4-Thiazolidinone Based 5-Arylidene Hybrids: Design, Synthesis, Antimicrobial Activity, and Molecular Docking Studies

References

• Evelina Tacconelli, Elena Carrara, Alessia Savoldi, Stephan Harbarth, Marc Mendelson, Dominique L. Monnet, Céline Pulcini, Gunnar Kahlmeter, Jan Kluytmans, Yehuda Carmeli, et al. “Discovery, Research, and Development of New Antibiotics: The WHO Priority List of Antibiotic-resistant Bacteria and Tuberculosis,” The Lancet. Infectious Diseases 18, no. 3 (2018): 318–27. doi:10.1016/S1473-3099(17)30753-3
   PubMed Web of Science ®Google Scholar
• Maria Magana, Muthuirulan Pushpanathan, Ana L. Santos, Leon Leanse, Michael Fernandez, Anastasios Ioannidis, Marc A. Giulianotti, Yiorgos Apidianakis, Steven Bradfute, Andrew L. Ferguson, et al. “The Value of Antimicrobial Peptides in the Age of Resistance,” The Lancet. Infectious Diseases 20, no. 9 (2020): e216–30. doi:10.1016/S1473-3099(20)30327-3
   PubMed Web of Science ®Google Scholar
• Katherine H. Luepke, J. Katie Suda, Helen Boucher, L. Rene Russo, W. Michael Bonney, D. Timothy Hunt, and F. John Mohr III, “Past, Present, and Future of Antibacterial Economics: Increasing Bacterial Resistance, Limited Antibiotic Pipeline, and Societal Implications,” Pharmacotherapy 37, no. 1 (2017): 71–84. doi:10.1002/phar.1868
   PubMed Web of Science ®Google Scholar
• Alexandria P. Taylor, Robinson P. Ralph, Fobian M. Yvette, Blakemore David, Jones H. Lyn, and Fadeyi Olugbeminiyi, “Modern Advances in Heterocyclic Chemistry in Drug Discovery,” Organic & Biomolecular Chemistry 14, no. 28 (2016): 6611–37. doi:10.1039/c6ob00936k
   PubMed Web of Science ®Google Scholar
• Nisheeth Desai, Jahnvi Monapara, Aratiba Jethawa, Vijay Khedkar, and Bapurao Shingate, “Oxadiazole: A Highly Versatile Scaffold in Drug Discovery,” Archiv Der Pharmazie 355, no. 9 (2022): e2200123. doi:10.1002/ardp.202200123
   PubMed Web of Science ®Google Scholar
• Nisheeth C. Desai, Dharmpalsinh J. Jadeja, Harsh K. Mehta, Ashvinkumar G. Khasiya, Keyur N. Shah, and Unnat P. Pandit “Synthesis and Biological Importance of Pyrazole, Pyrazoline, and Indazole as Antibacterial, Antifungal, Antitubercular, Anticancer, and Anti-inflammatory Agents,” N-Heterocycles (2022): 143–89. doi:10.1007/978-981-19-0832-3
   Google Scholar
• Nisheeth C. Desai, Hardik C. Somani, Harsh K. Mehta, Dharmpalsinh J. Jadeja, Ashvinkumar G. Khasiya, and Vijay M. Khedkar, “Microwave-assisted Organic Synthesis, Antimycobacterial Activity, Structure–Activity Relationship and Molecular Docking Studies of Some Novel Indole-oxadiazole Hybrids,” SAR and QSAR in Environmental Research 33, no. 2 (2022): 89–109. doi:10.1080/1062936X.2022.2032333
   PubMed Web of Science ®Google Scholar
• Nisheeth C. Desai, Abhay S. Maheta, Aratiba M. Jethawa, Unnat P. Pandit, Iqrar Ahmad, and Harun Patel, “Zeolite (Y‐H)‐Based Green Synthesis, Antimicrobial Activity, and Molecular Docking Studies of Imidazole Bearing Oxydibenzene Hybrid Molecules,” Journal of Heterocyclic Chemistry 59, no. 5 (2022): 879–89. doi:10.1002/jhet.4427
   Web of Science ®Google Scholar
• Nisheeth C. Desai, Dharmpalsinh J. Jadeja, and Vijay M. Khedkar, “Design, Synthesis, Antimicrobial Activity and in Silico Molecular Docking Studies of Some Sulfur Containing Pyrazole-pyridine Hybrids,” Phosphorus, Sulfur, and Silicon and the Related Elements 197, no. 12 (2022): 1226–37. doi:10.1080/10426507.2022.2085271
   Web of Science ®Google Scholar
• Nisheeth C. Desai, Kashyap R. Wadekar, Unnat P. Pandit, Harsh K. Mehta, Dharmpalsinh J. Jadeja, and Medha Pandya, “Design, Synthesis, Biological Evaluation and In-silico Docking Studies of Some Novel Imidazolone Derivatives as Potent Antimicrobial Containing Fluorine Agents,” Analytical Chemistry Letters 11, no. 4 (2021): 469–96. doi:10.1080/22297928.2021.1944310
   Google Scholar
• Nisheeth C. Desai, Niraj R. Shihory, Ashvinkumar G. Khasiya, Unnat P. Pandit, and Vijay M. Khedkar, “Quinazoline Clubbed Thiazole and 1, 3, 4-Oxadiazole Heterocycles: Synthesis, Characterization, Antibacterial Evaluation, and Molecular Docking Studies,” Phosphorus, Sulfur, and Silicon and the Related Elements 196, no. 6 (2021): 569–77. doi:10.1080/10426507.2021.1871732
   Web of Science ®Google Scholar
• Rahul Suryawanshi, Sushama Jadhav, Nandini Makwana, Dipen Desai, Devidas Chaturbhuj, Archana Sonawani, Susan Idicula-Thomas, Vanangamudi Murugesan, Seturam B. Katti, Srikanth Tripathy, et al. “Evaluation of 4-Thiazolidinone Derivatives as Potential Reverse Transcriptase Inhibitors against HIV-1 Drug Resistant Strains,” Bioorganic Chemistry 71 (2017): 211–8. doi:10.1016/j.bioorg.2017.02.007
   PubMed Web of Science ®Google Scholar
• V. Ravichandran, B.R. Prashantha Kumar, S. Sankar, and R.K. Agrawal, “Predicting Anti-HIV Activity of 1, 3, 4-Thiazolidinone Derivatives: 3D-QSAR Approach,” European Journal of Medicinal Chemistry 44, no. 3 (2009): 1180–7. doi:10.1016/j.ejmech.2008.05.036
   PubMed Web of Science ®Google Scholar
• Ahmed M. Shawky, Mohammed A.S. Abourehab, Ashraf N. Abdalla, and Ahmed M. Gouda, “Optimization of Pyrrolizine-based Schiff Bases with 4-Thiazolidinone Motif: Design, Synthesis and Investigation of Cytotoxicity and Anti-inflammatory Potency,” European Journal of Medicinal Chemistry 185 (2020): 111780. doi:10.1016/j.ejmech.2019.111780
   PubMed Web of Science ®Google Scholar
• Khaled R.A. Abdellatif, Mohamed A. Abdelgawad, Heba A.H. Elshemy, and Shahinda S.R. Alsayed, “Design, Synthesis and Biological Screening of New 4-Thiazolidinone Derivatives with Promising COX-2 Selectivity, Anti-inflammatory Activity and Gastric Safety Profile,” Bioorganic Chemistry 64 (2016): 1–12. doi:10.1016/j.bioorg.2015.11.001
   PubMed Web of Science ®Google Scholar
• Holota Serhii, Anna Kryshchyshyn, Derkach Halyna, Trufin Yaroslava, Inna Demchuk, Andrzej Gzella, Philippe Grellier, and Roman Lesyk, “Synthesis of 5-Enamine-4-Thiazolidinone Derivatives with Trypanocidal and Anticancer Activity,” Bioorganic Chemistry 86 (2019): 126–36. doi:10.1016/j.bioorg.2019.01.045
   PubMed Web of Science ®Google Scholar
• Konrad A. Szychowski, Marcin L. Leja, Danylo V. Kaminskyy, Anna P. Kryshchyshyn, Urszula E. Binduga, R. Pinyazhko, Roman B. Lesyk, Jakub Tobiasz, and Jan Gmiński, “Anticancer Properties of 4-Thiazolidinone Derivatives Depend on Peroxisome Proliferator-activated Receptor Gamma (PPARγ),” European Journal of Medicinal Chemistry 141 (2017): 162–8. doi:10.1016/j.ejmech.2017.09.071
   PubMed Web of Science ®Google Scholar
• Nisheeth C. Desai, Krunalsinh A. Jadeja, Dharmpalsinh J. Jadeja, Vijay M. Khedkar, and Prakash C. Jha, “Design, Synthesis, Antimicrobial Evaluation, and Molecular Docking Study of Some 4-Thiazolidinone Derivatives Containing Pyridine and Quinazoline Moiety,” Synthetic Communications 51, no. 6 (2020): 1–12. doi:10.1080/00397911.2020.1861302
   Web of Science ®Google Scholar
• Nisheeth C. Desai, Ashvinkumar G. Khasiya, Bharti P. Dave, and Vijay M. Khedkar, “Synthesis, Characterization In Vitro Antimicrobial Evaluation and In Silico Approach of Molecular Docking of Pyrazole Based Pyrimidine and Pyrazolone Motifs,” Anti-infective Agents 20, no. 5 (2022). doi:10.2174/2211352520666220616105540
   PubMedGoogle Scholar
• Nisheeth C. Desai, Yogesh M. Rupala, Ashvinkumar G. Khasiya, Keyur N. Shah, Unnat P. Pandit, and Vijay M. Khedkar, “Synthesis, Biological Evaluation, and Molecular Docking Study of Thiophene‐, Piperazine‐, and Thiazolidinone‐based Hybrids as Potential Antimicrobial Agents,” Journal of Heterocyclic Chemistry 59, no. 1 (2022): 75–87. doi:10.1002/jhet.4366
   Web of Science ®Google Scholar
• Shiben Wang, Hui Liu, Xuekun Wang, Kang Lei, Guangyong Li, and Zheshan Quan, “Synthesis and Evaluation of Antidepressant Activities of 5-Aryl-4, 5-Dihydrotetrazolo [1,5-a] Thieno [2,3-e] Pyridine Derivatives,” Molecules 24, no. 10 (2019): 1857. doi:10.3390/molecules24101857
   PubMed Web of Science ®Google Scholar
• Neetu Patel, A.K. Prajapati, R.N. Jadeja, I.P. Tripathi, and N. Dwivedi, “Synthesis, Characterization and In Vitro Antidiabetic Activity of Anionic Dioxidovanadium (V) complexes,” Journal of the Indian Chemical Society 98, no. 4 (2021): 100047. doi:10.1016/j.jics.2021.100047
   Web of Science ®Google Scholar
• Nisheeth C. Desai, Kandarp Bhatt, Jahnvi Monapara, Unnat Pandit, and Vijay M. Khedkar, “Conventional and Microwave-assisted Synthesis, Antitubercular Activity, and Molecular Docking Studies of Pyrazole and Oxadiazole Hybrids,” ACS Omega 6, no. 42 (2021): 28270–84. doi:10.1021/acsomega.1c04411
   PubMed Web of Science ®Google Scholar
• Nisheeth C. Desai, Kandarp Bhatt, Dharmpalsinh J. Jadeja, Harsh K. Mehta, Vijay M. Khedkar, and Dhiman Sarkar, “Conventional and Microwave‐assisted Organic Synthesis of Novel Antimycobacterial Agents Bearing Furan and Pyridine Hybrids,” Drug Development Research 83, no. 2 (2022): 416–31. doi:10.1002/ddr.21872
   PubMed Web of Science ®Google Scholar
• Karam Ahmed El-Sharkawy, Mohammed Mofreh AlBratty, and Hassan Ahmad Alhazmi, “Synthesis of Some Novel Pyrimidine, Thiophene, Coumarin, Pyridine and Pyrrole Derivatives and Their Biological Evaluation as Analgesic, Antipyretic and Anti-inflammatory Agents,” Brazilian Journal of Pharmaceutical Sciences 54, no. 4 (2018). doi:10.1590/s2175-97902018000400153
   Web of Science ®Google Scholar
• HimadriSekhar Chatterjee, Basudeb Dutta, Kunal Pal, Kuladip Jana, Pradip Kumar Mahapatra, and Chittaranjan Sinha, “Synthesis, Crystal Structure and Biological Application of a Cu (II) Coordination Compound of 2-Hydroxy-5-Methyl-3-(Pyridin-3-Yliminomethyl)-Benzaldehyde,” Journal of the Indian Chemical Society 98, no. 1 (2021): 100007. doi:10.1016/j.jics.2021.100007
   Web of Science ®Google Scholar
• Jovana B. Araškov, Milan Nikolić, Stevan Armaković, Sanja Armaković, Marko Rodić, Aleksandar Višnjevac, José M. Padrón, Tamara R. Todorović, and Nenad R. Filipović, “Structural, Antioxidant, Antiproliferative and In-silico Study of Pyridine-based Hydrazonyl–Selenazoles and Their Sulphurisosteres,” Journal of Molecular Structure 1240 (2021): 130512. doi:10.1016/j.molstruc.2021.130512
   Web of Science ®Google Scholar
• Bulut Nilufer, Umit M. Kocyigit, Ibrahim H. Gecibesler, Taner Dastan, Huseyin Karci, Parham Taslimi, Sevgi Durna Dastan, Ilhami Gulcin, and Ahmet Cetin, “Synthesis of Some Novel Pyridine Compounds Containing Bis‐1, 2, 4‐Triazole/Thiosemicarbazide Moiety and Investigation of Their Antioxidant Properties, Carbonic Anhydrase, and Acetylcholinesterase Enzymes Inhibition Profiles,” Journal of Biochemical and Molecular Toxicology 32, no. 1 (2018): e22006. doi:10.1002/jbt.22006
   Web of Science ®Google Scholar
• Guangqian Yang, Huanlin Zheng, Wubin Shao, Liwei Liu, and Zhibing Wu, “Study of the In Vivo Antiviral Activity against TMV Treated with Novel 1-(t-Butyl)-5-Amino-4-Pyrazole Derivatives Containing a 1,3,4-Oxadiazole Sulfide Moiety,” Pesticide Biochemistry and Physiology 171 (2021): 104740. doi:10.1016/j.pestbp.2020.104740
   PubMed Web of Science ®Google Scholar
• Zaibo Yang, Pei Li, and Xiuhai Gan, “Novel Pyrazole-hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity,” Molecules 23, no. 7 (2018): 1798. doi:10.3390/molecules23071798
   PubMed Web of Science ®Google Scholar
• Mohamed A. Abdelgawad, Rania B. Bakr, and Hany A. Omar, “Design, Synthesis and Biological Evaluation of Some Novel Benzothiazole/Benzoxazole and/or Benzimidazole Derivatives Incorporating a Pyrazole Scaffold as Antiproliferative Agents,” Bioorganic Chemistry 74 (2017): 82–90. doi:10.1016/j.bioorg.2017.07.007
   PubMed Web of Science ®Google Scholar
• RafatM. Mohareb, Yara R. Milad, and Reem A. El-Ansary, “New Approaches for the Synthesis of Fused Thiophene, Pyrazole, Pyran and Pyridine Derivatives with Anti-proliferative Together with c-Met Kinase and Prostate Cancer Cell Inhibitions,” Anti-Cancer Agents in Medicinal Chemistry 21, no. 13 (2021): 1751–66. doi:10.2174/1871520620999201110191056
   PubMed Web of Science ®Google Scholar
• N.C. Desai, and Amit M. Dodiya, “Synthesis, Characterization and Antimicrobial Screening of Quinoline Based Quinazolinone-4-Thiazolidinone Heterocycles,” Arabian Journal of Chemistry 7, no. 6 (2014): 906–13. doi:10.1016/j.arabjc.2011.08.007
   Web of Science ®Google Scholar
• Richard J. Reece, and Anthony Maxwell, “DNA Gyrase: Structure and Function,” Critical Reviews in Biochemistry and Molecular Biology 26, no. 3-4 (1991): 335–75. doi:10.3109/10409239109114072
   PubMed Web of Science ®Google Scholar
• Frédéric Collin, Shantanu Karkare, and Anthony Maxwell, “Exploiting Bacterial DNA Gyrase as a Drug Target: Current State and Perspectives,” Applied Microbiology and Biotechnology 92, no. 3 (2011): 479–97. doi:10.1007/s00253-011-3557-z
   PubMed Web of Science ®Google Scholar
• Yves Pommier, “Drugging Topoisomerases: Lessons and Challenges,” ACS Chemical Biology 8, no. 1 (2013): 82–95. doi:10.1021/cb300648v
   PubMed Web of Science ®Google Scholar
• David E. Ehmann, and Sushmita D. Lahiri, “Novel Compounds Targeting Bacterial DNA Topoisomerase/DNA Gyrase,” Current Opinion in Pharmacology 18 (2014): 76–83. doi:10.1016/j.coph.2014.09.007
   PubMed Web of Science ®Google Scholar
• Anthony Maxwell, and David M. Lawson, “The ATP-binding Site of Type II Topoisomerases as a Target for Antibacterial Drugs,” Current Topics in Medicinal Chemistry 3, no. 3 (2003): 283–303. doi:10.2174/1568026033452500
   PubMed Web of Science ®Google Scholar
• Brian K. Shoichet, Susan L. McGovern, Binqing Wei, and John J. Irwin, “Lead Discovery Using Molecular Docking,” Current Opinion in Chemical Biology 6, no. 4 (2002): 439–46. doi:10.1016/s1367-5931(02)00339-3
   PubMed Web of Science ®Google Scholar
• Nisheeth C. Desai, Hasit V. Vaghani, Aratiba M. Jethawa, and Vijay M. Khedkar, “In Silico Molecular Docking Studies of Oxadiazole and Pyrimidine Bearing Heterocyclic Compounds as Potential Antimicrobial Agents,” Archiv Der Pharmazie 354, no. 10 (2021): 2100134. doi:10.1002/ardp.202100134
   Web of Science ®Google Scholar
• Nisheeth C. Desai, Surbhi B. Joshi, and Vijay M. Khedkar, “Synthesis, Antimicrobial Activity and Molecular Docking of Pyrazole Bearing the Benzodiazepine Moiety,” Analytical Chemistry Letters 10, no. 3 (2020): 307–20. doi:10.1080/22297928.2020.1785325
   Google Scholar
• Richard A. Friesner, Robert B. Murphy, Matthew P. Repasky, Leah L. Frye, Jeremy R. Greenwood, Thomas A. Halgren, Paul C. Sanschagrin, and Daniel T. Mainz, “Extra Precision Glide: Docking and Scoring Incorporating a Model of Hydrophobic Enclosure for Protein − Ligand Complexes,” Journal of Medicinal Chemistry 49, no. 21 (2006): 6177–96. doi:10.1021/jm051256o
   PubMed Web of Science ®Google Scholar
• Thomas A. Halgren, Robert B. Murphy, Richard A. Friesner, Hege S. Beard, Leah L. Frye, W. Thomas. Pollard, and Jay L. Banks, “Glide: A New Approach for Rapid, Accurate Docking and Scoring. 2. Enrichment Factors in Database Screening,” Journal of Medicinal Chemistry 47, no. 7 (2004): 1750–9. doi:10.1021/jm030644s
   PubMed Web of Science ®Google Scholar
• Richard A. Friesner, Jay L. Banks, Robert B. Murphy, Thomas A. Halgren, Jasna J. Klicic, Daniel T. Mainz, Matthew P. Repasky, Eric H. Knoll, Mee Shelley, Jason K. Perry, et al. “Glide: A New Approach for Rapid, Accurate Docking and Scoring. 1. Method and Assessment of Docking Accuracy,” Journal of Medicinal Chemistry 47, no. 7 (2004): 1739–49. doi:10.1021/jm0306430
   PubMed Web of Science ®Google Scholar