Synthesis of Ni(II), Cu(II) and Zn(II) coumarin-3-carboxilic acid derivates and their and their physical-chemical properties

Authors

DOI:

https://doi.org/10.33448/rsd-v10i3.13430

Keywords:

Coumarin; Synthesis; Complexes; Antioxidant; Coordination.

Abstract

In the search for new drugs, coumarins are an important class of compounds due to their chemical and biological properties, such as their potential to reduce cancer, diabetes, and cardiovascular diseases. They are heterocyclic compounds that contain oxygen in their structure and are found in plants.To improve the chemical and biological properties of the coumarin-3-carboxilic acid, were prepared metal transition complexes of Cu(II), Ni(II) and Zn(II) of coumarin-3-carboxilic acid by a new synthetic route. All complexes were characterized by Ultraviolet (UV), Infrared (FTIR), and Raman spectroscopy; Scanning electronic microscopy (SEM); X-Ray diffraction (XRD), as well as conductivity and elemental analysis. Electron microscopy and X-ray analysis showed that the degree of crystallinity of the complexes changes when compared with the precursor, 3-carboxy-coumarin acid, and the degree of crystallinity depends on the nature of the metal ion attached to coumarin. In addition, the antioxidant action of the complexes was evaluated by the DPPH method, and the results showed a higher activity of the complexes when compared with the precursor, suggesting that these complexes may present biological properties of interest.

Author Biographies

Dirceu Aparecido Gonçalves de Souza, Universidade Anhanguera de São Paulo

Currently a PhD candidate and completed a Master's degree in Biotechnology and Innovation in Health (2015 -2017), Bachelor's degree in Pharmacy (2011 - 2014) from Universidade Anhanguera de São Paulo - (UNIAN) and technical course in Chemistry at Oswaldo Cruz technical school (2008 - 2009). He has experience in the pharmaceutical industry in the areas of drug production and quality control in the physical-chemical area. He has already worked in the academic area as a health laboratory technician preparing and monitoring practical classes in health laboratories. Currently he is a junior production analyst in the area of soft capsules (Softgel) in monitoring the production from weighing, handling, encapsulation, drying, inspection and corrections of the documentation used in the process.

Ricardo Luis Tranquilin, Universidade Federal de São Carlos

Bachelor's degree in Chemistry (2006) and full degree in Chemistry (2006) from the Federal University of São Carlos, Master's degree in Materials Science and Technology from the Paulista State University (2009), PhD in Materials Science and Technology from the Paulista State University (2013), Post Doctorate from the Federal University of São Carlos at the National Institute of Materials Sciences in Nanotechnology (2014), Post Doctorate from Federal University of Rio Grande do Norte in the project of composite materials with photocatalytic and hydrophobic properties for application in aircraft transparencies (2016), Post Doctorate from Federal University of Rio Grande do Norte in the project of development and technological applications of nanostructured functional materials (2018). He is currently a PhD/Unemployed Researcher. He has experience in the area of chemistry and materials engineering, where he worked with high resolution scanning electron microscopy, photoluminescent properties of materials, hydrothermalization and/or microwave-assisted hydrothermalization processes and their influences on physical and chemical properties of materials.

Marcio Luiz dos Santos, Universidade Anhanguera de São Paulo

Bachelor, Master and PhD in Chemistry. Has experience in techniques such as X-ray photoelectron spectroscopy (XPS/ESCA), mid-infrared spectroscopy, thermal analysis, dispersive and confocal Raman spectroscopy, X-ray diffraction, scanning electron microscopy. Works in the area of Biomaterials, Controlled Drug Delivery Systems in Polymeric and Inorganic Matrices, Bioceramics, Titanium and Titanium Alloys. Related topics: Biomolecules immobilization methods, sol-gel process, biomimetic process, hydrothermal-microwave synthesis, Synthesis and characterization of natural and synthetic polymers, Colloid chemistry, Bioceramic coatings, Physical-chemical and inorganic materials. Courses in Intellectual Property, Business Management, Project Management and Business Plan.

Regina Mara Silva Pereira, Universidade Anhanguera de São Paulo

I am B.S. in Chemistry from UFBA, a Ph.D. in Science from the State University of Campinas (1996) and a sandwich internship at the University of Kent (1994).  I have been teaching undergraduate courses at Anhanguera University of São Paulo (UNIAN-SP) since 2000, and I am a lecturer in the Professional Master's in Pharmacy, Master's in Science and Health Teaching, and in the Master's and Doctoral programs in Biotechnology at the same institution. Currently I am the coordinator of the Professional Master's Program in Pharmacy. I have research experience in the area of Coordination Chemistry and Bioinorganics.

References

Borges Bubols, G., da Rocha Vianna, D., Medina-Remon, A., von Poser, G., Maria Lamuela-Raventos, R., Lucia Eifler-Lima, V., & Cristina Garcia, S. (2013). The Antioxidant Activity of Coumarins and Flavonoids. Mini-Reviews in Medicinal Chemistry, 13(3), 318–334. https://doi.org/10.2174/1389557511313030002

Creaven, B. S., Devereux, M., Georgieva, I., Karcz, D., McCann, M., Trendafilova, N., & Walsh, M. (2011). Molecular structure and spectroscopic studies on novel complexes of coumarin-3-carboxylic acid with Ni(II), Co(II), Zn(II) and Mn(II) ions based on density functional theory. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 84(1), 275–285. https://doi.org/10.1016/j.saa.2011.09.041

Creaven, Bernadette S., Egan, D. A., Kavanagh, K., McCann, M., Noble, A., Thati, B., & Walsh, M. (2006). Synthesis, characterization and antimicrobial activity of a series of substituted coumarin-3-carboxylatosilver(I) complexes. Inorganica Chimica Acta, 359(12), 3976–3984. https://doi.org/10.1016/j.ica.2006.04.006

de Alcantara, F. C., Lozano, V. F., Vale Velosa, A. S., dos Santos, M. R. M., & Pereira, R. M. S. (2015). New coumarin complexes of Zn, Cu, Ni and Fe with antiparasitic activity. Polyhedron, 101, 165–170. https://doi.org/10.1016/J.POLY.2015.09.010

El-Wahab, Z. H. A., Mashaly, M. M., Salman, A. A., El-Shetary, B. A., & Faheim, A. A. (2004). Co(II), Ce(III) and UO2(VI) bis-salicylatothiosemicarbazide complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 60(12), 2861–2873. https://doi.org/10.1016/j.saa.2004.01.021

Elhusseiny, A. F., Aazam, E. S., & Al-Amri, H. M. (2014). Synthesis of new microbial pesticide metal complexes derived from coumarin-imine ligand. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 128, 852–863. https://doi.org/10.1016/j.saa.2014.03.003

Halli, M. B., Sumathi, R. B., & Kinni, M. (2012). Synthesis, spectroscopic characterization and biological evaluation studies of Schiff’s base derived from naphthofuran-2-carbohydrazide with 8-formyl-7-hydroxy-4-methyl coumarin and its metal complexes. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 99, 46–56. https://doi.org/10.1016/j.saa.2012.08.089

Ikeda, N. E. A., Novak, E. M., Maria, D. A., Velosa, A. S., & Pereira, R. M. S. (2015). Synthesis, characterization and biological evaluation of Rutin–zinc(II) flavonoid -metal complex. Chemico-Biological Interactions, 239, 184–191. https://doi.org/10.1016/j.cbi.2015.06.011

Islas, M. S., Martínez Medina, J. J., Piro, O. E., Echeverría, G. A., Ferrer, E. G., & Williams, P. A. M. (2018). Comparisons of the spectroscopic and microbiological activities among coumarin-3-carboxylate, o-phenanthroline and zinc(II) complexes. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 198(Ii), 212–221. https://doi.org/10.1016/j.saa.2018.03.003

Kadhum, A. A. H., Mohamad, A. B., Al-Amiery, A. A., & Takriff, M. S. (2011). Antimicrobial and antioxidant activities of new metal complexes derived from 3-aminocoumarin. Molecules, 16(8), 6969–6984. https://doi.org/10.3390/molecules16086969

Khan, M. I., Khan, A., Hussain, I., Khan, M. A., Gul, S., Iqbal, M., Inayat-Ur-Rahman, & Khuda, F. (2013). Spectral, XRD, SEM and biological properties of new mononuclear Schiff base transition metal complexes. Inorganic Chemistry Communications, 35, 104–109. https://doi.org/10.1016/j.inoche.2013.06.014

Lv, H. N., Wang, S., Zeng, K. W., Li, J., Guo, X. Y., Ferreira, D., Zjawiony, J. K., Tu, P. F., & Jiang, Y. (2015). Anti-inflammatory coumarin and benzocoumarin derivatives from Murraya alata. Journal of Natural Products, 78(2), 279–285. https://doi.org/10.1021/np500861u

Mueller, R. L. (2004). First-generation agents: Aspirin, heparin and coumarins. Best Practice and Research: Clinical Haematology, 17(1), 23–53. https://doi.org/10.1016/j.beha.2004.03.003

Musa, M., Cooperwood, J., & Khan, M. O. (2008). A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer. In Current Medicinal Chemistry 15(26). https://doi.org/10.2174/092986708786242877

Patil, S. A., Prabhakara, C. T., Halasangi, B. M., Toragalmath, S. S., & Badami, P. S. (2015). DNA cleavage, antibacterial, antifungal and anthelmintic studies of Co(II), Ni(II) and Cu(II) complexes of coumarin Schiff bases: Synthesis and spectral approach. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 137, 641–651. https://doi.org/10.1016/j.saa.2014.08.028

Paya, M., Goodwin, P. A., De Las Heras, B., & Hoult, J. R. S. (1994). Superoxide scavenging activity in leukocytes and absence of cellular toxicity of a series of coumarins. Biochemical Pharmacology, 48(3), 445–451. https://doi.org/10.1016/0006-2952(94)90273-9

Song, P. P., Zhao, J., Liu, Z. L., Duan, Y. B., Hou, Y. P., Zhao, C. Q., Wu, M., Wei, M., Wang, N. H., Lv, Y., & Han, Z. J. (2017). Evaluation of antifungal activities and structure–activity relationships of coumarin derivatives. Pest Management Science, 73(1), 94–101. https://doi.org/10.1002/ps.4422

Wang, T., Peng, T., We, X., Wang, G., Sun, Y., Liu, S., Zhang, S., & Wang, L. (2019). Design, synthesis and preliminary biological evaluation of benzylsulfone coumarin derivatives as anti-cancer agents. Molecules, 24(22). https://doi.org/10.3390/molecules24224034

Wang, Y. H., Avula, B., Nanayakkara, N. P. D., Zhao, J., & Khan, I. A. (2013). Cassia cinnamon as a source of coumarin in cinnamon-flavored food and food SUPPL.ements in the United States. Journal of Agricultural and Food Chemistry, 61(18), 4470–4476. https://doi.org/10.1021/jf4005862

Downloads

Published

22/03/2021

How to Cite

SOUZA, D. A. G. de .; TRANQUILIN, R. L.; SANTOS, M. L. dos .; PEREIRA, R. M. S. . Synthesis of Ni(II), Cu(II) and Zn(II) coumarin-3-carboxilic acid derivates and their and their physical-chemical properties. Research, Society and Development, [S. l.], v. 10, n. 3, p. e47910313430, 2021. DOI: 10.33448/rsd-v10i3.13430. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/13430. Acesso em: 16 apr. 2021.

Issue

Section

Exact and Earth Sciences