79
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Expeditious mechanochemical conversion of dihydronaphthalenyl-N-phenylhydrazine-1-carbothioamides into hydrazono-thiazolidin-4-one and hydrazono-dihydrothiazole derivatives—Spectroscopic, DFT, X-ray diffraction, and antibacterial studies

& ORCID Icon
Pages 615-626 | Received 22 Nov 2022, Accepted 22 Feb 2023, Published online: 20 Mar 2023

References

  • Shawky, A. M.; Abourehab, M. A. S.; Abdalla, A. N.; Gouda, A. M. Optimization of Pyrrolizine-Based Schiff Bases with 4-Thiazolidinone Motif: Design, Synthesis and Investigation of Cytotoxicity and Anti-inflammatory Potency. Eur. J. Med. Chem. 2020, 185, 111780. DOI: 10.1016/j.ejmech.2019.111780.
  • Pitta, E.; Tsolaki, E.; Geronikaki, A.; Petrovic, J.; Glamoclija, J.; Sokovic, M.; Crespan, E.; Maga, G.; Bhunia, S. S.; Saxena, A. K. 4-Thiazolidinone Derivatives as Potent Antimicrobial Agents: Microwave-Assisted Synthesis, Biological Evaluation and Docking Studies. Med. Chem. Commun. 2015, 6, 319–326. DOI: 10.1039/C4MD00399C.
  • Desai, C. N.; Rupala, Y. M.; Khasiya, A. G.; Shah, K. N.; Pandit, U. P.; Khedkar, V. M. Synthesis, Biological Evaluation, and Molecular Docking Study of Thiophene, Piperazine, and Thiazolidinone Based Hybrids as Potential Antimicrobial Agents. J. Heterocycl. Chem. 2022, 59, 75–87. DOI: 10.1002/jhet.4366.
  • Mishchenko, M.; Shtrygol, S.; Kaminskyy, D.; Lesyk, R. Thiazole-Bearing 4- Thiazolidinones as New Anticonvulsant Agents. Sci. Pharm. 2020, 88, 16–29. DOI: 10.3390/scipharm88010016.
  • Dincel, E. D.; Akdağ, Ç.; Kayra, T.; Coşar, E. D.; Aksoy, M. O.; Akalın-Çiftçi, G.; Ulusoy-Güzeldemirci, N. Design, Synthesis, Characterization, Molecular Docking Studies and Anticancer Activity Evaluation of Novel Hydrazinecarbothioamide, 1,2,4-Triazole-3-Thione, 4-Thiazolidinone and 1,3,4-Oxadiazole Derivatives. J. Mol. Struct. 2022, 1268, 133710. DOI: 10.1016/j.molstruc.2022.133710.
  • Holota, S.; Kryshchyshyn, A.; Derkach, H.; Trufin, Y.; Demchuk, I.; Gzella, A.; Grellier, P.; Lesyk, R. Synthesis of 5-Enamine-4-Thiazolidinone Derivatives with Trypanocidal and Anticancer Activity. Bioorg. Chem. 2019, 86, 126–136. DOI: 10.1016/j.bioorg.2019.01.045.
  • Abd El-Karim, S. S.; Mohamed, H. S.; Abdelhameed, M. F.; Amr, A. E.-G. E.; Almehizia, A. A.; Nossier, E. S. Design, Synthesis and Molecular Docking of New Pyrazole-Thiazolidinones as Potent Anti-inflammatory and Analgesic Agents with TNF-α Inhibitory Activity. Bioorg. Chem. 2021, 111, 104827. DOI: 10.1016/j.bioorg.2021.104827.
  • Suryawanshi, R.; Jadhav, S.; Makwana, N.; Desai, D.; Chaturbhuj, D.; Sonawani, A.; Idicula-Thomas, S.; Murugesan, V.; Katti, S. B.; Tripathy, S.; et al. Evaluation of 4-Thiazolidinone Derivatives as Potential Reverse Transcriptase Inhibitors against HIV-1 Drug Resistant Strains. Bioorg. Chem. 2017, 71, 211–218. DOI: 10.1016/j.bioorg.2017.02.007.
  • Kadagathur, M.; Patra, S.; Devabattula, G.; George, J.; Phanindranath, R.; Shaikh, A. S.; Sigalapalli, K. D.; Godugu, C.; Nagesh, N.; Tangellamudi, N. D.; Shankaraiah, N. Design, Synthesis of DNA-Interactive 4-Thiazolidinone-Based Indolo-/Pyrroloazepinone Conjugates as Potential Cytotoxic and Topoisomerase I Inhibitors. Eur. J. Med. Chem. 2022, 238, 114465. DOI: 10.1016/j.ejmech.2022.114465.
  • Oliveira, J. F.; Lima, T. S.; Vendramini-Costa, D. B.; Pedrosa, S. C. B.; Lafayette, E. A.; Ferreira da Silva, R.; Almeida, S. M. V.; Olímpio de Moura, R.; Ruiz, A. L. T.; Carvalho, J.; Alves de Lima, M. D. C. Thiosemicarbazones and 4-Thiazolidinones Indole-Based Derivatives: Synthesis, Evaluation of Antiproliferative Activity, Cell Death Mechanisms and Topoisomerase Inhibition Assay. Eur. J. Med. Chem. 2017, 136, 305–314. DOI: 10.1016/j.ejmech.2017.05.023.
  • Cordeiro, R.; Kachroo, M. Synthesis and Biological Evaluation of Anti-tubercular Activity of Schiff Bases of 2-Amino Thiazoles. Bioorg. Med. Chem. Lett. 2020, 30, 127655. DOI: 10.1016/j.bmcl.2020.127655.
  • Kaur, A.; Kaur, A. P.; Gautam, P.; Gautam, D.; Chaudhary, R. P. Ultrasound-Assisted Facile Synthesis and Antimicrobial Studies of Alkanediyl-Bis-Thiazolidin-4-Ones and Alkanediyl-Bis-Thiazinan-4-Ones. J. Heterocycl. Chem. 2019, 56, 2105–2110. DOI: 10.1002/jhet.3590.
  • Sahiba, N.; Sethiya, A.; Soni, J.; Agarwal, D. K.; Agarwal, S. Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications. Top. Curr. Chem. (Cham) 2020, 378, 34. DOI: 10.1007/s41061-020-0298-4.
  • Hajighasemi, H.; Foroughifar, N.; Khajeh-Amiri, A.; Balali, E. One Pot Reactions in the Synthesis of Thiazolidinone Derivatives by nano-Fe3O4-Cysteine Catalyst. J. Sulfur Chem. 2022, 43, 655–670. DOI: 10.1080/17415993.2022.2089038.
  • Mahmoodi, N. O.; Mohammadgholipour, S.; Pirbasti, F. G. Microwave-Assisted One-Pot Three-Component Synthesis of Thiazolidinones Using KSF@Ni as an Efficient Heterogeneous Catalyst. J. Sulfur Chem. 2017, 38, 668–678. DOI: 10.1080/17415993.2017.1343334.
  • Salim, J. K.; Hassan, Q. M. A.; Jassem, A. M.; Sultan, H. A.; Dhumad, A. M.; Emshary, C. A. An Efficient Ultrasound-Assisted CH3COONa Catalyzed Synthesis of Thiazolidinone Molecule: Theoretical and Nonlinear Optical Evaluations of Thiazolidinone-Schiff Base Derivative. Opt. Mater. 2022, 133, 112917. DOI: 10.1016/j.optmat.2022.112917.
  • Deshmukh, A. R.; Dhumal, S. T.; Nawale, L. U.; Khedkar, V. M.; Sarkar, D.; Mane, R. A. Dicationic Liquid Mediated Synthesis of Tetrazoloquinolinyl Methoxy Phenyl 4-Thiazolidinones and Their Antibacterial and Antitubercular Evaluation. Synth. Commun. 2019, 49, 587–601. DOI: 10.1080/00397911.2018.1564928.
  • Subhedar, D. D.; Shaikh, M. H.; Kalam Khan, F. A.; Sangshetti, J. N.; Khedkar, V. M.; Shingate, B. B. Facile Synthesis of New N-Sulfonamidyl-4-Thiazolidinone Derivatives and Their Biological Evaluation. New J. Chem. 2016, 40, 3047–3058. DOI: 10.1039/C6NJ00021E.
  • Kaur, N. Ionic Liquid Assisted Synthesis of S-Heterocycles. Phosphorus Sulfur Silicon Relat. Elem. 2019, 194, 165–185. DOI: 10.1080/10426507.2018.1539492.
  • Khan, J.; Muhammad, S.; Ali Shah, L.; Ali, J.; Ibrar, M.; Rehman, K. U. Synthesis, Characterization and Electrochemistry of Triethylammonium Sulphate Ionic Liquid. Z. Phys. Chem. 2021, 235, 1099–1111. DOI: 10.1515/zpch-2020-1704.
  • Elyasi, Z.; Safaei Ghomi, J.; Najafi, G. R.; Zand Monfared, M. R. The Influence of the Polymerization Approach on the Catalytic Performance of Novel Porous Poly (Ionic Liquid)s for Green Synthesis of Pharmaceutical Spiro-4-Thiazolidinones. RSC Adv. 2020, 10, 44159–44170. DOI: 10.1039/D0RA08647A.
  • Pinate, P.; Makone, S. Novel DABCO Based Acidic Ionic Liquid as a Green Protocol for the Synthesis of Thiazolidin-4-One Derivatives and Cytotoxic Activity Evaluation on Human Breast Cancer Cell Line. J. Sulfur Chem. 2023, 44, 20–36. DOI: 10.1080/17415993.2022.2099223.
  • Nikpassand, M.; Fekri, L. Z.; Taherkhorsand, H. Green Synthesis of Novel 2-Pyrazolyl-1,3-Thiazolidine-4-Ones Using 2-Oxoimidazolidine-1,3-Disulfonic Acid. Heterocycl. Commun. 2017, 23, 429–432. DOI: 10.1515/hc-2017-0124.
  • Apaydın, C. B.; Van Loy, B.; Stevaert, A.; Naesens, L. New Spirothiazolidinone Derivatives: Synthesis and Antiviral Evaluation. Phosphorus Sulfur Silicon Relat. Elem. 2021, 196, 294–299. DOI: 10.1080/10426507.2020.1828886.
  • Mic, M.; Pîrnău, A.; Floare, C. G.; Marc, G.; Franchini, A. H.; Oniga, O.; Vlase, L.; Bogdan, M. Synthesis and Molecular Interaction Study of a Diphenolic Hydrazinyl-Thiazole Compound with Strong Antioxidant and Antiradical Activity with HAS. J. Mol. Struct. 2021, 1244, 131278. DOI: 10.1016/j.molstruc.2021.131278.
  • Pop, B.; Ionut, I.; Marc, G.; Vodnar, D. C.; Pirnau, A.; Vlase, L.; Oniga, O. Development of New 2-Methyl-4-Salicylamide Thiazole Derivatives: Synthesis, Antimicrobial Activity Evaluation, Lipophilicity and Molecular Docking Study. Farmacia 2021, 69, 724–731. DOI: 10.31925/farmacia.2021.4.13.
  • Ali, S. H.; Sayed, A. R. Review of the Synthesis and Biological Activity of Thiazoles. Synth. Commun. 2021, 51, 670–700., DOI: 10.1080/00397911.2020.1854787.
  • Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 2015, 71, 3–8. DOI: 10.1107/S2053229614024218.
  • Zhang, I. Y.; Wu, J.; Xu, X. Extending the Reliability and Applicability of B3LYP. Chem. Commun. (Camb.) 2010, 46, 3057–3070. DOI: 10.1039/C000677G.
  • Tirado-Rives, J.; Jorgensen, W. L. Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules. J. Chem. Theory Comput. 2008, 4, 297–306. DOI: 10.1021/ct700248k.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B. GAUSSIAN 09, Revision, Gaussian, Inc.: Wallingford CT, 2009.
  • Lodewyk, M. W.; Matthew, R.; Siebert, M. R.; Tantillo, D. J. Computational Prediction of 1H and 13C Chemical Shifts: A Useful Tool for Natural Product, Mechanistic, and Synthetic Organic Chemistry. Chem. Rev. 2012, 112, 1839–1862., DOI: 10.1021/cr200106v.
  • Kaupp, M.; Buhl, M.; Malkin, V. G., Eds. Calculation of NMR and EPR Parameters: Theory and Applications, Wiley-VCH: Weinheim, 2004.
  • Koch, W.; Holthausen, M. C. A Chemist’s Guide to Density Functional Theory, Wiley-VCH: Weinheim, 2001.
  • Dennington, R.; II, Keith, T.; Millam, J. GaussView, Semichem Inc: Shawnee Mission, KS, 2007, Version 4.1.2.
  • Perez, C.; Paul, M.; Bazerque, P. Antibiotic Assay by Agar Well Diffusion Method, Acta Biol. Med. Exp. 1990, 15, 113–115.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.