Exploring the Potential of Substituted 4-Thiazolidinone Derivatives in the Treatment of Breast Cancer: Synthesis, Biological Screening and In Silico Studies

References

• World Health Organization, https://www.who.int/news-room/fact-sheets/detail/cancer (accessed May 15, 2020).
   Google Scholar
• W. Ding, Z. Li, C. Wang, J. Dai, G. Ruan, and C. Tu, “Anthracycline versus Nonanthracycline Adjuvant Therapy for Early Breast Cancer: A Systematic Review and Meta-Analysis,” Medicine 97, no. 42 (2018): e12908.
   PubMed Web of Science ®Google Scholar
• T.M. Abu Samaan, M. Samec, A. Liskova, P. Kubatka, and D. Büsselberg, “Paclitaxel’s Mechanistic and Clinical Effects on Breast Cancer,” Biomolecules 9, no. 12 (2019): 789.
   PubMed Web of Science ®Google Scholar
• J.A. O’Shaughnessy, “Oral Alkylating Agents for Breast Cancer Therapy,” Drugs 58, no. 3 (1999): 1–9.
   PubMedGoogle Scholar
• J.H. Yoon, “Systemic Overview of 5-FU Based Chemotherapy in Breast Cancer,” Korean Journal of Clinical Oncology 1, no. 1 (2005): 68–73.
   Google Scholar
• P. Koźmiński, P.K. Halik, R. Chesori, and E. Gniazdowska, “Overview of Dual-Acting Drug Methotrexate in Different Neurological Diseases, Autoimmune Pathologies and Cancers,” International Journal of Molecular Sciences 21, no. 10 (2020): 3483.
   PubMed Web of Science ®Google Scholar
• C. Karthikeyan, V.R. Solomon, H. Lee, and P. Trivedi, “Design, Synthesis and Biological Evaluation of Some Isatin-Linked Chalcones as Novel anti-Breast Cancer Agents: A Molecular Hybridization Approach,” Biomedicine & Preventive Nutrition 3, no. 4 (2013): 325–30.
   Google Scholar
• H. Zahreddine, and K. Borden, “Mechanisms and Insights into Drug Resistance in Cancer,” Frontiers in Pharmacology 4, no. 2013 (2013): 28.
   PubMedGoogle Scholar
• S. Dhawan, N. Kerru, P. Awolade, A. Singh-Pillay, S.T. Saha, M. Kaur, S.B. Jonnalagadda, and P. Singh, “Synthesis, Computational Studies and Antiproliferative Activities of Coumarin-Tagged 1, 3, 4-Oxadiazole Conjugates against MDA-MB-231 and MCF-7 Human Breast Cancer Cells,” Bioorganic & Medicinal Chemistry 26, no. 21 (2018): 5612–23.
   PubMed Web of Science ®Google Scholar
• M.M. Cepa, E.J. Tavares da Silva, G. Correia-da-Silva, F.M. Roleira, and N.A. Teixeira, “Structure − Activity Relationships of New A, D-Ring Modified Steroids as Aromatase Inhibitors: Design, Synthesis, and Biological Activity Evaluation,” Journal of Medicinal Chemistry 48, no. 20 (2005): 6379–85.
   PubMed Web of Science ®Google Scholar
• Y. Maximov, P. M. Lee, T. Craig Jordan, and V. “The Discovery and Development of Selective Estrogen Receptor Modulators (SERMs) for Clinical Practice,” Current Clinical Pharmacology 8, no. 2 (2013): 135–55.
   PubMedGoogle Scholar
• R.W. Brueggemeier, J.C. Hackett, and E.S. Diaz-Cruz, “Aromatase Inhibitors in the Treatment of Breast Cancer,” Endocrine Reviews 26, no. 3 (2005): 331–45.
   PubMed Web of Science ®Google Scholar
• H. Fang, W. Tong, L.M. Shi, R. Blair, R. Perkins, W. Branham, B.S. Hass, Q. Xie, S.L. Dial, C.L. Moland, et al., “Structure − Activity Relationships for a Large Diverse Set of Natural, Synthetic, and Environmental Estrogens,” Chemical Research in Toxicology 14, no. 3 (2001): 280–94.
   PubMed Web of Science ®Google Scholar
• C.P. Miller, “SERMs: Evolutionary Chemistry, Revolutionary Biology,” Current Pharmaceutical Design 8, no. 23 (2002): 2089–111.
   PubMed Web of Science ®Google Scholar
• M.A. Musa, O.F. Khan, and J.S. Cooperwood, “Medicinal Chemistry and Emerging Strategies Applied to the Development of Selective Estrogen Receptor Modulators (SERMs),” Current Medicinal Chemistry 14, no. 11 (2007): 1249–61.
   PubMed Web of Science ®Google Scholar
• A.W. Kung, E.Y. Chu, and L. Xu, “Bazedoxifene: A New Selective Estrogen Receptor Modulator for the Treatment of Postmenopausal Osteoporosis,” Expert Opinion on Pharmacotherapy 10, no. 8 (2009): 1377–85.
   PubMed Web of Science ®Google Scholar
• L. Gennari, D. Merlotti, F. Valleggi, and R. Nuti, “Ospemifene Use in Postmenopausal Women,” Expert Opinion on Investigational Drugs 18, no. 6 (2009): 839–49.
   PubMed Web of Science ®Google Scholar
• S.M. Gomha, N.A. Kheder, M.R. Abdelaziz, Y.N. Mabkhot, and A.M. Alhajoj, “A Facile Synthesis and Anticancer Activity of Some Novel Thiazoles Carrying 1, 3, 4-Thiadiazole Moiety,” Chemistry Central Journal. 11, no. 1 (2017): 1–9.
   PubMedGoogle Scholar
• M. Kos, G. Reid, S. Denger, and F. Gannon, “Minireview: Genomic Organization of the Human ERα Gene Promoter Region,” Molecular Endocrinology (Baltimore, Md.) 15, no. 12 (2001): 2057–63.
   PubMedGoogle Scholar
• P.A. Madureira, R. Varshochi, D. Constantinidou, R.E. Francis, R.C. Coombes, K.-M. Yao, and E.W.-F. Lam, “The Forkhead Box M1 Protein Regulates the Transcription of the Estrogen Receptor α in Breast Cancer Cells,” The Journal of Biological Chemistry 281, no. 35 (2006): 25167–76.
   PubMed Web of Science ®Google Scholar
• J. Millour, and E. Lam, “FOXM1 is a Transcriptional Target of ERα and Has a Critical Role in Breast Cancer Endocrine Sensitivity and Resistance,” Breast Cancer Research 12, no. S1 (2010): 1.
   Google Scholar
• D.P. Pandey, and D. Picard, “miR-22 Inhibits Estrogen Signaling by Directly Targeting the Estrogen Receptor α mRNA,” Molecular and Cellular Biology 29, no. 13 (2009): 3783–3790.
   PubMed Web of Science ®Google Scholar
• Leandro Castellano, Georgios Giamas, Jimmy Jacob, R.C. Coombes, Walter Lucchesi, Paul Thiruchelvam, Geraint Barton, L.R. Jiao, Robin Wait, Jonathan Waxman, et al., “The Estrogen Receptor-α-Induced microRNA Signature Regulates Itself and Its Transcriptional Response,” Proceedings of the National Academy of Sciences of the United States of America 106, no. 37 (2009): 15732–15737.
   PubMed Web of Science ®Google Scholar
• S.M. Gomha, A.O. Abdelhamid, O.M. Kandil, S.M. Kandeel, and N.A. Abdelrehem, “Synthesis and Molecular Docking of Some Novel Thiazoles and Thiadiazoles Incorporating Pyranochromene Moiety as Potent Anticancer Agents,” Mini Reviews in Medicinal Chemistry 18, no. 19 (2018): 1670–1682.
   PubMed Web of Science ®Google Scholar
• J.A. Caruso, R. Campana, C. Wei, C.H. Su, A.M. Hanks, W.G. Bornmann, and K. Keyomarsi, “Indole-3-Carbinol and Its N-Alkoxy Derivatives Preferentially Target ER α-Positive Breast Cancer Cells,” Cell Cycle 13, no. 16 (2014): 2587–2599.
   PubMed Web of Science ®Google Scholar
• R.K. Arafa, G.H. Hegazy, G.A. Piazza, and A.H. Abadi, “Synthesis and in Vitro Antiproliferative Effect of Novel Quinoline-Based Potential Anticancer Agents,” European Journal of Medicinal Chemistry 63 (2013): 826–832.
   PubMed Web of Science ®Google Scholar
• Chakrabhavi Dhananjaya Mohan, V. Srinivasa, Shobith Rangappa, Lewis Mervin, Surender Mohan, Shardul Paricharak, Sefer Baday, Feng Li, Muthu K. Shanmugam, Arunachalam Chinnathambi, et al., “Trisubstituted-Imidazoles Induce Apoptosis in Human Breast Cancer Cells by Targeting the Oncogenic PI3K/Akt/mTOR Signaling Pathway,” PLoS One 11, no. 4 (2016): e0153155.
   PubMed Web of Science ®Google Scholar
• Y. Dong, K. Nakagawa-Goto, C.Y. Lai, Y. Kim, S.L. Morris-Natschke, Y.H. Eva, K.F. Bastow, and K.H. Lee, “Antitumor Agents 279. Structure–Activity Relationship and In Vivo Studies of Novel 2-(Furan-2-yl) Naphthalen-1-ol (FNO) Analogs as Potent and Selective anti-Breast Cancer Agents,” Bioorganic & Medicinal Chemistry Letters 21, no. 1 (2011): 52–57.
   PubMed Web of Science ®Google Scholar
• M. El-Naggar, W.M. Eldehna, H. Almahli, A. Elgez, M. Fares, M.M. Elaasser, and H.A. Abdel-Aziz, “Novel Thiazolidinone/Thiazolo [3, 2-a] Benzimidazolone-Isatin Conjugates as Apoptotic anti-Proliferative Agents towards Breast Cancer: One-Pot Synthesis and in Vitro Biological Evaluation,” Molecules 23, no. 6 (2018): 1420.
   PubMed Web of Science ®Google Scholar
• S. Mamidala, V.S. Mudigunda, S.R. Peddi, K.K. Bokara, V. Manga, and R.R. Vedula, “Design and Synthesis of New Thiazoles by Microwave-Assisted Method: Evaluation as an anti-Breast Cancer Agents and Molecular Docking Studies,” Synthetic Communications 50, no. 16 (2020): 2488–2501.
   Web of Science ®Google Scholar
• Neil S. Cutshall, Christine O'Day, and Marina Prezhdo, “Rhodanine Derivatives as Inhibitors of JSP-1,” Bioorganic & Medicinal Chemistry Letters 15, no. 14 (2005): 3374–3379.
   PubMed Web of Science ®Google Scholar
• A. Degterev, A. Lugovskoy, M. Cardone, B. Mulley, G. Wagner, T. Mitchison, and J. Yuan, “Identification of Small-Molecule Inhibitors of Interaction between the BH3 Domain and Bcl-x L,” Nature Cell Biology 3, no. 2 (2001): 173–182.
   PubMed Web of Science ®Google Scholar
• D.K. Sigalapalli, V. Pooladanda, M. Kadagathur, S.D. Guggilapu, J.L. Uppu, C. Godugu, N.B. Bathini, and N.D. Tangellamudi, “Novel Chromenyl-Based 2-Iminothiazolidin-4-One Derivatives as Tubulin Polymerization Inhibitors: Design, Synthesis, Biological Evaluation and Molecular Modelling Studies,” Journal of Molecular Structure. 1225 (2021): 128847.
   Web of Science ®Google Scholar
• P.H. Carter, P.A. Scherle, J.K. Muckelbauer, M.E. Voss, R.Q. Liu, L.A. Thompson, A.J. Tebben, K.A. Solomon, Y.C. Lo, Z. Li, et al., “Photochemically Enhanced Binding of Small Molecules to the Tumor Necrosis Factor Receptor-1 Inhibits the Binding of TNF-α,” Proceedings of the National Academy of Sciences of the United States of America 98, no. 21 (2001): 11879–11884.
   PubMed Web of Science ®Google Scholar
• R. Tahmasvand, P. Bayat, S.M. Vahdaniparast, S. Dehghani, Z. Kooshafar, S. Khaleghi, A. Almasirad, and M. Salimi, “Design and Synthesis of Novel 4-Thiazolidinone Derivatives with Promising anti-Breast Cancer Activity: Synthesis, Characterization, In Vitro and In Vivo Results,” Bioorganic Chemistry 104 (2020): 104276.
   PubMed Web of Science ®Google Scholar
• D.K. Sigalapalli, V. Pooladanda, P. Singh, M. Kadagathur, S.D. Guggilapu, J.L. Uppu, N.D. Tangellamudi, P.K. Gangireddy, C. Godugu, and N.B. Bathini, “Discovery of Certain Benzyl/Phenethyl Thiazolidinone-Indole Hybrids as Potential Anti-Proliferative Agents: Synthesis, Molecular Modeling and Tubulin Polymerization Inhibition Study,” Bioorganic Chemistry 92 (2019): 103188.
   PubMed Web of Science ®Google Scholar
• R.M. Kassab, S.M. Gomha, S.A. Al-Hussain, A.S.A. Dena, M.M. Abdel-Aziz, M.E. Zaki, and Z.A. Muhammad, “Synthesis and in-Silico Simulation of Some New Bis-Thiazole Derivatives and Their Preliminary Antimicrobial Profile: Investigation of Hydrazonoyl Chloride Addition to Hydroxy-Functionalized Bis-Carbazones,” Arabian Journal of Chemistry 14, no. 11 (2021): 103396.
   Web of Science ®Google Scholar
• H.R. Rashdan, A.H. Abdelmonsef, I.A. Shehadi, S.M. Gomha, A.M.M. Soliman, and H.K. Mahmoud, “Synthesis, Molecular Docking Screening and anti-Proliferative Potency Evaluation of Some New Imidazo [2, 1-b] Thiazole Linked Thiadiazole Conjugates,” Molecules 25, no. 21 (2020): 4997.
   PubMed Web of Science ®Google Scholar
• S.M. Gomha, H.A. Abdelhady, D.Z. Hassain, A.H. Abdelmonsef, M. El-Naggar, M.M. Elaasser, and H.K. Mahmoud, “Thiazole-Based Thiosemicarbazones: Synthesis, Cytotoxicity Evaluation and Molecular Docking Study,” Drug Design, Development and Therapy 15 (2021): 659–677.
   PubMed Web of Science ®Google Scholar
• P. Chawla, R. Singh, and S.K. Saraf, “Syntheses and Evaluation of 2, 5-Disubstituted 4-Thiazolidinone Analogues as Antimicrobial Agents,” Medicinal Chemistry Research 21, no. 8 (2012): 2064–2071.
   Web of Science ®Google Scholar
• P. Chawla, R. Singh, and S.K. Saraf, “Effect of Chloro and Fluoro Groups on the Antimicrobial Activity of 2, 5-Disubstituted 4-Thiazolidinones: A Comparative Study,” Medicinal Chemistry Research 21, no. 10 (2012): 3263–3271.
   Web of Science ®Google Scholar
• B.F. Abdel-Wahab, and R.E. Khidre, “2-Chloroquinoline-3-Carbaldehyde II: Synthesis, Reactions, and Applications,” Journal of Chemistry 2013 (2013): 1–13.
   Web of Science ®Google Scholar
• P. Chawla, S. Kalra, R. Kumar, R. Singh, and S.K. Saraf, “Novel 2-(Substituted Phenyl Imino)-5-Benzylidene-4-Thiazolidinones as Possible Non-Ulcerogenic Tri-Action Drug Candidates: Synthesis, Characterization, Biological Evaluation and Docking Studies,” Medicinal Chemistry Research 28, no. 3 (2019): 340–359.
   Web of Science ®Google Scholar
• Q. Hou, X. Lin, X. Lu, C. Bai, H. Wei, G. Luo, and H. Xiang, “Discovery of Novel Steroidal-Chalcone Hybrids with Potent and Selective Activity against Triple-Negative Breast Cancer,” Bioorganic & Medicinal Chemistry 28, no. 23 (2020): 115763.
   PubMed Web of Science ®Google Scholar
• R. Pal, M.J. Akhtar, K. Raj, S. Singh, P. Sharma, S. Kalra, P.A. Chawla, and B. Kumar, “Design, Synthesis and Evaluation of Piperazine Clubbed 1, 2, 4-Triazine Derivatives as Potent Anticonvulsant Agents,” Journal of Molecular Structure. 1257 (2022): 132587.
   Web of Science ®Google Scholar
• K.S. Shukla, S. Pandey, and P.A. Chawla, “Thiazolidine-2, 4-Diones as Non-Hepatotoxic Tri-Action Drug Candidates: Design, Synthesis, Characterization, Biological Evaluation and Docking Studies,” Letters in Organic Chemistry 17, no. 9 (2020): 659–679.
   Web of Science ®Google Scholar
• Sander Pronk, Szilárd Páll, Roland Schulz, Per Larsson, Pär Bjelkmar, Rossen Apostolov, Michael R. Shirts, Jeremy C. Smith, Peter M. Kasson, David van der Spoel, et al., “GROMACS 4.5: A High-Throughput and Highly Parallel Open Source Molecular Simulation Toolkit,” Bioinformatics (Oxford, England) 29, no. 7 (2013): 845–854.
   PubMed Web of Science ®Google Scholar
• S. Abu-Melha, M.M. Edrees, S.M. Riyadh, M.R. Abdelaziz, A.A. Elfiky, and S.M. Gomha, “Clean Grinding Technique: A Facile Synthesis and in Silico Antiviral Activity of Hydrazones, Pyrazoles, and Pyrazines Bearing Thiazole Moiety against SARS-CoV-2 Main Protease (Mpro),” Molecules 25, no. 19 (2020): 4565.
   PubMed Web of Science ®Google Scholar