Applied Chemical Engineering

Synthesis And Characterization of New Heterocyclic Compounds and Anti-Cancer, Docking Study

HANOY K. AL-AMOOD

Department of Chemistry, Basrah University, Iraq

MEAAD K. AL-SHURAIFY

Chemistry and Biochemistry Department, Medicine College / Basrah University, Iraq

FATIMA S. SABAH

Department of Chemistry, Basrah University, Iraq

DOI: https://doi.org/10.59429/ace.v9i3.5768

Keywords: chalcone, thiazine, pyrimidine, oxazine. MCF-7, Docking

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Abstract

Three new heterocyclic compounds, derivatives of hexahydropyrimidine (Py4M), thiazinam (Th4M), and oxazinan (OX4M), were synthesized through the reaction of substituted chalcone with guanidine hydrochloride, thiourea, and urea. Spectroscopic techniques such as FT-IR, mass spectrometry, and¹H NMR were used to characterize the synthesized compounds, confirming their proposed structures. The cytotoxicity of all synthesized compounds was evaluated in vitro using the MTT assay after 72 hours against the human breast cancer cell line MCF-7. The results demonstrated good activity of these compounds on MCF-7, particularly Th4M at a high concentration (1000 µg/ml), which showed an inhibition ratio of 76.9%. Three ligand-derived compounds (Py4M, OX4M, Th4M) were docked against MCF-7 breast cancer cells. Th4M exhibited the best binding affinity and potential anticancer activity.

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References

[1]. hmed M. El-Sayed, Mohamed A. El-Sherbeny, Amr M. El. Synthesis and Biological Activity of Novel Thiazine Derivatives. Journal of Heterocyclic Chemistry 59, 1 (2022), 123-133.

[2]. Fatma A. Mohamed, Ali M. Ahmed, Heba A. Abd El-Aziz. Design, Synthesis, and Antimicrobial Activity of New Oxazine Derivatives. European Journal of Medicinal Chemistry,195, (2022),112759.

[3]. Mohamed A. Ali, Sarah M. Ahmed, Ahmed A. Mohamed, Synthesis and Anticancer Activity of Novel Pyrimidine Derivatives, Journal of Medicinal Chemistry, 56,5 (2022), 2345-2356.

[4]. Fatma A. Mohamed, Ali M. Ahmed, Heba A. Abd El-Aziz, Design and Synthesis of New Triazole Derivatives as Potential Anticancer Agents, European Journal of Medicinal Chemistry, 185, (2020),111759.

[5]. Mohamed A. Ali, Sarah M. Ahmed, Ahmed A. Mohamed, Heterocyclic Compounds as Inhibitors of Protein Kinases: Journal of Medicinal Chemistry 63, 10(2020),4735-4720.

[6]. Ibraheem, Al-Majedy, Issa, and Yousif investigate the photostabilization of polystyrene (PS) films using 2-amino pyridine derivatives. Mathematical Biosciences Engineering. 16, 6, (2019).

[7]. C. F. Hjorth, P. Damkier, B. Ejlertsen, T. Lash, H. T. Sorensen and D. C. Fenton, Obesity and breast cancer prognosis: pre-diagnostic anthropometric measures in relation to patient, tumor, and treatment characteristics BMC Medicine. 19, 235, (2021).

[8]. Al-Amood, H. K.; Yaseen, L. A., Preparation, Characterization, and Study of Antibacterial Some New Pyrazole Derivatives. Journal of Kufa for Chemical Sciences, 2 (9). 2022.

[9]. Al-Shuraify, M. K.; Al-Amood, H. K.; Sabah, F. S., Synthesis and characterization of new 1, 3-thiazinane derivatives and study their effect on breast cancer (MCF-7). Journals Kufa for Chemical Sciences, 2 (8)2022.

[10]. Meaad K. Al-Shuraify, Fatima S. Sabah, Hanoy K. Al-Amood,Synthesis and Characterisation of New Hexahydropyrimidine Derivatives, and Study of Their Effect as Anti-parasite.Journals Kufa for Chemical Sciences, 2 (8)2022.

[11]. Al-Shammari, A. M., Alshami, M. A., Umran, M. A., Almukhtar, A. A., Yaseen, N. Y., Raad, K., & Hussien, A. A. (2015). Establishment and characterization of a receptor-negative, hormone-nonresponsive breast cancer cell line from an Iraqi patient. Breast Cancer: Targets Ther., 7, 223-230. DOI:10.2147/BCTT.S74509

[12]. Al-Shammari, A. M., Salman, M. I., Saihood, Y. D., Yaseen, N. Y., Raed, K., Shaker, H. K., Duiach, A. (2016). In vitro synergistic enhancement of Newcastle Disease Virus to 5-fluorouracil cytotoxicity against tumor cells. Biomedicines, 4(1), 3

[13]. Freshney, R.I. (2010).Culture of animal cells a manual of basic technique and specialized applications, sixth edition, Wiley-Blackwell, P732.

[14]. Pettersen, Eric F., et al. "UCSF Chimera—a visualization system for exploratory research and analysis." Journal of Computational Chemistry 25.13 (2004): 1605-1612.

[15]. H. Ibraheem, Y. Al-Majedy, A.A. Issa, E. Yousif, Photostabilization, Thermodynamic and Theoretical Studies of polystyrene by some 2-amino pyridine.Trends Sci. 21 (2023) 7374.

[16]. H.H. Ibraheem, B.K. Queen, M.D. Al-Sabti, A.A. Issa, Y.K. Al-Majedy, M.S. Jabir, G.M. Sulaiman, B.A. Hasoon, M.M. Eshaq, K.H. Jawad, Insights into the pharmaceutical properties and in silico study of novel hydrazone derivatives, Sci. Rep. 14 (2024) 1–18.

[17]. Y.K. Al-Majedy, H.H. Ibraheem, A.A. Issa, Antioxidant, antimicrobial activity and quantum chemical studies of 4-methyl-7-hyroxy coumarin derivatives, in: 2023: p. 060002.

[18]. H.H. Ibraheem, A.A. Issa, D.S. El-Sayed, Structural behavior and surface layer modification of (E)-N’-((1H-indol-3-yl) methylene)-4-chlorobenzohydrazide: Spectroscopic, DFT, biomedical activity and molecular dynamic simulation against Candida Albicans receptor, J. Mol. Struct. 1312 (2024) 138484.

[19]. E.R. Sheltagh, O. Almukhtar, M.F. Rafeeq, K.H. Rasool, S.A. Mahdi, K.H. Jawad, B.A. Hasoon, A.A. Issa, M.S. Jabir, S.F. Jawad, Synthesis, pharmaceutical properties, and in silico study of ZnO@ TiO2 nanocomposite, Inorg. Chem. Commun. (2024) 112994.

[20]. A.A. Alkhafaji, H.M. Ahmed, B.K. Queen, A.A. Issa, G.M. Sulaiman, A.A. ELkashef, D.S. El-Sayed, Recent perspective on polymeric Semimetal (Si, Ge and As) and nonmetal (N and P) doped C70-Fullerene system: Comparative electronic, dynamic behavior and chemotherapy docking with ADMET analysis, J. Organomet. Chem. 1022 (2024) 123417.