SYNTHESIS, CHARACTERIZATION, AND STUDY OF BIOLOGICAL ACTIVITY OF OXAZEPINE COMPOUNDS DERIVED FROM 1,3,4-OXADIAZOLE
Abstract
This study involves the synthesis of pentagonal rings of oxazepine derivatives through the reaction of one mole of hydrazide base derivatives with two moles of malic anhydride. The validity of the compound structures was confirmed using physical and spectroscopic methods such as UV-Vis. spectroscopy, infrared spectroscopy, proton nuclear magnetic resonance spectroscopy. Additionally, melting points and purity were determined, and reaction progress was monitored by Thin-Layer Chromatography (TLC). The impact of some prepared compounds on the growth of two bacterial isolates, one Gram-negative (Escherichia coli) and the other Gram-positive (Staphylococcus aureus), was studied. Antibiotics amoxicillin, ampicillin, and ciprofloxacin were used as controls, and some of the prepared compounds showed good inhibitory effectiveness against the tested bacteria.
References
2. Serrano-Wu, M. H., Laurent, D. R. S., Chen, Y., Huang, S., Lam, K. R., Matson, J. A., ... & Balasubramanian, B. N. (2002). Sordarin oxazepine derivatives as potent antifungal agents. Bioorganic & medicinal chemistry letters, 12(19), 2757-2760.
3. Sunil, D., Ranjitha, C., Rama, M., & KSR, P. (2014). Oxazepine derivative as an antitumor agent and snail1 inhibitor against human colorectal adenocarcinoma. International Journal of Innovative Research in Science, Engineering and Technology, 3(8), 15357-15363.
4. Mohammad, A. T., Yeap, G. Y., & Osman, H. (2015). Synthesis, characterization and theoretical study of a new liquid crystal compound with an oxazepine core. Journal of Molecular Structure, 1087, 88-96.
5. Yang, X., Wei, L., Wu, Y., Zhou, L., Zhang, X., & Chi, Y. R. (2023). Atroposelective Access to 1, 3‐Oxazepine‐Containing Bridged Biaryls via Carbene‐Catalyzed Desymmetrization of Imines. Angewandte Chemie International Edition, 62(1), e202211977.
6. Hamak, K. F., & Eissa, H. H. (2013). Synthesis, characterization, biological evaluation and anti corrosion activity of some heterocyclic compounds oxazepine derivatives from Schiff bases. Organic Chemistry: Current Research, 2(3), 1.
7. Matsuzaki, H., Takeuchi, I., Hamada, Y., & Hatano, K. (2000). Studies on the 1, 4-oxazepine ring formation reaction using the molecular orbital method. CHEMICAL AND PHARMACEUTICAL BULLETIN-TOKYO-, 48(5), 755-756.
8. Al-Juburi, R. M. (2012). Synthesis and characterization of some heterocyclic compounds (oxazepine, tetrazole) derived from Schiff bases. Al-Nahrain Journal of Science, 15(4), 60-67.
9. Zaware, N., & Ohlmeyer, M. (2014). Recent advances in dibenzo [b, f][1, 4] oxazepine synthesis. Heterocyclic Communications, 20(5), 251-256.
10. Nagarajan, K., David, J., & Bhat, G. A. (1985). Synthesis of 10, 11-dihydrodibenz [b, f][l, 4] oxazepine derivatives as potential anticonvulsant & psychotropic agents. Indian Journal of Chemistry-Section B: Organic and Medicinal Chemistry, 24, 840-844.
11. Dalaf, A. H. (2018). 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 University, Tikrit, Iraq: 1-94 pp.
12. Dalaf, A. H., & Jumaa, F. H. (2018). Synthesis, Characterization of some 1,3-Oxazepane -4,7-Dione by Traditional and Microwave routes method and evaluation of their biological activity. Al-utroha for Pure Science. (8): 93-108.
13. Dalaf, A. H., Jumaa, F. H., & Jabbar, S. A. S. (2018). Synthesis and Characterization of some 2, 3-dihydroquinozoline and evaluation of their biological activity. Tikrit Journal of Pure Science, 23(8): 66-67. http://dx.doi.org/10.25130/tjps.23.2018.131.
14. Salwa, A. J., Ali, L. H., Adil, H. D., Hossam, S. A. (2020). Synthesis and Characterization of Azetidine and Oxazepine Compounds Using Ethyl-4-((4-Bromo Benzylidene) Amino) Benzoate as Precursor and Evalution of Their Biological Activity. Journal of Education and Scientific Studies, ISSN: 24134732. 16(5): 39-52.
15. Abd, I. Q., Ibrahim, H. I., Jirjes, H. M., & Dalaf, A. H. (2020). Synthesis and Identification of new compounds have Antioxidant activity Beta-carotene, from Natural Auxin Phenyl Acetic Acid. Research Journal of Pharmacy and Technology, 13(1): 40-46. https://doi.org/10.5958/0974-360X.2020.00007.4.
16. Dalaf, A. H., & Jumaa, F. H. (2020). Synthesis, Identification and Assess the Biological and Laser Efficacy of New Compounds of Azetidine Derived from Benzidine. Muthanna Journal of Pure Science (MJPS), 7(2):12-25. DOI: 10.18081/2226-3284/14-10/12-25.
17. Saleh, R. H., Rashid, W. M., Dalaf, A. H., Al-Badrany, K. A., & Mohammed, O. A. (2020). Synthesis of Some New Thiazolidinone Compounds Derived from Schiff Bases Compounds and Evaluation of Their Laser and Biological Efficacy. Ann Trop & Public Health, 23(7): 1012-1031. http://doi.org/10.36295/ASRO.2020.23728
18. Yass, I. A., Aftan, M. M., Dalaf, A. H., & Jumaa, F. H. (Nov. 2020). Synthesis and Identification of New Derivatives of Bis-1,3-Oxazepene and 1,3-Diazepine and Assess the Biological and Laser Efficacy for Them. The Second International & The Fourth Scientific Conference of College of Science – Tikrit University. (P4): 77-87.
19. Salih, B. D., Dalaf, A. H., Alheety, M. A., Rashed, W. M., & Abdullah, I. Q. (2021). Biological activity and laser efficacy of new Co (II), Ni (II), Cu (II), Mn (II) and Zn (II) complexes with phthalic anhydride. Materials Today: Proceedings, 43, 869-874. https://doi.org/10.1016/j.matpr.2020.07.083.
20. Aftan, M. M., Jabbar, M. Q., Dalaf, A. H., & Salih, H. K. (2021). Application of biological activity of oxazepine and 2-azetidinone compounds and study of their liquid crystalline behavior. Materials Today: Proceedings, 43, 2040-2050. https://doi.org/10.1016/j.matpr.2020.11.838.
21. Aftan, M. M., Talloh, A. A., Dalaf, A. H., & Salih, H. K. (2021). Impact para position on rho value and rate constant and study of liquid crystalline behavior of azo compounds. Materials Today: Proceedings. https://doi.org/10.1016/j.matpr.2021.02.298.
22. Aftan, M. M., Toma, M. A., Dalaf, A. H., Abdullah, E. Q., & Salih, H. K. (2021). 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(6), 2903-2911. https://dx.doi.org/10.21608/ejchem.2021.55296.3163.
23. Khalaf, S. D., Ahmed, N. A. A. S., & Dalaf, A. H. (2021). Synthesis, characterization and biological evaluation (antifungal and antibacterial) of new derivatives of indole, benzotriazole and thioacetyl chloride. Materials Today: Proceedings. 47(17), 6201-6210. https://doi.org/10.1016/j.matpr.2021.05.160.
24. Dalaf, A. H., Jumaa, F. H., & Salih, H. K. (2021). Preparation, Characterization, Biological Evaluation and Assess Laser Efficacy for New Derivatives of Imidazolidin-4-one. International Research Journal of Multidisciplinary Technovation, 3(4), 41-51. https://doi.org/10.34256/irjmt2145.
25. Dalaf, A. H., Jumaa, F. H., & Salih, H. K. (2021). MULTIDISCIPLINARY TECHNOVATION. Red, 15(A2), C44H36N10O8.
26. Dalaf, A. H., Jumaa, F. H., Aftana, M. M., Salih, H. K., & 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.
27. Alasadi, Y. Kh., Jumaa, F. H., Dalaf, A. H., Shawkat, S. M., & Mukhlif, M. Gh. (2022). Synthesis, Characterization, and Molecular Docking of New Tetrazole Derivatives as Promising Anticancer Agents. Journal of Pharmaceutical Negative Results. 13(3): 513-522. https://doi.10.47750/pnr.2022.13.03.079.
28. Dalaf, A. H., Jumaa, F. H., & Yass, I. A. (2022, November). Synthesis, characterization, biological evaluation, molecular docking, assess laser efficacy, thermal performance and optical stability study for new derivatives of bis-1, 3-oxazepene and 1, 3-diazepine. In AIP Conference Proceedings (Vol. 2394, No. 1, p. 040037). AIP Publishing LLC. https://doi.org/10.1063/5.0121213.
29. Alasadi, Y. K., Jumaa, F. H., & Dalaf, A. H. (2022, November). Synthesis, identification, antibacterial activity and laser effect of new derivatives of bis-1, 3-oxazepene-4, 7-dione and 1, 3-diazepine-4, 7-dione. In AIP Conference Proceedings (Vol. 2394, No. 1, p. 040019). AIP Publishing LLC. https://doi.org/10.1063/5.0121358.
30. Toma, M. A., Ibrahim, D. A., Dalaf, A. H., Abdullah, S. Q., Aftan, M. M., & Abdullah, E. Q. (2022, November). Study the adsorption of cyclopentanone on to natural polymers. In AIP Conference Proceedings (Vol. 2394, No. 1, p. 040007). AIP Publishing LLC. https://doi.org/10.1063/5.0121209.
31. Saleh, J. N., & 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), 231-239.
32. Hamad, A. M., Atiyea, Q. M., Hameed, D. N. A., & Dalaf, A. H. (2023). Green synthesis of copper nanoparticles using strawberry leaves and study of properties, anti-cancer action, and activity against bacteria isolated from Covid-19 patients. Karbala International Journal of Modern Science, 9(1), 12.
33. Jassim, A. S., Dalaf, A. H., and Abdullah, T. F. (2022). Studying the Biological Activity and Properties of Copper Nanoparticles Prepared by Pulsed Laser Ablation in Liquid. The Third International and The Fifth Scientific Conference for College of Science –Tikrit University. 1(25): 213-221.
34. Mohammed, L. J., Hamad, A. M., Atiyea, Q. M., Jwair, W. A., Dalaf, A. H., Jasim, A. S., Elsaigher, S. M., Ragab, A., and Hassan, Z. H. S. (2022). In vitro Comparison of the Effect of Zinc Oxide Nanoparticles and Hibiscus sabdariffa Extract on Streptococcus mutans Isolated from Human Dental Caries. The Third International and The Fifth Scientific Conference for College of Science –Tikrit University. 2(2): 5-14.
35. Najm, R. S., Shannak, Q. A. and Dalaf, A. H., (2023). Synthesis and Decoration of Aromatic Derivatives Nano Platelets by the Electric Method. Azerbaijan Pharmaceutical and Pharmacotherapy Journal. 22(2): 92-97. DOI https://doi.org/10.61336/appj/22-2-22.
36. Saleh, M. J., & 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), 222-230.