Synthesis and Characterization of New Derivatives of The Seven-Ring Oxazepine and Study of Their Bacterial Activity

Maan Ziadan  Khalaf

doi:10.51699/cajotas.v6i4.1613

Maan Ziadan Khalaf Education of Salah al-Din, Ministry of Education, Iraq.

DOI: https://doi.org/10.51699/cajotas.v6i4.1613

Keywords: Oxazepine, Biological Activity, Ciprofloxacin

Abstract

This article deals with the preparation and characterization of new derivatives of oxazepine compounds using the traditional method of sublimation. This study of this type of seven-membered rings comes due to its wide-ranging pharmacological and biological importance in various medical and pharmaceutical fields. These compounds were prepared by reacting 2-aminophenol with chalcones (prepared by reacting acetophenone substitutes with 4-chlorothiazole-5-carbaldehyde, which was considered the main core of this study). The results showed that these compounds have good physical properties and stability in laboratory conditions. Some spectroscopic methods such as (F.T-I.R , H-N.M.R and C-N.M.R) were used to prove the validity of the structures of these materials in addition to their purity. When testing their biological activity against two types of Gram- negative (Escherichia coil) and Gram- positive bacteria (Staphylococcus aureus). The results showed that the antibacterial activity varied, as compound M8 had the highest activity against negative bacteria, followed by compound M10, while the activity against positive bacteria was less clear compared to the antibiotics used as a control. Ciprofloxacin was used as a control sample, and its activity was higher than the prepared compounds. Despite this, the compounds can be considered promising materials for use as pharmaceutical antibiotics.

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References

D. M. Najim, K. A. Al-badrany, and M. K. Saleh, “Synthesis of some new oxazepine compounds derived from cyanoethyl acetate and study their inhibitory activity against some pathogenic bacterial species”

F. M. Muhammad, B. A. Khairallah, and K. A. Albadrany, “Synthesis, characterization and antibacterial evaluation of novel 1, 3-oxazepine derivatives using a cycloaddition approach,” J. Angiotherapy, vol. 8, no. 3, pp. 1–5, 2024.

A. S. T. Abdul Wahed, “Preparation and evaluation of bacterial activity and study of the crystalline properties of some 1, 3-oxazepine-4, 7-dione derivatives,” Central Asian J. Theor. Appl. Sci., vol. 5, no. 2, pp. 15–26, 2024.

S. A. Mohamed, M. S. Hussein, and K. A. Al-badrany, “Synthesis and characterization of pyrazolines and oxazapine derivatives using chalcones as precursor and evaluation of their biological activity,” Samarra J. Pure Appl. Sci., vol. 4, no. 4, 2022.

G. R. Newkome and P. W. Maudler, Contemporary Heterocyclic Chemistry. New York, USA: John Wiley & Sons, 1982, p. 375.

A. G. Borel and F. S. Abbott, “Metabolic profiling of clobazam, a 1, 5-benzodiazepine, in rats,” Drug Metab. Dispos., vol. 21, no. 3, pp. 415–427, 1993.

H. L. Yale and F. Sowinski, “Novel polycyclic heterocycles. II. Derivatives of 5, 11-dihydrodibenz[b, e][1, 4]oxazepine,” J. Med. Chem., vol. 7, no. 5, pp. 609–614, 1964.

W. Wan, J. Hou, H. Jiang, Y. Wang, S. Zhu, H. Deng, and J. Hao, “Concise synthesis of ω-fluoroalkylated ketoesters: A building block for the synthesis of six-, seven-, and eight-membered fluoroalkyl substituted 1, 2-diaza-3-one heterocycles,” Tetrahedron, vol. 65, no. 21, pp. 4212–4219, 2009.

C. V. C. Prasad et al., “2, 3-Benzodiazepin-1, 4-diones as peptidomimetic inhibitors of γ-secretase,” Bioorg. Med. Chem. Lett., vol. 14, no. 13, pp. 3535–3538, 2004.

N. A. Al-Joboury, K. A. Al-Badrany, A. S. Hamed, and W. M. Aljoboury, “Synthesis of some new thiazepine compounds derived from chalcones and evaluation of their biochemical and biological activity,” Biochem. Cell. Arch., vol. 19, no. 2, 2019.

S. S. Jasim, M. M. Al-tufah, and K. A. Al-badrany, “Synthesis and antibacterial evaluation of some new 1, 5-benzooxazepines derivatives,” Syst. Rev. Pharm., vol. 12, no. 3, pp. 270–285, 2021.

B. A. Khairallah, F. M. Muhammad, J. N. Saleh, and M. J. Saleh, “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.

A. B. Khalid, “Synthesis and characterization and biological study of some oxazepine derivatives from 2-acetylthiazole,” World Med.: J. Biomed. Sci., vol. 1, no. 8, pp. 40–48, 2024.

B. A. Khairallah, F. M. Muhammad, J. N. Saleh, and M. J. Saleh, “Preparation, characterization, biological activity evaluation, and liquid crystallography study of new diazepine derivatives,” World Med.: J. Biomed. Sci., vol. 7, p. 65, 2024.

M. J. Saleh, J. N. Saleh, K. Al-Badrany, A. H. Dalaf, R. S. Najm, and A. W. A. S. Talluh, “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. 4, pp. 130–138, 2024.

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. 7, pp. 15–23, 2024.

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. 7, pp. 155–168, 2024.

H. Al-Badrani, N. S. Ezzat, and Y. S. Al-Jawaheri, “Synthesis of oxazepino compound via electrophilic cyclization and evaluation of their biological activity,” Kimya Problemleri, vol. 3, pp. 343–355, 2025.

Z. Q. M. Hassan and M. G. Abdulkarim, “Synthesis, characterization, and biological activity evaluation of chalcones and pyrazole derivatives derived from indole,” AL-Yarmouk J., vol. 2, pp. 42–52, 2023.

F. M. Muhammad, B. A. Khairallah, and K. A. Albadrany, “Synthesis, characterization and antibacterial evaluation of novel 1, 3-oxazepine derivatives using a cycloaddition approach,” J. Angiotherapy, vol. 3, pp. 1–9, 2024.

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.

S. H. Abdullah, M. M. Salih, and A. Al-Badrany, “Synthesis, characterization and antibacterial evaluation of novel thiazolidine derivatives,” J. Angiotherapy, vol. 3, pp. 1–9, 2024.

A. A. M. Al Rashidy, K. A. Al Badrany, and G. M. Al Garagoly, “Spectrophotometric determination of sulphamethoxazole drug by new pyrazoline derived from 2, 4-dinitro phenyl hydrazine,” Mater. Sci. Forum, vol. 1002, pp. 1–7, 2020.