Synthesis and Characterization of New Thiazine Compounds Derivatized From 1-(Pyrazin-2-Yl)-3-(Benzylidene) Propanone and  Study of Their Biological Effectiveness

Saad Salim Jasim; Shakhawan Beebany; Jawdat Hilmi Abdulwahid; Khalid A. Al-Badrani

doi:10.61132/obat.v3i3.1236

Authors

Saad Salim Jasim University of Kirkuk
Shakhawan Beebany University of Kirkuk
Jawdat Hilmi Abdulwahid Northern Technical University of Kirkuk
Khalid A. Al-Badrani University of Tikrit

DOI:

https://doi.org/10.61132/obat.v3i3.1236

Keywords:

Heterocyclic Compounds, Chalcone Derivatives, Antibacterial Efficacy, Thiazine, Biological Activity.

Abstract

This study examines the synthesis and characterization of new compounds produced from chalcone, confirming their favorable yield and excellent purity utilizing Using FT-IR and 1H and 13C NMR spectroscopy. The compounds showed efficacy comparable to that of conventional antibiotics, demonstrating substantial bactericidal activity against Staphylococcus aureus and Escherichia coli. Interestingly, molecule S10 had stronger antibacterial activity, possibly as a result of its efficient electronic pairings. Furthermore, the compounds demonstrated resilience for up to 45 seconds when tested for stability under helium-neon laser irradiation. Longer exposure (60 seconds), however, caused discernible color and melting point alterations, suggesting thermal or photochemical deterioration. These results point to the possibility of additional pharmacological uses for molecules produced from chalcone.

Downloads

Download data is not yet available.

References

[1] D.N. Dhar, "The Chemistry of Chalcones and Related Compounds”, John Wiley and Sons, Inc., p. 54-47, (1981). ISBN 0471080071.

[2] Al-Tufah, M.M., Beebaeny, S., Jasim, S.S. and Mohammed, B.L., 2023. Synthesis, characterization of ethyl dioxoisoindolinyl cyclohexenone carboxylate derivatives from some chalcones and its biological activity assessment. Chemical Methodologies, 7, pp.408-418. https://doi.org/10.22034/chemm.2023.388126.1654

[3] Gutierrez, R.M.P., Muñiz-Ramirez, A. and Sauceda, J.V., 2015. The potential of chalcones as a source of drugs. African Journal of Pharmacy and Pharmacology, 9(8), pp.237-257. https://doi.org/10.5897/AJPP2015.%204267

[4] Hu, D., Zhang, N., Zhang, Y., Yuan, C., Gong, C., Zhou, Y. and Xue, W., 2023. Design, synthesis and biological activity of novel chalcone derivatives containing indole. Arabian Journal of Chemistry, 16(6), p.104776. https://doi.org/10.1016/j.arabjc.2023.104776

[5] Al-Mulla, A., 2017. A review: biological importance of heterocyclic compounds. Der Pharma Chem, 9(13), pp.141-147. Available online at www.derpharmachemica.com

[6] Amin, A., Qadir, T., Sharma, P.K., Jeelani, I. and Abe, H., 2022. A review on the medicinal and industrial applications of N-containing heterocycles. The Open Medicinal Chemistry Journal, 16(1). http://dx.doi.org/10.2174/18741045-v16-e2209010

[7] Asif, M., Imran, M. and Abida, 2022. Antimicrobial activities of various thiazine based heterocyclic compounds: a mini-review. Mini-Reviews in Organic Chemistry, 19(2), pp.166-172. https://doi.org/10.2174/1570193X18666210629102447

[8] Choudhary, S., Silakari, O. and Singh, P.K., 2018. Key updates on the chemistry and biological roles of thiazine scaffold: a review. Mini Reviews in Medicinal Chemistry, 18(17), pp.1452-1478. https://doi.org/10.2174/1389557518666180416150552

[9] Chaucer, P. and Sharma, P.K., 2020. Study of thiazines as potential anticancer agents. Plant Arch, 20(2), pp.3199-3202.

[10] Wiatrak, B., Krzyżak, E., Szczęśniak-Sięga, B., Szandruk-Bender, M., Szeląg, A. and Nowak, B., 2022. Effect of tricyclic 1, 2-thiazine derivatives in neuroinflammation induced by preincubation with lipopolysaccharide or coculturing with microglia-like cells. Pharmacological Reports, 74(5), pp.890-908. https://doi.org/10.1007/s43440-022-00414-8

[11] Jasim, S.S., Abdulwahid, J.H., Beebany, S. and Mohammed, B.L., 2023. Synthesis, identification, and antibacterial effect assessment of some new 1, 4-thiazepines, derived from substituted diphenyl acrylamides and diphenyl dienones. Chemical Methodologies, 7, pp.509-523. https://doi.org/10.22034/chemm.2023.392659.1668

[12] Dalaf, A.H., Jumaa, F.H., Aftana, M.M., Salih, H.K. and Abd, I.Q., 2022. Synthesis, Characterization, Biological Evaluation, and Assessment Laser Efficacy for New Derivatives of Tetrazole. In Key Engineering Materials (Vol. 911, pp. 33-39). Trans Tech Publications Ltd. https://doi.org/10.4028/p-6849u0

[13] Dabholkar, V.V. and Parab, S.D., 2011. Synthesis of chalcones, 1, 3-thiazines and 1, 3-pyrimidines derivatives and their biological evaluation for anti-inflammatory, analgesic and ulcerogenic activity. The Pharm. Res, 5, pp.127-143.

[14] Abdul Wahed Abdul, S.T., Mohammed Jwher, S. and Jamil Nadhem, S., 2024. Preparation, Characterisation and Study of the Molecular Docking of Some Derivatives of the Tetrazole Ring and Evaluation of their Biological Activity. World of Medicine: Journal of Biomedical Sciences, 1(7), pp.15-23. Available at http://eprints.umsida.ac.id/id/eprint/15687

[15] Saleh, M.J., Saleh, J.N. and Al-Badrany, K., 2024. Preparation, characterization, and evaluation of the biological activity of pyrazoline derivatives prepared using a solid base catalyst. European Journal of Modern Medicine and Practice, 4(7), pp.25-32.

[16] Saleh, J.N. and Khalid, A., 2023. Synthesis, characterization and biological activity evaluation of some new pyrimidine derivatives by solid base catalyst AL2O3-OBa. Central Asian Journal of Medical and Natural Science, 4(4), pp.231-239.

[17] Al-Hadidi, O.A.F., Al-Badrany, K.A. and Al-Bajari, S.A., 2022. Synthesis some of thiazepine compounds from 2-carbboxyaldehyde-5-methyl thiophene and study their biological activity on infected male rats epileptic. Journal of Education and Scientific Studies, 2(20).

[18] Najim, D.M., Al-badrany, K.A. and Saleh, M.K., 2022. Synthesis of some new oxazepine compounds derived from cyanoethyl acetate and study their inhibitory activity against some pathogenic bacterial species. International journal of health sciences, 6(S1), pp.14527-14541. https://doi.org/10.53730/ijhs.v6nS1.8901

[19] Al-Tufah, M.M., Jasim, S.S. and Al-Badrany, K.A., 2020. Synthesis and Antibacterial Evaluation of some New Pyrazole Derivatives. Prof.(Dr) RK Sharma, 20(3), p.178.

[20] Kumar, S., Arora, A., Sapra, S., Kumar, R., Singh, B.K. and Singh, S.K., 2024. Recent advances in the synthesis and utility of thiazoline and its derivatives. RSC advances, 14(2), pp.902-953. https://doi.org/10.1039/D3RA06444A

[21] Talluh, A.W.A.S., Saleh, J.N. and Saleh, M.J., 2024. Preparation, Characterization and Evaluation of Biological Ac-tivity and Study of Molecular Docking of Some New Thiazoli-dine Derivatives. World of Science: Journal on Modern Research Technologies, 3(2), pp.49-57. Available at https://univerpubl.com/index.php/woscience

[22] Saleh, M.J. and Al-Badrany, K.A., 2023. Preparation, characterization of new 2-oxo pyran derivatives by AL2O3-OK solid base catalyst and biological activity evaluation. Central Asian Journal of Medical and Natural Science, 4(4), pp.222-230.

[23] Abdul Wahed Abdul, S.T., Mohammed, J.S., Jamil Nadhem, S. and Khalid, A.B., 2024. Preparation, characterization, and evaluation of the biological activity of new 2, 3-dihydroquinazoline-4-one derivatives. European Journal of Modern Medicine and Practice, 4(4), pp.326-332. Available at http://eprints.umsida.ac.id/id/eprint/15678

[24] Talluh, A. W. A. S. (2024). Preparation, Characterization, Evaluation of Biological Activity, and Study of Molecular Docking of Azetidine Derivatives. Central Asian Journal of Medical and Natural Science, 5(1), 608-616.‏

[25] Al-Suhail, R.G.A. and Ali, L.F., 2021. Statistical analysis of COVID-19 pandemic across the provinces of Iraq. Iraqi Journal of Science, pp.811-824.