Synthesis, Characterization, and Biological Activity Evaluation of Thiazolidine-4-One Derivatives Derived From Schiff Bases
Keywords:
Schiff bases, thiazolidin-4-one, biological activityAbstract
In this study, a series of novel derivatives of thiazolidin-4-one ring (H11–H15) were synthesized via the reaction of Schiff bases with thioglycolic acid in tetrahydrofuran (THF) medium. The structures of the synthesized compounds were confirmed using various spectroscopic techniques, including FT-IR, ¹H-NMR, ¹³C-NMR, and UV-Vis. The obtained spectra revealed significant changes indicating the success of the reaction and the formation of the heterocyclic ring. The antibacterial activities of the synthesized compounds were evaluated against two clinically significant bacterial strains: Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). The results showed that compound H14 exhibited the highest activity against E. coli, whereas compound H15 showed strong activity against S. aureus, in some cases surpassing the efficacy of the reference antibiotic amoxicillin. This selective activity highlights the potential of these compounds as promising future antibiotics in combating resistance to conventional antimicrobial agents.
References
1. D. L. Hawksworth, “The magnitude of fungal diversity: the 1•5 million species estimate revisited,” Mycol. Res., vol. 105, no. 12, pp. 1422–1432, 2001.
2. N. Foroughifar and S. Ebrahimi, “One-pot synthesis of 1,3-thiazolidin-4-one using Bi(SCH₂COOH)₃ as catalyst,” Chin. Chem. Lett., vol. 24, no. 5, pp. 389–391, 2013.
3. S. Huber-Villaume et al., “2-(Thienothiazolylimino)-1,3-thiazolidin-4-ones inhibit cell division cycle 25 A phosphatase,” Bioorg. Med. Chem., vol. 24, no. 13, pp. 2920–2928, 2016.
4. G. Revelant et al., “Synthesis and biological evaluation of novel 2-heteroarylimino-1,3-thiazolidin-4-ones as potential anti-tumor agents,” Eur. J. Med. Chem., vol. 94, pp. 102–112, 2015.
5. A. Umar et al., “Design, synthesis, in vitro antiproliferative effect and in situ molecular docking studies of a series of new benzoquinoline derivatives,” J. King Saud Univ. Sci., vol. 34, no. 4, Art. no. 102003, 2022.
6. J. T. Hwang et al., “Apoptotic effect of EGCG in HT-29 colon cancer cells via AMPK signal pathway,” Cancer Lett., vol. 247, no. 1, pp. 115–121, 2007.
7. S. A. Hassan and D. M. Aziz, “Synthesis, in vitro Antimicrobial assay and Molecular Docking Studies of some new Symmetrical Bis-Schiff Bases and their 2-Azetidinones,” Zanco J. Pure Appl. Sci., vol. 33, no. 2, pp. 34–50, 2021.
8. R. H. Saleh et al., “Synthesis of some new thiazolidinone compounds derived from schiff bases compounds and evaluation of their laser and biological efficacy,” Ann. Trop. Public Health, vol. 23, no. 7, pp. 1012–1031, 2020.
9. S. H. Abdullah, M. M. Salih, and A. Al-Badrany, “Synthesis, Characterization and Antibacterial Evaluation of Novel Thiazolidine Derivatives,” J. Angiother., vol. 8, no. 3, pp. 1–9, 2024.
10. S. H. Abdullah, B. A. Khairallah, and K. A. Al-Badrany, “Preparation and characterization of some azetidine-2-one derivatives derived from benzothiazole-2-ol and evaluation of their biological activity,” Indian J. Heterocycl. Chem., vol. 35, no. 1, 2025.
11. B. A. Khairallah et al., “Preparation, Characterization, Biological Activity Evaluation, and Liquid Crystallography Study of New Diazepine Derivatives,” World Med. J. Biomed. Sci., vol. 1, no. 7, pp. 65–76, 2024.
12. M. J. Saleh et al., “Preparation And Evaluation Of The Biological Activity Of A 2-Amino Pyran Ring Using A Solid Base Catalyst,” Cent. Asian J. Med. Nat. Sci., vol. 5, no. 4, pp. 130–138, 2024.
13. A. W. A. S. Talluh, M. J. Saleh, and J. N. Saleh, “Preparation, Characterisation and Study of the Molecular Docking of Some Derivatives of the Tetrazole Ring and Evaluation of their Biological Activity,” World Med. J. Biomed. Sci., vol. 1, no. 7, pp. 15–23, 2024.
14. A. H. Dalaf, M. J. Saleh, and J. N. Saleh, “Green synthesis, characterization, and multifaceted evaluation of thiazolidinone derivatives: A study on biological and laser efficacy,” Eur. J. Mod. Med. Pract., vol. 4, no. 7, pp. 155–168, 2024.
15. M. J. Saleh, J. N. Saleh, and K. Al-Badrany, “Preparation, characterization, and evaluation of the biological activity of pyrazoline derivatives prepared using a solid base catalyst,” Eur. J. Mod. Med. Pract., vol. 4, no. 7, pp. 25–32, 2024.
16. A. W. A. S. Talluh et al., “Preparation, characterization, and evaluation of the biological activity of new 2,3-dihydroquinazoline-4-one derivatives,” Eur. J. Mod. Med. Pract., vol. 4, no. 4, pp. 326–332, 2024.
17. A. W. A. S. Talluh, J. N. Saleh, and M. J. Saleh, “Preparation, Characterization and Evaluation of Biological Activity and Study of Molecular Docking of Some New Thiazolidine Derivatives,” 2024.
18. A. W. A. S. Sattar Talluh et al., “Preparation and Characterization of New Imidazole Derivatives Derived From Hydrazones and Study of their Biological and Laser Efficacy,” Cent. Asian J. Theor. Appl. Sci., vol. 5, no. 4, pp. 202–211, 2024.
19. A. H. Dalaf, “Synthesis and Characterization of Some Quartet and Quinary Hetero cyclic Rings Compounds by Traditional Method and Microwave Routes Method and Evaluation of Their Biological Activity,” M.Sc. thesis, Tikrit Univ., Tikrit, Iraq, 2018.
20. A. H. Dalaf and F. H. Jumaa, “Synthesis, Characterization of some 1,3-Oxazepane-4,7-Dione by Traditional and Microwave routes method and evaluation of their biological activity,” Al-Utroha Pure Sci., no. 8, pp. 93–108, 2018.
21. A. H. Dalaf, F. H. Jumaa, and S. A. S. Jabbar, “Synthesis and Characterization of some 2,3-dihydroquinozoline and evaluation of their biological activity,” Tikrit J. Pure Sci., vol. 23, no. 8, pp. 66–67, 2018.
22. A. J. Salwa et al., “Synthesis and Characterization of Azetidine and Oxazepine Compounds Using Ethyl-4-((4-Bromo Benzylidene) Amino) Benzoate as Precursor and Evaluation of Their Biological Activity,” J. Educ. Sci. Stud., vol. 16, no. 5, pp. 39–52, 2020.
23. I. Q. Abd et al., “Synthesis and Identification of new compounds have Antioxidant activity Beta-carotene, from Natural Auxin Phenyl Acetic Acid,” Res. J. Pharm. Technol., vol. 13, no. 1, pp. 40–46, 2020.
24. B. D. Salih et al., “Biological activity and laser efficacy of new Co(II), Ni(II), Cu(II), Mn(II) and Zn(II) complexes with phthalic anhydride,” Mater. Today Proc., vol. 43, pp. 869–874, 2021.
