Synthesis, characterization, X-ray crystal structures, and antibacterial property of oxidovanadium(V) complexes with halide-containing hydrazones

References

• Barfeie, H.; Grivani, G.; Eigner, V.; Dusek, M.; Khalaji, A. D. Copper(II), Nickel(II), Zinc(II) and Vanadium(IV) Schiff Base Complexes: Synthesis, Characterization, Crystal Structure Determination, and Thermal Studies. Polyhedron 2018, 146, 19–25. DOI: 10.1016/j.poly.2018.02.012.
   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
• Jakusch, T.; Kozma, K.; Enyedy, E. A.; May, N. V.; Roller, A.; Kowol, C. R.; Keppler, B. K.; Kiss, T. Complexes of Pyridoxal Thiosemicarbazones Formed with Vanadium(IV/V) and Copper(II): Solution Equilibrium and Structure. Inorg. Chim. Acta 2018, 472, 243–253. DOI: 10.1016/j.ica.2017.08.018.
   Web of Science ®Google Scholar
• Reytman, L.; Hochman, J.; Tshuva, E. Y. Anticancer Diaminotris(Phenolato) Vanadium(V) complexes: Ligand-Metal Interplay. J. Coord. Chem. 2018, 71, 2003–2011. DOI: 10.1080/00958972.2018.1461848.
   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. ACSI. 2019, 66, 995–1001. DOI: 10.17344/acsi.2019.5247.
   Web of Science ®Google Scholar
• Heidari, F.; Fatemi, S. J. A.; Ebrahimipour, S. Y.; Ebrahimnejad, H.; Castro, J.; Dusek, M.; Eigner, V. Six-Coordinate Oxo-Vanadium(V) dimer Complex with Methoxy Bridging: Synthesis, Crystal Structure, Biological Activity and Molecular Docking. Inorg. Chem. Commun. 2017, 76, 1–4. DOI: 10.1016/j.inoche.2016.11.015.
   Web of Science ®Google Scholar
• Kober, E.; Janas, Z.; Jezierska, J. Oxidation of 1-Methyl-1-Phenylhydrazine with Oxidovanadium(V)-Salan Complexes: Insight into the Pathway to the Formation of Hydrazine by Vanadium Nitrogenase. Inorg. Chem. 2016, 55, 10888–10898. DOI: 10.1021/acs.inorgchem.6b01283.
   PubMed Web of Science ®Google Scholar
• Mba, M.; Pontini, M.; Lovat, S.; Zonta, C.; Bernardinelli, G.; KüNdig, P. E.; Licini, G. C3 Vanadium(V) amine Triphenolate Complexes: Vanadium Haloperoxidase Structural and Functional Models. Inorg. Chem. 2008, 47, 8616–8618. DOI: 10.1021/ic8015113.
   PubMed Web of Science ®Google Scholar
• Smith, T. S.; Pecoraro, V. L. Oxidation of Organic Sulfides by Vanadium Haloperoxidase Model Complexes. Inorg. Chem. 2002, 41, 6754–6760. DOI: 10.1021/ic025650d.
   PubMed Web of Science ®Google Scholar
• Kaczmarek, M. T.; Zabiszak, M.; Nowak, M.; Jastrzab, R. Lanthanides: Schiff Base Complexes, Applications in Cancer Diagnosis, Therapy, and Antibacterial Activity. Coord. Chem. Rev. 2018, 370, 42–54. DOI: 10.1016/j.ccr.2018.05.012.
   Web of Science ®Google Scholar
• Liu, X.; Manzur, C.; Novoa, N.; Celedon, S.; Carrillo, D.; Hamon, J.-R. Multidentate Unsymmetrically-Substituted Schiff Bases and Their Metal Complexes: Synthesis, Functional Materials Properties, and Applications to Catalysis. Coord. Chem. Rev. 2018, 357, 144–172. DOI: 10.1016/j.ccr.2017.11.030.
   Web of Science ®Google Scholar
• Qian, H. Y. Synthesis, Crystal Structures, and Biological Activity of Manganese(III) Complexes Derived from bis-Schiff Bases. Russ. J. Coord. Chem. 2018, 44, 32–38. DOI: 10.1134/S1070328418010074.
   Web of Science ®Google Scholar
• Rezaeivala, M.; Keypour, H. Schiff Base and non-Schiff Base Macrocyclic Ligands and Complexes Incorporating the Pyridine moiety - The First 50 Years. Coord. Chem. Rev. 2014, 280, 203–253. DOI: 10.1016/j.ccr.2014.06.007.
   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
• 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
• El-Sherif, A. A.; Fetoh, A.; Abdulhamed, Y. K.; Abu El-Reash, G. M. Synthesis, Structural Characterization, DFT Studies and Biological Activity of Cu(II) and Ni(II) Complexes of Novel Hydrazone. Inorg. Chim. Acta 2018, 480, 1–15. DOI: 10.1016/j.ica.2018.04.038.
   Web of Science ®Google Scholar
• Abdelgawad, M. A.; Labib, M. B.; Abdel-Latif, M. Pyrazole-Hydrazone Derivatives as anti-Inflammatory Agents: Design, Synthesis, Biological Evaluation, COX-1,2/5-LOX Inhibition and Docking Study. Bioorg. Chem. 2017, 74, 212–220. DOI: 10.1016/j.bioorg.2017.08.014.
   PubMed Web of Science ®Google Scholar
• Shankar, R.; Rawal, R. K.; Singh, U. S.; Chaudhary, P.; Konwar, R.; Hajela, K. Design, Synthesis and Biological Evaluation of Hydrazone Derivatives as anti-Proliferative Agents. Med. Chem. Res. 2017, 26, 1459–1468. DOI: 10.1007/s00044-017-1866-1.
   Web of Science ®Google Scholar
• Karaman, N.; Sıcak, Y.; Taşkın-Tok, T.; Öztürk, M.; Karaküçük-İyidoğan, A.; Dikmen, M.; Koçyiğit-Kaymakçıoğlu, B.; Oruç-Emre, E. E. New Piperidine-Hydrazone Derivatives: Synthesis, Biological Evaluations and Molecular Docking Studies as AChE and BChE Inhibitors. Eur. J. Med. Chem. 2016, 124, 270–283. DOI: 10.1016/j.ejmech.2016.08.037.
   PubMed Web of Science ®Google Scholar
• Amato, J.; Morigi, R.; Pagano, B.; Pagano, A.; Ohnmach, S.; De Magis, A.; Tiang, Y.-P.; Capranico, G.; Locatelli, A.; Graziadio, A.; et al. Toward the Development of Specific G-Quadruplex Binders: Synthesis, Biophysical, and Biological Studies of New Hydrazone Derivatives. J. Med. Chem. 2016, 59, 5706–5720. DOI: 10.1021/acs.jmedchem.6b00129.
   PubMed Web of Science ®Google Scholar
• Fekri, R.; Salehi, M.; Asadi, A.; Kubicki, M. Synthesis, Characterization, Anticancer and Antibacterial Evaluation of Schiff Base Ligands Derived from Hydrazone and Their Transition Metal Complexes. Inorg. Chim. Acta 2019, 484, 245–254. DOI: 10.1016/j.ica.2018.09.022.
   Web of Science ®Google Scholar
• Bera, P.; Brandao, P.; Mondal, G.; Jana, H.; Jana, A.; Santra, A.; Bera, P. Synthesis of a New Pyridinyl Thiazole Ligand with Hydrazone Moiety and Its Cobalt(III) Complex: X-Ray Crystallography, in Vitro Evaluation of Antibacterial Activity. Polyhedron 2017, 134, 230–237. DOI: 10.1016/j.poly.2017.06.024.
   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
• Sedaghat, T.; Yousefi, M.; Bruno, G.; Rudbari, H. A.; Motamedi, H.; Nobakht, V. Synthesis, Spectral Characterization, Crystal Structure and Antibacterial Studies of Diorganotin(IV) Complexes with Isonicotinoyl Hydrazone Derivatives. Polyhedron 2014, 79, 88–96. DOI: 10.1016/j.poly.2014.04.061.
   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
• Gopalakrishnan, M.; Thanusu, J.; Kanagarajan, V.; Govindaraju, R. Unexpected Formation of 3-Chloro-1-Hydroxy-2,6-Diarylpiperidin-4-Ones: Synthesis, Antibacterial and Antifungal Activities. J. Enzyme Inhib. Med. Chem. 2009, 24, 52–58. DOI: 10.1080/14756360801906632.
   PubMed Web of Science ®Google Scholar
• Shi, L.; Ge, H.-M.; Tan, S.-H.; Li, H.-Q.; Song, Y.-C.; Zhu, H.-L.; Tan, R.-X. Synthesis and Antimicrobial Activities of Schiff Bases Derived from 5-Chloro-Salicylaldehyde. Eur. J. Med. Chem. 2007, 42, 558–564. DOI: 10.1016/j.ejmech.2006.11.010.
   PubMed Web of Science ®Google Scholar
• Sheldrick, G. M. Crystal Structure Refinement with Shelxl. Acta Crystallogr. C Struct. Chem. 2015, 71, 3–8. DOI: 10.1107/S2053229614024218.
   PubMed Web of Science ®Google Scholar
• Yu, H.; Guo, S.; Cheng, J.-Y.; Jiang, G.; Li, Z.; Zhai, W.; Li, A.; Jiang, Y.; You, Z. Synthesis and Crystal Structures of Cobalt(III), Copper(II), Nickel(II) and Zinc(II) Complexes Derived from 4-methoxy-N’-(Pyridin-2-Ylmethylene)Benzohydrazide with Urease Inhibitory Activity. J. Coord. Chem. 2018, 71, 4164–4179. DOI: 10.1080/00958972.2018.1533959.
   Web of Science ®Google Scholar
• Guo, S.; Sun, N.; Ding, Y.; Li, A.; Jiang, Y.; Zhai, W.; Li, Z.; Qu, D.; You, Z. You, Z. Syntheses, Characterization, and Crystal Structures of Two Oxovanadium(V) complexes with Insulin-like Activity. Z. Anorg. Allg. Chem. 2018, 644, 1172–1176. DOI: 10.1002/zaac.201800060.
   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
• Zhu, X. W. Synthesis, Crystal Structure, and Antibacterial Activity of a Dinuclear Oxidovanadium(V) complexes Derived from 2-[(2-Methylaminoethylimini)Methyl]-4-trifluoromethoxyphenol1. Russ. J. Coord. Chem. 2018, 44, 335–339. DOI: 10.1134/S1070328418050081.
   Web of Science ®Google Scholar