Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones

Yıl: 2021 Cilt: 45 Sayı: 3 Sayfa Aralığı: 835 - 844 Metin Dili: İngilizce DOI: 10.3906/kim-2101-12 İndeks Tarihi: 29-06-2022

Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones

Öz:
Six nickel(II) complexes of the $N_2 O_2$ chelating thiosemicarbazones were synthesized using $N^1 -4-$benzyloxysalicylidene-Smethyl/propyl thiosemicarbazone and methoxy-substitute-salicylaldehydes in the presence of Ni(II) ion by template reaction. The structures of thiosemicarbazones and nickel(II) complexes were characterized by elemental analysis, UV-Vis, IR, and 1 H-NMR spectroscopies. The structure of the $N^1 -4-$benzyloxysalicylidene-S-propyl thiosemicarbazone (2) was determined by X-ray single-crystal diffraction method. The total antioxidant capacities of synthesized compounds were evaluated by using cupric reducing antioxidant capacity (CUPRAC) method. The thiosemicarbazones exhibited more potent antioxidant capacity than Ni(II) complexes. Trolox equivalent antioxidant capacity (TEAC) of 1c was found highest in tested nickel(II) complexes. In addition, antioxidant activities of tested compounds were evaluated by using the hydroxyl radical, DPPH radical, and ABTS radical scavenging abilities of these compounds.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 1. Weinert M, Prostenik M, Stanecev NZ. Identification of normal, higher aliphatic aldehydeby means of the melting point data of the thiosemicarbazone. Croatica Chemica Acta 1962; 34: 1-6.
  • 2. Padhye S, Kauffman GB. Transition metal complexes of semicarbazones and thiosemicarbazones. Coordination Chemistry Reviews 1985; 63: 127-160. doi:10.1016/0010-8545(85)80022-9
  • 3. Takjoo R, Hashemzadeh A, Rudbari HA, Nicola F. Copper(II) and molybdenum(VI) complexes with 5-bromosalicylaldehyde S-allylisothiosemicarbazone: Syntheses, characterizations and crystal structures. Journal of Coordination Chemistry 2013; 66 (2): 343- 357. doi:10.1080/00958972.2012.748191
  • 4. Revenco MD, Palamarciuc OV, Bourosh PN, Lipkowski J, Gdaniec M et al. New template reactions of salicylaldehyde S-methylisothiosemicarbazone with 2-formylpyridine promoted by Ni(II) or Cu(II) metal ions. Inorganica Chimica Acta 2011; 368: 157-164. doi:10.1016/j.ica.2010.12.068
  • 5. Eğlence-Bakır S, Şahin M, Salt BZ, Tüzün E, Mataracı-Kara E et al. Palladium (II) complexes with thione and thioalkylated thiosemicarbazones: Electrochemical, antimicrobial and thermogravimetric investigations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2020; 237: 118358. doi:10.1016/j.saa.2020.118358
  • 6. Şahin M, Eğlence-Bakır S, Alpay M, Alpay S, Özmerdivenli R et al. Effective copper (II) and nickel (II) complexes with $N_3O and ON_3$ thiosemicarbazidato ligands. Synthesis, structural analysis and in vitro cytotoxity on melanoma B16F10 cells. Inorganica Chimica Acta 2020; 502: 119347. doi:10.1016/j.ica.2019.119347
  • 7. Kalaivani P, Prabhakaran R, Kaveri MV, Huang R, Staples RJ et al. Synthesis, spectral, X-ray crystallography, electrochemistry, DNA/ protein binding and radical scavenging activity of new palladium(II) complexes containing triphenylarsine. Inorganica Chimica Acta 2013; 405: 415-426. doi:10.1016/j.ica.2013.06.038
  • 8. Leovac VM, Gerbeleu NV, Canic VD. Coordination compounds of cobalt (III), chromium (III), and vanadium (III) with salicylaldehyde S-methylthiosemicarbazone. Russian Journal of Inorganic Chemistry 1982; 27: 514-517.
  • 9. Meghdadi S, Amirnasr M, Majedi M, Bagheri M, Amiri A et al. Template synthesis, and X-ray crystal structures of copper(II)and nickel(II) complexes of new unsymmetrical tetradentate Schiff base ligands. Electrochemistry, antibacterial properties, and metal ion effection hydrolysis–recondensation of the ligand. Inorganica Chimica Acta 2015; 437: 64-69. doi:10.1016/j.ica.2015.08.006
  • 10. Bal-Demirci T, Şahin M, Kondakçı E, Özyürek M, Ülküseven B et al. Synthesis and antioxidant activities of transition metal complexes based 3-hydroxysalicylaldehyde-S-methylthiosemicarbazone. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015; 138: 866-872. doi:10.1016/j.saa.2014.10.088
  • 11. Gerbeleu V, Revenco MD. Russian Journal of Inorganic Chemistry 1971; 16: 1046.
  • 12. Bavin EM, Rees RJW, Robson JM, Seiler M, Seymour DE et al. The tuberculostatic activity of some thiosemicarbazones. Journal of Pharmacy and Pharmacology 1950; 2 (1): 764-772. doi:10.1111/j.2042-7158.1951.tb13043.x
  • 13. Pelosi G, Bisceglie F, Bignami F, Ronzi P, Schiavone P et al. Antiretroviral activity of thiosemicarbazone metal complexes. Journal of Medicinal Chemistry 2010, 53 (24): 8765-8769. doi:10.1021/jm1007616
  • 14. Gou Y, Wang J, Chen S, Zhang Z, Zhang Y et al. α-N-heterocyclic thiosemicarbazone Fe (III) complex: Characterization of its antitumor activity and identification of anticancer mechanism. European Journal of Medicinal Chemistry 2016; 123: 354-364. doi:10.1016/j. ejmech.2016.07.041
  • 15. Qi J, Yao Q, Qian K, Tian L, Cheng Z et al. Synthesis, antiproliferative activity and mechanism of gallium (III)-thiosemicarbazone complexes as potential anti-breast cancer agents. European Journal of Medicinal Chemistry 2018; 154: 91-100. doi:10.1016/j.ejmech.2018.05.016
  • 16. Kumar SM, Dhahagani K, Rajesh J, Nehru K, Annaraj J et al. Synthesis, characterization, structural analysis and DNA binding studies of nickel(II)–triphenylphosphine complex of ONS donor ligand–Multisubstituted thiosemicarbazone as highly selective sensor for fluoride ion. Polyhedron 2013; 59: 58-68. doi:10.1016/j.poly.2013.04.048
  • 17. Tang L, Zhou P, Zhang Q, Huang Z, Zhao J et al. A simple quinoline derivatized thiosemicarbazone as a colorimetic and fluorescent sensor for relay recognition of Cu2+ and sulfide in aqueous solution. Inorganic Chemistry Communications 2013; 36: 100-104. doi:10.1016/j. inoche.2013.08.011
  • 18. Tian Y-P, Yu W-T, Zhao C-Y, Jiang M-H, Cai Z-G et al. Structural characterization and second-order nonlinear optical properties of zinc halide thiosemicarbazone complexes. Polyhedron 2002; 21: 1217-1222. doi:10.1016/S0277-5387(02)01004-5
  • 19. Youssef NS, El-Seidy AMA, Schiavoni M, Castano B, Ragaini F et al. Thiosemicarbazone copper complexes as competent catalysts for olefin cyclopropanations. Journal of Organometallic Chemistry 2012; 714: 94-103. doi:10.1016/j.jorganchem.2012.03.018
  • 20. Li MX, Chen CL, Ling CS, Zhou J, Ji BS et al. Cytotoxicity and structure–activity relationships of four α-N-heterocyclic thiosemicarbazone derivatives crystal structure of 2-acetylpyrazine thiosemicarbazone. Bioorganic & Medicinal Chemistry Letters 2009; 19: 2704-2706. doi:10.1016/j.bmcl.2009.03.135
  • 21. Şahin M, Özdemir N, Bal-Demirci T, Ülküseven B, Dinçer M et al. Structural and spectroscopic characterization of a thiosemicarbazi datodioxouranium(VI) complex: A combined experimental and DFT study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015; 135: 994-1001. doi:10.1016/j.saa.2014.08.008
  • 22. Bal-Demirci T, Şahin M, Özyürek M, Kondakçı E, Ülküseven B. Synthesis, antioxidant activities of the nickel(II), iron(III) and oxovanadium(IV) complexes with $N_2O_2$ chelating thiosemicarbazones. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2014; 126: 317-323. doi:10.1016/j.saa.2014.02.039.
  • 23. Bal-Demirci T, Şahin M, Kondakçı E, Özyürek M, Ülküseven B et al. Synthesis and antioxidant activities of transition metal complexes based 3-hydroxysalicylaldehyde-S-methylthiosemicarbazone. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2015; 138: 866-872. doi:10.1016/j.saa.2014.10.088.
  • 24. İlhan-Ceylan B. Oxovanadium(IV) and Nickel(II) complexes obtained from 2,2′-dihydroxybenzophenone-S-methyl-thiosemicarbazone: Synthesis, characterization, electrochemistry, and antioxidant capability. Inorganica Chimica Acta 2020; 517: 120816. doi:10.1016/j. ica.2020.120186
  • 25. Eğlence S, Şahin M, Özyürek M, Apak R, Ülküseven B. Dioxomolybdenum(VI) complexes of S-methyl-5-bromosalicylidene-N-alkyl substituted thiosemicarbazones: Synthesis, catalase inhibition and antioxidant activities. Inorganica Chimica Acta 2018; 469: 495-502. doi:10.1016/j.ica.2017.10.007
  • 26. Apak R, Güçlü K, Özyürek M, Karademir SE. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of Agricultural and Food Chemistry 2004; 52 (26): 7970-7981. doi:10.1021/jf048741x
  • 27. Kaya Y, Erçağ A, Koca A. New square-planar nickel(II)-triphenylphosphine complexescontaining ONS donor ligands: Synthesis, characterization, electrochemical and antioxidant properties. Journal of Molecular Structure 2020; 1206: 127653. doi:10.1016/j. molstruc.2019.127653
  • 28. Sánchez‐Moreno C, Larrauri JA, Saura‐Calixto F. A procedure to measure the antiradical efficiency of polyphenols. Journal of the Science of Food and Agriculture 1998; 76 (2): 270-276. doi:10.1002/(SICI)1097-0010(199802)76:2<270::AID-JSFA945>3.0.CO;2-9
  • 29. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M et al. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free radical biology and medicine 1999; 26 (9-10): 1231-1237. doi:10.1016/S0891-5849(98)00315-3
  • 30. Özyürek M, Bektaşoğlu B, Güçlü K, Apak R. Hydroxyl radical scavenging assay of phenolics and flavonoids with a modified cupric reducing antioxidant capacity (CUPRAC) method using catalase for hydrogen peroxide degradation. Analytica Chimica Acta 2008; 616 (2): 196-206. doi:10.1016/j.aca.2008.04.033
  • 31. SHELXTL, version 6.14, Bruker AXS Inc.: Madison, WI; 2000.
  • 32. Farrugia L. J. ORTEP-3 for Windows-a version of ORTEP-III with a graphical user interface (GUI). Journal of Applied Crystallography 1997; 30 (5): 565-565. doi:10.1107/S0021889897003117
  • 33. Eğlence-Bakır S, Saçan Ö, Şahin M., Yanardağ R, Ülküseven B. Dioxomolybdenum(VI) complexes with 3-methoxy salicylidene-N-alkyl substituted thiosemicarbazones. Synthesis, characterization, enzyme inhibition and antioxidant activity. Journal of Molecular Structure 2019; 1194: 35-41. doi:10.1016/j.molstruc.2019.05.077
  • 34. Kumar LV, Nath GR. Synthesis, characterization and biological studies of cobalt(II), nickel(II), copper(II) and zinc(II) complexes of vanillin-4-methyl-4-phenyl-3-thiosemicarbazone. Journal of Chemical Sciences 2019; 131: 76. doi:10.1007/s12039-019-1658-x
  • 35. Fetoh A, Mohammaed MA, Youssef MM, El-rash GMA. Characterization, cyclic voltammetry and biological studies of divalent Co, Ni and Cu complexes of water-soluble, bioactive and photoactivethiosemicarbazone salt. Journal of Molecular Liquids 2019; 287: 110958. doi:10.1016/j.molliq.2019.110958
  • 36. Jacob JM, Prathapachandra-Kurup MR, Nisha K, Serdaroğlu G, Kaya S. Mixed ligand copper(II) chelates derived from an O, N, Sdonortridentate thiosemicarbazone: Synthesis, spectral aspects, FMO, and NBO analysis. Polyhedron 2020; 189: 114736. doi:10.1016/j. poly.2020.114736
  • 37. Bhowmick AC, Bikash DN, Moim MI. coordination complexes of transition metals and schiff base with potent medicinal activity. American Journal of Chemistry 2019; 9 (4): 109-114. doi:10.5923/j.chemistry.20190904.01
  • 38. Güveli Ş, Nickel(II)-PPh3 complexes of substituted benzophenone thiosemicarbazones: Electrochemistry, structural analysis, and antioxidant properties. Journal of Coordination Chemistry 2020; 73 (1): 137-153. doi:10.1080/00958972.2020.1711888
  • 39. Şahin M, Koca A, Özdemir N, Dinçer M, Büyükgüngör O et al. Synthesis, X-ray crystal structures, thermal and electrochemical properties of thiosemicarbazidatodioxouranium(VI) complexes. Dalton Transactions 2010; 39: 10228-10237. doi:10.1039/C0DT00265H
  • 40. Takjoo R, Centore R, Akbari A, Ahmadi M. Square planar nickel(II) complexes derived from 5-bromo-2-hydroxybenzaldehyde S-ethylisothiosemicarbazone: Preparation, characterization and structural studies. Polyhedron 2014; 80: 243-249. doi:10.1016/j. poly.2014.04.055
  • 41. Desiraju G. R. and Steiner T. The Weak Hydrogen Bond: In Structural Chemistry and Biology. 2001; Vol. 9. International Union of Crystal.
APA EGLENCE-BAKIR S (2021). Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. , 835 - 844. 10.3906/kim-2101-12
Chicago EGLENCE-BAKIR Songul Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. (2021): 835 - 844. 10.3906/kim-2101-12
MLA EGLENCE-BAKIR Songul Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. , 2021, ss.835 - 844. 10.3906/kim-2101-12
AMA EGLENCE-BAKIR S Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. . 2021; 835 - 844. 10.3906/kim-2101-12
Vancouver EGLENCE-BAKIR S Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. . 2021; 835 - 844. 10.3906/kim-2101-12
IEEE EGLENCE-BAKIR S "Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones." , ss.835 - 844, 2021. 10.3906/kim-2101-12
ISNAD EGLENCE-BAKIR, Songul. "Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones". (2021), 835-844. https://doi.org/10.3906/kim-2101-12
APA EGLENCE-BAKIR S (2021). Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. Turkish Journal of Chemistry, 45(3), 835 - 844. 10.3906/kim-2101-12
Chicago EGLENCE-BAKIR Songul Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. Turkish Journal of Chemistry 45, no.3 (2021): 835 - 844. 10.3906/kim-2101-12
MLA EGLENCE-BAKIR Songul Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. Turkish Journal of Chemistry, vol.45, no.3, 2021, ss.835 - 844. 10.3906/kim-2101-12
AMA EGLENCE-BAKIR S Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. Turkish Journal of Chemistry. 2021; 45(3): 835 - 844. 10.3906/kim-2101-12
Vancouver EGLENCE-BAKIR S Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones. Turkish Journal of Chemistry. 2021; 45(3): 835 - 844. 10.3906/kim-2101-12
IEEE EGLENCE-BAKIR S "Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones." Turkish Journal of Chemistry, 45, ss.835 - 844, 2021. 10.3906/kim-2101-12
ISNAD EGLENCE-BAKIR, Songul. "Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazones". Turkish Journal of Chemistry 45/3 (2021), 835-844. https://doi.org/10.3906/kim-2101-12