![Cover Image](https://medjchem.com/public/journals/1/cover_article_1780_en_US.png)
Transition metal (II) complexes of 2-(2,5-dimethoxy-benzylidene)hydrazine-1-carbothioamide: synthesis, characterization and their biological evaluation
Abstract
The current study involved synthesizing Schiff base ligand, 2-(2,5-dimethoxybenzylidene)hydrazine-1-carbothioamide (L) by combining thiosemicarbazide (Th) with 2,5-dimethoxybenzaldehyde (2,5-Dmb), and synthesizing its novel complexes of Co(II), Ni(II), and Cu(II) ions. Elemental analysis, conductance measurements, magnetic susceptibility, molecular weight estimations, FT-IR, ESI-Mass, and UV-Vis spectrum analysis have confirmed the ligand and its metal complexes. The experiment data demonstrated that the ligand binds to the metal atom in a bidentate manner through the N and S atoms. The cytotoxic activity of the synthesized complexes was tested against brine shrimp. All the complexes showed cytotoxic activity; among them, ligands showed a better result with LC50 value of 36.93 µg/mL than complexes. Using disc diffusion, the antibacterial action was tested against two Gram-positive bacteria and two Gram-negative bacteria. [Ni(L)2] was more effective against E. coli than the other compounds. The results verified the formation of the novel complexes, and the Ni-complex has the potential to generate novel antibacterial compounds for use in biomedical applications.
Full Text:
PDFReferences
N.A. Mazlan, T.B.S. Ravoof, E.R. Tiekink, M.I.M. Tahir, A. Veerakumarasivam, K.A. Crouse, Mixed-ligand metal complexes containing an ONS Schiff base and imidazole/benzimidazole ligands: Synthesis, characterization, crystallography and biological activity, Transition Metal Chemistry, 2014, 39, 633-639.
Y.Han, Y. Sun, A. Abdukader, B. Liu, D. Wang, PhI-catalyzed intramolecular oxidative coupling toward Synthesis of 2-amino-1, 3, 4-thiadizoles, Catalysis Letters, 2018, 148, 3486-3491.
A.D. Khalaji, G., Grivani, S.J. Akerdi, K. Gotoh, H. Ishida, H. Mighani, Synthesis, spectroscopic characterization, crystal structures, and theoretical studies of (E)-2-(2, 4-dimethoxybenzylidene) thiosemicarbazone and (E)-2-(2, 5-dimethoxybenzylidene) thiosemicarbazone, Structural Chemistry, 2010, 21, 995-1003.
K. Jayanthi, R.P. Meena, K. Chithra, S. Kannan, W. Shanthi, R. Saravanan, M. Suresh, D. Satheesh, Synthesis and microbial evaluation of copper (II) complexes of Schiff base ligand derived from 3-methoxysalicylaldehyde with semicarbazide and thiosemicarbazide, Journal of Pharmaceutical, Chemical and Biological Sciences, 2017, 5, 205-215.
A. Singh, P. Barman, Recent advances in Schiff base ruthenium metal complexes: Synthesis and applications, Topics in Current Chemistry, 2021, 379, 1-71.
K. Ajay, Studies and Synthesis of new drugs formed with fluoro-quinolones and metal ions, Int. J. of Life Sciences, 2018, 6, 446-452.
A.A. Ali, H. Nimir, C. Aktas, V. Huch, U. Rauch, K.H. Schäfer, M. Veith, Organoplatinum (II) complexes with 2-acetylthiophene thiosemicarbazone: synthesis, characterization, crystal structures, and in vitro antitumor activity, Organometallics, 2012, 31, 2256-2262
L.M. Aroua, S.K. Alhag, L.A. Al-Shuraym, S. Messaoudi, J.A. Mahyoub, M.Y. Alfaifi, W.M. Al-Otaibi, Synthesis and characterization of different complexes derived from Schiff base and evaluation as a potential anticancer, antimicrobial, and insecticide agent, Saudi Journal of Biological Sciences, 2023. 30, 103598.
A.J.M. Al-Karawi, Synthesis and characterization of a new N 2 S 2 Schiff base ligand and its complexes with nickel (II), copper (II) and cadmium (II) including the kinetics of complex formation, Transition metal chemistry, 2009, 34, 891-897.
H. Wang, P. Zhao, D. Shao, J. Zhang, Y. Zhu, Synthesis, characterization and spectra studies on Zn (II) and Cu (II) complexes with thiocarbamide ligand containing Schiff base group, Structural Chemistry, 2009, 20, 995-1003.
J. Joseph, N.L. Mary, R. Sidambaram, Synthesis, characterization, and antibacterial activity of the Schiff bases derived from thiosemicarbazide, Salicylaldehyde, 5-bromosalicylaldehyde and their copper (II) and nickel (II) complexes, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2010, 40, 930-933.
F.S. Tokalı, P. Taslimi, H. Usanmaz, M. Karaman, K. Şendil, Synthesis, characterization, biological activity and molecular docking studies of novel Schiff bases derived from thiosemicarbazide: Biochemical and computational approach, Journal of Molecular Structure, 2021, 1231, 129666.
H. Wang, A.M.S. Hossain, Q. Zhang, J. Wu, Y. Tian, Synthesis, crystal structures and third-order nonlinear optical properties of 4-formyl-pyridine Schiff base of thiosemicarbazide, and its dinuclear copper (I) and silver (I) complexes, Inorganica Chimica Acta, 2014, 414, 153-159.
N.N. Ishak, J. Jamsari, A.Z. Ismail, M.I. Tahir, E.R. Tiekink, A. Veerakumarasivam, T.B. Ravoof, Synthesis, characterisation and biological studies of mixed-ligand nickel (II) complexes containing imidazole derivatives and thiosemicarbazide Schiff bases, Journal of Molecular Structure, 2019, 1198, 126888.
A.A. Al-Amiery, Y.K. Al-Majedy, H.H. Ibrahim, A.A. Al-Tamimi, Antioxidant, antimicrobial, and theoretical studies of the thiosemicarbazone derivative Schiff base 2-(2-imino-1-methylimidazolidin-4-ylidene) hydrazinecarbothioamide (IMHC), Organic and medicinal chemistry letters, 2012, 2, 1-7.
M. Mohammadikish, M. Masteri-Farahani, S. Mahdavi, Immobilized molybdenum–thiosemicarbazide Schiff base complex on the surface of magnetite nanoparticles as a new nanocatalyst for the epoxidation of olefins, Journal of magnetism and magnetic materials, 2014, 354, 317-323.
I. Babahan, F. Eyduran, E.P. Coban, N. Orhan, D. Kazar, H. Biyik, Spectroscopic and biological approach of Ni (II), Cu (II) and Co (II) complexes of 4-methoxy/ethoxybenzaldehyde thiosemicarbazone glyoxime, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 121, 205-215.
D. Shobana, S. Sudha, D. Ramarajan, N. Ristivojević, A. Rakić, D. Dimić, Structural, spectroscopic (IR, Raman, and NMR), quantum chemical, and molecular docking analysis of (E)-2-(2, 5-dimethoxybenzylidene) hydrazinecarbothioamide and its dimers, Journal of Molecular Structure, 2022, 1247, 131277.
P.S. Zhao, H.Y. Wang, J. Song, L.D. Lu, Synthesis, structures, and property studies on Zn (II), Ni (II), and Cu (II) complexes with a Schiff base ligand containing thiocarbamide group, Structural Chemistry, 2010, 21, 977-987.
S. Feizpour, S.A. Hosseini-Yazdi, E. Safarzadeh, B. Baradaran, M. Dusek, M. Poupon, A novel water-soluble thiosemicarbazone Schiff base ligand and its complexes as potential anticancer agents and cellular fluorescence imaging, JBIC Journal of Biological Inorganic Chemistry, 2023, 1-16.
M.N. Al-Jibouri, S.M. Hasun, Synthesis and characterization of manganese (II), cobalt (II), nickel (II), copper (II) and zinc (II) complexes with new Schiff base derived from 6, 7-dimethyl-quinoxaline-2, 3 (1H, 4H)-dione and thiosemicarbazide, European Journal of Chemistry, 2015, 6, 44-47.
L.F. Chu, Y. Shi, D.F. Xu, H. Yu, J.R. Lin, Q.Z. He, Synthesis and biological studies of some lanthanide complexes of schiff base, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2015, 45, 1617-1626.
K.S. Abou-Melha, Octahedral Co (II) and Ni (II) complexes of Schiff bases, semicarbazone and thiosemicarbazone, Synthesis, biological, spectral, and thermal studies, Journal of Coordination Chemistry, 2008, 61, 2053-2067.
O.K. Nehar, R. Mahboub, S. Louhibi, T. Roisnel, M. Aissaoui, New thiosemicarbazone Schiff base ligands: Synthesis, characterization, catecholase study and hemolytic activity, Journal of Molecular Structure, 2020, 1204, 127566.
A.J.M Al-Karawi, Synthesis and characterization of a new N 2 S 2 Schiff base ligand and its complexes with nickel (II), copper (II) and cadmium (II) including the kinetics of complex formation, Transition metal chemistry, 2009, 34, 891-897.
S.H. Gordon, A. Mohamed, R.E. Harry-O'Kuru, S.H. Imam, A chemometric method for correcting Fourier transform infrared spectra of biomaterials for interference from water in KBr discs, Applied spectroscopy, 2010, 4, 448-457.
A.A. Al-Amiery, Synthesis and antioxidant, antimicrobial evaluation, DFT studies of novel metal complexes derivate from Schiff base, Research on Chemical Intermediates, 2012, 3, 745-759.
A. Çukurovali, I. Yilmaz, H. Özmen, M. Ahmedzade, Cobalt (II), copper (II), nickel (II) and zinc (II) complexes of two novel Schiff base ligands and their antimicrobial activity, Transition metal chemistry, 2002, 27, 171-176.
F.K. Camellia, M. Ashrafuzzaman, M.N. Islam, L.A. Banu, M.K. Zahan, Synthesis, characterization, antibacterial and antioxidant studies of isoniazid-based Schiff base ligands andtheir metal complexes. Asian Journal of Applied Chemistry Research, 2022, 11(3), 8-23.
S. Ramachandran, M. Vamsikrishna, K.V. Gowthami, B. Heera, M.D. Dhanaraju, Assessment of cytotoxic activity of Agave cantula using brine shrimp (Artemia salina) lethality bioassay, Asian J Sci Res, 2011, 4,
-104.
DOI: http://dx.doi.org/10.13171/mjc02407261780zahan
Refbacks
- There are currently no refbacks.
Copyright (c) 2024 Mediterranean Journal of Chemistry