SYNTHESIS, SPECTRAL CHARACTERIZATION OF SCHIFF BASE COMPLEXES BASED ON PYRIMIDINE MOIETY WITH MOLECULAR DOCKING WITH BIOMOLECULES
DOI:
https://doi.org/10.22159/ajpcr.2018.v11i10.26823Keywords:
Schiff base molecular structure, Nuclear magnetic resonance, Fourier transform infrared, Electron spin resonance study, Molecular docking with biomoleculesAbstract
Objective: Aim of this study is to synthesize new bidentate complexes of type MX2. nH2O with 4 amino antipyrine and ethyl 4-methyl-2-oxo-6- phenylhexahydropyrimidine-5-carboxylate (DHPM) and to characterize their properties, namely elemental analysis, conductivity measurements, and spectral characteristics and to establish the binding between the Schiff base ligands and complexes with human epidermis cancer cells (Hep-2) through molecular docking.
Method: A new bidentate complexes were synthesized by condensation reaction of MX2·nH2O (M = Cu (II), Zn (II), Co (II)) with 4-aminoantipyrine (A) and DHPM in methanol under atmospheric pressure.
Results: All the compounds have been characterized by elemental analysis, conductance measurements, magnetic moments, and spectroscopy techniques such as ultraviolet–visible, infrared (IR), 1H and 13C nuclear magnetic resonance, and electron spin resonance (ESR). The IR showed that nature of functional group present in the ligand (Lp) acts as neutral bidentate through the azomethane nitrogen atom and carbonyl oxygen moiety and its complexes formation. The ESR spectral data of copper complex provided information about their structure on the basis of Hamiltonian parameters and degree of covalency. The antimicrobial (Escherichia coli, Salmonella typhi, Bacillus subtilis, and aureus) and antifungal (Candida and Aspergillus niger) activities of the complexes were tested against various microorganism by disc diffusion method.
Conclusion: The antimicrobial activity indicates that the metal complexes are more active than the ligand. Molecular docking was used to predict the binding between the Schiff base ligands and complexes with human epidermis cancer cells (Hep-2).
Downloads
References
Alexander V. Design and synthesis of macrocyclic ligands and their complexes of lanthanides and actinides. Chem Rev 1995;95:273-342.
Rosu T, Pasculescu S, Lazar V, Chifiriuc C, Cernat R. Copper(II) complexes with ligands derived from 4-amino-2,3-dimethyl-1-phenyl- 3-pyrazolin-5-one: Synthesis and biological activity. Molecules 2006;11:904-14.
Hitoshi T, Tamao N, Hideyuki A, Manabu F, Takayuki M. Preparation and characterization of novel cyclic tetra nuclear manganese (III) complexes: MnIII 4(X-salmphen)6(X-salmphenH2=N,N′-di-substituted-salicylidene-1,3-diaminobenzene) (X=H, 5-Br). Polyhedron 1997;16:3787-94.
Hossain ME, Alam MN, Begum J, Akbar AM, Nazimuddin M, Smith FE, et al.The preparation, characterization, crystal structure and biological activities of some copper(II) complexes of the 2-benzoylpyridine schiff bases of S-methyl- and S-benzyldithiocarbazate. Inorg Chim Acta 1996;249:207-13.
Chiaramonte D, Steiner JM, Broussard JD, Baer K, Gumminger S, Moeller EM, et al. Use of a 13C-aminopyrine blood test: First clinical impressions. Can J Vet Res 2003;67:183-8.
Gudasi KB, Patil SA, Bakale RP, Nethaji M. Ligational behaviour of (E)-2-amino-N′-[1-(2-hydroxyphenyl) ethylidene] benzohydrazide towards later 3d metal ions: X-ray crystal structure of nickel (IV) complex. J Mol Struct 2014;1065:179-85.
Kandeel ZE, Abdelrazek FM, Eldin NE, Elnagdi MH. Activated nitriles in heterocyclic synthesis-novel synthesis of benzo[g]imidazo [1,2-c] pyrimidines and benzo[g]imidazo [1,2-a]pyridine derivatives. J Chem Soc Perkin Trans 1985;1499-501.
Manjula J, Maheswari R. Biological and studies of novel aroyl hydrazones. Int J Pharm Pharm Sci 2017;9:81-5.
Sekar S, Naik N, Mahalingappa SA, Peethamber SK. Synthesis and pharmacological evaluation of certain schiff bases of octahydro- 1H-pyrrolo [3, 4-b] pyridine derivatives. Int J Pharm Pharm Sci 2015;9:412-9.
Kowol CR, Berger R, Eichinger R, Roller A, Jakupec MA, Schmidt PP, et al. Gallium(III) and iron(III) complexes of alpha-N-heterocyclic thiosemicarbazones: Synthesis, characterization, cytotoxicity, and interaction with ribonucleotide reductase. J Med Chem 2007;50:1254-65.
Chitambar CR. Gallium nitrate for the treatment of non-hodgkin’s lymphoma. Expert Opin Investig Drugs 2004;13:531-41.
Fanagdi MH, Kandeel EM, Zayed EM, Kandil ZF. A novel synthesis of 3, 5-diacetamidopyrazole and of 2-aminopyrazolo [1, 5- a] pyrimidines. J Heterocycl Chem 1977;14:155-7.
Raman N, Sakthivel A, Rajasekaran K. Synthesis and spectral characterization of antifungal sensitive schiff base transition metal complexes. Mycobiology 2007;35:150-3.
Leelavathy C, Antony SA. Structural elucidation and thermal studies of some novel mixed ligand Schiff base metal (II) complexes. Int J Basic Appl Chem Sci 2013;3:88-95.
Elemike EE, Oviawe AP, Otuokere IE. Potentiation of the antimicrobial activity of 4-Benzylimino-2, 3- Dimethyl-1-Phenyl-pyrazal-5-One by metal chelation. Res J Chem Sci 2011;1:6-11.
Prakash D, Kumar C, Prakash S, Gupta AK, Singh KR. Synthesis, spectral characterization and antimicrobial studies of some new binuclear complexes of Cu II and Ni II Schiff base. J Indian Chem Soc 2009;86:1257-61.
Huheey JE, Keiter EA, Keiter RL. Inorganic Chemistry. 4th ed. India: Addison-Wesley Publishing Company; l993.
Drago RS. Physical Methods in Inorganic Chemistry. New York: Reinhold Publishing Corporation; 1965.
Dutta RL, Syamal A. Elements of Magnetochemistry. 2th ed. New Delhi: East-West Press; 1993.
Akkasali R, Patil N, Angadi SD. Synthesis, characterization and microbial activities of metal complexes with. Coumarine derivatives. Rasayan J Chem 2009;2:81-6.
Raman N, Muthuraj V, Ravichandran S, Kulandaisamy A. Synthesis, characterization and electrochemical behaviour of. Cu (II), Co (II), Ni (II) and Zn (II) complexes derived from acetyl acetone and p-anisidine and their antimicrobial activity. Proc Indian Acad Sci (Chem Sci) 2003;115:161-7.
Malik WU, Tuli GD, Madan RD. Selected Topics in Inorganic Chemistry. 1st ed New Delhi: S. Chand and Company Ltd.; 1976, 2004. p. 390.
Annapoorani S. Synthesis and spectroscopic characterization of some copper (ii) trinuclear complexes involving nitrogen as bridging atoms. Asian J Chem 2012;24:3347-51.
Chandra S, Sangeetika X. EPR, magnetic and spectral studies of copper(II) and nickel(II) complexes of schiff base macrocyclic ligand derived from thiosemicarbazide and glyoxal. Spectrochim Acta A 2004;60:147.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.
