Synthesis, Antimicrobial, Antioxidant, Toxicity and Anticancer Activity of a New Azetidinone, Thiazolidinone and Selenazolidinone Derivatives Based on Sulfonamide

https://doi.org/10.22146/ijc.72454

Zainab Kadhim Al-Khazragie(1), Bushra Kamel Al-Salami(2), ِAdnan Jassim Mohammed Al-Fartosy(3*)

(1) Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq, PO BOX 781, Basrah, Iraq
(2) Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq, PO BOX 781, Basrah, Iraq
(3) Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq, PO BOX 781, Basrah, Iraq
(*) Corresponding Author

Abstract


A new series of azetidinone (Z2a-Z2e, Z2g), thiazolidinone and selenazolidinone derivatives (Z2B, Z2E, Z2B', Z2E') based on sulfonamide have been synthesized and characterized by different instrumental techniques, such as elemental analyses, FTIR, multinuclear NMR (1H, 13C) and mass spectrometry. The tested compound containing selenium (Z2E') was less toxic than its analogs containing sulfur (Z2E) based on the LD50 value determined by Dixon's up and down method. All compounds showed antibacterial properties, however, Z2E' was more active against Gram-negative bacteria: Escherichia coli and Pseudomonas aeruginosa than Gram-positive ones: Streptococcus aureus and Bacillus, with the lowest MIC value of 5 mg/mL. All compounds showed good antioxidant activity at a lower rate than the standard compound BHT (82%). More precisely, Z2b was the main compound that possess strong activity as an antioxidant (73%). MTT viability assay showed that all tested compounds had cytotoxic effects on MCF-7 cells after 72 h of treatment. Our results revealed that Z2E' and Z2E compounds possessed strong activity (IC50 = 24.8 and 90.9 µg/mL, respectively) against MCF-7 cells at a higher rate than the standard compound 5-FU (IC50 = 97.47 µg/mL). Our results indicated that Z2E' had a promising bioactive scaffold of great medicinal interest due to their numerous pharmacological and biological activities.

Keywords


2-azetidinone; 4-thiazolidinone; 4-selenazolidinone; Sulfonamide; Acute toxicity; Antioxidant; Antibacterial; Anticancer activity

Full Text:

Full Text PDF


References

[1] Mansour, A.M., 2014, Selective coordination ability of sulfamethazine Schiff-base ligand towards copper (II): Molecular structures, spectral and SAR study, Spectrochim. Acta, Part A, 123, 257–266.

[2] Claudel, M., Schwarte, J.V., and Fromm, K.M., 2020, New antimicrobial strategies based on metal complexes, Chemistry, 2 (4), 849–899.

[3] Tačić, A., Nikolić, V., Nikolic, L., and Savić, I., 2017, Antimicrobial sulfonamide drugs, Adv. Technol., 6 (1), 58–71.

[4] Al-Atbi, H.S., Al-Assadi, I.J., Al-Salami, B.K., and Badr, S.Q., 2020, Study of new azo-azomethine derivatives of sulfanilamide: Synthesis, characterization, spectroscopic, antimicrobial, antioxidant and anticancer activity, Biochem. Cell. Arch., 20 (2), 4161–4174.

[5] Bytyqi-Damoni, A., Genç, H., Zengin, M., Demir, D., Gençer, N., and Arslan, O., 2020, Novel β-lactam compounds as activators for polyphenoloxidase, ChemistrySelect, 5 (25), 7671–7674.

[6] Elkanzi, N.A.A., 2013, Short review on synthesis of thiazolidinone and β-lactam, World J. Org. Chem., 1 (2), 24–51.

[7] Martelli, G., and Giacomini, D., 2018, Antibacterial and antioxidant activities for natural and synthetic dual-active compounds, Eur. J. Med. Chem., 158, 91–105.

[8] Piens, N., 2017, Synthesis of new β-lactam building blocks and their application in heterocyclic Chemistry, Dissertation, Faculty of Bioscience Engineering, Ghent University, Belgium.

[9] Elkanzi, N.A.A., and Mohamed, N.M.M., 2014, Synthesis and antimicrobial activity of β-lactams: Antibacterial activities and antifungal activities, Heterocycl. Lett., 4 (1), 153–182.

[10] Salamanca, C.H., Yarce, C.J., Roman, Y., Davalos, A.F., and Rivera, G.R., 2018, Application of nanoparticle technology to reduce the anti-microbial resistance through β-lactam antibiotic-polymer inclusion nano-complex, Pharmaceuticals, 11 (1), 19.

[11] Bhalla, A., Bari, S.S., Berry, S., Bhalla, J., Vats, S., Mandal, S., and Khullar, S., 2015, Facile synthesis of novel monocyclic trans- and cis-3-oxy/thio/seleno-4-pyrazolyl-β-lactams, ARKIVOC, 2015 (7), 10–27.

[12] Patel, J.A., Mistry, B.D., and Desai, K.R., 2008, Conventional and microwave induced synthesis of various azetidinone and thiazolidinone derivatives from 3-[(1E)-1-aza-2-(2-chloro-7-methoxy-3-quinolyl)-vinyl]-4-(aryldiazenyl) phenol and their antimicrobial screening, Indian J. Chem., Sect. B, 47B (10), 1695–1700.

[13] Chaban, Z., Harkov, S., Chaban, T., Klenina, O., Ogurtsov, V., and Chaban, I., 2017, Recent advances in synthesis and biological activity evaluation of condensed thiazoloquinazolines: A review, Pharmacia, 64 (3), 52–66.‏

[14] Neri, R., and Bossmann, S.H., 2021, Isoselenocyanates: Synthesis and their use for preparing selenium-based heterocycles, Synthesis, 53 (12), 2015–2028.

[15] Nirwan, S., Chahal, V., and Kakkar, R., 2019, Thiazolidinones: Synthesis, reactivity, and their biological applications, J. Heterocycl. Chem., 56 (4), 1239–1253.

[16] Trotsko, N., 2021, Antitubercular properties of thiazolidin-4-ones–A review, Eur. J. Med. Chem., 215, 113266.

[17] Banerjee, B., and Koketsu, M., 2017, Recent developments in the synthesis of biologically relevant selenium-containing scaffolds, Coord. Chem. Rev., 339, 104–127.

[18] Abd Al-khaliq, Z.M., 2015, Synthesis, characterization and antibacterial activity of new series of sulfamethoxazole derivatives, Thesis, College of Pharmacy, University of Al-Mustansiriyah, Baghdad, Iraq.

[19] Sahu, P.K., Kim, G., Yu, J., Ahn, J.Y., Song, J., Choi, Y., Jin, X., Kim, J.H., Lee, S.K., Park, S., and Jeong, L.S., 2014, Stereoselective synthesis of 4′-selenonucleosides via seleno-Michael reaction as potent antiviral agents, Org. Lett., 16 (21), 5796–5799.

[20] Desai, N.C., Harsora, J.P., Monapara, J.D., and Khedkar, V.M., 2021, Synthesis, antimicrobial capability and molecular docking of heterocyclic scaffolds clubbed by 2-azetidinone, thiazole and quinoline derivatives, Polycyclic Aromat. Compd., 0, 1–15.

[21] Ramachandran, S., Cheriyan, B.V., and Aanandhi, M.V., 2021, Activities of thiazolidine-4-one and azetidine-2-one derivatives-A review, Res. J. Pharm. Technol., 14 (8), 4513–4516.

[22] Jarrahpour, A., Rezaei, S., Sinou, V., Latour, C., and Brunel, J.M., 2017, Synthesis of some novel 3-spiro monocyclic β-lactams and their antibacterial and antifungal investigations, Iran. J. Sci. Technol., Trans. A: Sci., 41 (2), 337–342.

[23] Al-Masoudi, W.A., Al-Diwan, M.A., and Hassan, I.J., 2015, Synthesis, acute toxicity and modelling docking studies of azo compound derived from sulphonamide and pyrimidine derivative, Pharma Chem., 7 (9), 1–5.

[24] Ahmad, M.F., 2018, Ganoderma lucidum: Persuasive biologically active constituents and their health endorsement, Biomed. Pharmacother., 107, 507–519.

[25] Al-Fregi, A.A., Al-Fadhly, A.L., and Al-Salami, B.K., 2017, Synthesis, characterization and biological activity study of some new palladium(II) complexes containing amine or azomethine groups, Eur. J. Chem., 8 (2), 155–161.

[26] Rusmana, D., Wahyudianingsih, R., Elisabeth, M., Balqis, B., Maesaroh, M., and Widowati, W., 2017, Antioxidant activity of Phyllanthus niruri extract, rutin and quercetin, InaBJ, 9 (2), 84–90.

[27] Al-Fartosy, A.J.M., 2011, Antioxidant properties of methanolic extract from Inula graveolens L., Turk. J. Agric. For., 35 (6), 591–596.

[28] Al-Shammari, A.M., Al-Esmaeel, W.N., Al-Ali, A.A., Hassan, A.A., and Ahmed, A.A., 2019, Enhancement of oncolytic activity of Newcastle disease virus through combination with retinoic acid against digestive system malignancies, Mol. Ther., 27 (4), 126–127.

[29] Sharma, A., and Puhar, A., 2019, Gentamicin protection assay to determine the number of intracellular bacteria during infection of human TC7 intestinal epithelial cells by Shigella flexneri, Bio-Protoc., 9 (13), e3292.‏

[30] Liu, K., Liu, P.C., Liu, R., and Wu, X., 2015, Dual AO/EB staining to detect apoptosis in osteosarcoma cells compared with flow cytometry, Med. Sci. Monit. Basic Res., 21, 15–20.

[31] Mahdi, I.S., Yousif, S.A., and Khammas, S.J., 2019, Synthesis and characterization of some new (tetrazole, thiazolidin-4-one) compounds derived from drugs and evaluation of their biological activities, Int. J. Pharm. Qual. Assur., 10 (4), 720–727.

[32] Bhaskar, V.H., and Mohite, P.B., 2011, Synthesis analgesic, Anti-Inflammatory and antimicrobial activities of some 1-[5-(substituted phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-5-phenyl-1H-tetrazole, J. Optoelectron. Biomed. Mater., 3 (1), 7–16.

[33] Verma, V.A., Saundane, A.R., Meti, R.S., Shamrao, R., and Katkar, V., 2020, Synthesis, biological evaluation and docking studies of some new indolyl-pyridine containing thiazolidinone and azetidinone analogs, Polycyclic Aromat. Compd., 42 (4), 1545–1559.

[34] Al-Rubaie, A.Z., Al-Masoudi, W.A., Hameed, A.J., Yousif, L.Z., and Graia, M., 2008, Synthesis, reaction and antiviral activity of 2,4-diaryl-1,3-selenazoles, J. Korean Chem. Soc., 52 (1), 36–46.

[35] Alam, S., Hasan, P., Aneja, B., Ahmad, M.B., and Abid, M., 2016, POCl3 mediated Staudinger reaction of imines with ketenes: Synthesis of monocyclic β-lactam and 1,3-oxazinone derivatives, Rasayan J. Chem., 9 (2), 101–111.

[36] Xie, Y., Liu, J., and Li, J., 2011, Selective synthesis of novel 2-imino-1,3-selenazolidin-4-ones and 2-amino-1,3,4-selenadiazin-5-ones from isoselenocyanates, Tetrahedron Lett., 52 (8), 932–935.

[37] Saini, N., Sharma, A., Thakur, V.K., Makatsoris, C., Dandia, A., Bhagat, M., and Sharma, P.C., 2020, Microwave assisted green synthesis of thiazolidin-4-one derivatives: A perspective on potent antiviral and antimicrobial activities, Curr. Res. Green Sustainable Chem., 3, 100021.

[38] Rafique, J., Canto, F.S.R., Saba, S., Barbosa, F.A.R., and Braga, A.L., 2016, Recent advances in the synthesis of biologically relevant selenium-containing 5-membered heterocycles, Curr. Org. Chem., 20 (2), 166–188.

[39] Sharp, D.J., Rogers, G.C., and Scholey, J.M., 2000, Microtubule motors in mitosis, Nature, 407 (6800), 41–47.

[40] Usui, K., Nishida, S., Sugita, T., Ueki, T., Matsumoto, Y., Okumura, H., and Sekimizu, K., 2016, Acute oral toxicity test of chemical compounds in silkworms, Drug Discoveries Ther., 10 (1), 57–61.

[41] Thomba, D.U., Mirgane, S.R., Ambhure, R.U., Pawar, R.P., and Ameta, K.L., 2017, Synthesis and antimicrobial study of novel Schiff bases and metal complexes, Biochem. Biophys., 3, 7–11.

[42] Sevgi, F., Bagkesici, U., Kursunlu, A. N., and Guler, E., 2018, Fe (III), Co (II), Ni (II), Cu (II) and Zn (II) complexes of Schiff bases based-on glycine and phenylalanine: Synthesis, magnetic/thermal properties and antimicrobial activity, J. Mol. Struct., 1154, 256–260.‏

[43] Opoku-Temeng, C., Naclerio, G.A., Mohammad, H., Dayal, N., Abutaleb, N.S., Seleem, M.N., and Sintim, H.O., 2018, N-(1,3,4-oxadiazol-2-yl)benzamide analogs, bacteriostatic agents against methicillin-and vancomycin-resistant bacteria, Eur. J. Med. Chem., 155, 797–805.

[44] Dhanya, S., and Aravind, A., 2015, Synthesis, characterization and evaluation of antioxidant activities of some new quinazolino-acetidinone derivatives, J. Chem. Pharm. Res., 7 (12), 849–856.

[45] AL-Salami, B.K., AL-Khazragie, Z.K., and Al-Fregi, A.A., 2018, Synthesis, characterization, antimicrobial activity and antioxidant of azo Schiff bases containing sulfanilamide, J. Global Pharma Technol., 10 (3), 952–962.

[46] Kuhn, D., Coates, C., Daniel, K., Chen, D., Bhuiyan, M., Kazi, A., Turos, E., and Ping Dou, Q., 2004, Beta-lactams and their potential use as novel anticancer chemotherapeutics drugs, Front. Biosci., 9 (4), 2605–2617.

[47] Mohana, K.N., and Kumar, C.B.P., 2013, Synthesis and antioxidant activity of 2-amino-5-methylthiazol derivatives containing 1,3,4-oxadiazole-2-thiol moiety, Int. Scholarly Res. Not., 2013, 620718.

[48] Singh, F.V., and Wirth, T., 2018, “Synthesis of Organoselenium Compounds with Potential Biological Activities” in Organoselenium Compounds in Biology and Medicine: Synthesis, Biological and Therapeutic Treatments, Eds. Jain V.K., and Priyadarsini K.I., The Royal Society of Chemistry, London, UK, 77–121.

[49] Eruygur, N., Koçyiğit, U.M., Taslimi, P., Ataş, M., Tekin, M., and Gülçin, İ., 2019, Screening the in vitro antioxidant, antimicrobial, anticholinesterase, antidiabetic activities of endemic Achillea cucullata (Asteraceae) ethanol extract, S. Afr. J. Bot., 120, 141–145.

[50] Bhattacharjee, M.K., 2016, “Antibiotics That Inhibit Cell Wall Synthesis” in Chemistry of Antibiotics and Related Drugs, Springer, Cham, Switzerland, 49–94.

[51] Al-Fartosy, A.J.M., and Ati, M.H., 2021, A Predictive clinical markers to make prostate cancer and benign prostate hyperplasia easy diagnosis, Biochem. Cell. Arch., 21 (2), 2939–2947.

[52] El-Desoky, S.I., Badria, F.A., Abozeid, M.A., Kandeel, E.A., and Abdel-Rahman, A.H., 2013, Synthesis and antitumor studies of novel benzopyrano-1,2,3-selenadiazole and spiro[benzopyrano]-1,3,4-thiadiazoline derivatives, Med. Chem. Res., 22 (5), 2105–2114.



DOI: https://doi.org/10.22146/ijc.72454

Article Metrics

Abstract views : 2111 | views : 1035


Copyright (c) 2022 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.