Green synthesis, antibacterial and antifungal evaluation of new thiazolidine-2,4-dione derivatives: molecular dynamic simulation, POM study and identification of antitumor pharmacophore sites

References

• Akhavan, M., Foroughifar, N., Pasdar, H., & Bekhradnia, A. (2019). Green synthesis, biological activity evaluation, and molecular docking studies of aryl alkylidene 2, 4-thiazolidinedione and rhodanine derivatives as antimicrobial agents. Combinatorial Chemistry & High Throughput Screening, 22(10), 716–727. https://doi.org/10.2174/1386207322666191127103122
   PubMed Web of Science ®Google Scholar
• Alegaon, S. G., & Alagawadi, K. R. (2012). New thiazolidinedione-5-acetic acid amide derivatives: Synthesis, characterization and investigation of antimicrobial and cytotoxic properties. Medicinal Chemistry Research, 21(6), 816–824. https://doi.org/10.1007/s00044-011-9598-0
   Web of Science ®Google Scholar
• Alnajjar, R., Mostafa, A., Kandeil, A., & Al-Karmalawy, A. A. (2020). Molecular docking, molecular dynamics, and in vitro studies reveal the potential of angiotensin II receptor blockers to inhibit the COVID-19 main protease. Heliyon, 6(12), e05641. https://doi.org/10.1016/j.heliyon.2020.e05641
   PubMed Web of Science ®Google Scholar
• Al-Sanea, M. M., Hamdi, A., Mohamed, A. A. B., El-Shafey, H. W., Moustafa, M., Elgazar, A. A., Eldehna, W. M., Rahman, H., Parambi, D. G. T., Elbargisy, R. M., Selim, S., Bukhari, S. N. A., Hendawy, O. M., & Tawfik, S. S. (2023). New benzothiazole hybrids as potential VEGFR-2 inhibitors: Design, synthesis, anticancer evaluation, and in silico study. Journal of Enzyme Inhibition and Medicinal Chemistry, 38(1), 2166036. https://doi.org/10.1080/14756366.2023.2166036
   PubMed Web of Science ®Google Scholar
• Andres, C. J., Bronson, J. J., D'Andrea, S. V., Deshpande, M. S., Falk, P. J., Grant-Young, K. A., Harte, W. E., Ho, H. T., Misco, P. F., Robertson, J. G., Stock, D., Sun, Y., & Walsh, A. W. (2000). 4-thiazolidinones: Novel inhibitors of the bacterial enzyme MurB. Bioorganic & Medicinal Chemistry Letters, 10(8), 715–717. https://doi.org/10.1016/s0960-894x(00)00073-1
   PubMed Web of Science ®Google Scholar
• Bansal, G., Singh, S., Monga, V., Thanikachalam, P. V., & Chawla, P. (2019). Synthesis and biological evaluation of thiazolidine-2,4-dione-pyrazole conjugates as antidiabetic, anti-inflammatory and antioxidant agents. Bioorganic Chemistry, 92, 103271. https://doi.org/10.1016/j.bioorg.2019.103271
   PubMed Web of Science ®Google Scholar
• Barry, A.L. (2000). The antimicrobial susceptibility test: Principle and practices, Illus Lea and Febiger, Philadelphia, PA 180.b) European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID) (2000) Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by agar dilution. Clinical Microbiology and Infection, 6, 509–515.
   PubMed Web of Science ®Google Scholar
• Berredjem, M., Bouzina, A., Bahadi, R., Bouacida, S., Rastija, V., Djouad, S. E., Sothea, T. O., Almalki, F. A., Hadda, T. B., & Aissaoui, M. (2022). Antitumor activity, X-ray crystallography, in silico study of some-sulfamido-phosphonates. Identification of pharmacophore sites. Journal of Molecular Structure, 1250, 131886. https://doi.org/10.1016/j.molstruc.2021.131886
   Web of Science ®Google Scholar
• Bondock, S., Khalifa, W., & Fadda, A. A. (2007). Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3, 4-dihydronaphthalene-2-carboxaldehyde. European Journal of Medicinal Chemistry, 42(7), 948–954. https://doi.org/10.1016/j.ejmech.2006.12.025
   PubMed Web of Science ®Google Scholar
• Bhat, A. R., Dongre, R. S., Almalki, F. A., Berredjem, M., Aissaoui, M., Touzani, R., Hadda, T. B., & Akhter, M. S. (2021). Synthesis, biological activity and POM/DFT/docking analyses of annulated pyrano[2,3-d]pyrimidine derivatives: Identification of antibacterial and antitumor pharmacophore sites. Bioorganic Chemistry, 106, 104480. https://doi.org/10.1016/j.bioorg.2020.104480
   PubMed Web of Science ®Google Scholar
• Bowers, K. J., Chow, E., Xu, H., Dror, R. O., Eastwood, M. P., Gregersen, B. A., Klepeis, J. L., Kolossvary, I., Moraes, M. A., Sacerdoti, F. D., & Shaw, D. E. (2006). Scalable algorithms for molecular dynamics simulations on commodity clusters. In Proceedings of the 2006 ACM/IEEE Conference on Supercomputing (pp. 84). https://doi.org/10.1145/1188455.1188544
   Google Scholar
• Burghout, P., Cron, L. E., Gradstedt, H., Quintero, B., Simonetti, E., Bijlsma, J. J., Bootsma, H. J., & Hermans, P. W. (2010). Carbonic anhydrase is essential for Streptococcus pneumoniae growth in environmental ambient air. Journal of Bacteriology, 192(15), 4054–4062. https://doi.org/10.1128/JB.00151-10
   PubMed Web of Science ®Google Scholar
• Capobianco, J. O., Cao, Z., Shortridge, V. D., Ma, Z., Flamm, R. K., & Zhong, P. (2000). Studies of the novel ketolide ABT-773: Transport, binding to ribosomes, and inhibition of protein synthesis in Streptococcus pneumoniae. Antimicrobial Agents and Chemotherapy, 44(6), 1562–1567. https://doi.org/10.1128/AAC.44.6.1562-1567.2000
   PubMed Web of Science ®Google Scholar
• Chander, S., Tang, C.-R., Al-Maqtari, H. M., Jamalis, J., Penta, A., Hadda, T. B., Sirat, H. M., Zheng, Y.-T., & Sankaranarayanan, M. (2017). Synthesis and study of anti-HIV-1 RT activity of 5-benzoyl-4-methyl-1, 3, 4, 5-tetrahydro-2H-1, 5-benzodiazepin-2-one derivatives. Bioorganic Chemistry, 72, 74–79. https://doi.org/10.1016/j.bioorg.2017.03.013
   PubMed Web of Science ®Google Scholar
• Chohan, Z. H., Youssoufi, M. H., Jarrahpour, A., & Hadda, T. B. (2010). Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: Indolenyl sulfonamide derivatives. European Journal of Medicinal Chemistry, 45(3), 1189–1199. https://doi.org/10.1016/j.ejmech.2009.11.029
   PubMed Web of Science ®Google Scholar
• Chopra, I. (2001). Glycylcyclines: Third-generation tetracycline antibiotics. Current Opinion in Pharmacology, 1(5), 464–469. https://doi.org/10.1016/S1471-4892(01)00081-9
   PubMedGoogle Scholar
• Choudhry, A. E., Mandichak, T. L., Broskey, J. P., Egolf, R. W., Kinsland, C., Begley, T. P., Seefeld, M. A., Ku, T. W., Brown, J. R., Zalacain, M., & Ratnam, K. (2003). Inhibitors of pantothenate kinase: Novel antibiotics for staphylococcal infections. Antimicrobial Agents and Chemotherapy, 47(6), 2051–2055. https://doi.org/10.1128/AAC.47.6.2051-2055.2003
   PubMed Web of Science ®Google Scholar
• Colca, J. R., McDonald, W. G., Waldon, D. J., Thomasco, L. M., Gadwood, R. C., Lund, E. T., Cavey, G. S., Mathews, W. R., Adams, L. D., Cecil, E. T., Pearson, J. D., Bock, J. H., Mott, J. E., Shinabarger, D. L., Xiong, L., & Mankin, A. S. (2003). Cross-linking in the living cell locates the site of action of oxazolidinone antibiotics. Journal of Biological Chemistry, 278(24), 21972–21979. https://doi.org/10.1074/jbc.M302109200
   PubMed Web of Science ®Google Scholar
• da Silva, D. I M., da Silva Filho, J., Santiago, P. B. G. D. S., do Egito, M. S., de Souza, C. A., Gouveia, F. L., Ximenes, R. M., de Sena, K. X. D. F. R., de Faria, A. R., Brondani, D. J., & de Albuquerque, J. F. C. (2014). Synthesis and antimicrobial activities of 5-arylidene-thiazolidine-2, 4-dione derivatives. BioMed Research International, 2014, 316082. https://doi.org/10.1155/2014/316082
   PubMed Web of Science ®Google Scholar
• Deep, A., Jain, S., & Sharma, P. C. (2010). Synthesis and anti-inflammatory activity of some novel biphenyl-4-carboxylic acid 5-(arylidene)-2-(aryl)-4-oxothiazolidin-3-yl amides. Acta Poloniae Pharmaceutica, 67(1), 63–67.
   PubMed Web of Science ®Google Scholar
• Dewar, M. J., Zoebisch, E. G., Healy, E. F., & Stewart, J. J. (1985). Development and use of quantum mechanical molecular models. 76. AM1: A new general purpose quantum mechanical molecular model. Journal of the American Chemical Society, 107(13), 3902–3909. https://doi.org/10.1021/ja00299a024
   Web of Science ®Google Scholar
• Dongre, R. S., Meshram, J. S., Selokar, R. S., Almalki, F. A., & Hadda, T. B. (2018). Antibacterial activity of synthetic pyrido [2, 3-d] pyrimidines armed with nitrile groups: POM analysis and identification of pharmacophore sites of nitriles as important pro-drugs. New Journal of Chemistry, 42(19), 15610–15617. https://doi.org/10.1039/C8NJ02081G
   Web of Science ®Google Scholar
• DYa, H., Lesyk, R. B., Zimenkovsky, B. S., & VYu, P. (2006). Synthesis and anticancer studying of 4-(2, 4-thiazolidinedione-5-acetoxy) benzylidenehydrazones of benzazol-2-thioacetic acids. Farm Zh (Kiev), 2, 53–58.
   Google Scholar
• El-Barbary, A. A., Khodair, A. I., Pedersen, E. B., & Nielsen, C. (1994). Synthese und Testung der antiviralen Aktivität von 2′-Deoxyuridinen mit 5-Methylen-2-thiohydantoin-Substituenden in der 5-Position. Monatshefte für Chemie Chemical Monthly, 125(5), 593–598. https://doi.org/10.1007/BF00811853
   Google Scholar
• Esharkawy, E. R., Almalki, F., & Hadda, T. B. (2022). In vitro potential antiviral SARS-CoV-19-activity of natural product thymohydroquinone and dithymoquinone from Nigella sativa. Bioorganic Chemistry, 120, 105587. https://doi.org/10.1016/j.bioorg.2021.105587
   PubMed Web of Science ®Google Scholar
• Fung-Tomc, J. C., Clark, J., Minassian, B., Pucci, M., Tsai, Y.-H., Gradelski, E., Lamb, L., Medina, I., Huczko, E., Kolek, B., Chaniewski, S., Ferraro, C., Washo, T., & Bonner, D. P. (2002). In vitro and in vivo activities of a novel cephalosporin, BMS-247243, against methicillin-resistant and-susceptible staphylococci. Antimicrobial Agents and Chemotherapy, 46(4), 971–976. https://doi.org/10.1128/AAC.46.4.971-976.2002
   PubMed Web of Science ®Google Scholar
• Genc, M., Genc, Z. K., Tekin, S., Sandal, S., Sirajuddin, M., Hadda, T. B., & Sekerci, M. (2016). Design, synthesis, in vitro antiproliferative activity, binding modeling of 1, 2, 4,-triazoles as new anti-breast cancer agents. Acta Chimica Slovenica, 63(4), 726–737. https://doi.org/10.17344/acsi.2016.2428
   PubMed Web of Science ®Google Scholar
• Gibb, J., & Wong, D. W. (2021). Antimicrobial treatment strategies for stenotrophomonas maltophilia: A focus on novel therapies. Antibiotics (Basel, Switzerland), 10(10), 1226. https://doi.org/10.3390/antibiotics10101226
   PubMed Web of Science ®Google Scholar
• Ha, Y. M., Park, Y. J., Kim, J. A., Park, D., Park, J. Y., Lee, H. J., Lee, J. Y., Moon, H. R., & Chung, H. Y. (2012). Design and synthesis of 5-(substituted benzylidene) thiazolidine-2, 4-dione derivatives as novel tyrosinase inhibitors. European Journal of Medicinal Chemistry, 49, 245–252. https://doi.org/10.1016/j.ejmech.2012.01.019
   PubMed Web of Science ®Google Scholar
• Hadda, T. B., Ali, M. A., Masand, V., Gharby, S., Fergoug, T., & Warad, I. (2013). Tautomeric origin of dual effects of N 1-nicotinoyl-3-(4′-hydroxy-3′-methyl phenyl)-5-[(sub) phenyl]-2-pyrazolines on bacterial and viral strains: POM analyses as new efficient bioinformatics’ platform to predict and optimize bioactivity of drugs. Medicinal Chemistry Research, 22(3), 1438–1449. https://doi.org/10.1007/s00044-012-0143-6
   Web of Science ®Google Scholar
• Hadda, T. B., Fathi, J., Chafchaouni, I., Masand, V., Charrouf, Z., Chohan, Z. H., Jawarkar, R., Fergoug, T., & Warad, I. (2013). Computational POM and 3D-QSAR evaluation of experimental in vitro HIV-1-integrase inhibition of amide-containing diketoacids. Medicinal Chemistry Research, 22(3), 1456–1464. https://doi.org/10.1007/s00044-012-0120-0
   Web of Science ®Google Scholar
• Hadda, T. B., Rastija, V., AlMalki, F., Titi, A., Touzani, R., Mabkhot, Y. N., Khalid, S., Zarrouk, A., & Siddiqui, B. S. (2021). Petra/osiris/molinspiration and molecular docking analyses of 3-hydroxy-indolin-2-one derivatives as potential antiviral agents. Current Computer-Aided Drug Design, 17(1), 123–133. https://doi.org/10.2174/1573409916666191226110029
   PubMed Web of Science ®Google Scholar
• Harder, E., Damm, W., Maple, J., Wu, C., Reboul, M., Xiang, J. Y., Wang, L., Lupyan, D., Dahlgren, M. K., Knight, J. L., Kaus, J. W., Cerutti, D. S., Krilov, G., Jorgensen, W. L., Abel, R., & Friesner, R. A. (2016). OPLS3: A force field providing broad coverage of drug-like small molecules and proteins. Journal of Chemical Theory and Computation, 12(1), 281–296. https://doi.org/10.1021/acs.jctc.5b00864
   PubMed Web of Science ®Google Scholar
• Hasan, A. H., Murugesan, S., Amran, S. I., Chander, S., Alanazi, M. M., Hadda, T. B., Shakya, S., Pratama, M. R. F., Das, B., Biswas, S., & Jamalis, J. (2022). Novel thiophene chalcones-coumarin as acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, molecular docking, ADMET prediction and molecular dynamics simulation. Bioorganic Chemistry, 119, 105572. https://doi.org/10.1016/j.bioorg.2021.105572
   PubMed Web of Science ®Google Scholar
• Hassan, S. A., Aziz, D. M., Abdullah, M. N., Bhat, A. R., Dongre, R. S., Hadda, T. B., Almalki, F. A., Kawsar, S. M. A., Rahiman, A. K., Sumeer, A., Abdellattif, M. H., Berredjem, M., Sheikh, S. A., & Jamalis, J. (2023). In vitro and in vivo evaluation of the antimicrobial, antioxidant, cytotoxic, hemolytic activities and insilico POM/DFT/DNA-binding and pharmacokineticanalyses of new sulfonamide bearing thiazolidin-4-ones. Journal of Biomolecular Structure & Dynamics, 41, 1–18. https://doi.org/10.1080/07391102.2023.2226713
   PubMedGoogle Scholar
• 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., & Jamalis, J. (2023b). Design and synthesis of oxazepine derivatives from sulfonamide Schiff bases as antimicrobial and antioxidant agents with low cytotoxicity and hemolytic prospective. Journal of Molecular Structure, 1292, 136121. https://doi.org/10.1016/j.molstruc.2023.136121
   Web of Science ®Google Scholar
• Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Day, C. W., Smee, D. F., Grellier, P., & Lesyk, R. (2013). Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones. European Journal of Medicinal Chemistry, 66, 228–237. https://doi.org/10.1016/j.ejmech.2013.05.044
   PubMed Web of Science ®Google Scholar
• Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Zaprutko, L., Gzella, A., & Lesyk, R. (2009). Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity. European Journal of Medicinal Chemistry, 44(4), 1396–1404. https://doi.org/10.1016/j.ejmech.2008.09.032
   PubMed Web of Science ®Google Scholar
• Hocquet, A., & Langgård, M. (1998). An evaluation of the MM + force field. Journal of Molecular Modeling, 4(3), 94–112. https://doi.org/10.1007/s008940050128
   Web of Science ®Google Scholar
• Hsu, K. C., Chen, Y. F., Lin, S. R., & Yang, J. M. (2011). iGEMDOCK: A graphical environment of enhancing GEMDOCK using pharmacological interactions and post-screening analysis. BMC Bioinformatics, 12 Suppl 1(Suppl 1), S33. https://doi.org/10.1186/1471-2105-12-s1-s33
   PubMedGoogle Scholar
• Hussain, F., Khan, Z., Jan, M. S., Ahmad, S., Ahmad, A., Rashid, U., Ullah, F., Ayaz, A., & Sadiq, A. (2019). Synthesis, in-vitro α-glucosidase inhibition, antioxidant, in-vivo antidiabetic and molecular docking studies of pyrrolidine-2,5-dione and thiazolidine-2,4-dione derivatives. Bioorganic Chemistry, 91, 103128. https://doi.org/10.1016/j.bioorg.2019.103128
   PubMed Web of Science ®Google Scholar
• Ibrahim, D., Jabbour, J. F., & Kanj, S. S. (2020). Current choices of antibiotic treatment for Pseudomonas aeruginosa infections. Current Opinion in Infectious Diseases, 33(6), 464–473. https://doi.org/10.1097/qco.0000000000000677
   PubMed Web of Science ®Google Scholar
• Kaminskyy, D., Zimenkovsky, B., & Lesyk, R. (2009). Synthesis and in vitro anticancer activity of 2, 4-azolidinedione-acetic acids derivatives. European Journal of Medicinal Chemistry, 44(9), 3627–3636. https://doi.org/10.1016/j.ejmech.2009.02.023
   PubMed Web of Science ®Google Scholar
• Kêsia, X. F. R. S., Raudiney, F. V. M., Evillyn, X. B., Rosilma, O. A., Camila, J. A. S., Henrique, N. P. C., Bruno, A., Igor, Z. D., Matheus, F. F., Jaciana, S. A., Teresinha, G. S., Gláucia, M. S. L., Julianna, F. C. A., & Rafael, M. X. (2022). Antibacterial and antibiofilm activities of thiazolidine‐2,4‐dione and 4‐thioxo‐thiazolidin‐2‐one derivatives against multidrug‐resistant Staphylococcus aureus clinical isolates. Journal of Applied Microbiology, 133, 3558–3572. https://doi.org/10.1111/jam.15790
   PubMed Web of Science ®Google Scholar
• Khan, H., Khan, Z., Amin, S., Mabkhot, Y. N., Mubarak, M. S., Hadda, T. B., & Maione, F. (2017). Plant bioactive molecules bearing glycosides as lead compounds for the treatment of fungal infection: A review. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 93, 498–509. https://doi.org/10.1016/j.biopha.2017.06.077
   PubMed Web of Science ®Google Scholar
• Kumar, A., Salahuddin Mazumder, A., Kumar, R., Sahu, R., Mishral, S., Singh, C., Yar, M., & Ahsan, M. (2021). Synthesis, characterization, and antidiabetic evaluation of substituted 5-(2-chloro-quinolin-3-ylmethylene)-thiazolidine-2,4-dione. Indian Journal of Heterocyclic Chemistry, 31, 357–364.
   Web of Science ®Google Scholar
• Kumar, H., Deep, A., & Marwaha, R. K. (2020). Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives. BMC Chemistry, 14(1), 25. https://doi.org/10.1186/s13065-020-00678-2
   PubMed Web of Science ®Google Scholar
• Lafridi, H., Almalki, F. A., Ben Hadda, T., Berredjem, M., Kawsar, S. M., Alqahtani, A. M., Esharkawy, E. R., Lakhrissi, B., & Zgou, H. (2023). In silico evaluation of molecular interactions between macrocyclic inhibitors with the HCV NS3 protease. Docking and identification of antiviral pharmacophore site. Journal of Biomolecular Structure & Dynamics, 41(6), 2260–2273. https://doi.org/10.1080/07391102.2022.2029571
   PubMed Web of Science ®Google Scholar
• Lesyk, R., Zimenkovsky, B., Atamanyuk, D., Jensen, F., Kieć-Kononowicz, K., & Gzella, A. (2006). Anticancer thiopyrano [2, 3-d][1, 3] thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies. Bioorganic & Medicinal Chemistry, 14(15), 5230–5240. https://doi.org/10.1016/j.bmc.2006.03.053
   PubMed Web of Science ®Google Scholar
• Liu, H.-L., Lieberzeit, Z., & Anthonsen, T. (2000). Synthesis and fungicidal activity of 2-imino-3-(4-arylthiazol-2-yl)-thiazolidin-4-ones and their 5-arylidene derivatives. Molecules, 5(12), 1055–1061. https://doi.org/10.3390/50901055
   Google Scholar
• Liu, Y., Jing, F., Xu, Y., Xie, Y., Shi, F., Fang, H., Li, M., & Xu, W. (2011). Design, synthesis and biological activity of thiazolidine-4-carboxylic acid derivatives as novel influenza neuraminidase inhibitors. Bioorganic & Medicinal Chemistry, 19(7), 2342–2348. https://doi.org/10.1016/j.bmc.2011.02.019
   PubMed Web of Science ®Google Scholar
• Lotlikar, S. R., Hnatusko, S., Dickenson, N. E., Choudhari, S. P., Picking, W. L., & Patrauchan, M. A. (2013). Three functional β-carbonic anhydrases in Pseudomonas aeruginosa PAO1: Role in survival in ambient air. Microbiology, 159(Pt_8), 1748–1759. https://doi.org/10.1099/mic.0.066357-0
   PubMedGoogle Scholar
• Mahajan, D. T., Masand, V. H., Patil, K. N., Hadda, T. B., Jawarkar, R. D., Thakur, S. D., & Rastija, V. (2012). CoMSIA and POM analyses of anti-malarial activity of synthetic prodiginines. Bioorganic & Medicinal Chemistry Letters, 22(14), 4827–4835. https://doi.org/10.1016/j.bmcl.2012.05.115
   PubMed Web of Science ®Google Scholar
• Marc, G., Araniciu, C., Oniga, S. D., Vlase, L., Pîrnău, A., Nadăș, G. C., Novac, C. Ș., Matei, I. A., Chifiriuc, M. C., Măruțescu, L., & Oniga, O. (2019). Design, synthesis and biological evaluation of new piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) norfloxacin analogues as antimicrobial agents. Molecules (Basel, Switzerland), 24(21), 3959. https://doi.org/10.3390/molecules24213959
   PubMed Web of Science ®Google Scholar
• Mark, P., & Nilsson, L. (2001). Structure and dynamics of the TIP3P, SPC, and SPC/E water models at 298 K. Journal of Physical Chemistry A, 105(43), 9954–9960. https://doi.org/10.1021/jp003020w
   Web of Science ®Google Scholar
• Marshall, P. G., & Vallance, D. K. (1954). Derivatives of succinimide, glutarimide, thiazolidinedione and methanol, and some miscellaneous compounds. Journal of Pharmacy and Pharmacology, 6(10), 740–746. https://doi.org/10.1111/j.2042-7158.1954.tb11011.x
   PubMed Web of Science ®Google Scholar
• Menazea, A. A., Eid, M. M., & Ahmed, M. K. (2020). Synthesis, characterization, and evaluation of antimicrobial activity of novel chitosan/tigecycline composite. International Journal of Biological Macromolecules, 147, 194–199. https://doi.org/10.1016/j.ijbiomac.2020.01.041
   PubMed Web of Science ®Google Scholar
• Mousavi, S. M., Zarei, M., Hashemi, S. A., Babapoor, A., & Amani, A. M. (2019). A conceptual review of rhodanine: Current applications of antiviral drugs, anticancer and antimicrobial activities. Artificial Cells, Nanomedicine, and Biotechnology, 47(1), 1132–1148. 10.1080/21691401.2019.1573824
   PubMed Web of Science ®Google Scholar
• Murray, A. B., Aggarwal, M., Pinard, M., Vullo, D., Patrauchan, M., Supuran, C. T., & McKenna, R. (2018). Structural mapping of anion inhibitors to β‐carbonic anhydrase psCA3 from Pseudomonas aeruginosa. ChemMedChem, 13(19), 2024–2029. https://doi.org/10.1002/cmdc.201800375
   PubMed Web of Science ®Google Scholar
• Nagano, R., Shibata, K., Adachi, Y., Imamura, H., Hashizume, T., & Morishima, H. (2000). In vitro activities of novel trans-3, 5-disubstituted pyrrolidinylthio-1β-methylcarbapenems with potent activities against methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa. Antimicrobial Agents and Chemotherapy, 44(3), 489–495. https://doi.org/10.1128/AAC.44.3.489-495.2000
   PubMed Web of Science ®Google Scholar
• Navarrete-Vázquez, G., Torres-Gómez, H., Hidalgo-Figueroa, S., Ramírez-Espinosa, J. J., Estrada-Soto, S., Medina-Franco, J. L., León-Rivera, I., Alarcón-Aguilar, F. J., & Almanza-Pérez, J. C. (2014). Synthesis, in vitro and in silico studies of a PPARγ and GLUT-4 modulator with hypoglycemic effect. Bioorganic & Medicinal Chemistry Letters, 24(18), 4575–4579. https://doi.org/10.1016/j.bmcl.2014.07.068
   PubMed Web of Science ®Google Scholar
• Oliva, B., Miller, K., Caggiano, N., O'Neill, A. J., Cuny, G. D., Hoemann, M. Z., Hauske, J. R., & Chopra, I. (2003). Biological properties of novel antistaphylococcal quinoline-indole agents. Antimicrobial Agents and Chemotherapy, 47(2), 458–466. https://doi.org/10.1128/AAC.47.2.458-466.2003
   PubMed Web of Science ®Google Scholar
• Olsson, M. H., Søndergaard, C. R., Rostkowski, M., & Jensen, J. H. (2011). PROPKA3: Consistent treatment of internal and surface residues in empirical p K a predictions. Journal of Chemical Theory and Computation, 7(2), 525–537. https://doi.org/10.1021/ct100578z
   PubMed Web of Science ®Google Scholar
• Ottana, R., Maccari, R., Barreca, M. L., Bruno, G., Rotondo, A., Rossi, A., Chiricosta, G., Di Paola, R., Sautebin, L., Cuzzocrea, S., & Vigorita, M. G. (2005). 5-Arylidene-2-imino-4-thiazolidinones: Design and synthesis of novel anti-inflammatory agents. Bioorganic & Medicinal Chemistry, 13(13), 4243–4252. https://doi.org/10.1016/j.bmc.2005.04.058
   PubMed Web of Science ®Google Scholar
• Patil, V., Tilekar, K., Mehendale-Munj, S., Mohan, R., & Ramaa, C. S. (2010). Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2, 4-thiazolidinedione derivatives. European Journal of Medicinal Chemistry, 45(10), 4539–4544. https://doi.org/10.1016/j.ejmech.2010.07.014
   PubMed Web of Science ®Google Scholar
• Rachedi, K. O., Bahadi, R., Aissaoui, M., Ben Hadda, T., Belhani, B., Bouzina, A., & Berredjem, M. (2020). DFT study, POM analyses and molecular docking of novel oxazaphosphinanes: Identification of antifungal pharmacophore site. Indonesian Journal of Chemistry, 20(2), 440–450. https://doi.org/10.22146/ijc.46375
   Web of Science ®Google Scholar
• Rahim, M. A., Shoukat, A., Khalid, W., Ejaz, A., Itrat, N., Majeed, I., Koraqi, H., Imran, M., Nisa, M. U., Nazir, A., Alansari, W. S., Eskandrani, A. A., Shamlan, G., & Al-Farga, A. (2022). A narrative review on various oil extraction methods, encapsulation processes, fatty acid profiles, oxidative stability, and medicinal properties of black seed (Nigella sativa). Foods (Basel, Switzerland), 11(18), 2826. https://doi.org/10.15413/ajfr.2020.0104
   PubMed Web of Science ®Google Scholar
• Rauf, A., Liaqat, S., Qureshi, A. M., Yaqub, M., Rehman, A. U., Hassan, M. U., Chohan, Z. H., Nasim, F. U., & Hadda, T. B. (2012). Synthesis, characterization, and urease inhibition of 5-substituted-8-methyl-2 H-pyrido [1, 2-a] pyrimidine-2, 4 (3 H)-diones. Medicinal Chemistry Research, 21(1), 60–74. https://doi.org/10.1007/s00044–010–9491–2
   Web of Science ®Google Scholar
• Sameeh, M. Y., Khowdiary, M. M., Nassar, H. S., Abdelall, M. M., Alderhami, S. A., Elhenawy, A. A. (2021). Discovery potent of thiazolidinedione derivatives as antioxidant, α-amylase inhibitor, and antidiabetic agent. Biomedicines, 10(1), 24, 1–18.
   Google Scholar
• Santos, F. A., Almeida, M. L., Silva, V. A. S., Viana, D. C. F., Pereira, M. C., Lucena, A. S. L., Pitta, M. G. R., Galdino-Pitta, M. R., de Melo Rêgo, M. J. B., Pitta, I. R. (2022). Synthesis and biological activities of new phthalimide and thiazolidine derivatives. Medicinal Chemistry Research, 31(1), 108–119. 10.1007/s00044-021-02821-7
   Web of Science ®Google Scholar
• Sen, P., Sindelo, A., Mafukidze, D. M., & Nyokong, T. (2019). Synthesis and photophysicochemical properties of novel axially di-substituted silicon (IV) phthalocyanines and their photodynamic antimicrobial chemotherapy (PACT) activity against Staphylococcus aureus. Synthetic Metals, 258, 116203. https://doi.org/10.1016/j.synthmet.2019.116203
   Web of Science ®Google Scholar
• Sheikh, J., & Hadda, T. B. (2013). Antibacterial, antifungal and antioxidant activity of some new water-soluble β-diketones. Medicinal Chemistry Research, 22(2), 964–975. https://doi.org/10.1007/s00044-012-0089-8
   Web of Science ®Google Scholar
• Sucheta Tahlan, S., & Verma, P. K. (2018). Synthesis, SAR and in vitro therapeutic potentials of thiazolidine-2,4-diones. Chemistry Central Journal, 12(1), 129. https://doi.org/10.1186/s13065-018-0496-0
   PubMedGoogle Scholar
• Tanaka, T., Okuyama-Dobashi, K., Motohashi, R., Yokoe, H., Takahashi, K., Wiriyasermkul, P., Kasai, H., Yamashita, A., Maekawa, S., Enomoto, N., Ryo, A., Nagamori, S., Tsubuki, M., & Moriishi, K. (2021). Inhibitory effect of a novel thiazolidinedione derivative on hepatitis B virus entry. Antiviral Research, 194, 105165. https://doi.org/10.1016/j.antiviral.2021.105165
   PubMed Web of Science ®Google Scholar
• Taranalli, A. D., Bhat, A. R., Srinivas, S., & Saravanan, E. (2008). Antiinflammatory, analgesic and antipyretic activity of certain thiazolidinones. Indian Journal of Pharmaceutical Sciences, 70(2), 159–164. https://doi.org/10.4103/0250-474X.41448
   PubMed Web of Science ®Google Scholar
• Uttarkar, A., Kishore, A. P., Srinivas, S. M., Rangappa, S., Kusanur, R., & Niranjan, V. (2023). Coumarin derivative as a potent drug candidate against triple negative breast cancer targeting the frizzled receptor of wingless-related integration site signaling pathway. Journal of Biomolecular Structure & Dynamics, 41(5), 1561–1573. https://doi.org/10.1080/07391102.2021.2022536
   PubMed Web of Science ®Google Scholar
• Vicini, P., Geronikaki, A., Anastasia, K., Incerti, M., & Zani, F. (2006). Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorganic & Medicinal Chemistry, 14(11), 3859–3864. https://doi.org/10.1016/j.bmc.2006.01.043
   PubMed Web of Science ®Google Scholar
• Volkova, T. V., Simonova, O. R., & Perlovich, G. L. (2021). Thiazolidine-2,4-dione derivative in 2-hydroxypropyl-β-cyclodextrin solutions: Complexation/solubilization, distribution and permeability. Journal of Molecular Liquids, 333, 115931. https://doi.org/10.1016/j.molliq.2021.115931
   Web of Science ®Google Scholar
• Youssoufi, M. H., Sahu, P. K., Sahu, P. K., Agarwal, D. D., Ahmad, M., Messali, M., Lahsasni, S., & Hadda, T. B. (2015). POM analyses of antimicrobial activity of 4 H-pyrimido [2, 1-b] benzothiazole, pyrazole, and benzylidene derivatives of curcumin. Medicinal Chemistry Research, 24(6), 2381–2392. https://doi.org/10.1007/s00044-014-1297-1
   Web of Science ®Google Scholar