Preparation, Characterization, Theoretical and Biological Study of new Complexes with mannich base , 2chloro –N-5-(Piperidin -1-ylmethylthio)-1, 3, 4- Thiadiazol-2-yl)acetamide
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Abstract
A new Mannich base ligand was prepared by reacting the 2-chloro.-N-(5-mercapto-1, 3, 4-thiadazol -2-yl) acetamide and Piperidine in the presence (formaldehyde) (L) ligand. A series of ligand complexes were prepared from (L) with the metal ion Co (II), Ni (II), Cu (II), Pd (II), Pt (IV), and Au (III). Various spectroscopic techniques such as C.H.N.S, FTIR, UV-VIS, , 1HNMR, 13CNMR, Magnetic moment, and molar conductivity successfully characterize the obtained compounds. The M: L ratio was determined using the molar ratio method in solution. All prepared compounds' antibacterial and antifungal activity was studied against two types of bacteria and one type of fungi at a rate of 0.02M. The standard ΔH° f and ΔEb of the ligands and all the prepared complexes were calculated using Hyperchem 8.0.7 program, and the study proved that the complexes are more stable than the ligands. In addition, the vibrational frequencies of the ligand were calculated, and the theoretical error rate of the process was calculated.
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Jia, X.; Liu, Q.; Wang, S.; Zeng, B.; Du, G.; Zhang, C.; Li, Y. Synthesis, Cytotoxicity, and in Vivo Antitumor Activity Study of Parthenolide Semicarbazones and Thiosemicarbazones. Bioorganic & Medicinal Chemistry 2020, 28, 115557, doi:10.1016/j.bmc.2020.115557.
Roder, C.; Thomson, M.J. Auranofin: Repurposing an Old Drug for a Golden New Age. Drugs R D 2015, 15, 13–20, doi:10.1007/s40268-015-0083-y.
Jain, A.K.; Sharma, S.; Vaidya, A.; Ravichandran, V.; Agrawal, R.K. 1,3,4-Thiadiazole and Its Derivatives: A Review on Recent Progress in Biological Activities. Chemical Biology & Drug Design 2013, 81, 557–576, doi:10.1111/cbdd.12125.
Ainsworth, C. The Condensation of Aryl Carboxylic Acid Hydrazides with Orthoesters. J Am Chem Soc 1955, 77, 1148–1150, doi:10.1021/ja01610a019.
de Andrade Danin Barbosa, G.; Palermo de Aguiar, A. Synthesis of 1,3,4-Thiadiazole Derivatives and Microbiological Activities: A Review. Revista Virtual de Química 2019, 11, 806–848, doi:10.21577/1984-6835.20190058.
Pandey, A.; Rajavel, R.; Chandraker, S.; Dash, D. Synthesis of Schiff Bases of 2-Amino-5-Aryl-1,3,4-Thiadiazole and Its Analgesic, Anti-Inflammatory and Anti-Bacterial Activity. E-Journal of Chemistry 2012, 9, 2524–2531, doi:10.1155/2012/145028.
Schweinfurth, D.; Krzystek, J.; Schapiro, I.; Demeshko, S.; Klein, J.; Telser, J.; Ozarowski, A.; Su, C.-Y.; Meyer, F.; Atanasov, M.; et al. Electronic Structures of Octahedral Ni(II) Complexes with “Click” Derived Triazole Ligands: A Combined Structural, Magnetometric, Spectroscopic, and Theoretical Study. Inorganic Chemistry 2013, 52, 6880–6892, doi:10.1021/ic3026123.
G. Pyne, S.; Tang, M. The Boronic Acid Mannich Reaction. In Organic Reactions, John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2013, 211–498.
Singh, B.N.; Shukla, S.K.; Singh, M. Synthesis and Biological Activity of Sulphadiazine Schiff’{} s Bases of Isatin and Their N-Mannich Bases. asian Journal of chemistry 2007, 19, 5013.
Sumrra, S.H.; Arshad, Z.; Zafar, W.; Mahmood, K.; Ashfaq, M.; Hassan, A.U.; Mughal, E.U.; Irfan, A.; Imran, M. Metal Incorporated Aminothiazole-Derived Compounds: Synthesis, Density Function Theory Analysis, in Vitro Antibacterial and Antioxidant Evaluation. Royal Society Open Science 2021, 8, doi:10.1098/rsos.210910.
Rehman, M. ur Metal-Based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes. Science Journal of Chemistry 2013, 1, 56, doi:10.11648/j.sjc.20130105.12.
Pishawikar, S.A.; More, H.N. Synthesis, Docking and, in-Vitro Screening, of Mannich Bases of Thiosemicarbazide, for Anti-Fungal Activity. Arabian Journal of Chemistry 2017, 10, S2714–S2722, doi:10.1016/j.arabjc.2013.10.016.
Evans, A.; Kavanagh, K.A. Evaluation of Metal-Based Antimicrobial, Compounds for the Treatment of Bacterial, Pathogens. Journal of Medical Microbiology 2021, 70, doi:10.1099/jmm.0.001363.
Hadeel Hamid Mahmood, S.R.B. PREPARATION, PHYSICOCHEMICAL, AND BIOLOGICAL STUDY OF SCHIFF BASE DERIVED, FROM 2- AMINO-5-MERCPTO-1,3,4 THIADIAZOLE WITH, SOME METAL IONS. Biochem. Cell. Arch 2021.
Karcz, D.; Matwijczuk, A.; Kamiński, D.; Creaven, B.; Ciszkowicz, E.; Lecka-Szlachta, K. Starzak, K. Structural Features of 1,3,4-Thiadiazole-Derived, Ligands and Their Zn(II) and Cu(II) , Complexes Which Demonstrate Synergistic Antibacterial Effects with Kanamycin,. International Journal of Molecular Sciences 2020, 21, 5735, doi:10.3390/ijms21165735.
Guo, J.; Zhou, J.; Guorui, Fu; He, Y.; Li, W.; Lü, X. Two Efficient Near-Infrared (NIR) Luminescent [Ir(C^N)2(N^O)]-Characteristic, Complexes with 8-Hydroxyquinoline (8-Hq) as, the Ancillary Ligand. Inorganic Chemistry Communications 2019, 101, 69–73, doi:10.1016/j.inoche.2019.01.019.
Lotfi, S.; Brgoch, J. Predicting Pressure-Stabilized Alkali, Metal Iridides: A−Ir (A = Rb, Cs). Computational Materials, Science 2019, 158, 124–129, doi: ,10.1016/j.commatsci.2018.11.018.
Guo, J.; Zhou, J.; Guorui Fu; He, Y.; Li, W.; Lü, X. Two Efficient, Near-Infrared (NIR) Luminescent [Ir(C^N)2(N^O)]-Characteristic Complexes, with 8-Hydroxyquinoline (8-Hq) as the Ancillary, Ligand. Inorganic Chemistry, Communications 2019, 101, 69–73, doi:10.1016/j.inoche.2019.01.019.
Ibraheem, I.H.; Sadiq, A.S.; Al-Tameemi, M.; Alias, M.F. Synthesis, Spectral, Identification, Antibacterial Evaluationand Theoretical, Study of Co, Fe, Rh and Pd Complexes for 2-Benzoylthiobenzimidazol. Baghdad Science Journal 2022, 1326–1334, doi:10.21123/bsj.2022.6704.
Baqer, S.R.; Hassan, S.S.; Hassan, N.M.; Saleh, A.M. Biological, Evaluation, and Theoretical Study of Bi-Dentate Ligand, for Amoxicillin, Derivative with Some, Metal Ions. Baghdad Science Journal 2021, 18, doi:10.21123/bsj.2021.18.4.1269.
Gülfen, M.; Özdemir, A. Monitoring Cu(II)-Insulin, and Mn(II)-Insulin Complexes Using Potentiometric, Chromatographic, UV–Vis Absorption and Fluorescence, Emission Spectroscopic Techniques. Journal of Molecular Structure 2022, 1259, 132763, doi:10.1016/j.molstruc.2022.132763.
Alias, M.F.; Murtadha, J.H.; Abdul ALrazzaq, I.H. Study of Cytotoxic, Effect of Aqueous Extract Fenugreek, (Trigonella Foenum Graecum L.S) Seeds and The New, Complexes of Rh (II) and Pd (II) on Cancer Cell Lines,. Baghdad Science Journal 2018, 9, 289–295.
Mortazavi, S.Z.; Parvin, P.; Reyhani, A.; Golikand, A.N.; Mirershadi, S. Effect of Laser, Wavelength at IR (1064 Nm) and UV (193 Nm) on the Structural Formation, of Palladium Nanoparticles in Deionized Water. The Journal of Physical Chemistry C 2011, 115, 5049–5057, doi:10.1021/jp1091224.
Lopez, T.; Villa, M.; Gomez, R. UV-Visible Diffuse Reflectance, Spectroscopic Study of Platinum, Palladium, and Ruthenium, Catalysts Supported on Silica. The Journal of, Physical Chemistry 1991, 95, 1690–1693, doi:10.1021/j100157a038.
Phillips, J.P.; Mackey, N.M.; Confait, B.S.; Heaps, , D.T.; Deng, X.; Todd, M.L.; Stevenson, S.; Zhou, H.; Hoyle, C.E. Dispersion of Gold, Nanoparticles in UV-Cured, Thiol−Ene Films by, Precomplexation of Gold−Thiol. Chemistry, of Materials 2008, 20, 5240–5245, doi:10.1021/cm8007842.
Zhao, X.; Zhan, X.; Zhang, H.; Wan, Y.; Yang, H.; Wang,, Y.; Chen, Y.; Xie, W. Synthesis and Biological Evaluation, of Isatin Derivatives Containing 1,3,4-Thiadiazole as, Potent a-Glucosidase Inhibitors. Bioorganic & Medicinal, Chemistry Letters 2021, 54, 128447, doi:10.1016/j.bmcl.2021.128447
R. A. M. Al-Hasani MANNICH BASE, DERIVED FROM 1,3,4-THIADIAZOLE AS, CHELATING LIGAND FOR SOME TRANSITION METAL, COMPLEXES. ANJS 2008, 11, 42–56, DOI:10.22401/JNUS.11.2.06.