Molecular structure and biological activities of 4-thiazolidinone derivatives: a combined theoretical and experimental study

References

• Sung, H.; Ferlay, J.; Siegel, R. L.; Mathieu, L.; Soerjomataram, I.; Jemal, A.; Bray, F. Global Cancer Statistics 2020: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries. CA A Cancer J. Clin. 2021, 71, 209–249. DOI: 10.3322/caac.21660.
   PubMed Web of Science ®Google Scholar
• Weaver, B. A. How Taxol/Paclitaxel Kills Cancer Cells. Mol. Biol. Cell. 2014, 25, 2677–2681. DOI: 10.1091/mbc.E14-04-0916.
   PubMed Web of Science ®Google Scholar
• Astolfi, L.; Ghiselli, S.; Guaran, V.; Chicca, M.; Simoni, E.; Olivetto, E.; Lelli, G.; Martini, A. Correlation of Adverse Effects of Cisplatin Administration in Patients Affected by Solid Tumours: A Retrospective Evaluation. Oncol. Rep. 2013, 29, 1285–1292. DOI: 10.3892/or.2013.2279.
   PubMed Web of Science ®Google Scholar
• Ai, Y.; Obianom, O. N.; Kuser, M.; Li, Y.; Shu, Y.; Xue, F. Enhanced Tumor Selectivity of 5-Fluorouracil Using a Reactive Oxygen Species-Activated Prodrug Approach. ACS Med. Chem. Lett. 2019, 10, 127–131. DOI: 10.1021/acsmedchemlett.8b00539.
   PubMed Web of Science ®Google Scholar
• Fahmy, H. H.; Srour, A. M.; Ismail, M. A.; Khater, M. A.; Serrya, R. A.; El-Manawaty,.; M.; A. Design and Synthesis of Some New Tri-Substituted Pyrazole Derivatives as Anticancer Agents. Res. Chem. Intermed. 2016, 42, 6881–6892. DOI DOI: 10.1007/s11164-016-2502-2.
   Web of Science ®Google Scholar
• Hamzehloueian, M.; Sarrafi, Y.; Darroudi, M.; Arani, M.; Darestani, A.; Safari, R. N.; Foroumadi, F.; Synthesis, A. Antibacterial and Anticancer Activities Evaluation of New 4-Thiazolidinone-Indolin-2- One Analogs. Biointerface Res. Appl. Chem. 2022, 12, 8094–8104. doi:10.33263/BRIAC126.80948104.
   Web of Science ®Google Scholar
• Szychowski, K. A.; Leja, M. L.; Kaminskyy, D. V.; Binduga, U. E.; Pinyazhko, R.; Lesyk, R. B.; Gmińsk, J. I. Study of Novel Anticancer 4-Thiazolidinone Derivatives. Chem. Biol. Interact. 2017, 262, 46–56. DOI: 10.1016/j.cbi.2016.12.008.
   PubMed Web of Science ®Google Scholar
• Chawla, P. A.; Teli, G.; Pathania, S.; Singh, S.; Srivastava, V.; et.al. Exploration of Antioxidant, anti-Inflammatory and Anticancer Potential of Substituted 4-Thiazolidinone Derivatives: Synthesis, Biological Evaluation and Docking Studies. Polycycl. Aromat. Compd. 2022, 1–22. DOI: 10.1080/10406638.2021.2019796.
   Web of Science ®Google Scholar
• Kulkarni, P. S.; Karale, S. N.; Khandebharad, A. U.; Agrawal, B. R.; Sarda, S. R.; et.al. Design, Synthesis, and Biological Evaluation of Newer Arylidene Incorporated 4-Thiazolidinones Derivatives as Potential Antimicrobial Agents. Polycycl. Aromat. Compd. 2020, 42, 2031-2044. DOI: 10.1080/10406638.2020.1823861.
   Web of Science ®Google Scholar
• Alves, J. E. F.; Lucena, M. L.; C.; de Souza Lucena, A. E.; das Merces, A. A.; D.; de Azevedo, R. D. S.; Sousa, G. L.; S.; de Moura, R. O.; de Lima, M.; A.; de Carvalho Júnior, L. B.; de Almeida, S. M. V. A Simple Method for Obtaining Human Albumin and Its Use for in Vitro Interaction Assays with Indole-Thiazole and Indole-Thiazolidinone Derivatives. Int. J. Biol. Macromol. 2021, 192, 126–137. DOI: 10.1016/j.ijbiomac.2021.09.109.[PMC].[34562539.
   PubMed Web of Science ®Google Scholar
• Szychowski, K. A.; Skóra, B.; Kryshchyshyn-Dylevych, A.; Kaminskyy, D.; Tobiasz, J.; Lesyk, R. B.; Gmiński, J. 4-Thiazolidinone-Based Derivatives Do Not Affect Differentiation of Mouse Embryo Fibroblasts (3T3-L1 Cell Line) into Adipocytes. Chem. Biol. Interact. 2021, 345, 109538. DOI: 10.1016/j.cbi.2021.109538.
   PubMed Web of Science ®Google Scholar
• Haroun, M.; Tratrat, C.; Petrou, A.; Geronikaki, A.; Ivanov, M.; Ciric, A.; Sokovic, M. 2-Aryl-3-(6-Trifluoromethoxy) Benzo [d] Thiazole-Based Thiazolidinone Hybrids as Potential anti-Infective Agents: Synthesis, Biological Evaluation and Molecular Docking Studies. Bioorg. Med. Chem. Lett. 2020, 35, 127718. DOI: 10.1016/j.bmcl.2020.127718.
   Google Scholar
• Tahmasvand, R.; Bayat, P.; Vahdaniparast, S. M.; Dehghani, S.; Kooshafar, Z.; Khaleghi, S.; Almasirad, A.; Salimi, M. Design and Synthesis of Novel 4-Thiazolidinone Derivatives with Promising anti-Breast Cancer Activity: Synthesis, Characterization, In Vitro and In Vivo Results. Bioorg. Chem. 2020, 104, 104276. DOI: 10.1016/j.bioorg.2020.104276.
   PubMed Web of Science ®Google Scholar
• Wang, S.; Zhao, Y.; Zhang, G.; Lv, Y.; Zhang, N.; Gong, P. Design, Synthesis and Biological Evaluation of Novel 4-Thiazolidinones Containing Indolin-2-One Moiety as Potential Antitumor Agent. Eur. J. Med. Chem. 2011, 46, 3509–3518. DOI: 10.1016/j.ejmech.2011.05.017.
   PubMed Web of Science ®Google Scholar
• Gouda, M. A.; Abu‐Hashem, A. A. Synthesis, Characterization, Antioxidant and Antitumor Evaluation of Some New Thiazolidine and Thiazolidinone Derivatives. Arch. Pharm. (Weinheim) 2011, 344, 170–177. DOI: 10.1002/ardp.201000165.
   PubMed Web of Science ®Google Scholar
• Unangst, P. C.; Connor, D. T.; Cetenko, W. A.; Sorenson, R. J.; Kostlan, C. R.; Sircar, J. C.; Wright, C. D.; Schrier, D. J.; Dyer, R. D. Synthesis and Biological Evaluation of 5-[[3, 5-Bis (1, 1-Dimethylethyl)-4-Hydroxyphenyl] Methylene] Oxazoles,-Thiazoles, and-Imidazoles: novel Dual 5-Lipoxygenase and Cyclooxygenase Inhibitors with Antiinflammatory Activity. J. Med. Chem. 1994, 37, 322–328. DOI: 10.1021/jm00028a017.
   PubMed Web of Science ®Google Scholar
• Ottanà, R.; Maccari, R.; Barreca, M. L.; Bruno, G.; Rotondo, A.; Rossi, A.; Chiricosta, G.; Di Paola, R.; Sautebin, L.; Cuzzocrea, S.; Vigorita, M. G. 5-Arylidene-2-Imino-4-Thiazolidinones: Design and Synthesis of Novel anti-Inflammatory Agents. Bioorg. Med. Chem. 2005, 13, 4243–4252. DOI: 10.1016/j.bmc.2005.04.058.
   PubMed Web of Science ®Google Scholar
• Johnson, A. R.; Marletta, M. A.; Dyer, R. D.; et.al. Slow-Binding Inhibition of Human Prostaglandin Endoperoxide Synthase-2 with Darbufelone, an Isoform-Selective Antiinflammatory di-Tert-Butyl Phenol. J. Biochem. 2001, 40, 7736–7745. DOI: 10.1021/bi002343f.
   Google Scholar
• Mushtaque, M.; Avecilla, F.; Azam, A. Azam A. Synthesis, Characterization and Structure Optimization of a Series of Thiazolidinone Derivatives as Entamoeba histolytica Inhibitors. Eur. J. Med. Chem. 2012, 55, 439–448. DOI: 10.1016/j.ejmech.2012.06.052.
   PubMed Web of Science ®Google Scholar
• Önen-Bayram, F. E.; Buran, K.; Durmaz, I.; Berk, B.; Cetin-Atalay, R. Cetin-Atalay, R. 3-Propionyl-Thiazolidine-4-Carboxylic Acid Ethyl Esters: A Family of Antiproliferative Thiazolidines. Med. Chem. Commun. 2015, 6, 90–93. DOI: 10.1039/C4MD00306C.
   Google Scholar
• Ottanà, R.; Carotti, S.; Maccari, R.; Landini, I.; Chiricosta, G.; Caciagli, B.; Vigorita, M. G.; Mini, E. In Vitro Antiproliferative Activity against Human Colon Cancer Cell Lines of Representative 4-Thiazolidinones. Bioorg. Med. Chem. Lett. 2005, 15, 3930–3933. DOI: 10.1016/j.bmcl.2005.05.093.
   PubMed Web of Science ®Google Scholar
• Havrylyuk, D.; Mosula, L.; Zimenkovsky, B.; Vasylenko, O.; Gzella, A.; Lesyk, R. Synthesis and Anticancer Activity Evaluation of 4-Thiazolidinones Containing Benzothiazole Moiety. Eur. J. Med. Chem. 2010, 45, 5012–5021. DOI: 10.1016/j.ejmech.2010.08.008.
   PubMed Web of Science ®Google Scholar
• Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Gzella, A.; Lesyk, R. Synthesis of Novel Thiazolone-Based Compounds Containing Pyrazoline Moiety and Evaluation of Their Anticancer Activity. Eur. J. Med. Chem. 2009, 44, 1396–1404. DOI: 10.1016/j.ejmech.2008.09.032.
   PubMed Web of Science ®Google Scholar
• Kaminskyy, D.; Zimenkovsky, B.; Lesyk, R. Synthesis and in Vitro Anticancer Activity of 2, 4-Azolidinedione-Acetic Acids Derivatives. Eur. J. Med. Chem. 2009, 44, 3627–3636.
   PubMed Web of Science ®Google Scholar
• Ansari, M. F.; Idrees, D.; Hassan, M. I.; Ahmad, K.; Avecilla, F.; Azam, A. Azam, A. Design, Synthesis and Biological Evaluation of Novel Pyridine-Thiazolidinone Derivatives as Anticancer Agents: targeting Human Carbonic Anhydrase IX. Eur. J. Med. Chem. 2018, 144, 544–556. DOI: 10.1016/j.ejmech.2017.12.049.
   PubMed Web of Science ®Google Scholar
• Zhou, H.; Wu, S.; Zhai, S.; Liu, A.; Sun, Y.; Li, R.; Zhang, Y.; Ekins, S.; Swaan, P. W.; Fang, B.; et al. Design, Synthesis, Cytoselective Toxicity, Structure–Activity Relationships, and Pharmacophore of Thiazolidinone Derivatives Targeting Drug-Resistant Lung Cancer Cells. J. Med. Chem. 2008, 51, 1242–1251. DOI: 10.1021/jm7012024.
   PubMed Web of Science ®Google Scholar
• Mushtaque, M.; Avecilla, F.; Hafeez, Z. B.; Jahan, M.; Khan, M.; S.; Rizvi, M. M. A.; Khan, M.; S.; Srivastava, A.; Mallik, A.; Verma, S. Synthesis, Stereochemistry Determination, Pharmacological Studies and Quantum Chemical Analyses of Bisthiazolidinone Derivative. J. Mol. Struct. 2017, 1127, 99–113. DOI: 10.1016/j.molstruc.2016.07.089.
   Web of Science ®Google Scholar
• Mushtaque, M.; Avecilla, F.; Pingale, S. S.; Kamble, K. M.; Yab, Z.; Rizvi,.; M. M.; A. Computational and Experimental Studies of 4-Thiazolidinone-Cyclopropyl Hybrid. J. Mol. Liq. 2017, 241, 912–921. DOI: 10.1016/j.molliq.2017.06.041.
   Web of Science ®Google Scholar
• Gududuru, V.; Hurh, E.; Dalton, J. T.; Miller, D. D. Synthesis and Antiproliferative Activity of 2-Aryl-4-Oxo-Thiazolidin-3-yl-Amides for Prostate Cancer. Bioorg. Med. Chem. Lett. 2004, 14, 5289–5293. DOI: 10.1016/j.bmcl.2004.08.029.
   PubMed Web of Science ®Google Scholar
• Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior. Phys. Rev. A Gen. Phys. 1988, 38, 3098–3100. DOI: 10.1103/PhysRevA.38.3098.
   PubMedGoogle Scholar
• Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B Condens. Matter. 1988, 37, 785–789. DOI: 10.1103/PhysRevB.37.785.
   PubMed Web of Science ®Google Scholar
• Frisch, M.; Clemente, F.; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Gaussian 09, Revision A. 01.; et al. UNIVIS-2000: An Indigenously Developed Comprehensive Visualization Package. Curr. Sci.(India) 2001, 80, 1296–1300. https://www.jstor.org/stable/24105043.
   Web of Science ®Google Scholar
• Miertuš, S.; Scrocco, E.; Tomasi, J. Electrostatic Interaction of a Solute with a Continuum. A Direct Utilizaion of AB Initio Molecular Potentials for the Prevision of Solvent Effects. J. Chem. Phys. 1981, 55, 117–129. DOI: 10.1016/0301-0104(81)85090-2.
   Web of Science ®Google Scholar
• Knutsen, L. J. S.; Hobbs, C. J.; Earnshaw, C. G.; Fiumana, A.; Gilbert, J.; Mellor, S. L.; Radford, F.; Smith, N. J.; Birch, P. J.; Russell Burley, J.; et al. Synthesis and SAR of Novel 2-Arylthiazolidinones as Selective Analgesic N-Type Calcium Channel Blockers. Bioorg. Med. Chem. Lett. 2007, 17, 662–667. DOI: 10.1016/j.bmcl.2006.10.098.
   PubMed Web of Science ®Google Scholar
• Foster, J.; Weinhold, F. Natural Hybrid Orbitals. J. Am. Chem. Soc. 1980, 102, 7211–7218. DOI: 10.1021/ja00544a007.
   Web of Science ®Google Scholar
• Gil, D. M.; Lestard, M. D.; Estévez-Hernández, O.; Duque, J.; Reguera, E. Quantum Chemical Studies on Molecular Structure, Spectroscopic (IR, Raman, UV–Vis), NBO and Homo–Lumo Analysis of 1-Benzyl-3-(2-Furoyl) Thiourea. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2015, 145, 553–562. DOI: 10.1016/j.saa.2015.02.071.
   PubMed Web of Science ®Google Scholar
• Mushtaque, M.; Jahan, M.; Ali, M.; Khan, M.; S.; Khan, M.; S.; Sahay, P.; Kesarwani, A. Synthesis, Characterization, Molecular Docking, DNA Binding, Cytotoxicity and DFT Studies of 1-(4-Methoxyphenyl)-3-(Pyridine-3-Ylmethyl) Thiourea. J. Mol. Struct. 2016, 1122, 164–174. DOI: 10.1016/j.molstruc.2016.05.087.
   Web of Science ®Google Scholar
• Kavitha, E.; Sundaraganesan, N.; Sebastian, S.; Kurt, M. Molecular Structure, Anharmonic Vibrational Frequencies and NBO Analysis of Naphthalene Acetic Acid by Density Functional Theory Calculations. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2010, 77, 612–619. DOI: 10.1016/j.saa.2010.06.034.
   PubMed Web of Science ®Google Scholar
• Parr, R. G.; Szentpaly, L.; Liu, S. Electrophilicity Index. J. Am. Chem. Soc. 1999, 121, 1922–1924. DOI: 10.1021/ja983494x.
   Web of Science ®Google Scholar
• Sheldrick, G. SADABS, Program for Empirical Absorption Correction of Area Detectors (Version 2.10); University of Göttingen: Göttingen, Germany, 2004.
   Google Scholar
• Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. A 2008, 64, 112–122. DOI: 10.1107/S0108767307043930.
   PubMed Web of Science ®Google Scholar
• Gupta, M. K.; Neelakantan, T.; Sanghamitra, M.; Tyagi, R. K.; Dinda, A.; Maulik, S.; Mukhopadhyay, C. K.; Goswami,.; S.; K. An Assessment of the Role of Reactive Oxygen Species and Redox Signaling in Norepinephrine-Induced Apoptosis and Hypertrophy of H9c2 Cardiac Myoblasts. Antioxid. Redox Signal 2006, 8, 1081–1093. DOI: 10.1089/ars.2006.8.1081.
   PubMed Web of Science ®Google Scholar
• Irshad, M.; Mehdi, S. J.; Al-Fatlawi, A. A.; Zafar yab, M.; Ali, A.; Ahmad, I.; Singh, M.; Rizvi, M. M. A. Phytochemical Composition of Cassia Fistula Fruit Extracts and Its Anticancer Activity against Human Cancer Cell Lines. J. Biol. Act. Prod. Nat. 2014, 4, 158–170. DOI: 10.1080/22311866.2014.933084.
   Google Scholar