One pot synthesis and spectral characterization of 5-Substitutedfuran-2-carbaldehyde N4-cyclohexyl thiosemicarbazones and their Ni(II) complexes

Yıl 2020, , 81 - 86, 29.12.2020

Ayşegül İyidoğan , Emine Elçin Oruç-emre , Ülkü Çakır

https://doi.org/10.51435/turkjac.813792

Öz

In this work, the synthesis of thiosemicarbazones (I-V) was carried out using one pot method, multicomponent and catalyst-free reaction of cyclohexyl isothiocyanate, hydrazine monohydrate and 5-substituted-2-furancarbaldehydes in good yields. The chemical structures of 5-substituted-2-furancarbaldehyde thiosemicarbazones were eludicated using UV‐Vis, IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. Also, the reaction of NiCl2.6H2O with thiosemicarbazones in 1:2 molar ratio by refluxing gave the nickel (II) complexes (Ia-Va) as binuclear and their structures characterized by UV-Vis, IR, and elemental analysis.

Anahtar Kelimeler

one pot synthesis, thiosemicarbazones, nickel complexes

Destekleyen Kurum

Scientific Research Projects Governing Unit Council of Scientific Research Projects

Proje Numarası

Grant no. FEF.08.10

Teşekkür

This work was supported by Scientific Research Projects Governing Unit Council of Scientific Research Projects (Grant no. FEF.08.10), Gaziantep, Turkey.

Kaynakça

• [1] T.S. Lobana, R. Sharma, G. Bawa, S. Khanna, Bonding and structure trends of thiosemicarbazone derivatives of metals-An overview, Coord Chem Rev, 253, 2009, 977-1055.
• [2] S. Savir, Z.J. Wei, J.W.K. Liew, I. Vythilingam, Y.A.L. Lim, H.M. Saad, K.S. Sim, K.W. Tan, Synthesis, cytotoxicity and antimalarial activities of thiosemicarbazones and their nickel (II) complexes, J Mol Struct, 1211, 2020, 128090.
• [3] C. Bonaccorso, T. Marzo, D. La Mendola, Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review, Pharmaceuticals, 13(4), 2020, 1-19.
• [4] A.l. Matesanz, P. Albacete, P. Souza, Synthesis and characterization of a new bioactive mono(thiosemicarbazone) ligand based on 3,5-diacetyl-1,2,4-triazol diketone and its palladium and platinum complexes, Polyhedron 109, 2016, 161-165.
• [5] T.P. Stanojkovic, D. Kovala-Demertzi, A. Primikyri, I. Garcia-Santos, A. Castineiras, Z.Juranic, M.A. Demertzis, Zinc(II) complexes of 2-acetyl pyridine 1-(4-fluorophenyl)-piperazinyl thiosemicarbazone: Synthesis, spectroscopic study and crystal structures– Potential anticancer drugs J. Inorg. Biochem. 104 (2010) 467- 476.
• [6] V.M. Leovac, S.B. Novakovic, G.A. Bogdanovic, M.D. Joksovic, K.M. Szecsenyi, V.I. Cesljevic, Transition metal complexes with thiosemicarbazide-based ligands. Part LVI: Nickel(II) complex with 1,3-diphenylpyrazole-4-carboxaldehyde thiosemicarbazone and unusually deformed coordination geometry, Polyhedron, 26, 2007, 3783-3792.
• [7] Z. Piri, Z. Moradi-Shoeili, A. Assoud, Ultrasonic assisted synthesis, crystallographic, spectroscopic studies and biological activity of three new Zn(II), Co(II) and Ni(II) thiosemicarbazone complexes as precursors for nano-metal oxides Inorg Chim Acta, 484, 2019, 338- 346.
• [8] N.P. Prajapati, H.D. Patel, Novel thiosemicarbazone derivatives and their metal complexes: Recent development, Synthetic Commun Rev, 2019, 1-38.
• [9] A. Karaküçük-İyidoğan, D. Taşdemir, E.E. Oruç-Emre, J. Balzarini, Novel platinum(II) and palladium(II) complexes of thiosemicarbazones derived from 5-substitutedthiophene-2-carboxaldehydes and their antiviral and cytotoxic activities, Eur J Med Chem, 46, 2011, 5616-5624.
• [10] A. Akbari, H. Ghateazadeh, R. Takjoo, B. Sadeghi-Nejad, M. Mehrvar, J.T. Mague, Synthesis & crystal structures of four new biochemical active Ni(II) complexes of thiosemicarbazone and isothiosemicarbazone-based ligands: In vitro antimicrobial study, J Mol Struct 181, 2019, 287-294.
• [11] E. Bozgeyik, D. Taşdemir-Kahraman, K. Arman, İ. Bozgeyik, A. Karaküçük-İyidoğan, E.A. Çakmak, Novel thiosemicarbazone derivative 17B interferes with the cell cycle progression and induce apoptosis through modulating downstream signaling pathways, Gene Reports, 18, 2020, 100578.
• [12] A. Karaküçük-İyidoğan, Z. Mercan, E.E. Oruç-Emre, D. Taşdemir, D. İşler, İ.H. Kılıç, M. Özaslan, Synthesis, characterization, and biological evaluation of some novel thiosemicarbazones as possible antibacterial and antioxidant agents, Phosphorous, Sulfur and Silicon and Related Elements, 189, 2014, 661-673.
• [13] M.T. Shehzad, A.Imranb, G.S.S. Njateng, A. Hameed , M. Islam , M. al-Rashida, M. Uroos, A. Asari, Z. Shafiq, J. Iqbal, Benzoxazinone-thiosemicarbazones as antidiabetic leads via aldose reductase inhibition: Synthesis, biological screening and molecular docking study, Bioorg Chem, article in press, doi: 10.1016/j.bioorg.2018.12.006.
• [14] H.B. Shawish, W.Y. Wong, Y.L. Wong, S.W. Loh, C.Y. Looi, P. Hassandarvish, A.Y.L. Phan, W.F. Wong, H. Wang, I.C. Paterson, C.K. Ea, M.R. Mustafa, M.J. Maah, Nickel(II) Complex of Polyhydroxybenzaldehyde N4- Thiosemicarbazone Exhibits Anti-Inflammatory Activity by Inhibiting NF-kB Transactivation, PLoS One, 9(6), 2014, e100933.
• [15] J.S. Casas, M.S. Garcia-Tasende, J. Sordo, Main group metal complexes of semicarbazones and thiosemicarbazones. A structural review, Coord Chem Rev, 209, 2000, 197-261.
• [16] V.V. Bon, S.I. Orysyk, V.I. Pekhnyo, S.V. Volkov, Square-planer 1:2 Ni(II) and Pd(II) complexes with different coordination mode of salicylaldehyd (4)-phenylthiosemicarbazone: synthesis, structure and spectral properties, J Mol Struct, 984, 2010, 15-22.
• [17] E. Pahontu, C. Paraschivescu, D.-C. Ilieş, D. Poirier, C. Oprean, V. Paunescu, A. Gulea, T. Roşu, O. Bratu, Synthesis and characterization of novel Cu(II), Pd(II) and Pt(II) complexes with 8-ethyl-2-hydroxytricyclo(7.3.1.02,7)tridecan-13-one thiosemicarbazone: antimicrobial and in vitro antiproliferative activity, Molecules, 21, 674, 2016, 1-18.
• [18] I. Pal, F. Basuli, S. Bhattacharya, Thiosemicarbazone complexes of the platinum metals. A story of variable coordination modes, Proc Indian Acad Sci (Chem Sci), 114, 2002, 255-268.
• [19] S. Cunha, T.L. da Silva, One-pot and catalyst-free synthesis of thiosemicarbazones via multicomponent coupling reactions, Tetrahedron Lett, 50, 2009, 2090-2093.
• [20] D. Taşdemir, A. Karaküçük-İyidoğan, M. Ulaşlı, T. Taşkın-Tok, E.E. Oruç-Emre, H. Bayram, Synthesis, molecular modeling, and biological evaluation of novel chiral thiosemicarbazone derivatives as potent anticancer agents, Chirality, 27, 2015, 177-188.
• [21] A. Karaküçük-İyidoğan, B. Aydınöz, T. Taşkın-Tok, E.E. Oruç-Emre, J. Balzarini, Synthesis, biological evaluation and ligand based pharmacophore modeling of new aromatic thiosemicarbazones as potential anticancer agents, Pharm Chem J, 53(2), 2019, 139-149.
• [22] M.-H. Shih, Y.-Y. Xu, Y.-S. Yang, T.-T. Lin, Syntheses of Nickel (II) complexes from novel semicarbazone ligands with chloroformylarylhydrazine, benzimidazole and salicylaldehyde moieties, Molecules, 20, 2015, 5184-5201.
• [23] D. Bahl, F. Athar, M.B.P. Soares, M.S. de Sa, D.R.M. Moreira, R.M. Srivastava, A.C.L. Leite, A. Azam, Structure–activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities, Bioorg Med Chem, 18, 2010, 6857-6864.
• [24] E.M. Jouad, A. Riou, M. Allain, M.A. Khan, G.M. Bouet, Synthesis, structural and spectral studies of 5-methyl 2-furaldehyde thiosemicarbazone and its Co, Ni, Cu and Cd complexes, Polyhedron, 20, 2001, 67-74.
• [25] E. Viñuelas-Zahínos, F. Luna-Giles, P. Torres-García, M.C. Fernández-Calderón, Co(III), Ni(II), Zn(II) and Cd(II) complexes with 2-acetyl-2-thiazoline thiosemicarbazone: synthesis, characterization, X-ray structures and antibacterial activity, Eur J Med Chem, 46, 2011, 150-159.
• [26] M.B. Ferrari, S. Capacchi, F. Bisceglie, G. Pelosi, P. Tarasconi, Synthesis and characterization of square planar nickel(II) complexes with p-fluorobenzaldehyde thiosemicarbazone derivatives, Inorg Chim Acta, 312, 2001, 81-87.
• [27] Y. Li, Z.-Y. Yang, J.-C. Wu, Synthesis, crystal structures, biological activities and fluorescence studies of transition metal complexes with 3-carbaldehyde chromone thiosemicarbazone, Eur J Med Chem, 45, 2010, 5692-5701.
• [28] L. Latheef, M.R.P. Kurup, Spectral and structural studies of nickel(II) complexes of salicylaldehyde 3-azacyclothiosemicarbazones, Polyhedron, 27, 2008, 35-43.
• [29] U.M. Osman, S. Silvarajoo, K.H. Kamarudin, M.I.M. Tahir, K.H. Chong, Ni(II) complex containing a thiosemicarbazone ligand: Synthesis, spectroscopy, single-crystal X-ray crystallographic and conductivity studies, J Mol Struct, 2020, article in press, doi: 10.1016/j.molstruc.2020.128994.
• [30] M.C. Rodríguez-Argüelles, P. Tourón-Touceda, R. Cao, A.M. García-Deibe, P. Pelagatti, C. Pelizzi, F. Zani, Complexes of 2-acetyl-γ-butyrolactone and 2-furancarbaldehyde thiosemicarbazones: Antibacterial and antifungal activity, J Inorg Biochem, 103, 2009, 35-42.
• [31] A.H. Pathan, R.P. Bakale, G.N. Naik, C.S. Frampton, K.B. Gudasi, Synthesis, crystal structure, redox behavior and comprehensive studies on DNA binding and cleavage properties of transition metal complexes of a fluorosubstituted thiosemicarbazone derived from ethyl pyruvate, Polyhedron, 34, 2012, 149-156.