Vanadium complexes derived from fluoro-substituted Schiff bases: Synthesis, crystal structures, and antimicrobial activity

References

• Rocha, M.; Ruiz, M. C.; Echeverria, G. A.; Piro, O. E.; Di Virgilio, A. L.; León, I. E.; Frontera, A.; Gil, D. M. Diethylaminophenyl-Based Schiff Base Cu(II) and V(IV) Complexes: Experimental and Theoretical Studies and Cytotoxicity Assays. New J. Chem. 2019, 43, 18832–18842. DOI: 10.1039/C9NJ04975D.
   Web of Science ®Google Scholar
• Monga, V.; Thompson, K. H.; Yuen, V. G.; Sharma, V.; Patrick, B. O.; McNeill, J. H.; Orvig, C. Vanadium Complexes with Mixed O,S Anionic Ligands Derived from Maltol: Synthesis, Characterization, and Biological Studies. Inorg. Chem. 2005, 44, 2678–2688. DOI: 10.1021/ic0486926.
   PubMed Web of Science ®Google Scholar
• Thakur, S.; Drew, M. G. B.; Franconetti, A.; Frontera, A.; Chattopadhyay, S. Stabilization of Two Conformers via Intra- or Inter-Molecular Hydrogen Bonds in a Dinuclear Vanadium(v) Complex with a Pendant Schiff Base: theoretical Insight. RSC Adv. 2019, 9, 35165–35175. DOI: 10.1039/C9RA07006K.
   PubMed Web of Science ®Google Scholar
• Thakur, S.; Drew, M. G. B.; Franconetti, A.; Frontera, A.; Chattopadhyay, S. Analysis of Energies of Halogen and Hydrogen Bonding Interactions in the Solid State Structures of Vanadyl Schiff Base Complexes. RSC Adv. 2018, 142, 83–92. DOI: 10.1039/C8RA09947B.
   Web of Science ®Google Scholar
• Qian, H. Y. Synthesis, Characterization and Crystal Structures of Oxidovanadium(V)complexes Derived from Hydrazone Ligands with Antibacterial Activity. Inorg. Nano-Met. Chem. 2018, 48, 461–466. DOI: 10.1080/24701556.2019.1569689.
   Web of Science ®Google Scholar
• Qian, H. Y. Synthesis, Characterization, Crystal Structures, and Antibacterial Activity of 8-Hydroxyquinoline-Coordinated Oxidovanadium(V) complexes with Tridentate Hydrazone Ligands. Russ. J. Coord. Chem. 2017, 43, 780–786. DOI: 10.1134/S1070328417110070.
   Web of Science ®Google Scholar
• Sonmez, M.; Celebi, M.; Berber, I. Synthesis, Spectroscopic and Biological Studies on the New Symmetric Schiff Base Derived from 2,6-Diformyl-4-Methylphenol with N-Aminopyrimidine. Eur. J. Med. Chem. 2010, 45, 1935–1940. DOI: 10.1016/j.ejmech.2010.01.035.
   PubMed Web of Science ®Google Scholar
• Qian, H.-Y. Synthesis, Characterization, X-Ray Crystal Structures and Antibacterial Activities of Oxidovanadium(V) complexes with Hydrazone and Hydroxamate Ligands. Acta Chim. Slov 2019, 66, 995–1001. DOI: 10.17344/acsi.2019.5247.
   PubMed Web of Science ®Google Scholar
• Sinha, D.; Tiwari, A. K.; Singh, S.; Shukla, G.; Mishra, P.; Chandra, H.; Mishra, A. K. Synthesis, Characterization and Biological Activity of Schiff Base Analogues of Indole-3-Carboxaldehyde. Eur. J. Med. Chem. 2008, 43, 160–165. DOI: 10.1016/j.ejmech.2007.03.022.
   PubMed Web of Science ®Google Scholar
• Qian, H. Y.; Sun, N. Synthesis and Crystal Structures of Manganese(III) Complexes Derived from bis-Schiff Bases with Antibacterial Activity. Transit. Met. Chem. 2019, 44, 501–506. DOI: 10.1007/s11243-018-00296-x.
   Web of Science ®Google Scholar
• Qian, H. Y. Synthesis, Crystal Structures and Antibacterial Activities of Nickel(II) Complexes Derived from 2-Bromo-4-Chloro-6[(2-Diethylaminoethylimino)Methyl]Phenol. Inorg. Nano-Met. Chem. 2018, 48, 615–619. DOI: 10.1080/24701556.2019.1567542.
   Web of Science ®Google Scholar
• Bagihalli, G. B.; Avaji, P. G.; Patil, S. A.; Badami, P. S. Synthesis, Spectral Characterization, in Vitro Antibacterial, Antifungal and Cytotoxic Activities of Co(II), Ni(II) and Cu(II) Complexes with 1,2,4-Triazole Schiff Bases. Eur. J. Med. Chem. 2008, 43, 2639–2649. DOI: 10.1016/j.ejmech.2008.02.013.
   PubMed Web of Science ®Google Scholar
• Sun, Y.-X. Synthesis, Crystal Structures and Antibacterial Activities of Two Schiff Base Copper(II) Complexes. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 2006, 36, 621–625. DOI: 10.1080/15533170600910546.
   Web of Science ®Google Scholar
• Zhang, M.; Xian, D.-M.; Li, H.-H.; Zhang, J.-C.; You, Z.-L. Synthesis and Structures of Halo-Substituted Aroylhydrazones with Antimicrobial Activity. Aust. J. Chem. 2012, 65, 343–350. DOI: 10.1071/CH11424.
   Web of Science ®Google Scholar
• SMART and SAINT, Area Detector Control and Integration Software; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1997.
   Google Scholar
• Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1997.
   Google Scholar
• North, A. C. T.; Phillips, D. C.; Mathews, F. S. A Semi-Empirical Method of Absorption Correction. Acta Cryst. A. 1968, 24, 351–352. DOI: 10.1107/S0567739468000707.
   Web of Science ®Google Scholar
• Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
   Google Scholar
• Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. 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. J. Chem. Soc. Dalton Trans. 1984, (7), 1349–1356. DOI: 10.1039/DT9840001349.
   Google Scholar
• Rahchamani, J.; Behzad, M.; Bezaatpour, A.; Jahed, V.; Dutkiewicz, G.; Kubicki, M.; Salehi, M. Oxidovanadium Complexes with Tetradentate Schiff Bases: Synthesis, Structural, Electrochemical and Catalytic Studies. Polyhedron 2011, 30, 2611–2618. DOI: 10.1016/j.poly.2011.07.011.
   Web of Science ®Google Scholar
• Hernandez-Benitez, L. J.; Jimenez-Cruz, P.; Cureno-Hernandez, K. E.; Solano-Peralta, A.; Flores-Alamo, M.; Flores-Parra, A.; Gracia-Mora, I.; Castillo-Blum, S. E. [VIVO]2+ Complexes: Structure, Unusual Magnetic Properties and Cytotoxic Effect. Inorg. Chim. Acta 2018, 480, 197–206. DOI: 10.1016/j.ica.2018.05.013.
   Web of Science ®Google Scholar
• Romanowski, G.; Wera, M. Mononuclear and Dinuclear Chiral Vanadium(V) complexes with Tridentate Schiff Bases Derived from R(-)-1,2-Diaminopropane: Synthesis, Structure, Characterization and Catalytic Properties. Polyhedron 2010, 29, 2747–2754. DOI: 10.1016/j.poly.2010.06.030.
   Web of Science ®Google Scholar
• You, Z.-L.; Shi, D.-H.; Zhang, J.-C.; Ma, Y.-P.; Wang, C.; Li, K. Synthesis, Structures, and Urease Inhibitory Activities of Oxovanadium(V) complexes with Schiff Bases. Inorg. Chim. Acta. 2012, 384, 54–61. DOI: 10.1016/j.ica.2011.11.039.
   Web of Science ®Google Scholar
• Nejo, A. A.; Kolawole, G. A.; Opoku, A. R.; Wolowska, J.; O’Brien, P. Synthesis, Characterization and Preliminary Insulin-Enhancing Studies of Symmetrical Tetradentate Schiff Base Complexes of Oxovanadium(IV). Inorg. Chim. Acta. 2009, 362, 3993–4001. DOI: 10.1016/j.ica.2009.05.039.
   Web of Science ®Google Scholar
• Mondal, B.; Drew, M. G. B.; Ghosh, T. Synthesis, Structure and Solution Chemistry of Quaternary Oxovanadium(V) complexes Incorporating Hydrazone Ligands. Inorg. Chim. Acta 2009, 362, 3303–3308. DOI: 10.1016/j.ica.2009.02.043.
   Web of Science ®Google Scholar
• Barry, A. Antibiotics in Laboratory Medicine; Victor, L., Ed.; Williams and Wilkins: Baltimore, 1991; p. 1.
   Google Scholar
• Rosu, T.; Negoiu, M.; Pasculescu, S.; Pahontu, E.; Poirier, D.; Gulea, A. Metal-Based Biologically Active Agents: Synthesis, Characterization, Antibacterial and Antileukemia Activity Evaluation of Cu(II), V(IV) and Ni(II) Complexes with Antipyrine-Derived Compounds. Eur. J. Med. Chem. 2010, 45, 774–781. DOI: 10.1016/j.ejmech.2009.10.034.
   PubMed Web of Science ®Google Scholar
• Taheri, O.; Behzad, M.; Ghaffari, A.; Kubicki, M.; Dutkiewicz, G.; Bezaatpour, A.; Nazari, H.; Khaleghian, A.; Mohammadi, A.; Salehi, M. Synthesis, Crystal Structures and Antibacterial Studies of Oxidovanadium(IV) Complexes of Salen-Type Schiff Base Ligands Derived from Meso-1,2-Diphenyl-1,2-Ethylenediamine. Transition Met. Chem. 2014, 39, 253–259. DOI: 10.1007/s11243-014-9798-9.
   Web of Science ®Google Scholar
• Sharma, N.; Kumari, M.; Kumar, V.; Chaudhry, S. C.; Kanwar, S. S. Synthesis, Characterization, and Antimicrobial Activity of Oxovanadium(IV)Hydroxamate Complexes. J. Coord. Chem 2010, 63, 1940–1950. DOI: 10.1080/00958972.2010.495986.
   Web of Science ®Google Scholar
• Bhattacharjee, C. R.; Goswami, P.; Sengupta, M. Synthesis, Electrochemical and Antimicrobial Studies of Mono and Binuclear Iron(III) and Oxovanadium(IV) Complexes of [ONO] Donor Tridentate Schiff-Base Ligands. J. Coord. Chem. 2010, 63, 3969–3980. DOI: 10.1080/00958972.2010.525703.
   Web of Science ®Google Scholar
• Searl, J. W.; Smith, R. C.; Wyard, S. Electron Spin Resonance Absorption for Polycrystalline Substances. J. Proc. Phys. Soc. 1961, 78, 1174–1177. DOI: 10.1088/0370-1328/78/6/311.
   Web of Science ®Google Scholar