Synthesis a Novel Complexes of VO(II),Mn(II),Fe(II) ,Co(II), Ni(II), Cu(II)and Pt(IV) Derived from Schiff’s Base of Pyridoxal and 2-amino-4-nitrophenol and Study their Biological Activates
Main Article Content
Abstract
This work describes the synthesis of novel ligand (H2L2) (4-((2-hydroxy-5-nitrophenyl)imino)methyl)-5(hydroxymethyl)-2methylpyridin-3-ol) type (NOO) donor atoms. When it coordinates with metal ions[V2+,Mn2+,Fe2+,Co2+,Ni2+,Cu2+and Pt4+] with the general formula K2[M(L2)2].XH2O and K2[VO(L2)(OSO3)].H2O . This ligand can form tridentate structures. The ligand was synthesized from the reaction of pyridoxal hydrochloride with 2-amino-4-nitrophenol in ethanol (as a solvent) at a mole ratio of 1:1 and thoroughly mixed and refluxed for 6-8 hrs . The reaction was monitored using TLC (Ethylactate/hexane 1:1). The structures of the ligand and the complexes were characterised using spectroscopic techniques such as (FT-IR, 1HNMR, 13CNMR, UV-Vis, and Mass spectroscopy). In addition, molar conductance, magnetic susceptibility, elemental analysis, and thermo gravimetric, melting points were also measured for complexes. The antibacterial activities of the obtained products were tested against G- bacteria (Klebsiella pneumoniae and pseudomonas), G+ bacteria (Staphylococcus aureus and Bacillus subtilis). In addition, antifungal action was tested against (Candida albicans). The results were good in both tests.
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
licenseTerms
Publication Dates
References
Farshbaf, S.; Sreerama, L.; Khodayari, T.; Vessally, E. Propargylic ureas as powerful and versatile building blocks in the synthesis of various key medicinal heterocyclic compounds. Chemical Review and Letters, 2018. ,1(2),5667.doi10.22034/crl.2018.85120
Siddiquee, S., Recent advancements on the role and analysis of volatile compounds (VOCs) from Trichoderma, in Biotechnology and biology of trichoderma. 2014, Elsevier. 139-175. https://doi.org/10.1016/b978-0-444-59576-8.00011-4
Rajasekar, K., T. Ramachandramoorthy, and S. Balasubramaniyan, Synthesis, spectral characterization and biological activities of Cr (III), Co (II), Ni (II) and Zn (II) complexes with 4-aminoantipyrine and azide ion as ligands. Chem. Sci. Trans., 2013. 2(3), 877-882. doi:10.7598/cst2013.487
Bushra Karim Hamad*, M.R.A., Synthesis of new compounds with seven rings (oxazepine) through the ring closure of Schiff bases with study of biological activity. Eurasian Chemical Communications, 2022. 4(12): 1306-1317. 10.22034/ecc.2022.332079.1343
Hadi, M.A.; M.S. Mohammed; Kadhium, A.J., Synthesis, characterization and spectral studies and Biological screening study of Transition Metal complexes with new Heterocyclic Ligand Derived from pyridoxal Hydrochloride. Systematic Reviews in Pharmacy, 2021. 12(1): 371-383. doi:10.31838/srp.2021.1.58
Mukhtorov, L.; Georgy Pestsov; Maria Nikishina; Evgenia Ivanova; Yury Atroshchenko; Leonid Perelomov, Fungicidal Properties of 2-Amino-4-nitrophenol and Its Derivatives. Bulletin of environmental contamination and toxicology, 2019. 102(6): p. 880-886. https://doi.org/10.1007/s00128-019-02602-4
Radecka-Paryzek, W.; Patroniak, V.; Lisowski , J., Metal complexes of polyaza and polyoxaaza Schiff base macrocycles. Coordination Chemistry Reviews, 2005. 249(21-22): 2156-2175. https://doi.org/10.1016/j.ccr.2005.02.021
Anand, T., A.S. Kumar, and S.K. Sahoo, A novel Schiff base derivative of pyridoxal for the optical sensing of Zn2+ and cysteine. Photochemical & Photobiological Sciences, 2018. 17(4): 414-422. https://doi.org/10.1039/c7pp00391a
Mandal, S.; Sikdar, Y.; Sanyal, R.; Goswami, S.,. Experimental and theoretical study on a new copper (II) complex derived from pyridoxal hydrochloride and 1, 2-diaminocyclohexane. Journal of Molecular Structure, 2017,1128,471-480. https://doi.org/10.1016/j.molstruc.2016.09.011
Suku, S. ; Ravindran, R.,. Synthesis, characterization and antimicrobial studies of 1d hetero-bimetallic coordination polymers of pyridine-2, 6-dicarboxylic acid with iron and alkaline earth metals. Journal of MolecularStructure, 2022,1252,132083. https://doi.org/10.1016/j.molstruc.2021.132083
Al-Talib, M.; Al-Soud, Y.A.; Abussaud, M.; Khshashneh, S.,. Synthesis.and biological evaluation of new benzothiazoles as antimicrobial agents. Arabian Journal of chemistry, 2016, 9, pp.S926-S930. https://doi.org/10.1016/j.arabjc.2011.09.003
Azzam, R.A.; Elgemeie, G.H.; Elsayed, R.E.; Gad, N.M.; Jones, P.G.,. Crystal structure of 2-(benzo [d] thiazol-2-yl)-3, 3-bis (ethylsulfanyl) acrylonitrile. Acta Crystallographica Section E: Crystallographic Communications, 2022,78(4). https://doi.org/10.1107/S2056989022002572
Blasco, R.; Castillo, F., Light-dependent degradation of nitrophenols by the phototrophic bacterium Rhodobacter capsulatus E1F1. Applied and environmental microbiology, 1992. 58(2): p. 690-695. https://doi.org/10.1128/aem.58.2.690-695.1992
Suryanti, V.; Wibowo, F.R.; Isnaeni, S.R.; Sari, M.R.K.; Handayani, S.,. Addition reaction of methyl cinnamate with 2-amino-4-nitrophenol. In IOP Conference Series: Materials Science and Engineering 2016, 107, No. 1, 012062.doi:10.1088/1757-899X/107/1/012062
Patil, A.R.; Donde, K.J.; Raut, S.S.; Patil, V.R.; Lokhande, R.S.,. Synthesis, characterization and biological activity of mixed ligand Co (II) complexes of schiff base 2-amino-4-nitrophenol-n-salicylidene with some amino acids. Journal of Chemical and Pharmaceutical Research, 2012,4(2),1413-1425.https://www.semanticscholar.org/paper/Synthesis-%2C-characterization-and-biological-of-Co-(-Patil- Donde/e2d4f047f9a14f8c09d83fb9ca992116b0774193
Cotton, F.A.; Wilkinson, G.; Murillo, C.A.; Bochmann, M., Advanced inorganic chemistry. John Wiley and Sons, Inc. 1999, http://repository.vnu.edu.vn/handle/VNU_123/85212.
Anupama, B.; Padmaja, M.; Kumari, C.G.,. Synthesis, characterization, biological activity and DNA binding studies of metal complexes with 4-aminoantipyrine Schiff base ligand. E-Journal of Chemistry, 2012,9(1),389-400. https://scholar.google.com/citations?view_op=view_citation&hl=en&user=31Zn0B4AAAAJ&citation_for_view=31Zn0B4AAAAJ:zYLM7Y9cAGgC
Abbas, G.; Irfan, A.; Ahmed, I.; Al-Zeidaneen, F.K.; Muthu, S.; Fuhr, O.; Thomas, R.,. Synthesis and investigation of anti-COVID19 ability of ferrocene Schiff base derivatives by quantum chemical and molecular docking. Journal of molecular structure, 2022,1253,.132242. https://doi.org/10.1016/j.molstruc.2021.132242
Maher, K.A.; Mohammed, S.R., Metal complexes of Schiff base derived from salicylaldehyde-A review. International Journal of Current Research and Review, 2015,7(2),6. https://ijcrr.com/article_html.php?did=647
Ommenya, F.K.; Nyawade, E.A.; Andala, D.M.; Kinyua, J., 2020. Synthesis, characterization and antibacterial activity of Schiff base, 4-Chloro-2-{(E)-[(4-fluorophenyl) imino] methyl} phenol metal (II) complexes. Journal of Chemistry, 2020. https://doi.org/10.1155/2020/1745236
Diab, M.A.; Mohamed, G.G.; Mahmoud, W.H.; El‐Sonbati, A.Z.; Morgan, S.M.; Abbas, S.Y.,. Inner metal complexes of tetradentate Schiff base: Synthesis, characterization, biological activity and molecular docking studies. Applied Organometallic Chemistry, 2019,33(7), e4945. https://doi.org/10.1002/aoc.4945
Raman, N.; Dhaveethu Raja, J.; Sakthivel, A., Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies. Journal of Chemical sciences, 2007,119(4),303-310. https://link.springer.com/article/10.1007/s12039-007-0041-5
Lateef, S.M.; Sarhan, B.M.; Al-Saedi, W.A., Synthesis, Characterization and Biological Activity for Complexes VO (II), Mn (II), Co (II) and Ni (II) with new multidentate ligand [2-((E)-3-(2-hydroxyphenylimino)-1, 5-dimethyl-2-phenyl-2, 3-dihydro-1H-pyrazol-4-ylimino) acetic acid][H2L] type (N2). Diyala Journal For Pure Science, 2016,12(1).https://scholar.google.com/citations?view_op=view_citation&hl=en&user=n8UrjGAAAAAJ&citation_for_view=n8UrjGAAAAAJ:d1gkVwhDpl0C
Cowley, A.R.; Dilworth, J.R.; Donnelly, P.S.; White, J.M., Copper complexes of thiosemicarbazone− pyridylhydrazine (THYNIC) hybrid ligands: a new versatile potential bifunctional chelator for copper radiopharmaceuticals. Inorganic chemistry, 2006, 45(2),496-498. https://doi.org/10.1021/ic0514492
Osowole, A.A.; Ekennia, A.C.; Achugbu, B.O.; Etuk, G.H.,. Synthesis, spectroscopic characterization and structure related antibacterial activities of some metal (II) complexes of substituted triflurobutenol. Elixir Appl Chem, 2013, 59,15848-15852. https://www.rroij.com/open-access/synthesis-spectroscopic-characterization-and-antibacterial-properties-of-some-metal-ii-complexes-of-26methoxybenzothiazol2-ylimino-.php?aid=34639
Hassan, S.A., Lateef, S.M. and Majeed, I.Y.,. Structural, Spectral and Thermal studies of new bidentate Schiff base ligand type (NO) derived from Mebendazol and 4-Aminoantipyrine and it's metal complexes and evaluation of their biological activity. Research Journal of Pharmacy and Technology, 2020,13(6),3001-3006. DOI: 10.5958/0974-360X.2020.00531.4
Kuate, M.; Conde, M.A.; Ngandung Mainsah, E.; Paboudam, A.G.; Tchieno, F.M.M.; Ketchemen, K.I.; Tonle Kenfack, I.; Ndifon, P.T., 2020. Synthesis, Characterization, Cyclic Voltammetry, and Biological Studies of Co (II), Ni (II), and Cu (II) Complexes of a Tridentate Schiff Base, 1-((E)-(2-Mercaptophenylimino) Methyl) Naphthalen-2-ol (H2L1). Journal of Chemistry, 2020. https://doi.org/10.1155/2020/5238501