Abstract
Objective: This study involved the synthesis of new Schiff bases and 1,3-oxazepine derivatives from the baclofen drug and study the anticancer activities. Methods: Baclofen was initially reacted with aromatic aldehydes to create Schiff base derivatives (Ia–Ib), which were then closed in the next step using anhydrous acids to form oxazepine derivatives (IIa–IId). Results: The title compounds were synthesized successfully and identified using FT-IR, 1H NMR, and 13C NMR spectroscopy. Additionally, compound (IIc)’s (3-(4-chloro-phenyl)-4-[2-(4nitro-phenyl)-4,7-dioxo-4,7-dihydro-[1,3] oxazepin-3-yl]butyric acid) anticancer activity was assessed using MTT assay against FTC-133 (thyroid cancer) compared with WRL-68 (normal cell line). Discussion: The results showed that the viability of the FTC-133 cell was found to be greatest at 12.5 g/mL (96.52 ± 0.70) and lowest at 400 g/mL (35.378 ± 5.07). The effect of compound (IIc) on the normalizing of the WRL-68 cell line resulted in an IC50 for 62.39 ϻg/mL. Conclusions: It has been found that the compound (IIc) has good efficiency against thyroid cancer (FTC-133).
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DATA AVAILABILITY
The data that support the findings of this study are available from the corresponding author upon reasonable request.
REFERENCES
Sachan, A., Singh, V.K., Kalita, J., and Misra, U.K., Postgrad Med. J., 2020, vol. 26, pp. 780–781. https://doi.org/10.1136/postgradmedj-2020-137487
Wang, T., Huang, Y., and Chen, F., Life Sci., 2008, vol. 28, pp. 536–541. https://doi.org/10.1016/j.lfs.2007.12.014
Garbutt, J.C., Kampov-Polevoy, A.B., Pedersen, C., Stansbury, M., Jordan, R., Willing, L., and Gallop, R.J., Neuropsychopharmacol., 2021, vol. 46, pp. 2250–2256. https://doi.org/10.1038/s41386-021-01055-w
Bschor, T., Henssler, J., Müller, M., and Baethge, C., Acta Psychiatr Scand., 2018, vol. 138, pp. 232–242. https://doi.org/10.1111/acps.12905
Da Silva, M.N., Da Silva, J.V.B., Da Fonseca, N.F., Junior, J.A.O., and Mederios, A.C.D., Curr. Pharm. Anal., 2023, vol. 19, pp. 353–370. https://doi.org/10.2174/1573412919666230502124837
Agabio, R., Baldwin, D.S., Amaro, H., Leggio, L., and Sinclair, J.M.A., Neurosci. Biobehav. Rev., 2021, vol. 125, pp. 296–313. https://doi.org/10.1016/j.neubiorev.2020.12.030
Abraham, M., Gold, J., Dweck, J., Ward, M., Gendreau, J., Panse, N., Holani, K., Gupta, P., and Mammis, A., World Neurosurg., 2020, vol. 139, pp. e652–e657. https://doi.org/10.1016/j.wneu.2020.04.070
Imerci, A., Rogers, K., Dixit, D., McManus, M., Miller, F., and Sees, J.P., Paediatr. Anaesth., 2020, vol. 30, pp. 153–160. https://doi.org/10.1111/pan.13791
Couvrat, N., Sanselme, M., Poupard, M., Bensakoun, C., Drouin, S.H., Schneider, J.M., and Coquerel, G., J. Pharm. Sci., 2021, vol. 110, pp. 3457–3463. https://doi.org/10.1016/j.xphs.2021.06.018
Dario, A., Pisani, R., Sangiorgi, S., Soragna, A., Reguzzoni, M., Protasoni, M., Pessina, F., Fesc, R., Peres, A., and Tomei, G., Eur. J. Pharmacol., 2006, vol. 550, pp. 33–38. https://doi.org/10.1016/j.ejphar.2006.08.068
Ahmed, R.S., Ali, R.A., and Ahamed, L.S., JGPT, 2019, vol. 11, pp. 437–444. https://www.jgpt.co.in/index.php/jgpt/article/view/2664
Mahmood, A.A., Iraqi J. Pharm., 2021, vol. 18, pp. 180– 193. https://doi.org/10.33899/iphr.2022.170406
Hassan, Z.M. and Abbas, A.K., Iraqi J. Sci., 2020, vol. 61, pp. 2762–2775. https://doi.org/10.24996/ijs.2020.61.11.2
Albayati, M.R., Int. J. Eng. Sci. Technol., 2017, vol. 6, pp. 93–101. https://www.researchgate.net/publication/340038649
Al-Shaheen, A.J., Albayati, M.R., and Ali, A.M., Int. J. Eng. Sci. Technol., 2018, vo. l7, pp. 10–16. https://www.researchgate.net/publication/340038658
Al-Khazriaji, Sh. I., AIP Conference Proceed., 2020, vol. 2290, pp. 1–9. https://doi.org/10.1063/5.0027534
Ali, R.A., Al-Tamimi, E.O., and Abdul-Wadood, S., Iraqi J. Sci., 2023, vol. 64, pp. 6104–6118. https://doi.org/10.24996/ijs.2023.64.12.3
Abbas, A.M., Taib, AS.M., and Saeed, N.H.M., Egypt. J. Chem., 2020, vol. 63, pp. 2999–3013. https://doi.org/10.21608/ejchem.2020.25217.2526
Hashim, D.J. and Mahdi, S.M., J. Med. Chem. Sci., 2023, vol. 6, pp. 1555–1576. https://doi.org/10.26655/JMCHEMSCI.2023.7.8
Mohammed, A.Y. and Ahamed, L.S., IJDDT, 2022, vol. 12, pp. 1279–1281. https://doi.org/10.25258/ijddt.12.3.58
Ahamed, L.S., Ali, R.A., and Ahmed, R.S., Egypt. J. Chem., 2021, vol. 64, pp. 2963–2968. https://doi.org/10.21608/ejchem.2021.55742.3176
Al-Azzawi, A.M., and Yaseen, K.H., Iraqi J. Sci., 2016, vol. 57, pp. 2604–2616.
AL-Tamimi, E.O., Muslih, R.M., and Thejeel, KH.A., Baghdad Sci. J., 2015, vol. 12, pp. 546–554. https://doi.org/10.21123/bsj.2015.12.3.546-554
Mahmoud, S.S. and Khaleel, A.M.N., Iraqi J. Sci., 2023, vol. 64, pp. 5501–5516. https://doi.org/10.24996/ijs.2023.64.11.4
Sabah, A.A., Ameen, A.M., and Al-Daher, A., Iraqi J. Sci., 2022, vol. 63, pp. 1885–1893. https://doi.org/10.24996/ijs.2022.63.5.3
Hassan, S.A., Aziz, D.M., Abdullah, M.N., Bhat, A.R., Dongre, R.S., Ahmed, S., Rahiman, A.K., Hadda, T.B., Berredjem, M., and Jamalis, J., J. Mol. Struct., 2023, vol. 1292, p. 136121. https://doi.org/10.1016/j.molstruc.2023.136121
Zhuang, Y., Zhu, L., Chen, X., Chen, J., Ye, Z., Kang, J., Wang, X., and Han, Z., RSC Adv., 2024, vol. 14, pp. 1952–1961. https://doi.org/10.1039/D3RA06411E
Ali, A.M., Aswathy, K.A., Munuswamy-Ramanujam, G., and Jaisankar, V., Int. J. Biol. Macromol., 2023, vol. 225, pp. 1575–1587. https://doi.org/10.1016/j.ijbiomac.2022.11.214
Ahamed, L.S., JGPT, 2019, vol. 10, pp. 298–304. https://www.jgpt.co.in/index.php/jgpt/article/view/1795
Salih, N., Yahya, W., Al-Labban, H., and Aljanaby, A.A.J., Res. J. Pharm. Tech., 2022, vol. 15, pp. 3595–359. https://doi.org/10.52711/0974-360X.2022.00602
Abdel-Rahman, L.H., Abu-Dief, A.M., Adam, M.S.S., and Hamdan, S.K., Catal. Lett., 2016, vol. 146, pp. 1373– 1396. https://link.springer.com/article/10.1007/s10562-016-1755-0
Lasalle, B., Kamalesh, T., Karuppasamy, P., Pandian, M.S., and Ramasamy, P., J. Mater. Sci. Mater. Electron, 2023, vol. 33, pp. 1–16. https://doi.org/10.1007/s10854-022-09179-5
Aljamali, N.M., Aati, S.A., Obaid, H., and Wannas, F.A., Am. Int. J. Sci. Eng. Res., 2019, vol. 2, pp. 9–21. https://doi.org/10.46545/aijser.v2i1.41
Banik, B.K., Sahoo, B.M., Kumar, B.R., Panda, J., and Kumar, A., Green Approach. Med. Chem. Sust. Drug Des., 2020, pp. 713–736. https://doi.org/10.1016/B978-0-12-817592-7.00020-4
Eftekhari, S., Foroughifar, N., Hallajian, S., and Khajeh-Amiri, A., Curr. Microw. Chem., 2020, vol. 7, pp. 207–215. https://doi.org/10.2174/2213335607999200520124245
Hamad, B.K. and Ahamed, M.R., Eurasian Chem. Commun., 2022, vol. 4, pp. 1306–1317. https://doi.org/10.22034/ecc.2022.332079.1343
Kshash, A.H., Acta Chim. Slov., 2020, vol. 67, pp. 113–118. https://doi.org/10.17344/acsi.2019.5264
Abbas, A.K. and Jber, N.R., ANJS, 2020, vol. 23, pp. 17 –23. https://doi.org/10.22401/ANJS.23.3.03
Jawad, M. and Adnan, S., HIV Nurs., 2023, vol. 23, pp. 18–25.
Jasim, S.S., KUJSS, 2018, vol. 13, pp. 149–165. https://doi.org/10.32894/kujss.2018.145725
Al-Salami, A.M., Al-Khafaf, N.I., and Al-Jaboure, A.K., KUJSS, 2017, vol. 12, pp. 435–446. https://doi.org/10.32894/kujss.2017.129730
Jasim, S.S., KUJSS, 2019, vol. 14, pp. 249–272. https://doi.org/10.32894/kujss.2019.14.2.15
Hussein, M.S. and Al-Lami, N., Iraqi J. Sci., 2022, vol. 63, pp. 4620–4636. https://doi.org/10.24996/ijs.2022.63.11.1
Singh, S.A., ishra, N., Nayak, G., and Mehta, P., Orginal J. Chem., 2023, vol. 39, pp. 1367–1372. https://doi.org/10.13005/ojc/390534
Rehan, T.A., Al-Lami, N. and Alanee, R.S., Eur. Chem. Commun., 2021, vol. 3, pp. 339–351. https://doi.org/10.22034/ecc.2021.277531.1151
Berber, N., Arslam, M., Vural, F., Ergun, A., and Gencer, N., J. Biochem. Mol. Toxicol., 2020, vol. 34, pp. 1–9. https://doi.org/10.1002/jbt.22596
AbdelFattah, B.A., Khalifa, M.M.A, El-Sehrawi, H., Fayed, E., Bayoumi, A., and Said, M., Lett. Drug Des. Discov., 2021, vol. 8, pp. 330–338. https://doi.org/10.2174/157018011794839448
Liu, K., Lu, X., Zhang, H.J., Sun, J., and Zhu, H.L., Eur. J. Med. Chem., 2012, vol.47, pp.73–478. https://doi.org/10.1016/j.ejmech.2011.11.015
Khadem, Z., Al-Smhammaree, S.A., and Abdulretha, M., Eur. Chem. Commun., 2022, vol. 4, pp. 625–635. https://doi.org/10.22034/ecc.2022.328706.1321
Ali, R.A, Al-Tamimi, E.O., and Abdul Wadood, S., Russ. J. Bioorg. Chem., 2023, vol. 49, pp. 882–884. https://doi.org/10.1134/S1068162023040040
ACKNOWLEDGMENTS
The authors is thankful to Department of Chemistry at the College of Science, Iraq, for their help and cooperation throughout this research, and to the Biotechnology research centre at Al-Nahrain University, Iraq, for assistance with an anti-cancer assay.
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The author RAA—designed the experiments. The authors RAA and LSA synthesized the samples and carried out their electrochemical study.
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Ali, R.A., Ahamed, L.S. & AL-Khazraji, S.I.C. Synthesis, Characterization, and Study of Anticancer Activities of New Schiff Bases and 1,3-Oxazepine Containing Drug. Russ J Bioorg Chem 50, 28–33 (2024). https://doi.org/10.1134/S1068162024010102
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DOI: https://doi.org/10.1134/S1068162024010102