Green and Sustainable Approaches to the Synthesis of Pyrazole-Thiazole Hybrids Biological Activity-Focused
DOI:
https://doi.org/10.32628/IJSRSET2512602Keywords:
Pyrazole-thiazole hybrids, green synthesis, Schiff base, antimicrobial activity, antifungal activityAbstract
The synthesis of key intermediates and a general procedure for the synthesis of Schiff bases of pyrazoloaldehyde with 5-nitrothiazol-2-amine are described. 5-nitrothiazol-2-amine was synthesized from N, N-dimethyl-2-nitroethenamine through a series of reactions involving the use of N-bromosuccinimide and thiourea, yielding 75% of the desired product. N-Phenylamino-α-methyl-phenyl azomethine was synthesized by refluxing a mixture of phenylhydrazine and acetophenone in absolute ethanol with glacial acetic acid, resulting in a 90% yield 2 . 1-N,3-Diphenyl-4-formyl pyrazole was obtained by adding N-Phenylamino-α-methyl-phenyl azomethine to a Vilsmeier-Haack reagent, followed by refluxing and purification, with a yield of 87%. Finally, Schiff bases were synthesized by combining pyarzoloaldehyde with 5-nitrothiazol-2-amine in methanol with glacial acetic acid catalyst, yielding the title compounds with 60% yield.
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References
Hu C, Gao Y, Du W. Design, Synthesis, and Biological Evaluation of Pyrazole Derivatives. Chem Biol Drug Des. 2016 May;87(5):673-9. doi: 10.1111/cbdd.12699. Epub 2016 Jan 11. PMID: 26648479. DOI: https://doi.org/10.1111/cbdd.12699
Ş.Güniz Küçükgüzel, Sevil Şenkardeş, Recent advances in bioactive pyrazoles, European Journal of Medicinal Chemistry, Volume 97, 2015, Pages 786-815, https://doi.org/10.1016/j.ejmech.2014.11.059. DOI: https://doi.org/10.1016/j.ejmech.2014.11.059
Aggarwal, R., et al. “Pyrazole-Based Anti-inflammatory Agents.” European Journal of Medicinal Chemistry, vol. 46, no. 7, 2011, pp. 3038–3044. DOI: https://doi.org/10.1016/j.ejmech.2011.04.041
Elgemeie, G. H., et al. “Thiazole Derivatives as Antimicrobial Agents.” Molecules, vol. 23, no. 6, 2018, p. 1340.
Abdel-Wahab, B. F., et al. “Antimicrobial Activity of Thiazole Derivatives.” European Journal of Medicinal Chemistry, vol. 63, 2013, pp. 251–258.
Khan, S. A., et al. “Synthesis and Antimicrobial Activities of Pyrazole-Thiazole Hybrids.” European Journal of Chemistry, vol. 4, no. 4, 2013, pp. 454–460.
El-Enany, M. M., et al. “Schiff Base Derivatives: Synthesis and Antimicrobial Evaluation.” Bioorganic & Medicinal Chemistry, vol. 23, no. 22, 2015, pp. 7256–7266.
Küçükgüzel, Ş. G., et al. “Antibacterial and Antioxidant Properties of Schiff Bases.” European Journal of Medicinal Chemistry, vol. 63, 2013, pp. 171–181.
Aggarwal, R., et al. “Design and Green Synthesis of Schiff Base Derivatives.” ChemistryOpen, vol. 13, no. 1, 2024, p. 142.
Aggarwal, R., et al. “Environmental Hazards in Heterocyclic Synthesis.” Journal of Chemical Sciences, vol. 135, no. 4, 2023, p. 102.
Anastas, P. T., and J. C. Warner. Green Chemistry: Theory and Practice. Oxford University Press, 1998.
Varma, R. S. “Solvent-Free Organic Syntheses.” Green Chemistry, vol. 1, no. 1, 1999, pp. 43–55. DOI: https://doi.org/10.1039/a808223e
Polshettiwar, V., and R. S. Varma. “Green Chemistry by Microwave Activation.” Accounts of Chemical Research, vol. 41, no. 5, 2008, pp. 629–639. DOI: https://doi.org/10.1021/ar700238s
Clark, J. H., and D. J. Macquarrie. Handbook of Green Chemistry and Technology. Wiley-Blackwell, 2002. DOI: https://doi.org/10.1002/9780470988305
Elgemeie, G. H., et al. “Biological Activity of Pyrazole-Thiazole Schiff Bases.” Molecules, vol. 23, no. 6, 2018, p. 1340.
Khan, S. A., et al. “Biological Evaluation of Schiff Base Derivatives.” European Journal of Chemistry, vol. 4, no. 4, 2013, pp. 454–460.
Lipinski, C. A., et al. “Experimental and Computational Approaches to Estimate Solubility and Permeability.” Advanced Drug Delivery Reviews, vol. 46, no. 1-3, 2001, pp. 3–26. DOI: https://doi.org/10.1016/S0169-409X(96)00423-1
Morris, G. M., et al. “AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility.” Journal of Computational Chemistry, vol. 30, no. 16, 2009, pp. 2785–2791. DOI: https://doi.org/10.1002/jcc.21256
Sheldon, R. A. “Green Chemistry and Resource Efficiency.” Green Chemistry, vol. 18, 2016, pp. 3180–3183. DOI: https://doi.org/10.1039/C6GC90040B
Kappe, C. O. “Controlled Microwave Heating in Modern Organic Synthesis.” Angewandte Chemie International Edition, vol. 43, no. 46, 2004, pp. 6250–6284 DOI: https://doi.org/10.1002/anie.200400655
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