New Metal Complexes with Mannich -β-amino carbonyl ligand; Preparation, spectral Characterisation and Biological Activity
Baraa Kasim Mohammed, Enaam Ismail Yousif*
Department of Chemistry, College of Education for Pure Science (Ibn Al-Haitham), University of Baghdad, Adhamiyah, Baghdad, Iraq.
Received: 15th March, 2024; Revised: 23rd May, 2024; Accepted: 13th August, 2024; Available Online: 25th September, 2024
ABSTRACT
New metal complexes and a new beta-amino maniche carbonyl ligand were prepared and characterized. (((4-(tert-butyl)-2-((S)- (phenylamino) (p-tolyl) methyl)cyclohexan-1-one)) (HL) was formed from the reaction of aniline and 4-methylbesaldehyde with 4- (tert-butyl)cyclohexane-1-one at a 1:1:1 mol ratio respectively reaction of (4-methyl-2-((R)-(phenylamino)(p-tolyl) methyl)cyclohexan-1-one (HL) and MnII, CoII, NiII, CuII, ZnII and CdII metal ions in a 2:1 (L:M) ratio led to the isolation of monomeric complexes from analytical and spectroscopic techniques including; elemental microanalysis, magnetic susceptibility, conductivity, TGA, and FTIR, electronic and mass spectra and 1H, 13C-NMR characterization data indicated to a four- and six-coordinate isolate.Complexes Many bacterial and fungal strains were tested, and the data obtained showed that these complexes are more active against a variety of organisms, under experiment, than free associations.
Keywords: 4-(tert-butyl)cyclohexan-1-one, β-amino carbonyl, Thermal analysis, Candida and Rhizopus porium, Metal Complexes.
International Journal of Drug Delivery Technology (2024); DOI: 10.25258/ijddt.14.3.60
How to cite this article: Mohammed BK, Yousif EI. New Metal Complexes with Mannich -β-amino carbonyl ligand; Preparation, spectral Characterisation and Biological Activity. International Journal of Drug Delivery Technology. 2024;14(3):1676-1682.
REFERENCES
- Arend M, Estermann BW, Risch N, Angew. Chem., Int. Ed. 1998; 37: 1044.
- Kobayashi S, Ishitani H, Rev. 1999; 99: 1069.
- Mannich C, Krosche W, Arch. 1912; 250: 674.
- Muller R, Goesmann H, Waldmann H, Angew. Chem., Int. Ed. 1999; 38: 184.
- Bohme H, Haake M, Advances in Organic Chemistry, in: E.C. Taylor (Ed.), John Wiley and Sons, New York, 1976, p. 107.
- Ishitani H, Ueno M, Kobayashi S, Am Chem. Soc. 1997; 119: 7153.
- Wenzel A.G, Jacobsen E.N, Am J. Chem. Soc. 2002; 124:12964.
- Josephsohn N.S, Carswell E.L, Snapper M.L, Hoveyda A.H, Org. Lett. 2005; 7: 2711.
- Takashi O, Minoru K., Fujii J.I, Maruoka K., Org. Lett. 2004; 6: 2397.
- Josephsohn N S, Snapper M L, Hoveyda A H, Am Chem. Soc. 2004; 126: 3734.
- Bhusare S R, Pawar R P, and Vibhute Y B, “Synthesis and antibacterial activity of some new 2-(substituted phenyl sulfonamido)-6-substituted benzothiazoles,” Indian Journal of Heterocyclic Chemistry. 2001; 11(1): pp 79–80,.
- Raman N, Esthar S, Thangaraja C, “A new Mannich base and its transition metal (II) complexes—synthesis, structural characterization and electrochemical study,” Journal of Chemical Sciences. 2004; 116(4): pp. 209–213.
- Karthikeyan NS, Sathiyanarayanan KI, Aravindan PG Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14 - tetrahydrodibenzo[a,i] phenanthridines,2,4-Diaryl-6,7-benzo-3- azabicyclo[3.3.1]nonan- 9-ones and α,α’-Bis (substituted benzylidene) cycloalkanones, Korean Chem. Soc. 2009; 30(11): 2555-2558.
- Memona S, Bhattia AA, Ocakb U, Ocakb M. Cu2+ Selective Chromogenic Behavior of Calix[4]arene Derivative, PolycyclicAromatic Compounds. 2015: 1-15.
- Jia P, Hu L, Shang Q, Wang R, Zhang M, Zhou Y. Self- Plasticization of PVC Materials via Chemical Modification of Mannich Base of Cardanol Butyl Ether, ACS Sustainable Eng. 2017; 5: 6665- 6673.
- Bhirud RG, Srivastava TS Superoxide Dismutase Activity of Cu(II)2(aspirinate), and Its Adducts with Nitrogen and Oxygen Donors, Inorganica Chimica. 1990; 173: 121-125.
- Ramadevi P, Singh R, Jana SS, Devkar R, Chakraborty D . Ruthenium complexes of ferrocene mannich bases: DNA/BSA interactions and cytotoxicity against A549 cell line, Journal of Photochemistry and Photobiology A: 2015; 305: 1-10.
- Berk B, Ertaş M, Biltekin Synthesis, Antimicrobial Activity Studies and Molecular Property Predictions of Schiff Bases Derived from ortho-Vanillin, Acta Pharmaceutica Sciencia. 2017; 55(1): 83-96.
- Baraa Kasim Mohammed and Yousif E I. Synthesis, Structural Characterisation and Biological Activity; New Metal Complexes Derived from Semicarbazone Ligand. Latin American J. Biotechnology & Life Sciences. 2023; 8(2).
- Abu-Dief AM, Mohamed A review on versatile applications of transition metal complexes incorporating Schiff bases, beni-suef university journal of basic and applied sciences. 2015; 4: 119-133.
- Yousif E I, Hasan N K, Synthesis, Structural Characterization, Thermal properties and Biological Activity of New Complexes Derived from Ligand with N, O Donor Atoms. Journal of Global Pharma Technology. 2019; 11( 9): 613-621.
- Hussein S A, Yousif E ( New Mannich Base (2R)-4-methyl-2- ((S)(phenylamino)(p-tolyl) methyl)cyclohexan-1-one; Synthesis and Spectral Characterisation). Journal of Physics: Conference Series 1999 (2021) 012019 IOP Publishing doi:10.1088/1742- 6596/1999/1/012019.
- Al-Jeboori M J, Hussain S A, New Metal Complexes Derived from Mannich-Base Ligand; Synthesis, Spectral Characterisation and Biological Activity. Journal of Global Pharma Technology. 2019; 11(02): 548-560.
- Liaqat M, Mahmud T, Imran M, Iqbal M, Muddassar M, Ahmad T, Mitu Synthesis, Characterization and Biological Study of a New Mannich Base, 2-[(4- fluorophenyl) (phenylamino)methyl] cyclopentanone (FPC) and its Transition Metal Complexes with Cu(II), Ni(II), Co(II), Fe(II) and Zn(II), REV.CHIM.(Bucharest). 2017; 68(11): 25560- 2565.
- Yousif, I., Hasan, N. K., Al-Jeboori, M. J., & Mohammed, B.(2022). Synthesis, Characterisation, Thermal Properties and Biological Activity of Mannich-Bases (HL And HL) and HL Complexes with Zn (II) and Cd (II). Synthesis, 15(1).
- Sundaravadivel E, Reddy GR, Manoj D, Rajendran S, Kandaswamy M, Janakiraman M. DNA binding and cleavage studies of copper(II) complex containing N2O2 Schiff base ligand, Inorganica Chimica Acta. 2018; 482: 170-178.
- Chaisuwan T, Komalwanich T, Luangsukrerk S, WongkasemjitS (2010) Role of para-substitution in controlling phosphatase activity of dinuclear NiII complexes of Mannich-base ligands: experimental and DFT studies Desalination, 256: 108-114.
- Muhammad L, Tariq M, Ashraf M, Muddassar M, Imran M, Ahmad T, Mitu L. Synthesis, Characterization and Biological Activities of a Novel Mannich Base 2-[(3,4- dimethoxyphenyl) (pyrrolidinyl) methyl]cyclohexanone and its Complexes with Cu(II), Ni(II), Co(II) and Fe(II) Ions, REV.CHIM.(Bucharest). 2017; 68(12): 2845-2849.
- Baron EJ, Finegold Diagnostic Microbiology. 8th Ed. Mosby Company. London.1990; 53-62.
- Nair MS, Arish D, Johnson J. Synthesis, characterization and biological studies on some metal complexes with Schiff base ligand containing pyrazolone moiety, Journal of Saudi Chemical Society. 2016; 20: 591-598.
- Enaam YI, Ahmed HK, Hasan HA. Metal Complexes Derived from Mixed Azo-linked Schiff-base Ligand with Dithiocarbamate Derivative: Formation, Spectral Characterization and Biological Study. J. Chem. 2018; 34(3): 1492-1503.
- Sharghi H, Jokar Highly stereo selective facile synthesis of β-amino carbonyl compounds via a Mannich-type reaction catalyzed by γ-Al2O3/MeSO3H (alumina/methanesulfonic acid: AMA) as a recyclable, efficient, and versatile heterogeneous catalyst, Can. J. Chem. 2009; 88: 14-26.
- Ramachandran E, Gandin V, Bertani R, Sgarbossa P, Natarajan K, Bhuvanesh NSP, Venzo A, Zoleoe A, Glisenti A, Dolmella A, Albinati A, Marzano Synthesis, characterization and cytotoxic activity of novel copper(II) complexes with aroylhydrazone derivatives of 2-Oxo-1,2- dihydrobenzo[h] quinoline-3-carbaldehyde, Journal of Inorganic Biochemistry. 2018; 182: 18-28.
- Ho J, Lee WY, Koh KJT, Lee PPF, Yan YK. Rhenium(I) tricarbonyl complexes of salicylaldehyde semicarbazones: Synthesis, crystal structures and cytotoxicity, Journal of Inorganic Biochemistry. 2013; 119: 10-20.
- Lever ABP. Inorganic Electronic Spectroscopy, New York. 1984; 2nd Ed.
- Mohamad Al-Jeboori J, Baidaa Al-Rubaye K, Nasry JH, Abdul Salam A, Abul R, Siti FM Yusoff, EYI. New Organotin(Iv) Complexes Derived From 3,4-Dihydroxybenzaldehyden(4)- Ethyl-3-Semicarbazone Ligand :Synthesis, Characterisation And Biological Activity Cell. Arch. 2020; 20(2): pp. 6571-6579.
- Singh RV, Dwivedi R, Joshi SC. Synthetic, magnetic, spectral, antimicrobial and antifertility studies of dioxomolybdenum (VI) unsymmetrical imine complexes having a 𝑁 ∩ 𝑁 donor system, Transition Met. Chem. 2004; 29(1): 70-74.
- Ramesh R, Maheswaran Synthesis, spectra, dioxygen affinity and antifungal activity of Ru(III) Schiff base complexes, J. Inorg. Biochem. 2003; 96: 457-462.
- Rahman A, Choudhary M, Thomsen W. Bioassay Techniques for Drug Development, Harwood Academic, 2001.