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A study of mononuclear 3d transition metal bis-Schiff base complexes: Synthesis, characterization, and evaluation of their antibacterial activity

Mithun Kori, Kaushal Kumar, Karuna Chourasia, Atish Roy, Ritu Yadav, Krishna Kumar Raj

Abstract


In this study, we have outlined a conventional and user-friendly procedure for the production of (E)-1-(((5-ethyl-1,3,4-thiadiazol-2-yl)imino)methyl)naphthalen-2-ol (HL-1) and (E)-1-((thiazol-2-ylimino)methyl)-naphthalen-2-ol (HL-2) by the reaction of heterocyclic amine, aldehyde in the presence of ethanol as a solvent and acid as the catalyst. The synthesis of new HL-1 and HL-2 may be accomplished with ease using this approach, which is also very efficient. In the presence of dipositive Co, Ni, and Cu metal complexation, HL-1 and HL-2 were carried out in the presence of metal: ligand (1:2). HL-1, HL-2, and metal complexes are characterized with the assistance of UV/visible, FT-IR, Mass, and 1H NMR spectroscopy respectively. Furthermore, the ligands mentioned above (HL-1 and HL-2) and their metal complexes were tested for the antimicrobial study and showed an excellent inhibitory zone. These investigations indicated that HL1-Co (II), HL-1Cu (II), complexes and ligands HL-2Co (II), and HL-1Ni(II) had positive effects on Escherichia coli causing severe stomach cramps (Gram-negative- MTCC 1610) and positive impact on Staphylococcus aureus (Gram-positive MTCC-96) due to skin infections.


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- S. T. Tsantis, D. I. Tzimopoulos, M. Holyńska, S. P. Perlepes, Oligonuclear Actinoid Complexes with Schiff Bases as Ligands—Older Achievements and Recent Progress, Int. J. Mol. Sci., 2020, 21,555.

- A. Singh, P. Barman, Recent Advances in Schiff Base Ruthenium Metal Complexes: Synthesis and Applications, Top Curr Chem., 2021, 379, 1-71.

- L. Fabbrizzi, Beauty in Chemistry: Making Artistic Molecules with Schiff Bases, J. Org. Chem., 2020, 85 (19), 12212–12226.

- P. G. Cozzi, Metal-Salen Schiff Base Complexes in Catalysis: Practical Aspects, Chem. Soc. Rev., 2004, 33 (7), 410–421.

- J. D. Chellaian, S. S. Salin Raj, Co(II), Ni(II), Cu(II), and Zn(II) Complexes of 4-Aminoantipyrine-Derived Schiff Base. Synthesis, Structural Elucidation, Thermal, Biological Studies, and Photocatalytic Activity, J. Heterocycl. Chem., 2021, 58 (4), 928–941.

- P. Sathyadevi, P. Krishnamoorthy, R. R. Butorac, A. H. Cowley, N. Dharmaraj, Synthesis of Novel Heterobimetallic Copper(i) Hydrazone Schiff Base Complexes: A Comparative Study on the Effect of Heterocyclic Hydrazides towards Interaction with DNA/Protein, Free Radical Scavenging and Cytotoxicity, Metallomics, 2012, 4 (5), 498–511.

- X. Zhang, X. Zhang, X. Sun, R. Jiang, E. Y. Zeng, E. M. Sunderland, D. C. G. Muir, D. C. G. Muir, D. C. G. Muir, Screening New Persistent and Bioaccumulative Organics in China’s Inventory of Industrial Chemicals, Environ. Sci. Technol., 2020, 54 (12), 7398–7408.

- A. W. Holland, R. G. Bergman, Unusual Base-Induced Metalation within a Chelate Ring versus Activation of a Methyl Group, 2002, 21 (11), 5–8.

- X. Kong, B. Zhang, J. Wang, Multiple Roles of Mesoporous Silica in Safe Pesticide Application by Nanotechnology: A Review, J. Agric. Food Chem., 2021, 69 (24), 6735–6754.

- P. Ghamari Kargar, S. Aryanejad, G. Bagherzade, Simple Synthesis of the Novel Cu-MOF Catalysts for the Selective Alcohol Oxidation and the Oxidative Cross-Coupling of Amines and Alcohols, Appl. Organomet. Chem., 2020, 34 (12), 1–12.

- A. L. Nuzhdin, M. V. Bukhtiyarova, G. A. Bukhtiyarova, Cu-Al Mixed Oxide Derived from Layered Double Hydroxide as an Efficient Catalyst for Continuous-Flow Reductive Amination of Aromatic Aldehydes, J. Chem. Technol. Biotechnol., 2020, 95 (12), 3292–3299.

- A. Das, Y. Ren, C. Hessin, M. D. Murr, Copper Catalysis with Redox-Active Ligands, Beilstein J. Org. Chem., 2020, 16, 858–870.

- J. Linnemann, K. Kanokkanchana, K. Tschulik, Design Strategies for Electrocatalysts from an Electrochemist’s Perspective, ACS Catal., 2021, 11 (9), 5318–5346.

- W. Filipowska, B. Jaskula-Goiris, M. Ditrych, P. Bustillo Trueba, G. De Rouck, G. Aerts, C. Powell, D. Cook, L. De Cooman, On the Contribution of Malt Quality and the Malting Process to the Formation of Beer Staling Aldehydes: A Review, J. Inst. Brew., 2021, 127 (2), 107–126.

- A. Arunadevi, N. Raman, Biological Response of Schiff Base Metal Complexes Incorporating Amino Acids–a Short Review, J. Coord. Chem., 2020, 73 (15), 2095–2116.

- S. A. Elsayed, H. M. El-Gharabawy, I. S. Butler, F. M. Atlam, Novel Metal Complexes of 3-Acetylcoumarin-2-Hydrazinobenzothiazole Schiff Base: Design, Structural Characterizations, DNA Binding, DFT Calculations, Molecular Docking and Biological Studies, Appl. Organomet. Chem., 2020, 34 (6), 1–18.

- M. Amjad, S. H. Sumrra, M. S. Akram, Z. H. Chohan, Metal-Based Ethanolamine-Derived Compounds: A Note on Their Synthesis, Characterization and Bioactivity, J. Enzyme Inhib. Med. Chem. 2016, 31, 88–97.

- R. Patel, S. Park, An Evolving Role of Piperazine Moieties in Drug Design and Discovery, Mini-Reviews Med. Chem., 2015, 13 (11), 1579–1601.

- L. V. Zhilitskaya, B. A. Shainyan, N. O. Yarosh, Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives, Molecules, 2021, 26 (8).

- N. Mishra, S. S. Gound, R. Mondal, R. Yadav, R. Pandey, Synthesis, Characterization and Antimicrobial Activities of Benzothiazole-Imino-Benzoic Acid Ligands and Their Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) Complexes, Results Chem., 2019, 1, 100006.

- S. H. Sumrra, Z. H. Chohan, Antibacterial and Antifungal Oxovanadium(IV) Complexes of Triazole-Derived Schiff Bases, Med. Chem. Res., 2013, 22 (8), 3934–3942.

- K. Merschjohann, D. Steverding, In Vitro Trypanocidal Activity of the Anti-Helminthic Drug Niclosamide, Exp. Parasitol, 2008, 118 (4), 637–640.

- H. K. Jebur, M. Z. Khalaf, N. F. Alheety, Synthesis, Characterizations of Some New 6-Flouro-2-Amino Benzothiazole Derivatives and Study Their Biological Activity, 2019, 12 (3), 1–11.

- S. Matsuda, H. Iwata, N. Se, Y. Ikada, Bioadhesion of Gelatin Films Crosslinked with Glutaraldehyde, J. Biomed. Mater. Res., 1999, 45 (1), 20–27.

- S. E. A. El-Razek, S. M. El-Gamasy, M. Hassan, M. S. Abdel-Aziz, S. M. Nasr, Transition Metal Complexes of a Multidentate Schiff Base Ligand Containing Guanidine Moiety: Synthesis, Characterization, Anti-Cancer Effect, and Antimicrobial Activity, J. Mol. Struct., 2020, 1203, 127381.

- K. Dodou, R. J. Anderson, W. J. Lough, D. A. P. Small, M. D. Shelley, P. W. Groundwater, Synthesis of Gossypol Atropisomers and Derivatives and Evaluation of Their Anti-Proliferative and Anti-Oxidant Activity, Bioorganic Med. Chem., 2005, 13 (13), 4228–4237.

- S. Noreen, S. H. Sumrra, Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations, ACS Omega 2021, 6 (48), 33085–33099.

- Y. Manojkumar, S. Ambika, R. Arulkumar, B. Gowdhami, P. Balaji, G. Vignesh, S. Arunachalam, P. Venuvanalingam, R. Thirumurugan, M. A. Akbarsha, Synthesis, DNA and BSA Binding: In Vitro Anti-Proliferative and in Vivo Anti-Angiogenic Properties of Some Cobalt(Iii) Schiff Base Complexes, New J. Chem., 2019, 43 (28), 11391–11407.

- A. Pandey, R. Rajavel, D. Dash, S. Chandraker, Synthesis of Schiff Bases of 2-Amino-5-Aryl-1, 3, 4-Thiadiazole and Its Analgesic, Anti-Inflammatory and Anti-Bacterial Activity, E-Journal Chem., 2012, 9 (4), 2524–2531.

- R. Pignatello, A. Panico, P. Mazzone, M. Pinizzotto, A. Garozzo, P. M. Furneri, Schiff Bases of N-Hydroxy-N′-Aminoguanidines as Antiviral, Antibacterial and Anticancer Agents, Eur. J. Med. Chem., 1994, 29 (10), 781–785.

- A. R. Nekoei, M. Vatanparast, An Intramolecular Hydrogen Bond Study in Some Schiff Bases of Fulvene: A Challenge between the RAHB Concept and the σ-Skeleton Influence, New J. Chem., 2014, 38 (12), 5886–5891.

- A. Aragón-Muriel, Y. Liscano, Y. Upegui, S. M. Robledo, M. T. Ramírez-Apan, D. Morales-Morales, J. Oñate-Garzón, D. Polo-Cerón, In Vitro Evaluation of the Potential Pharmacological Activity and Molecular Targets of New Benzimidazole-Based Schiff Base Metal Complexes, Antibiotics, 2021, 10 (6), 1–27.

- S. S. Tajudeen, G. Kannappan, Indian Journal of Advances in Chemical Science Schiff Base – Copper ( II ) Complexes: Synthesis, Spectral Studies and Anti-Tubercular and Antimicrobial Activity, Indian J. Adv. Chem. Sci., 2016, 4 (1), 40–48.

- S. V. Bhandari, K. G. Bothara, M. K. Raut, A. A. Patil, A. P. Sarkate, V. J. Mokale, Design, Synthesis and Evaluation of Antiinflammatory, Analgesic and Ulcerogenicity Studies of Novel S-Substituted Phenacyl-1,3,4-Oxadiazole-2-Thiol and Schiff Bases of Diclofenac Acid as Nonulcerogenic Derivatives. Bioorganic Med. Chem., 2008, 16 (4), 1822–1831.

- Q. L. Zhang, J. Guo, X. Y. Deng, F. Wang, J. Y. Chen, L. B. Lin, Comparative Transcriptomic Analysis Provides Insights into the Response to the Benzo(a)Pyrene Stress in Aquatic Firefly (Luciola Leii), Sci. Total Environ., 2019, 661, 226–234.

- J. Zhu, G. Teng, D. Li, R. Hou, Y. Xia, Synthesis and Antibacterial Activity of Novel Schiff Bases of Thiosemicarbazone Derivatives with Adamantane Moiety, Med. Chem. Res., 2021, 30 (8), 1534–1540.

- A. Akelah, E. R. Kenawy, D. C. Sherrington, Agricultural Polymers with Herbicide/Fertilizer Function-III. Polyureas and Poly(Schiff Base)s Based Systems, Eur. Polym. J., 1993, 29 (8), 1041–1045.

- N. Patel, A. K. Prajapati, R. N. Jadeja, R. N. Patel, S. K. Patel, I. P. Tripathi, N. Dwivedi, V. K. Gupta, R. J. Butcher, Dioxidovanadium(V) Complexes of a Tridentate ONO Schiff Base Ligand: Structural Characterization, Quantum Chemical Calculations and in-Vitro Antidiabetic Activity, Polyhedron, 2020, 180, 114434.

- T. R. Daniels, T. Delgado, J. A. Rodriguez, G. Helguera, M. L. Penichet, The Transferrin Receptor Part I: Biology and Targeting with Cytotoxic Antibodies for the Treatment of Cancer, Clin. Immunol., 2006, 121 (2), 144–158.

- S. H. Sumrra, A. U. Hassan, M. N.; Zafar, S. S. Shafqat, G. Mustafa, M. N. Zafar, M. Zubair, M. Imran, Metal Incorporated Sulfonamides as Promising Multidrug Targets: Combined Enzyme Inhibitory, Antimicrobial, Antioxidant and Theoretical Exploration, J. Mol. Struct., 2022, 1250.

- S. H. Sumrra, M. Hanif, Z. H. Chohan, Design, Synthesis and in Vitro Bactericidal/Fungicidal Screening of Some Vanadyl(IV)Complexes with Mono- and Di-Substituted ONS Donor Triazoles, J. Enzyme Inhib. Med. Chem., 2015, 30 (5), 800–808.

- R. Diana, B. Panunzi, The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review. Molecules, 2020, 25 (21).

- A. A. A. Al-Dulimia, R. A. M. Al-Hasani, E. A. Yousif, Synthesis, Characterization, Theoretical Studies and Photostabilization of Mefenamic Acid Derivative with Some Divalent Metal Ions, Eur. Chem. Bull., 2016, 5 (10), 456–464.

- R. V. Patel, P. K. Patel, P. Kumari, D. P. Rajani, K. H. Chikhalia, Synthesis of Benzimidazolyl-1,3,4-Oxadiazol-2ylthio-N-Phenyl (Benzothiazolyl) Acetamides as Antibacterial, Antifungal and Antituberculosis Agents, Eur. J. Med. Chem., 2012, 53, 41–51.

- M. T. Basha, R. M. Alghanmi, M. R. Shehata, L. H. Abdel-Rahman, Synthesis, Structural Characterization, DFT Calculations, Biological Investigation, Molecular Docking and DNA Binding of Co(II), Ni(II) and Cu(II) Nanosized Schiff Base Complexes Bearing Pyrimidine Moiety, J. Mol. Struct., 2019, 1183, 298–312.

- M. Nikoorazm, M. Khanmoradi, Application of Cu (II)-Guanine Complexes Anchored on SBA-15 and MCM-41 as Efficient Nanocatalysts for One-Pot, Four-Component Domino Synthesis of Phenazine Derivatives and Investigation of Their Antimicrobial Behavior, Catal. Letters, 2020, 150 (10), 2823–2840.

- N. Mishra, K. Kumar, H. Pandey, S. Raj, Synthesis, Characterization, Optical and Anti-Bacterial Properties of Benzothiazole Schiff Bases and Their Lanthanide ( III ) Complexes, 2020, 0–8.

- N. Mishra, S. S. Gound, R. Mondal, R. Yadav, R. Pandey, Ur Na l P, Results Chem., 2019, 100006.

- P. Kosti, G. Ahmad, N. Ratnesh, D. Neha, M. Sushil, And ­ Cd 2 + Metal Complexes of Schiff Base Ligand Derived from 4 ‑ Amino Benzoic Acid and Isonicotinic Hydrazide, 2021, 1773–1780.

- K. Chourasia, B. P. Prajapati, M. Kori, K. Kumar, R. Yadav, Synthesis, Spectral Characterization and Antimicrobial Activity of Two Novel Schiff Bases Derived from Thiosemicarbazide and Mononuclear 3d Transition Metal Complexes, 2022.

- S. H. Sumrra, W. Zafar, H. Javed, M. Zafar, M. Z. Hussain, M. Imran, M. A. Nadeem, Facile Synthesis, Spectroscopic Evaluation and Antimicrobial Screening of Metal Endowed Triazole Compounds, BioMetals 2021, 34 (6), 1329–1351.

- Z. Fallah, E. N. Zare, M. A. Khan, S. Iftekhar, M. Ghomi, E. Sharifi, M. Tajbakhsh, N. Nikfarjam, P. Makvandi, E. Lichtfouse, M. Sillanpaa, R. S. Varma, Ionic Liquid-Based Antimicrobial Materials for Water Treatment, Air Filtration, Food Packaging and Anticorrosion Coatings, Adv. Colloid Interface Sci., 2021, 294.




DOI: http://dx.doi.org/10.13171/mjc02304231686kori

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