy, S. K. Nidasanametla, R. Korupolu, Molecular hybrid design, synthesis and biological evaluation of N-phenyl sulfonamide linked N-acyl hydrazone derivatives functioning as COX-2 inhibitors: New anti-inflammatory, antioxidant and anti-bacterial agents, New Journal of Chemistry, 2017, 41, 13516–13532.

- M. de Freitas Silva, E. T. Lima, L. Pruccoli, N. G. Castro, M. J. R. Guimarães, F. M. R. da Silva, N. F. Nadur, L. L. de Azevedo, A. E. Kümmerle, I. A. Guedes, L. E. Dardenne, V. S. Gontijo, A. Tarozzi, C. Viegas, Design, synthesis and biological evaluation of novel triazole

N-acylhydrazone hybrids for Alzheimer’s disease, Molecules, 2020, 25 doi:10.3390/molecules25143165.

- C. G. L. Nongpiur, L. Dkhar, D. K. Tripathi, K. M. Poluri, W. Kaminsky, M. R. Kollipara, Half-sandwich platinum group metal complexes containing coumarin-N-acylhydrazone hybrid ligands: Synthesis and biological evaluation studies, Inorganica Chim Acta, 2021, 525 doi:10.1016/j.ica.2021.120459.

- C. G. L. Nongpiur, D. F. Diengdoh, N. Nagar, K. M. Poluri, P. M. Gannon, W. Kaminsky, M. R. Kollipara, Mono and dinuclear ruthenium, rhodium and iridium metal complexes containing N-acylhydrazone moiety: Synthesis and in vitro biological studies, Polyhedron, 2022, 221 doi:10.1016/j.poly.2022.115855.

- N. Belkheiri, B. Bouguerne, F. Bedos-Belval, H. Duran, C. Bernis, R. Salvayre, A. Négre-Salvayre, M. Baltas, Synthesis and antioxidant activity evaluation of a syringic hydrazones family, Eur J Med Chem, 2010, 45, 3019–3026.




DOI: http://dx.doi.org/10.13171/mjc02303071666souza

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