Synthesis and Evaluation of the Anti-Inflammatory Activity of the Schiff Base Ligand (2-(1H-Benzo[d]imidazol-2-Yl)phenol) and Its Co(II) and Mn(III) Complexes
Coordination complexes are inorganic compounds that play an important role in medicinal chemistry. They possess numerous properties such as denticity, flexibility, reactivity, and stability. Schiff base ligands are organic compounds obtained from the condensation reaction between a carbonyl compound and a primary amine. They are used in many fields, including analytical, biological, organic, and inorganic industries. In this context, we synthesized a Schiff base ligand as well as two dinuclear complexes of cobalt and manganese. Various techniques such as IR, 1H and 13C NMR, UV-visible, conductimetry, magnetism, and XRD were used to characterize these compounds. The local anti-inflammatory activity of these compounds and the reference indomethacin was evaluated in mice by measuring the inflammatory response to the topical application of an irritant (croton oil) to the ear. The results of the comparative study of the anti-inflammatory properties of the free ligand and its complexes led to the conclusion that the complexes are more active than the ligand.
References
[1]
Badouard, C. (2006) Nucleic Acid Lesions: Detection by HPLC-MS/MS in Human Bio-Logical Environments and Interest as Biomarkers of Oxidative Stress and Inflammation. Doctoral Thesis, Joseph Fourier University, 229 p.
[2]
Gerster, J. (2007) Traitement des arthropathies chondrocalcinosiques. RevueduRhumatisme, 74, 194-198. https://doi.org/10.1016/j.rhum.2006.11.010
[3]
Muster, D. (2005) Médicaments de l’inflammation. EMC—Stomatologie, 1, 21-29. https://doi.org/10.1016/j.emcsto.2005.01.005
[4]
Arora, M., Choudhary, S. and Silakari, O. (2020) InSilico Guided Designing of 4-(1h-Benzo[d]Imidazol-2-Yl)phenol-Based Mutual-Prodrugs of Nsaids: Synthesis and Biological Evaluation. SARandQSARinEnvironmentalResearch, 31, 761-784. https://doi.org/10.1080/1062936x.2020.1810117
[5]
Bansal, Y. and Silakari, O. (2012) The Therapeutic Journey of Benzimidazoles: A Review. Bioorganic&MedicinalChemistry, 20, 6208-6236. https://doi.org/10.1016/j.bmc.2012.09.013
[6]
Küçükbay, H. and Durmaz, B. (1997) Antifungal Activity of Organic and Organometallic Derivatives of Benzimidazole and Benzothiazole. Arzneimittelforschung, 47, 667-670.
[7]
Saber, A. and Sebbar, N.K. (2019) Synthesis, Reactivities and Biological Properties of Benzimidazole Derivatives. MoroccanJournalofHeterocyclicChemistry, 18, 1-50.
[8]
Gavisiddegowda, P., Kollur, S.P., Syed, I. and Revanasiddappa. H.D. (2020) Novel Benzimidazole Derived Imine-Based Ligand and Its Co(III), Ni(II), Cu(II) and Pt(II) Complexes: Chemical Synthesis, Structure, Antimicrobial, DNA Interaction Studies and Nuclease Activity. Letters in Applied NanoBioScience, 9, 1655-1672.
[9]
Ansar, M., Zellou, A., Faouzi, M.E.A., Zahidi, A., Serroukh, S., Lmimouni, B.E., etal. (2009) Synthèse, étude chimique et toxicologique d’un nouveau dérivé benzimidazole. AnnalesPharmaceutiquesFrançaises, 67, 78-83. https://doi.org/10.1016/j.pharma.2008.11.001
[10]
Dupuy, M. (2020) Synthesis, Structure and Study of the Antitumor Activity of Original Derivatives of Pyrido[1,2-a] Benzimidazoles. Thèse de doctorat, Université de Montpellier I. https://theses.fr/2000MON13524
[11]
Guerret, P. and Langlois, M. (1979) Nouveaux dérivés tricycliques du benzimidazole. JournalofHeterocyclicChemistry, 16, 1163-1168. https://doi.org/10.1002/jhet.5570160615
[12]
Li, Y., Zhang, J., Xie, H., Ge, Y., Wang, K., Song, Z., etal. (2021) Discovery of New 2-Phenyl-1H-Benzo[d]Imidazole Core-Based Potent Α-Glucosidase Inhibitors: Synthesis, Kinetic Study, Molecular Docking, and in Vivo Anti-Hyperglycemic Evaluation. BioorganicChemistry, 117, Article ID: 105423. https://doi.org/10.1016/j.bioorg.2021.105423
[13]
Hernández-Morales, A., Rivera, J.M., López-Monteon, A., Lagunes-Castro, S., Castillo-Blum, S., Cureño-Hernández, K., etal. (2019) Complexes Containing Benzimidazolyl-Phenol Ligands and Ln(III) Ions: Synthesis, Spectroscopic Studies and Preliminary Cytotoxicity Evaluation. JournalofInorganicBiochemistry, 201, Article ID: 110842. https://doi.org/10.1016/j.jinorgbio.2019.110842
[14]
Munteanu, C.R. and Suntharalingam, K. (2015) Advances in Cobalt Complexes as Anticancer Agents. DaltonTransactions, 44, 13796-13808. https://doi.org/10.1039/c5dt02101d
[15]
Belkhalfa, H. and Mebarkia, C. (2022) Synthèse, caractérisation et application biologique des complexes de cuivre et de manganèse. Master’s Thesis, Université Kasdi Merbah Ouargla.
[16]
Tubaro, A., Dri, P., Delbello, G., Zilli, C. and Loggia, R.D. (1986) The Croton Oil Ear Test Revisited. AgentsandActions, 17, 347-349. https://doi.org/10.1007/bf01982641
[17]
Dutta, A.K., Samanta, S., Dutta, S., Lucas, C.R., Dawe, L.N., Biswas, P., etal. (2016) Iron(III) Complexes of 2-(1H-Benzo[d]Imidazol-2-Yl)Phenol and Acetate or Nitrate as Catalysts for Epoxidation of Olefins with Hydrogen Peroxide. JournalofMolecularStructure, 1115, 207-213. https://doi.org/10.1016/j.molstruc.2016.02.101
[18]
Yarkandi, N.H., El-Ghamry, H.A. and Gaber, M. (2017) Synthesis, Spectroscopic and DNA Binding Ability of CoII, NiII, CuII and ZnII Complexes of Schiff Base Ligand (E)-1-(((1h-Benzo[d]imidazol-2-Yl)methylimino)methyl)naphthalen-2-ol. X-Ray Crystal Structure Determination of Cobalt (II) Complex. MaterialsScienceandEngineering: C, 75, 1059-1067. https://doi.org/10.1016/j.msec.2017.02.171
[19]
Mautner, F.A., Louka, F.R., LeGuet, T. and Massoud, S.S. (2009) Pseudohalide Copper(II) Complexes Derived from Polypyridyl Ligands: Synthesis and Characterization. JournalofMolecularStructure, 919, 196-203. https://doi.org/10.1016/j.molstruc.2008.09.015
[20]
Bhaumik, P.K., Harms, K. and Chattopadhyay, S. (2013) Synthesis and Characterization of Four Dicyanamide Bridged Copper(II) Complexes with N2O Donor Tridentate Schiff Bases as Blocking Ligands. InorganicaChimicaActa, 405, 400-409. https://doi.org/10.1016/j.ica.2013.06.025
[21]
Sarr, M., Diop, M., Thiam, I.E., Gaye, M., Barry, A.H., Alvarez, N., et al. (2018) Co-crystal Structure of a Dinuclear (Zn-Y) and a Trinuclear (Zn-Y-Zn) Complexes Derived from a Schiff Base Ligand. European Journal of Chemistry, 9, 67-73. https://doi.org/10.5155/eurjchem.9.2.67-73.1688
[22]
Al-Adilee, K. and Dakheel, H. (2018) Synthesis, Spectral and Biological Studies of Ni(II), Pd(II), and Pt(IV) Complexes with New Heterocyclic Ligand Derived from Azo-Schiff Bases Dye. EurasianJournalofAnalyticalChemistry, 13, em64. https://doi.org/10.29333/ejac/97267
[23]
Geary, W.J. (1971) The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. CoordinationChemistryReviews, 7, 81-122. https://doi.org/10.1016/s0010-8545(00)80009-0
[24]
Ghosh, K., Roy, S., Ghosh, A., Banerjee, A., Bauzá, A., Frontera, A., etal. (2016) Three Mononuclear Octahedral Cobalt(III) Complexes with Salicylaldimine Schiff Bases: Synthesis, Characterization, Phenoxazinone Synthase Mimicking Activity and DFT Study on Supramolecular Interactions. Polyhedron, 112, 6-17. https://doi.org/10.1016/j.poly.2016.02.035
[25]
Banerjee, A., Herrero, S., Gutiérrez, Á. and Chattopadhyay, S. (2020) Synthesis, Structure and Magnetic Property of a Dinuclear Cobalt(II/III) Complex with a Reduced Schiff Base Ligand. Polyhedron, 190, Article ID: 114756. https://doi.org/10.1016/j.poly.2020.114756
[26]
Bartyzel, A. (2013) Synthesis, Crystal Structure and Characterization of Manganese(III) Complex Containing a Tetradentate Schiff Base. JournalofCoordinationChemistry, 66, 4292-4303. https://doi.org/10.1080/00958972.2013.867029
[27]
Orton, J.B., Diouf, N., Gueye, R.S., Gaye, M., Thiam, I.E. and Coles, S.J. (2023) Synthesis and Crystal Structures of Two Related Co and Mn Complexes: A Celebration of Collaboration between the Universities of Dakar and Southampton. ActaCrystallographicaSectionECrystallographicCommunications, 79, 1109-1114. https://doi.org/10.1107/s2056989023009805
[28]
Addison, A.W., Rao, T.N., Reedijk, J., van Rijn, J. and Verschoor, G.C. (1984) Synthesis, Structure, and Spectroscopic Properties of Copper(II) Compounds Containing Nitrogen-Sulphur Donor Ligands; the Crystal and Molecular Structure of Aqua[1,7-Bis(N-Methylbenzimidazol-2’-Yl)-2,6-Dithiaheptane]Copper(II) Perchlorate. Journal of the Chemical Society, Dalton Transactions, 7, 1349-1356. https://doi.org/10.1039/dt9840001349
[29]
Thakurta, S., Butcher, R.J., Gómez-García, C.J., Garribba, E. and Mitra, S. (2010) Synthesis, Structural Aspects and Magnetic Properties of an Unusual 2D Thiocyanato-Bridged Cobalt(II)-Schiff Base Network. InorganicaChimicaActa, 363, 3981-3986. https://doi.org/10.1016/j.ica.2010.07.069
[30]
Macrae, C.F., Sovago, I., Cottrell, S.J., Galek, P.T.A., McCabe, P., Pidcock, E., etal. (2020) Mercury 4.0: From Visualization to Analysis, Design and Prediction. JournalofAppliedCrystallography, 53, 226-235. https://doi.org/10.1107/s1600576719014092
[31]
Diouf, N., Thiam, I.E., Sylla-Gueye, R., Retailleau, P. and Gaye, M. (2022) Syntheses, Characterization, and X-Ray Crystal Structure of a Co-Crystal Containing One Neutral Mononuclear Copper (II) Unit and One Cationic Dinuclear Copper (II) Unit Assembled with Schiff Base and Perchlorate Copper(II) Salt. EarthlineJournalofChemicalSciences, 8, 35-52. https://doi.org/10.34198/ejcs.8122.3552