Preparation, Characterization, Anti-cancer and Antibacterial Evaluation of New Schiff base and Tetrazole Derivatives

Main Article Content

Yuosra Khalaf Alasadi
Fawzi Hameed Jumaa
Mohammed Ghanam Mukhlif
Safa Mahmood Shawkat

Abstract

This work involved the synthesis of tetrazole derivatives 4,4'-(((sulfonylbis(4,1-phenylene))bis(diazene-2,1-dil))bis(2-(1-(4-R)phenyl]-4),5-Dihydro-1H-tetrazol-5-yl(phenol) (where R = OH or OCH3) through the reaction of the substituted amine in THF as a solvent with sodium azide. FT-IR 1H-NMR Spectrophotometric methods were used to characterize the prepared compounds. The antibacterial activity against four types of bacteria was studied. It was proven that tetrazole compounds were more effective than the compounds from which they were derived. The anticancer activity was measured against MCF-7 strains of human breast cells of the synthesized compounds.

Article Details

How to Cite
Yuosra Khalaf Alasadi, Fawzi Hameed Jumaa, Mohammed Ghanam Mukhlif, & Safa Mahmood Shawkat. (2023). Preparation, Characterization, Anti-cancer and Antibacterial Evaluation of New Schiff base and Tetrazole Derivatives. Tikrit Journal of Pure Science, 28(2), 12–19. https://doi.org/10.25130/tjps.v28i2.1333
Section
Articles

References

[1] S. Hugo, Mittheilungen aus dem Universitätslaboratorium in Pisa: eine neue Reihe organischer Basen, Justus Liebigs Annalen der Chemie 131.1 (1864): 118-119. [2] B. Ahmed, B. M. Yamin, Y. O. Ben Amer, G. SH Ghaith, A. A. Almughery, A. Zarrouk, and I. Warad., Crystal interaction, Hirshfeld surface analysis, and spectral analysis of new Dithiocarbazate Schiff bases derivative (LH) and its neutral cis-Cu (L) 2 complex., Journal of Molecular Structure 1224 (2021): 129207. [3] A. A. Irzoqi, M. M. Salih, H. M. Jirjes, and M. K. Mensoor., Synthesis, Characterization, and Antibacterial Activity of Complexes of Hg (II) with Mixtures of 3-Hydrazonoindolin-2-one and Diphosphine, or Diimine Ligands., Russian Journal of General Chemistry 90, no. 6 (2020): 1069-1073. [4] L. Z. Qiao, P. Xie, M. Zhi Rong, and M. Qiu Zhang., Catalyst-free dynamic exchange of aromatic Schiff base bonds and its application to self-healing and remolding of crosslinked polymers., Journal of Materials Chemistry A 3, no. 39 (2015): 19662-19668. [5] D. A. Hussein, F. H. Jumaa, H. K. Salih, Preparation, Characterization, Biological Evaluation and Assess Laser Efficacy for New Derivatives of Imidazolidin-4-one. International Research Journal of Multidisciplinary Technovation, 3(4), (2021) 41-51. [6] S. Zhaoqing, Q. Li, and L. Mei., pH-Sensitive nanoscale materials as robust drug delivery systems for cancer therapy., Chinese Chemical Letters 31, no. 6 (2020): 1345-1356. [7] D. Sanchari, S. Karim, S. Banerjee, M. Saha, K. D. Saha, and D. Das., Designing of novel zinc (II) Schiff base complexes having acyl hydrazone linkage: study of phosphatase and anti-cancer activities., Dalton Transactions 49, no. 4 (2020): 1232-1240. [8] L. V. Myznikov, , A. Hrabalek, and G. I. Koldobskii., Drugs in the tetrazole series., Chemistry of Heterocyclic Compounds 43, no. 1 (2007). [9] Y. Manju, S. Sharma, and J. Devi., Designing, spectroscopic characterization, biological screening and antioxidant activity of mononuclear transition metal complexes of bidentate Schiff base hydrazones., Journal of Chemical Sciences 133, no. 1 (2021): 1-22. [10] L. V. Myznikov, J. Roh, T. V. Artamonova, A. Hrabalek, G. I. Koldobskii., Drugs in the tetrazole series. Chemistry of Heterocyclic Compounds, 43(1), (2007)1-9. [11] R. Satyajit, S. Kumar Das, H. Khatua, S. Das, and B. Chattopadhyay., Road Map for the Construction of High-Valued N-Heterocycles via Denitrogenative Annulation., Accounts of chemical research 54, no. 23 (2021): 4395-4409. [12] C. Ajay, and A. Dömling., Convergent Three‐Component Tetrazole Synthesis., (2016): 2383-2387.

[13] P. Jigar, S. Jain, P. K. Jain, D. Kishore, and J. Dwivedi., Greener approach toward synthesis of biologically active s‐Triazine (TCT) derivatives: A recent update., Journal of Heterocyclic Chemistry 58, no. 11 (2021): 2049-2066. [14] S. J. Khudhair, Q. MA Hassan, A. M. Jassem, H. A. Sultan, A. Dhumad, and C. A. Emshary., An efficient ultrasound-assisted CH3COONa catalyzed synthesis of thiazolidinone molecule: Theoretical and nonlinear optical evaluations of thiazolidinone-Schiff base derivative., Optical Materials 133 (2022): 112917. [15] J. Sameer, R. B. Mane, K. R. Pulagam, V. Gomez-Vallejo, J. Llop, and C. Rode., The microwave-assisted synthesis of 5-substituted 1 H-tetrazoles via [3+ 2] cycloaddition over a heterogeneous Cu-based catalyst: application to the preparation of 13 N-labelled tetrazoles., New Journal of Chemistry 41, no. 16 (2017): 8084-8091. [16] M. J. Azarnia, K. Azizi, M. S. Jalali, and A. Heydari., Choline Azide: New Reagent and Ionic Liquid in Catalyst‐Free and Solvent‐Free Synthesis of 5‐Substituted‐1H‐Tetrazoles: A Triple Function Reagent., ChemistrySelect 3, no. 1 (2018): 116-121. [17] R. A. Manoj, K. Banik, V. Deshpande, G. Padmavathi, N. K. Roy, G. Sethi, L. Fan, A. P. Kumar, and A. B. Kunnumakkara., Magnolol: a neolignan from the magnolia family for the prevention and treatment of cancer., International Journal of Molecular Sciences 19, no. 8 (2018): 2362. [18] H. Fahmi, Z. P. Demko, L. Noodleman, and K. B. Sharpless., Mechanisms of tetrazole formation by addition of azide to nitriles., Journal of the American Chemical Society 124, no. 41 (2002): 12210-12216. [19] J. Peter, and S. B. Baylin., The epigenomics of cancer., Cell 128, no. 4 (2007): 683-692. [20] Y. Jie, Y. Xu, M. Jiang, D. Zou, G. Yang, L. Shen, and J. Zou., Photochemical property of two Ru (II) compounds based on 5-(2-pyrazinyl) tetrazole for cancer phototherapy by changing auxiliary ligand., Journal of Inorganic Biochemistry 193 (2019): 124-129. [21] C. Bruce, and T. G. Roberts., Chemotherapy and the war on cancer., Nature Reviews Cancer 5, no. 1 (2005): 65-72. [22] A. Mohammed, M. A. Toma, A. H. Dalaf, E. Q. Abdullah, and H. K. Salih., Synthesis and characterization of new azo dyes based on thiazole and assess the biological and laser efficacy for them and study their dyeing application., Egyptian Journal of Chemistry 64, no. 6 (2021): 2903-2911. [23] A. M. Mezher, M. Q. Jabbar, A. H. Dalaf, and H. K. Salih., Application of biological activity of oxazepine and 2-azetidinone compounds and study of their liquid crystalline behavior., Materials Today: Proceedings 43 (2021): 2040-2050. [24] S. D. Salman, S. Adnan., Eurasian Chemico-Technological Journal, 20(3), (2018), 264-276. [25] W. A. Fadllallah, M. B. Hussein, and M. M. Mohammed., Synthesis, characterization of Schiff bases derived from salicylaldehyde with some amino acids by a new developed method., Sch. Int. J. Chem. Mater. Sci 4 (2021): 46-53. [26] H. A. Soliman, A. Kalmouch, H. M. Awad, and N. A. M. Abdel Wahed., Synthesis of new tetrazole derivatives and their biological evaluation., Russian Journal of General Chemistry 88, no. 8 (2018): 1726-1733. [27] Z. T. Tryfon, A. L. Chandgude, and A. Dömling., Multicomponent reactions, union of MCRs and beyond., The Chemical Record 15, no. 5 (2015): 981-996. [28] E. Łukowska-Chojnacka, and A. Kowalkowska., Gizi nska, M.; Koronkiewicz, M.; Staniszewska, M. Synthesis of tetrazole derivatives bearing pyrrolidine scaffold and evaluation of their antifungal activity against Candida albicans., Eur. J. Med. Chem 164 (2019): 106-120. [29] K. G. Şeker, E. K. Akkol, Y. Genç, H. Bardakcı, Ç. Yücel, and E. Sobarzo-Sánchez., Combretastatins: an overview of structure, probable mechanisms of action and potential applications., Molecules 25, no. 11 (2020): 2560.