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Research Articles

Synthesis, X-Ray Structure Analysis, Computational Investigations, and In Vitro Biological Evaluation of New Thiazole-Based Heterocycles as Possible Antimicrobial Agents

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Pages 261-274 | Received 12 Dec 2022, Accepted 14 Jan 2023, Published online: 01 Feb 2023

References

  • M. Gümüş, M. Yakan, and I. Koca, “Recent Advances of Thiazole Hybrids in Biological Applications,” Future Medicinal Chemistry 11, no. 15 (2019): 1979–98. doi:10.4155/fmc-2018-0196
  • T. Wright, 2001. “Pharmaceutical Substances: Syntheses, Patents, Applications,” Axel Kleemann, Jurgen Engel (eds), B. Kutscher and D. Reichert. (Stuttgart: Georg Thieme, 2001): xxxiv+ 2488 pages (2 volumes). DM 998. ISBN 3‐13‐558404‐6.
  • P. Maienfisch, and A. J. Edmunds, “Thiazole and Isothiazole Ring–Containing Compounds in Crop Protection,” Advances in Heterocyclic Chemistry 121 (2017): 35–88.
  • N. Jain, and B. Singh, “An Overview of Biological and Synthetic Aspects of Thiazole Derivatives in Heterocyclic Chemistry,” World Journal of Research and Review 3, no. 5 (2016): 52–7.
  • K. Masui, A. Mori, K. Okano, K. Takamura, M. Kinoshita, and T. Ikeda, “Syntheses and Properties of Donor-Acceptor-Type 2,5-Diarylthiophene and 2, 5-Diarylthiazole,” Organic Letters 6, no. 12 (2004): 2011–4. doi:10.1021/ol049386z
  • I. M. El-Deeb, and S. H. Lee, “Design and Synthesis of New Potent Anticancer Pyrazoles with High FLT3 Kinase Inhibitory Selectivity,” Bioorganic & Medicinal Chemistry 18, no. 11 (2010): 3961–73. doi:10.1016/j.bmc.2010.04.029
  • A. E. Rashad, M. I. Hegab, R. E. Abdel-Megeid, J. A. Micky, and F. M. Abdel-Megeid, “Synthesis and Antiviral Evaluation of Some New Pyrazole and Fused Pyrazolopyrimidine Derivatives,” Bioorganic & Medicinal Chemistry 16, no. 15 (2008): 7102–6. doi:10.1016/j.bmc.2008.06.054
  • A. El-Hashim, S. Yousefi, I. Edafiogho, R. Raghupathy, M. Yousif, and H. U. Simon, “Anti-Inflammatory and Immunosuppressive Effects of the Enaminone E121,” European Journal of Pharmacology 632, no. 1–3 (2010): 73–8. doi:10.1016/j.ejphar.2009.12.004
  • E. Azzali, D. Machado, A. Kaushik, F. Vacondio, S. Flisi, C. S. Cabassi, et al, “Substituted N-Phenyl-5-(2-(Phenylamino)Thiazol-4-yl)Isoxazole-3-Carboxamides Are Valuable Antitubercular Candidates That Evade Innate Efflux Machinery,” Journal of Medicinal Chemistry 60, no. 16 (2017): 7108–22.
  • K. Chaudhari, S. Surana, P. Jain, and H. M. Patel, “Mycobacterium Tuberculosis (MTB) GyrB Inhibitors: An Attractive Approach for Developing Novel Drugs against TB,” European Journal of Medicinal Chemistry 124 (2016): 160–85. doi:10.1016/j.ejmech.2016.08.034
  • P. Khloya, S. Kumar, P. Kaushik, P. Surain, D. Kaushik, and P. K. Sharma, “Synthesis and Biological Evaluation of Pyrazolylthiazole Carboxylic Acids as Potent Anti-Inflammatory–Antimicrobial Agents,” Bioorganic & Medicinal Chemistry Letters 25, no. 6 (2015): 1177–81. doi:10.1016/j.bmcl.2015.02.004
  • S. J. Takate, A. D. Shinde, B. K. Karale, H. Akolkar, L. Nawale, D. Sarkar, and P. C. Mhaske, “Thiazolyl-Pyrazole Derivatives as Potential Antimycobacterial Agents,” Bioorganic & Medicinal Chemistry Letters 29, no. 10 (2019): 1199–202. doi:10.1016/j.bmcl.2019.03.020
  • K. Vaarla, R. K. Kesharwani, K. Santosh, R. R. Vedula, S. Kotamraju, and M. K. Toopurani, “Synthesis, Biological Activity Evaluation and Molecular Docking Studies of Novel Coumarin Substituted Thiazolyl-3-Aryl-Pyrazole-4-Carbaldehydes,” Bioorganic & Medicinal Chemistry Letters 25, no. 24 (2015): 5797–803. doi:10.1016/j.bmcl.2015.10.042
  • H. H. Wang, K. M. Qiu, H. E. Cui, Y. S. Yang, Y. Luo, M. Xing, X. Y. Qiu, L. F. Bai, and H. L. Zhu, “Synthesis, Molecular Docking and Evaluation of Thiazolyl-Pyrazoline Derivatives Containing Benzodioxole as Potential Anticancer Agents,” Bioorganic & Medicinal Chemistry 21, no. 2 (2013): 448–55. doi:10.1016/j.bmc.2012.11.020
  • A. A. Altaf, A. Shahzad, Z. Gul, N. Rasool, A. Badshah, B. Lal, and E. Khan, “A Review on the Medicinal Importance of Pyridine Derivatives,” Journal of Drug Design and Medicinal Chemistry 1, no. 1 (2015): 1–11.
  • T. B. Chaston, and D. R. Richardson, “Interactions of the Pyridine-2-Carboxaldehyde Isonicotinoyl Hydrazone Class of Chelators with Iron and DNA: Implications for Toxicity in the Treatment of Iron Overload Disease,” Journal of Biological Inorganic Chemistry 8, no. 4 (2003): 427–38. doi:10.1007/s00775-002-0434-3
  • Y. L. Jin, M. C. Rho, K. Gajulapati, H. Y. Jung, S. K. Boovanahalli, J. H. Lee, G. Y. Song, J. H. Choi, Y. K. Kim, K. Lee, et al, “Synthesis of a Novel Series of Imidazo[1,2-α] Pyridines as Acyl-CoA: Cholesterol Acyltransferase (ACAT) Inhibitors,” Bulletin of the Korean Chemical Society 30, no. 6 (2009): 1297–304.
  • M. López‐Martínez, H. Salgado‐Zamora, E. R. San‐Juan, S. Zamudio, O. Picazo, M. E. Campos, and E. B. Naranjo‐Rodriguez, “Anti‐Anxiety and Sedative Profile Evaluation of Imidazo[1,2‐a] Pyridine Derivatives,” Drug Development Research 71, no. 6 (2010): 371–81. doi:10.1002/ddr.20382
  • Y. Tsurumi, H. Ueda, K. Hayashi, S. Takase, M. Nishikawa, S. Kiyoto, and M. Okuhara, “WS75624 A and B, New Endothelin Converting Enzyme Inhibitors Isolated from Saccharothrix sp. No. 75624,” Journal of Antibiotics 48, no. 10 (1995): 1066–72. doi:10.7164/antibiotics.48.1066
  • (a) J. V. Greenhill, “Enaminones,” Chemical Society Reviews 6, no. 3 (1977): 277–94. doi:10.1039/cs9770600277. (b) A.-Z A. Elassar, and A. A. El-Khair, “Recent Developments in the Chemistry of Enaminones,” Tetrahedron 59, no. 43 (2003): 8463–80. (c) H. Seki, and G. I. Georg, “Synthesis of Amino Acid Derived Enaminones via Wolff Rearrangement Using Vinylogous Amides as Carbon Nucleophiles,” Journal of the American Chemical Society 132, no. 44 (2010): 15512–3. (d) Y.-W. Kang, Y. J. Cho, S. J. Han, and H.-Y. Jang, “Tunable and Diastereoselective Brønsted Acid Catalyzed Synthesis of β-Enaminones,” Organic Letters 18, no. 2 (2016): 272–5. (e) Z. Dong, X. W. Zhang, W. Li, Z. M. Li, W. Y. Wang, Y. Zhang, W. Liu, and W. B. Liu, “Synthesis of N-Fused Polycyclic Indoles via Ligand-Free Palladium-Catalyzed Annulation/Acyl Migration Reaction,” Organic Letters 21, no. 4 (2019): 1082–6.
  • (a) M. Rueping, and A. Parra, “Fast, Efficient, Mild, and Metal-Free Synthesis of Pyrroles by Domino Reactions in Water,” Organic Letters 12, no. 22 (2010): 5281–3. doi:10.1021/ol102247n. (b) K. Hu, P. Qian, J. Su, Z. Li, J. Wang, Z. Zha, and Z. Wang, “Multifunctionalization of Unactivated Cyclic Ketones via an Electrochemical Process: Access to Cyclic α-Enaminones,” Journal of Organic Chemistry 84, no. 3 (2019): 1647–53. (c) Biping Xu, Yaping Shang, Xiaoming Jie, Xiaofeng Zhang, Jian Kan, Subhash Laxman Yedage, and Weiping Su, “Synthesis of α-Enaminones from Cyclic Ketones and Anilines Using Oxoammonium Salt as an Oxygen Transfer Reagent,” Green Chemistry 22, no. 6 (2020): 1827–31.
  • Y. I. Asiri, A. B. Muhsinah, A. Alsayari, H. A. Ghabbour, Z. M. Almarhoon, F. A. Al-Aizari, K. Venkatesan, S. Tasqeeruddin, S. S. Sulthana, and Y. N. Mabkhot, “Design, Synthesis, X-Ray Analysis, and Biological Screening of New Oxime and Enaminone Thiazoline-2-Thione Derivatives,” Journal of Molecular Structure 1223 (2021): 128977. doi:10.1016/j.molstruc.2020.128977
  • M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka, and M. A. Spackman, Crystal Explorer (University of Western Australia, 2017). crystalexplorer.net
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, and G. A. Petersson, GAUSSIAN 09; Revision A02 (Wallingford, CT: Gaussian Inc., 2009); GaussView; Version 4.1; Dennington II, R., Keith, T., Millam, J., Eds. (Shawnee Mission, KS: Semichem Inc, 2007).
  • A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint,” Chemical Reviews 88, no. 6 (1988): 899–926. ‏ doi:10.1021/cr00088a005
  • Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Susceptibility Testing (Wayne, PA: CLSI, 2012).
  • M. M. Ghorab, M. S. Alsaid, M. S. El-Gaby, N. A. Safwat, M. M. Elaasser, and A. M. Soliman, “Biological Evaluation of Some New N-(2,6-Dimethoxypyrimidinyl)Thioureido Benzenesulfonamide Derivatives as Potential Antimicrobial and Anticancer Agents,” European Journal of Medicinal Chemistry 124 (2016): 299–310. doi:10.1016/j.ejmech.2016.08.060
  • Xiaoming Li, Mark Hilgers, Mark Cunningham, Zhiyong Chen, Michael Trzoss, Junhu Zhang, Lucy Kohnen, Thanh Lam, Chris Creighton, Kedar G C, et al, “Structure-Based Design of New DHFR-Based Antibacterial Agents: 7-Aryl-24-Diaminoquinazolines,” Bioorganic & Medicinal Chemistry Letters 21, no. 18 (2011): 5171–6. doi:10.1016/j.bmcl.2011.07.059
  • M. Sabet, S. Tanreh, A. Khosravi, M. Astaraki, M. Rezvani, and M. D. Ganji, “Theoretical Assessment of the Solvent Effect on the Functionalization of Au32 and C60 Nanocages with Fluorouracil Drug,” Diamond and Related Materials 126 (2022): 109142. doi:10.1016/j.diamond.2022.109142
  • M. Rasoolidanesh, M. Astaraki, M. Mostafavi, M. Rezvani, and M. D. Ganji, “Toward Efficient Enantioseparation of Ibuprofen Isomers Using Chiral BNNTs: Dispersion Corrected DFT Calculations and DFTB Molecular Dynamic Simulations,” Diamond and Related Materials 119 (2021): 108561. doi:10.1016/j.diamond.2021.108561
  • J. B. Foresman, and AE. Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed. (Pittsburgh, PA: Gaussian, 1996).
  • R. Chang, Chemistry, 7th ed. (New York, NY: McGraw-Hill, 2001).
  • B. Kosar, and C. Albayrak, “Spectroscopic Investigations and Quantum Chemical Computational Study of (E)-4-Methoxy-2-[(p-Tolylimino) Methyl] Phenol,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 78, no. 1 (2011): 160–7. doi:10.1016/j.saa.2010.09.016
  • T. A. Koopmans, “Ordering of Wave Functions and Eigenenergies to the Individual Electrons of an Atom,” Physica 1, no. 1–6 (1934): 104–13. doi:10.1016/S0031-8914(34)90011-2
  • R. G. Parr, and W. Yang, Density-Functional Theory of Atoms and Molecules (New York, NY: Oxford University Press, 1989).
  • R. G. Parr, L. V. Szentpaly, and S. Liu, “Electrophilicity Index,” Journal of the American Chemical Society 121, no. 9 (1999): 1922–4. doi:10.1021/ja983494x
  • N. C. Desai, V. V. Joshi, K. M. Rajpara, H. V. Vaghani, and H. M. Satodiya, “Facile Synthesis of Novel Fluorine Containing Pyrazole Based Thiazole Derivatives and Evaluation of Antimicrobial Activity,” Journal of Fluorine Chemistry 142 (2012): 67–78. doi:10.1016/j.jfluchem.2012.06.021

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