Abstract
Antibiotic resistance has emerged as a formidable public health challenge, being recognized as a paramount priority demanding urgent resolution. Consequently, to augment the therapeutic armamentarium in combating recalcitrant microorganisms, the synthesis of novel molecules derived from pre-existing drugs has demonstrated substantial promise as an alternative approach. Herein, five novel thiazolidin-4-one derivatives based on sulfamethoxazole were successfully synthesized. The chemical structures were well characterized using FT-IR, 1H NMR, and 13C NMR and CHNS. Adjectives are predicted for ADMET properties and study the molecular docking for synthesis derivatives, percentage hemolysis ratio was within range (2.5–60%). Biological activity was also evaluated against two types of bacteria, Pseudomonas aeruginosa and Staphylococcus aureus, the results show that the synthesis compounds have good activity against Pseudomonas aeruginosa. Liver enzymes results show that synthesis compounds have a significant effect on raising liver enzymes compared with the reference and the healthy person.
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REFERENCES
Ferouni, G., Nacer, A., Ameur, N., Bachir, R., and Ziani-Cherif, C., J. Chin. Chem. Soc., 2017, vol. 65, p. 459. https://doi.org/10.1002/jccs.201700334
Al-Anazi, K.M., Mahmoud, A.H., Abul Farah, M., Allam, A.A., Fouda, M.M., and Gaffer, H.E., Chem. Select., 2019, vol. 4, p. 5570. https://doi.org/10.1002/slct.201901148
Aatif, M., Raza, M.A., Javed, K., Nashre-ul-Islam, S.M., and Alam, M.W., Antibiotics, 2022, vol. 11, p. 1750. https://doi.org/10.3390/antibiotics11121750
Siraj, I.T., and Ado, H.B., Chem. Search J., 2021, vol. 12, p. 27.
Khan, A.K., Hamdi, M.D., and Razik, B.M.A., Pak. J. Pharm Sci. 2021, vol. 34, p. 825.
Molina, D., Cossio-perez, R., Rocha-Roa, C., Pedraza, L., Cortes, E., Hernandez, A., and Gómez-Marín, J.E., BMC Genomics, 2019, vol.19, p.856. https://doi.org/10.1186/s12864-018-5223-7
Gupta, A., Singh, R., Sonar, P.K., and Saraf, S.K., Biochem. Res. Int. 2016. https://doi.org/10.1155/2016/8086762
Khaldan, A., El-Khatabi, K., El-Mernissi, R., Ghaleb, A., Hmamouchi, R.A., Sbai, A., Bouachrine, M, and Lakhlifi, T., J. Mater. Enνiron. Sci., 2020, vol. 11, p. 429.
Khaldan, A., Bouamrane, S., El-Mernissi, R., Ajana, M.A., Sbai, A., Bouachrine, M., and Lakhifi, T., Mor. J. Chem., 2022, vol. 10, p. 022. https://doi.org/10.48317/IMIST.PRSM/morjchem-v10i1.31722
Khaldan, A., Bouamrane, S., El-Mernissi, R., Maghat, H., Ajana, M.A., Sbai, A., Bouachrine, M., and Lakhifi, T., Mater. Today, 2021, vol. 45, p. 7643. https://doi.org/10.1016/j.matpr.2021.03.113
Khaleel, R.A., Alfuraiji, N., Hussain, B.W., Nassar, M.F., and Ebrahimzadeh, F., J. Renal Injury Preνent., 2021, vol. 11, p. e8. https://doi.org/10.34172/jrip.2022.08
Akram, Z.M., Khalid, K.B., Oraibi, Q.K., and Nassar, M.F., J. Med. Life, 2022, vol.15. https://doi.org/10.25122/jmL-2021-0149
El-Mernissi, R., El Khatabi, K., Haldean, K., El Mchichi, A., Shahinozzaman, L.M., Ajana, M.A., Lakhifi, T., and Bouachrine, M., J. Mex. Chem. Soc., 2021, vol. 66, p. 79. https://doi.org/10.29356/jmcs.v66i1.1578
Bouamrane, S., Khaldan, A., Hajji, H., El-Mernissi, R., Maghat, H., Ajana, M.A., Sbai, A., Bouachrine, M., and Lakhlifi, T., Mor. J. Chem. 2022, vol. 10, p. 523. https://doi.org/10.48317/IMIST.PRSM/morjchem-v10i3.33141
El-Mernissi, R., El Khatabi, K., Khaldan, A., El Mchichi, L., Ajana, M.A., Lakhlifi, T., and Bouachrine, M., Mater. Today, 2021, vol. 45, p. 7608. https://doi.org/10.1016/j.matpr.2021.03.080
Khaleel, R.A., Shareef, S.M., Hameed, Z.E., Alsaraf, K.M., and Nassar, M.F., Sci. Rise Pharm. Sci., 2021, vol. 5, p. 79. https://doi.org/10.15587/2519-4852.2021.243526
Wasfi, A., Al-Masoudi, Safana, K., Jassim, H., and Khassaf, K., Bas. J. Νet. Res. 2021, vol. 20, p. 1. https://doi.org/10.23975/bvetr.2021.170495
Abd alazez, E.K., Raauf, A.M.R., and Ali, K.F., J. Pharm. Sci., 2019, vol. 19. https://doi.org/10.32947/ajps.19.04.0433
Han, Y., Zhang, J, Hu, C.Q., Zhang, X., Ma, B., and Zhang, P., Front. Pharmacol., 2019, vol. 10. https://doi.org/10.3389/fphar.2019.00434
El Jery, A., Nassar, M.F., Hassan, A., Saadoon, M.A., Ilhan, A., Roy, H., and Khedher, K.M., Comput. Theor. Chem., 2022, vol. 1214, p. 113760. https://doi.org/10.1016/j.comptc.2022.113760
Harismah, K., Hassan, A., Nassar, M.F., Hamid, O.T., and Zandi, H., Biointerface Res. Appl. Chem., 2023, vol. 13, p. 421. https://doi.org/10.33263/BRIAC135.421
Matloob, A.H., Al-Hamami, A., Al-Zaubai, N.M.S., Alfuraiji, N., and Nassar, M.F., Nanomed. Res. J., 2023, vol. 8, p. 141. https://doi.org/10.22034/NMRJ.2023.02.003
Amoda, O., Alexander, E., and Uwagbale, E., J. Med. Case Rep. Case Series. 2021, vol. 2. https://doi.org/10.38207/Jmcrcs20210062
Slim, R., Asmar, N., Yaghi, C., Honein, K., Sayegh, R., Chelala, D., Indian J. Nephrol., 2017, vol. 27, no. 6, p. 482. https://doi.org/10.4103/ijn.IJN_339_16
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Hamdan, I.A.A., Matloob, A.H., Gatea, E.A. et al. Synthesis, Spectroscopic Characterization, and Biological Evaluation of Thiazolidin-4-one Derivatives of Sulfamethoxazole: Insights into ADMET Properties and Molecular Docking Studies. Russ J Gen Chem 93, 2917–2925 (2023). https://doi.org/10.1134/S1070363223110233
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DOI: https://doi.org/10.1134/S1070363223110233