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Synthesis, structure and properties of V(IV) complex with N’-[(E)-(2,3-dihydroxyphenyl)metylidene]-2- phenylacetohydrazide

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Języki publikacji
EN
Abstrakty
EN
The synthesis and physicochemical properties of new vanadium(IV) complex of formula [VO(L)(phen)] is described. The L denotes ONO tridentate Schiff base derived from 2,3-dihydroxybenzaldehyde and phenylacetic hydrazide, while phen = 1,10-phenanthroline used as a co-ligand to stabilize the V(IV) oxidation state. The single crystal X-Ray crystal structure indicates on octahedral geometry of vanadium centre, with 1,10-phenanthroline nitrogen trans to the V=O bond. The complex crystalizes in a monoclinic P21/c space group, very unusual is that only one isomer is present in the crystal structure. The structure is stabilized by very weak hydrogen bonds and H··π and π···π interactions. The phenyl ring of hydrazide is strongly curved from ONO ligand plane by 70.95˚. The spectroscopic characterization (IR, UV-Vis) as well as the cyclic voltammetry measurements are presented and discussed
Rocznik
Strony
1--8
Opis fizyczny
Bibliogr. 38 poz., rys., tab.
Twórcy
  • Jagiellonian University, Faculty of Chemistry, Gronostajowa 2, 30-387 Kraków, Poland
  • Jagiellonian University, Faculty of Chemistry, Gronostajowa 2, 30-387 Kraków, Poland
  • Jagiellonian University, Faculty of Chemistry, Gronostajowa 2, 30-387 Kraków, Poland
  • Jagiellonian University, Faculty of Chemistry, Gronostajowa 2, 30-387 Kraków, Poland
Bibliografia
  • 1. Mukherjee T, Costa Pessoa J, Kumar A, Sarkar AR. Oxidovanadium (IV) Schiff base complex derived from vitamin B6: synthesis, characterization, and insulin enhancing properties. Inorganic Chemistry. 2011; 50:4349-4361.
  • 2. Holder AA, Taylor P, Magnusen AR, Moffett ET, Meyer K, Hong Y, Ramsdale SE, Gordon M, Stubbs J, Seymour LA, Acharya D, Weber RT, Smith PF, Dismukes GC, Ji P, Menocal L, Bai F, Williams JL, Cropek DM, Jarrett WL. Preliminary anti-cancer photodynamic therapeutic in vitro studies with mixed-metal binuclear ruthenium (II)–vanadium (IV) complexes. Dalton Transactions 2013; 42:11881-11899.
  • 3. León IE, Parajón-Costa BS, Franca CA, Etcheverry SB, Baran EJ. A New Oxidovanadium (IV) Complex of Oxodiacetic Acid and dppz: Spectroscopic and DFT Study. Antitumor Action on MG-63 Human Osteosarcoma Cell Line. Biological Trace Element Research 2015; 164:198-204.
  • 4. Abaszadeh M, Seifi M, Ebrahimipour SY. Two ligand oxidio-vanadium (IV) complexes as novel efficient catalysts in multicomponent reactions for synthesis of tetrahydrobenzopyran derivatives. Bulletin of the Chemical Society of Ethiopia. 2016; 30:253-262.
  • 5. Bikas R, Shahmoradi E, Noshiranzadeh N, Emami M, Reinoso S. The effects of halogen substituents on the catalytic oxidation of benzyl-alcohols in the presence of dinuclear oxidovanadium (IV) complex. Inorganica Chimica Acta. 2017; 466:100-109.
  • 6. Sakurai H, Fujii K, Watanabe H, Tamura H. Orally active and long-term acting insulin-mimetic vanadyl complex: bis (picolinato) oxovanadium (IV). Biochemical and Biophysical Research Communications. 1995; 214:1095-1101.
  • 7. Melchior M, Thompson KH, Jong JM, Rettig SJ, Shuter E, Yuen VG, Zhou Y, McNeill JH, Orvig C. Vanadium complexes as insulin mimetic agents: coordination chemistry and in vivo studies of oxovanadium (IV) and dioxovanadate (V) complexes formed from naturally occurring chelating oxazolinate, thiazolinate, or picolinate units. Inorganic Chemistry. 1999; 38:2288-2293.
  • 8. Rehder D, Pessoa JC, Geraldes CF, Castro MM, Kabanos T, Kiss T, Meier B, Micera G, Pettersson L, Rangel M, Salifoglou A, Turel I, Wang D. In vitro study of the insulin-mimetic behaviour of vanadium (IV, V) coordination compounds. JBIC Journal of Biological Inorganic Chemistry. 2002; 7:384-396.
  • 9. Halevas E, Tsave O, Yavropoulou MP, Hatzidimitriou A, Yovos JG, Psycharis V, Gabriel C, Salifoglou A. Design, synthesis and characterization of novel binary V (V)-Schiff base materials linked with insulin-mimetic vanadium-induced differentiation of 3T3-L1 fibroblasts to adipocytes. Structure–function correlations at the molecular level. Journal of Inorganic Biochemistry. 2015; 147:99-115.
  • 10. Li SY, Zhai WQ, Li ZW, Li A, Jiang YM, Li W. Synthesis, Crystal Structures and Insulin-Enhancing Activity of Vanadium (V) Complexes with Hydrazone Ligands. Russian Journal of Coordination Chemistry. 2018; 44:701-706.
  • 11. Yuen VG, Orvig C, McNeill JH. Glucose-lowering effects of a new organic vanadium complex, bis (maltolato) oxovanadium (IV). Canadian Journal of Physiology and Pharmacology. 1993; 71:263-269.
  • 12. Cong XQ, Piao MH, Li Y, Xie L, Liu Y. Bis (maltolato) oxovanadium (IV)(BMOV) attenuates apoptosis in high glucose-treated cardiac cells and diabetic rat hearts by regulating the unfolded protein responses (UPRs). Biological Trace Element Research. 2016; 173:390-398.
  • 13. Wang J, Yuen VG, McNeill JH. Effect of vanadium on insulin and leptin in Zucker diabetic fatty rats. Molecular and Cellular Biochemistry. 2001; 218:93-96.
  • 14. Facchini DM, Yuen VG, Battell ML, McNeill JH, Grynpas MD. The effects of vanadium treatment on bone in diabetic and non-diabetic rats. Bone. 2016; 38:368-377.
  • 15. Jakusch T, Kiss T. In vitro study of the antidiabetic behavior of vanadium compounds. Coordination Chemistry Reviews. 2017; 351:118-126.
  • 16. Patra D, Paul S, Sepay N, Kundu R, Ghosh T. Structure-activity relationship on DNA binding and anticancer activities of a family of mixed-ligand oxidovanadium (V) hydrazone complexes. Journal of Biomolecular Structure and Dynamics. 2017; 13:1-13.
  • 17. Torabi S, Mohammadi M, Shirvani M. Antidiabetic, Antioxidant, Antibacterial, and Antifungal Activities of Vanadyl Schiff Base Complexes. Trends in Pharmaceutical Sciences. 2018; 4:87-94.
  • 18. Farzanfar J, Ghasemi K, Rezvani AR, Delarami HS, Ebrahimi A, Hosseinpoor H, Eskandari A, Rudbari HA, Bruno G. Synthesis, characterization, X-ray crystal structure, DFT calculation and antibacterial activities of new vanadium (IV, V) complexes containing chelidamic acid and novel thiourea derivatives. Journal of Inorganic Biochemistry. 2015; 147:54-64.
  • 19. Chen XF, Wang TR, Ma Z, Yu Y, Tang L, Jin LY, Sheng GH, Zhu HL. Synthesis, crystal structures and insulin-like activity of two new oxidovanadium (V) complexes with aroylhydrazones and maltol mixed-ligands. Polyhedron. 2017; 137:321-324.
  • 20. Zhao X, Chen X, Li J, Chen J, Sheng G, Niu F, Qu D, Huo Y, Zhu H, You Z. Synthesis, structures and insulin-like activity of oxidovanadium (V) complexes with aroylhydrazones and ethylmaltol mixed-ligands. Polyhedron. 2015; 97:268-272.
  • 21. Thompson, K.H., Lichter J, LeBel K, Scaife MC, McNeill JH, Orvig C, Vanadium treatment of type 2 diabetes: A view to the future. Journal of Inorganic Biochemistry, 2009; 103:554-558
  • 22. Prakash A, Adhikari D. Application of Schiff bases and their metal complexes-A Review. International Journal of ChemTech Research. 2011; 3:1891-1896.
  • 23. Zaheer M, Shah A, Akhter Z, Qureshi R, Mirza B, Tauseef M, Bolte M. Synthesis, characterization, electrochemistry and evaluation of biological activities of some ferrocenyl Schiff bases. Applied Organometallic Chemistry. 2011; 25:61-69.
  • 24. Hranjec M, Starčević K, Pavelić SK, Lučin P, Pavelić K, Zamola GK. Synthesis, spectroscopic characterization and antiproliferative evaluation in vitro of novel Schiff bases related to benzimidazoles. European Journal of Medicinal Chemistry. 2011; 46:2274-2279.
  • 25. Dümmling S, Eichhorn E, Schneider S, Speiser B, Würde M. Recycling of the Supporting Electrolyte Tetra(n-butyl)ammonium Hexafluorophosphate from Used Electrolyte Solutions. Current Separations. 1996; 5:53-56.
  • 26. Nonius COLLECT. Nonius BV, Delft, The Netherlands; 1998.
  • 27. Otwinowski Z, Minor W., Processing of X-ray diffraction data collected in oscillation mode. Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by Carter Jr CW, Sweet RM, New York: Academic Press; 1997. p. 307–326.
  • 28. Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallographica C Structural Chemistry. 2015; 71:3-8.
  • 29. Brandenburg K, Putz H. DIAMOND. Crystal Impact GbR, Bonn, Germany; 2015.
  • 30. Repich HH, Orysyk SI, Orysyk VV, Zborovskii YL, Melnyk AK, Trachevskyi VV, Pekhnyo VI, Vovk MV. Influence of synthesis conditions on complexation of Cu (II) with O,N,O tridentate hydrazone ligand. X-ray diffraction and spectroscopic investigations. Journal of Molecular Structure. 2017; 1146:222- 232.
  • 31. Luo W, Meng X-G, Xiang J-F, Duan Y, Cheng G-Z, Ji Z-P. Synthesis, characterization and bioactivity of four novel trinuclear copper(II) and nickel(II) complexes with pentadentate ligands derived from Nacylsalicylhydrazide. Inorganica Chimica Acta. 2008; 361:2667-2676.
  • 32. Wilde F, Lemmerhirt H, Emmrich T, Bednarski PJ, Link A. Microwave-assisted synthesis and evaluation of acylhydrazones as potential inhibitors of bovine glutathione peroxidase. Molecular Diversity. 2014;18:307-322.
  • 33. Repich HH, Orysyk SI, Orysyk VV, Zborovskii YL, Pekhnyo VI, Vovk MV. Synthesis, crystal structure and spectral characterization of the first Ag+ complex compounds involving O,N,O-coordinated N-acylhydrazones of salicylaldehyde. Journal of Molecular Structure. 2017; 1144:225-236.
  • 34. Luo W, Wang XT, Meng X-G, Cheng G-Z, Ji Z-P. Metal coordination architectures of N-acylsalicylhydrazides: The effect of metal ions and steric repulsion of ligands to their structures of polynuclear metal complexes. Polyhedron. 2009; 28:300- 306.
  • 35. Gryboś R, Szklarzewicz J, Jurowska A, Hodorowicz M. Properties, structure and stability of V(IV) hydrazide Schiff base ligand complex. Journal of Molecular Structure. 2018; 1171:880-887.
  • 36. Mathew M, Carty AJ, Palenik GJ. An Unusual Complex Containing Bridging Vanadyl Groups. The Crystal Structure of N,N′-Propylenebis(salicylaldiminato)oxovanadium(IV). Journal of the American Chemical Society 1970; 92:3197–3198.
  • 37. Cashin B, Cunningham D, Daly P, McArdle P, Munroe M, Ní Chonchubhair N. Donor properties of the vanadyl ion: Reactions of vanadyl salicylaldimine β-ketimine and acetylacetonato complexes with groups 14 and 15 Lewis acids. Inorganic Chemistry. 2002; 41:773–782.
  • 38. Schilt A, Taylor RC. Infra-red spectra of 1: 10-phenanthroline metal complexes in the rock salt region below 2000 cm-1. Journal of Inorganic and Nuclear Chemistry. 1959; 9:211-221.
Uwagi
Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-67815f86-21cb-49b8-945a-d23dbed09c35
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