Co(II), Ni(II), and Cu(II) metal complexes based on thiourea ligand: synthesis, characterization, thermal behaviors, anticancer, and antioxidant activities

References

• Abdlseed, F. A.; El-Ajaily, M. M. Preparation and spectroscopic investigation of a schiff base metal complexes. Int. J. Chem. Tech. Res. 2009, 1, 1097–1103.
   Google Scholar
• Benzet, G.; Arslan, H.; Kulcu, N. Synthesis and thermal behaviour of Co(II), Ni(II) and Cu(II) complexes of N,N-di-n-propyl-N’-(2-chlorobenzoyl)thiourea. Asian J. Chem. 2007, 19, 5711–5717.
   Google Scholar
• Bailey, R. A.; Rothaupt, K. L.; Kullnig, R. K. Synthesis and structure of bis(1,1-diethyl-3-(2-chlorobenzoyl)thioureido)nickel(II). InorganicChimicaActa 1988, 147, 233–236. DOI: 10.1016/S0020-1693(00)83377-0.
   Google Scholar
• Bensch, W.; Schuster, M. Komplexierungvon gold mit N,N-dialkyl-N’-Benzoylthioharnstoffen: DieKristallstrukturvonN,N-diethyl-N_-Benzoylthioureatogold(I)-Chlorid. J. Inorg. Gen. Chem. 1992, 611, 99–102. DOI: 10.1002/zaac.19926110517.
   Google Scholar
• Che, D.-J.; Li, G.; Yao, X.-L.; Wu, Q.-J.; Wang, W.-L.; Zhu, Y. Photochemicalgeneration of a novel(O, N_ N_) coordinatediron(II) complex [Fe(FT-py)2] from a ferrocenoyl-functionalized thiourea ligand: N-ferrocenylcarbonyl-N’-(2-pyridyl)thiourea (HFT-py):crystal and molecular structures of HFT-Pyand [Fe(FT-py)2]. J. Organometa. Chem. 1999, 584, 190–196. DOI: 10.1016/S0022-328X(99)00138-2.
   Web of Science ®Google Scholar
• Pérez, H.; Corrêa, R. S.; Plutín, A. M.; Calderon, O.; Duque, J. cis-Bis[N-(2-furoyl)-N',N'-diphenyl-thio-ureato-κO,S]nickel(II) ). Acta Crystallogr. Sect. E Struct. Rep. Online 2009, 65, m242. DOI: 10.1107/S160053680900302X.
   PubMedGoogle Scholar
• Pérez, H.; Corrêa, R. S.; O’Reilly, B.; Plutín, A. M.; Silva, C. C. P.; Mascarenhas, Y. P. Spectroscopic characterization and crystal structure of cis-Bis(N-(2-benzoyl)-N’,N’-diphenylthioureato-κ2O,S)nickel(II). J. Struct. Chem. 2012, 53, 921–926. DOI: 10.1134/S0022476612050137.
   Web of Science ®Google Scholar
• Muller, J.; Limban, C.; Stadelmann, B.; Missir, A. V.; Chirita, I. C.; Chifiriuc, M. C.; Nitulescu, G. M.; Hemphill, A. Thioureides of 2-(phenoxymethyl) benzoic acid 4-r substituted: a novel class of anti-parasitic compounds. Parasitol. Int. 2009, 58, 128–135. DOI: 10.1016/j.parint.2008.12.003.14.
   PubMed Web of Science ®Google Scholar
• Shing, J. C.; Choi, J. W.; Chapman, R.; Schroeder, M. A.; Sarkaria, J. N.; Fauq, A.; Bram, R. J. A novel synthetic 1,3-phenyl bis-thiourea compound targets microtubule polymerization to cause cancer cell death. Cancer Biol. Ther. 2014, 15, 895–905. DOI: 10.4161/cbt.28881.
   PubMed Web of Science ®Google Scholar
• Koçyiğit-Kaymakçıoğlu, B.; Rollas, S.; Körceğez, E.; Arıcıoğlu, F. Synthesis and biological evaluation of new N-substituted-N’-(3,5-di/1,3,5-trimethylpyrazole-4-yl)thiourea/urea derivatives. Eur. J. Pharm. Sci. 2005, 26, 97–103. DOI: 10.1016/j.ejps.2005.04.017.
   PubMed Web of Science ®Google Scholar
• Saturnino, C.; Auria, M. D.; Paesano, N.; Saponiero, D.; Cioffi, G.; Buonerba, M.; De Martino, G. Antioxidant activity of thioureidic derivatives I. Farmaco 2003, 58, 823–828. DOI: 10.1016/S0014-827X(03)00139-3.
   Google Scholar
• Ngaini, Z.; Mohd Arif, M. A.; Hussain, H.; Mei, E. S.; Tang, D.; Kamaluddin, D. H. A. Synthesis and antibacterial activity of acetoxybenzoyl thioureas with aryl and amino acid side chains. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 1–7. DOI: 10.1080/10426507.2011.562398.
   Web of Science ®Google Scholar
• Wan Zullkiplee, W. S. H.; Abd Halim, A. N.; Ngaini, Z.; Mohd Ariff, M. A.; Hussain, H. Bis-thiourea bearing aryl and amino acids side chains and their antibacterial activities. Phosphorus, Sulfur Silicon Relat. Elem. 2014, 189, 832–838. DOI: 10.1080/10426507.2013.858250.
   Web of Science ®Google Scholar
• Saeed, S.; Rashid, N.; Jones, P. G.; Hussain, R.; Bhatt, M. H. Synthesis, spectroscopic characterization, crystal structure and antifungal activity of thiourea derivatives containing a thiazole moiety. Central Eur. J. Chem. 2010, 8, 550–558. DOI: 10.2478/s11532-010-0014-2.
   Web of Science ®Google Scholar
• Kucukguzel, I.; Tatar, E.; Kucukguzel, S. G.; Rollas, S.; De Clercq, E. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur. J. Med. Chem. 2008, 43, 381–392. DOI: 10.1016/j.ejmech.2007.04.010.
   PubMed Web of Science ®Google Scholar
• Ke, S. Y.; Xue, S. J. Synthesis and herbicidal activity of N-(o-fluoro phenoxyacetyl)thioureas derivatives and related fused heterocyclic compounds. Arkivoc 2006, 10, 63–70.
   Web of Science ®Google Scholar
• Zhang, Y. M.; Wei, T. B.; Xian, L.; Gao, L. M. An efficient synthesis of polymethylene-bis-aroyl thioure derivatives under the condition of phase transfer catalysis. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 2007–2019. DOI: 10.1080/10426500490473456.
   Web of Science ®Google Scholar
• Duan, L.-P.; Xue, J.; Xu, L.-L.; Zhang, H.-B. Synthesis 1-acyl-3-(2'-aminophenyl) thioureas as anti-intestinal nematode prodrugs . Molecules 2010, 15, 6941–6947. DOI: 10.3390/molecules15106941.
   PubMed Web of Science ®Google Scholar
• Saeed, A.; Rafique, H.; Hameed, A.; Rasheed, S. Synthesis and antibacterial activity of somenew1-aroyl-3-(substituted-2-benzothiazolyl)thioureas. Pharmacet. Chem. J. 2008, 42, 191. DOI: 10.1007/s11094-008-0094-x.
   Google Scholar
• Cunha, S.; Macedo, F. C.; Costa, G. A. N.; Rodrigues, M. T.; Verde, R. B. V.; de Souza Neta, L. C.; Vencato, I.; Lariucci, C.; Sá, F. P. Antimicrobial activity and structural study of disubstituted thiourea derivatives. Monatsh. Chem. 2007, 138, 511–516. DOI: 10.1007/s00706-007-0600-y.
   Web of Science ®Google Scholar
• Atiş, M.; Karipcin, F.; Sarıboğa, B.; Taş, M.; Çelik, H. Structural, antimicrobial and computational characterization of 1-benzoyl-3-(5-chloro-2-hydroxyphenyl)thiourea. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2012, 98, 290–301. DOI: 10.1016/j.saa.2012.08.020.
   PubMed Web of Science ®Google Scholar
• Saeed, S.; Rashid, N.; Jones, P. G.; Ali, M.; Hussain, R. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents. Eur. J. Med. Chem. 2010, 45, 1323–1331. DOI: 10.1016/j.ejmech.2009.12.016.
   PubMed Web of Science ®Google Scholar
• Mishra, A.; Srivastava, K.; Tripathi, R.; Puri, S. K.; Batra, S. Search for new pharmacophores for antimalarial activity. part III: synthesis and bioevaluation of new 6-thioureido-4-anilinoquinazolines . Eur. J. Med. Chem. 2009, 44, 4404–4412. DOI: 10.1016/j.ejmech.2009.06.001.
   PubMed Web of Science ®Google Scholar
• Ke, S.-Y.; Xue, S.-J. Synthesis and herbicidal activity of N-(o-fluorophenoxyacetyl) thioure as derivatives and related fused heterocyclic compounds. Arkivoc J. 2006, x, 63.
   Google Scholar
• Du, X.; Hansell, E.; Engel, J. C.; Caffrey, C. R.; Cohen, F. E.; McKerrow, J. H. Arylureas represent a new class of antitrypanosomalagents. Cell Chem. Biol. 2000, 7, 733–742. DOI: 10.1016/S1074-5521(00)00018-1.
   Google Scholar
• Sun, C.; Huang, H.; Feng, M.; Shi, X.; Zhang, X.; Zhou, P. A Novel class of potent influenza virus inhibitors: polysubstitutedacylthiourea and its fused heterocycle derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 162–166. DOI: 10.1016/j.bmcl.2005.09.033.
   PubMed Web of Science ®Google Scholar
• Yeşilkaynak, T. 2-Chloro-N-((5-chloropyridine-2-yl)carbamothioyl)benzamide and its Co(II), Ni(II) and Cu(II) metal complexes: synthesis, characterization, thermal decomposition, electrochemical behavior and antioxidant activity. J. Therm. Anal. Calorim. 2016, 124, 1029–1037. DOI: 10.1007/s10973-015-5221-9.
   Web of Science ®Google Scholar
• Gunasekaran, N.; Jerome, P.; Ng, S. W.; Tiekink, E. R. T.; Karvembu, R. J. Tris-chelatecomplexes of cobalt (III) with N-[di (alkyl/aryl) carbamothioyl] benzamidederivatives: synthesis, crystallography and catalytic activity in TBHP oxidation of alcohols. J. Mol. Catal. A: Chem. 2012, 353–354, 156–162. DOI: 10.1016/j.molcata.2011.11.019.
   Web of Science ®Google Scholar
• Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. A 2008, 64, 112–122. DOI: 10.1107/S0108767307043930.
   PubMed Web of Science ®Google Scholar
• Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A.; et al. Mercury CSD2.0: new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 2008, 41, 466–470. DOI: 10.1107/S0021889807067908.
   Web of Science ®Google Scholar
• Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Food Sci. Technol.-Lebensmittel-Wissenschaft&Technolgie 1995, 28, 25–30. DOI: 10.1016/S0023-6438(95)80008-5.
   Web of Science ®Google Scholar
• Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 1999, 26, 1231–1237. DOI: 10.1016/S0891-5849(98)00315-3.
   PubMed Web of Science ®Google Scholar
• Oyaizu, M. Antioxidative activities of browning products of glucosamineactionated by organic solvent and thinlayer chromatography. J. Food. Sci. Technol. 1988, 35, 771–775. DOI: 10.3136/nskkk1962.35.11_771.
   Web of Science ®Google Scholar
• Han, J.; Talorete, P. N. T.; Yamada, P.; Isoda, H. Anti-proliferative and apoptotic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cells. Cytotechnology 2009, 59, 45–53. DOI: 10.1007/s10616-009-9191-2.
   PubMed Web of Science ®Google Scholar
• Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; et al. Gaussian 09. Gaussian, Inc.: Wallingford, CT, 2009.
   Google Scholar
• Grimme, S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J. Comput. Chem. 2006, 27, 1787–1799. DOI: 10.1002/jcc.20495.
   PubMed Web of Science ®Google Scholar
• Schäfer, A.; Huber, C.; Ahlrichs, R. Fully optimized contracted gaussian-basis sets of triplezeta valence quality for atoms Li to Kr. J. Chem. Phys. 1994, 100, 5829–5835. DOI: 10.1063/1.467146.
   Web of Science ®Google Scholar
• O'Boyle, N. M.; Tenderholt, A. L.; Langner, K. M. Cclib: a library for package-independent computational chemistry algorithms. J. Comput. Chem. 2008, 29, 839–845. DOI: 10.1002/jcc.20823.
   PubMed Web of Science ®Google Scholar
• Legault, C. Y. CYLview, 1.0b. Université de Sherbrooke: Québec, 2009. (http://www.cylview.org).
   Google Scholar
• Arslan, H.; Külcü, N.; Flörke, U. Synthesis and characterization of copper(II), nickel(II) and cobalt(II) complexes with novel thiourea derivatives. Trans. Metal Chem. 2003, 28, 816–819. DOI: 10.1023/A:1026064232260.
   Web of Science ®Google Scholar
• Binzet, G.; Arslan, H.; Florke, U.; Kulcu, N.; Duran, N. Synthesis, characterization and antimicrobial activities of transition metal complexes of N,N-dialkyl-N'-(2-chlorobenzoyl) thiourea derivatives. J. Coord. Chem. 2006, 59, 1395–1406. DOI: 10.1080/00958970500512633.
   Web of Science ®Google Scholar
• Arslan, H.; Florke, U.; Kulcu, N.; Emen, F. M. Crystal structure and thermal behaviour of copper(II) and zinc(II) complexes with N-pyrrolidine-N'-(2-chloro-benzoyl)thiourea. J. Coord. Chem. 2006, 59, 223–228. DOI: 10.1080/00958970500270992.
   Web of Science ®Google Scholar
• Ugur, D.; Arslan, H.; Kulcu, N. Synthesis, characterization and thermal behavior of 1,1-dialkyl-3-(4-(3,3-dialkylthioureidocarbonyl)benzoyl)thioureaandits Cu(II), Ni(II), and Co(II) complexes. Russ. J. Coord. Chem. 2006, 32, 669–675. DOI: 10.1134/S1070328406090089.
   Web of Science ®Google Scholar
• Emen, F. M.; Arslan, H.; Kulcu, N.; Florke, U.; Duran, N. Synthesis, characterization and antimicrobial activities of some metal complexes with N '-(2-chloro-benzoyl)thiourea ligands: the crystal structure of Fac-[CoL3] and Cis-[PdL2]. Pol. J. Chem. 2005, 79, 1615.
   Google Scholar
• Yeşilkaynak, T.; Flörke, U.; Külcü, N.; Arslan, H. 1-Benzoyl-3-(4-methylpyridin-2-yl)thiourea. Acta Crystallogr. Sect. E 2006, E62, 3934. DOI: 10.1107/S1600536806032302.
   Google Scholar
• Mohamadou, A.; Dechamps, I.; Barbier, J. Copper, nickel and cobalt complexes with N,N-disubstituted, N’benzoylthioureas. Polyhedron 1994, 13, 1363–1370. DOI: 10.1016/S0277-5387(00)81702-7.
   Web of Science ®Google Scholar
• Marcu, A.; Stanila, A.; Rusu, D.; Rusu, M.; Cozar, O. Spectroscopic studies of copper(II) complexes with some amino acids. J. Optoelectron. Adv. Mater. 2007, 9, 741.
   Web of Science ®Google Scholar
• Rao, T. S.; Reddy, K. L.; Lingaiah, P. Synthesis and structural studies of complexes of Co(ll), Ni(ll), Cu(ll), Zn(II) and Cd(ll) with substituted chalcones. Proc. Indian Acad. Sci. (Chem. Sci.) 1988, 100, 363–373.
   Google Scholar
• Selwin, J. R.; Sivasankaran, N. M. Synthesis, characterization and biological studies of some Co(II), Ni(II) and Cu(II) complexes derived from indole-3-carboxaldehyde and glycylglycine as schiff base. Arabian J. Chem. 2010, 3, 195–204. DOI: 10.1016/j.arabjc.2010.05.001.
   Web of Science ®Google Scholar
• Alaghaz, A. M. A.; Bayoumi, H. A.; Ammar, Y. A.; Aldhlmani, S. A. Synthesis, characterization, and antipathogenic studies of some transition metal complexes with N,O-chelating schiff’s base ligand incorporating azo and sulfonamide moieties. J. Mol. Struct. 2013, 1035, 383–399. DOI: 10.1016/j.molstruc.2012.11.030.
   Web of Science ®Google Scholar
• Alaghaz, A. M. A.; Ammar, R. A. New dimeric cyclodiphosph(V)azane complexes of Cr(III), Co(II), Ni(II), Cu(II), and Zn(II): preparation, characterization and biological activity studies. Eur. J. Med. Chem. 2010, 45, 1314–1322. DOI: 10.1016/j.ejmech.2009.12.008.
   PubMed Web of Science ®Google Scholar
• Sönmez, M. Synthesis and characterization of copper(II), nickel(II), cadmium(II), cobalt(II) and zinc(II) complexes with 2-benzoyl-3-hydroxy-1-naphthylamino-3-phenyl-2- propen-1-on. Turk J. Chem. 2001, 25, 181–185.
   Web of Science ®Google Scholar
• Binzet, G.; Emen, F. M.; Flörke, U.; Yeşilkaynak, T.; Külcü, N.; Arslan, H. 4-Chloro-N-[N-(6-methyl-2-pyrid-yl)car-bamo-thio-yl]benzamide. Acta Crystallogr. Sect. E Struct. Rep. Online 2008, 65, o81–o82. DOI: 10.1107/S1600536808041123.
   Google Scholar
• Emen, F. M.; Flörke, U.; Külcü, N.; Arslan, H. cis-Bis(N,N-dimethyl-N'-2- chlorobenzoylthioureato)Nickel(II). Acta Crystallogr. Sect. E 2003, E59, 582. DOI: 10.1107/S1600536803014934.
   Google Scholar
• Ozpozan, N.; Ozpozan, T.; Arslan, H.; Karipçin, F.; Külcü, N. Thermal behaviours of Co(II),Ni(II), Cu(II) and Pb(II) complexes of N,N-dipropyl-N’-benzoylthiourea. Thermochim. Acta 1999, 336, 97–103. DOI: 10.1016/S0040-6031(99)00208-7.
   Web of Science ®Google Scholar
• Breviglieri, T. S.; Cavalheiro, E. T. G.; Chierice, G. O. Correlation between ionic radius and thermal decomposition of Fe(II), Co(II), Ni(II), Cu(II) and Zn(II) diethanoldithiocarbamates. Thermochim. Acta 2000, 356, 79–84. DOI: 10.1016/S0040-6031(00)00465-2.
   Web of Science ®Google Scholar
• Mosselmans, J. F. W.; Pattrick, R. A. D.; van der Laan, G.; Charnock, J. M.; Vaughan, D. J.; Henderson, C. M. B.; Garner, C. D. X-ray absorption near-edge spectra of transition metal disulfides FeS2 (PyriteandMarcasite), CoS2, NiS2 and CuS2 and their isomorphs FeAsS and CoAsS. Phys. Chem. Minerals 1995, 22, 311–317. DOI: 10.1007/BF00202771.
   Web of Science ®Google Scholar
• Liu, W.; Zhou, J.; Zhang, T.; Zhu, H.; Qian, H.; Zhang, H.; Huang, W.; Gust, R. Design and synthesis of thiourea derivatives containing a benzo[5,6]cyclohepta[1,2-b]pyridine moiety as potential antitumor and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2012, 22, 2701–2704. DOI: 10.1016/j.bmcl.2012.03.002.
   PubMed Web of Science ®Google Scholar
• Muslu, H.; Golcu, A.; Tumer, M.; Özsöz, M. Electrochemical investigation and DNA-binding studies of pefloxacin-metal(II/III) complexes. J. Coord. Chem. 2011, 64, 3393–3407. DOI: 10.1080/00958972.2011.610103.
   Web of Science ®Google Scholar
• König, K. H.; Schuster, M.; Steinbrech, B.; Schneeweis, G.; Schlodder, R. N,N-Dialkyl-N′Benzoylthioharnstoffe Als Selektive Extraktionsmittel Zur Abtrennung Und Anreicherung Von Platinmetallen. Z. Anal. Chem. 1985, 321, 457–460. DOI: 10.1007/BF00487079.
   Google Scholar
• Schuster, M. Inaugural-dissertation Zu Erlangung des Doktor grades der Naturwissens- Chaften Vorgelegtbeim Fachbereich Chemie de Johann Wolfrang Goethe-Universitatzu Frankfurt am Main 1986.
   Google Scholar