Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Latest Articles
0
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis, in vitro-antimicrobial investigation, molecular docking, and DFT studies of novel bis-thiazole derivatives

, , &
Received 15 May 2024, Published online: 09 Aug 2024

References

  • Niu, Z.-X.; Wang, Y.-T.; Zhang, S.-N.; Li, Y.; Chen, X.-B.; Wang, S.-Q.; Hong-Min, L. Application and Synthesis of Thiazole Ring in Clinically Approved Drugs. Eur. J. Med. Chem. 2023, 250, 115172. DOI: 10.1016/j.ejmech.2023.115172.
  • Djukic, M.; Fesatidou, M.; Xenikakis, I.; Geronikaki, A.; Angelova, V. T.; Savic, V.; Pasic, M.; Krilovic, B.; Djukic, D.; Gobeljic, B.; et al. In Vitro Antioxidant Activity of Thiazolidinone Derivatives of 1, 3-Thiazole and 1,3,4-Thiadiazole. Chem. Biol. Interact. 2018, 286, 119–131. DOI: 10.1016/j.cbi.2018.03.013.
  • Abd El-Sattar, N. E. A.; Badawy, E. H. K.; Abdel-Mottaleb, M. S. A. Synthesis of Some Pyrimidine, Pyrazole, and Pyridine. J. Chem. 2018, 23, 234. DOI: 10.1155/2018/8795061.
  • Marković, A.; Živković, A.; Atanasova, M.; Doytchinova, I.; Hofmann, B.; George, S.; Kretschmer, S.; Rödl, C.; Steinhilber, D.; Stark, H.; Šmelcerović, A. Thiazole Derivatives as Dual Inhibitors of Deoxyribonuclease I and 5-Lipoxygenase: A Promising Scaffold for the Development of Neuroprotective Drugs. Chem. Biol. Interact. 2023, 381, 110542. DOI: 10.1016/j.cbi.2023.110542.
  • Abhale, Y. K.; Shinde, A.; Deshmukh, K. K.; Nawale, L.; Sarkar, D.; Mhaske, P. C. Synthesis, Antitubercular and Antimicrobial Potential of Some New Thiazole Substituted Thiosemicarbazide Derivatives. Med. Chem. Res. J. 2017, 10, 2557. DOI: 10.1007/s00044-017-1955-1.
  • Khatik, G. L.; Datusalia, A. K.; Ahsan, W.; Kaur, P.; Vyas, M.; Mittal, A.; Nayak, S. K. A Retrospect Study on Thiazole Derivatives as the Potential Antidiabetic Agents in Drug Discovery and Developments. CDDT. 2018, 15, 163–177. DOI: 10.2174/1570163814666170915134018.
  • Osman, H.; Yusufzai, S. K.; Khan, M. S.; Abd Razik, B. M.; Sulaiman, O.; Mohamad, S.; Gansau, J. A.; Ezzat, M. O.; Parumasivam, T.; Hassan, M. Z. New Thiazolyl-Coumarin Hybrids: Design, Synthesis, Characterization, X-Ray Crystal Structure, Antibacterial and Antiviral Evaluation. J. Mol. Struct. 2018, 1166, 147–154. DOI: 10.1016/j.molstruc.2018.04.031.
  • Mohamed, A. M.; Abdel-Hafez, N. A.; Kassem, A. F.; Abbas, E. M. H.; Mounier, M. M. Synthesis of Some New Thiazole Derivatives and Their Cytotoxicity on Different Human Tumor Cell Lines. Russ. J. Gen. Chem. 2017, 87, 2391–2400. DOI: 10.1134/S1070363217100218.
  • Pember, S. O.; Mejia, G. L.; Price, T. J.; Pasteris, R. J. Piperidinyl Thiazole Isoxazolines: A New Series of Highly Potent, Slowly Reversible FAAH Inhibitors with Analgesic Properties. Bioorg. Med. Chem. Lett. 2016, 26, 2965–2973. DOI: 10.1016/j.bmcl.2016.02.061.
  • Shikha, A.; Priyanka, K.; Divyani, G.; Prakash, P. Thiazole Containing Heterocycles with CNS Activity. Curr. Drug Discov. Technol. 2018, 15, 178. DOI: 10.2174/1570163814666170724170152.
  • Sharma, R. N.; Xavier, F. P.; Vasu, K. K.; Chaturvedi, S. C.; Pancholi, S. S. Synthesis of 4-Benzyl-1,3-Thiazole Derivatives as Potential anti-Inflammatory Agents: An Analog- Based Drug Design Approach. J. Enzyme Inhib. Med. Chem. 2009, 24, 890–897. DOI: 10.1080/14756360802519558.
  • Hantzsch, A.; Weber, J. Uber Verbindungen Des Thiazols (Pyridins Der Thiophenreihe). Ber. Dtsch. Chem. Ges. 1887, 20, 3118–3132. DOI: 10.1002/cber.188702002200.
  • Ayati, A.; Emami, S.; Asadipour, A.; Shafiee, A.; Foroumadi, A. Recent Applications of 1,3-Thiazole Core Structure in the Identification of New Lead Compounds and Drug Discovery. Eur. J. Med. Chem. 2015, 97, 699–718. DOI: 10.1016/j.ejmech.2015.04.015.
  • Borcea, A.-M.; Ionuț, I.; Crișan, O.; Oniga, O. An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives. Molecules 2021, 26, 624. DOI: 10.3390/molecules26030624.
  • Ozturk, T.; Ertas, E.; Mert, O. Use of Lawesson’s Reagent in Organic Syntheses. Chem. Rev. 2007, 107, 5210–5278. DOI: 10.1021/cr040650b.
  • Castagnolo, D.; Pagano, M.; Bernardini, M.; Botta, M. Domino Alkylation-Cyclization Reaction of Propargyl Bromides with Thioureas/Thiopyrimidinones: A New Facile Synthesis of 2-Aminothiazoles and 5H-Thiazolo[3,2-a]Pyrimidin-5-Ones. Synlett, 2009, 2009, 2093–2096. DOI: 10.1055/s-0029-1217700.
  • Singh, A.; Malhotra, D.; Singh, K.; Chadha, R.; Bedi, P. M. S. Thiazole Derivatives in Medicinal Chemistry: Recent Advancements in Synthetic Strategies, Structure Activity Relationship and Pharmacological Outcomes. J. Mol. Struct. 2022, 1266, 133479. DOI: 10.1016/j.molstruc.2022.133479.
  • Thierbach, G.; Reichenbach, H. Myxothiazol, a New Antibiotic Interfering with Respiration. Antimicrob. Agents Chemother. 1981, 19, 504–507. DOI: 10.1128/AAC.19.4.504.
  • Wellington, K.; Curran, M. P. Cefditoren Pivoxil. Drugs 2004, 64, 2597–2618. DOI: 10.2165/00003495-200464220-00009.
  • Grassi, G. G. Cefodizime in Clinical Use: A Review of the Clinical Trial Reports. J. Antimicrob. Chemother. 1990, 26, 117–125. DOI: 10.1093/jac/26.suppl_c.117.
  • Cameron, D. W.; Heath-Chiozzi, M.; Danner, S.; Cohen, C.; Kravcik, S.; Maurath, C.; Sun, E.; Henry, D.; Rode, R.; Potthoff, A.; Leonard, J. Randomised Placebo-Controlled Trial of Ritonavir in Advanced HIV-1 Disease. Lancet 1998, 351, 543–549. DOI: 10.1016/S0140-6736(97)04161-5.
  • Horby, P. W.; Mafham, M.; Bell, J. L.; Linsell, L.; Staplin, N.; Emberson, J.; Palfree-Man, A.; Raw, J.; Elmahi, E.; Prudon, B. Lopinavir–Ritonavir in Patients Admitted to Hospital with COVID-19 (RECOVERY): A Randomised, Controlled, Open-Label, Platform Trial. Lancet 2020, 396, 1345–1352. DOI: 10.1016/S0140-6736(20)32013-4.
  • Mohamed Ahmed, M. S.; Mekky, A. E. M.; Sanad S. M. H. Regioselective [3 + 2] Cycloaddition Synthesis and Theoretical Calculations of New Chromene-Pyrazole Hybrids: A DFT-Based Parr Function, Fukui Function, Local Reactivity Indexes, and MEP Analysis. J. Mol. Struct. 2022, 1267, 133583. DOI: 10.1016/j.molstruc.2022.133583.
  • Katariya, K. D.; Reddy, D. V. Oxazolyl-Pyrimidines as Antibacterial and Antitubercular Agents: Synthesis, Biological Evaluation, in-Silico ADMET and Molecular Docking Study. J. Mol. Struct. 2022, 1253, 132240. DOI: 10.1016/j.molstruc.2021.132240.
  • Yusuf, M.; Kaur, M.; Jain, P.; Solanki, I. New 1,3,4-Bisthiadiazolines: Synthesis, Characterization and Antimicrobial Evaluations. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2012, 97, 470–478. DOI: 10.1016/j.saa.2012.06.030.
  • Halle, J. C.; Pouet, M. J.; Simonnin, M. P.; Debleds, F.; Terrier, F. Ambident Nucleophiles. 11. Nitrogen-Bonded and Carbon-Bonded o-Complex Formation in the Reaction of Pyrrolide Anions with 1,3,5-Trinitrobenzen. Can. J. Chem. 1982, 60, 1988–1995. DOI: 10.1139/v82-280.
  • Mohil, R.; Kumar, D.; Mor, S. Synthesis and Antimicrobial Activity of Some 1,3‐Disubstituted Indeno[1,2‐c]Pyrazoles. Journal of Heterocyclic Chem. 2014, 51, 203–211. DOI: 10.1002/jhet.
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B. G. E.; Scuseria, M. A.; Robb, J. R.; Cheeseman, G.; Scalmani, V.; Barone, B.; Mennucci, G. A.; Petersson, H.; et al. Gaussian 09, Revision A.02. Fox, Gaussian, Inc.: Wallingford, CT, 2016.
  • Becke, A. D. A New Mixing of Hartree-Fock and Local Density-Functional Theories. J. Chem. Phys. 1993, 98, 1372–1377. DOI: 10.1063/1.464304.
  • 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.
  • Miar, M.; Shiroudi, A.; Pourshamsian, K.; Oliaey, A. R.; Hatamjafari, F. Theoretical Investigations on the HOMO–LUMO Gap and Global Reactivity Descriptor Studies, Natural Bond Orbital, and Nucleus-Independent Chemical Shifts Analyses of 3-Phenylbenzo[d]Thiazole-2(3H)-Imine and its Para-Substituted Derivatives: Solvent and Substituent Effects. J. Chem. Res. 2021, 45, 147–158. DOI: 10.1177/1747519820932091.
  • Chamorro, E.; Pérez, P.; Domingo, L. R. On the Nature of Parr Functions to Predict the Most Reactive Sites along Organic Polar Reactions. Chem. Phys. Lett. 2013, 582, 141–143. DOI: 10.1016/j.cplett.2013.07.020.
  • Koopmans, T. Über Die Zuordnung Von Wellenfunktionen Und Eigenwerten zu Den Einzelnen Elektronen Eines Atoms. Physica 1934, 1, 104–113. DOI: 10.1016/S0031-8914(34)90011-2.
  • Pearson, R. G.; Songstad, J. Application of the Principle of Hard and Soft Acids and Bases to Organic Chemistry. J. Am. Chem. Soc. 1967, 89, 1827–1836. DOI: 10.1021/ja00984a014.
  • Pearson, R. G. Hard and Soft Acids and Bases-the Evolution of a Chemical Concept Author Links Open Overlay Panel. Coord. Chem. Rev. 1990, 100, 403–425. DOI: 10.1016/0010-8545(90)85016-L.
  • Parr, R. G.; Pearson, R. G. J. Absolute Hardness: Companion Parameter to Absolute Electronegativity. J. Am. Chem. Soc. 1983, 105, 7512–7516. DOI: 10.1021/ja00364a005.
  • Mulliken, R. S. J. A New Electroaffinity Scale; Together with Data on Valence States and Valence Ionization Potentials and Electron Affinities. Chem. Phys. 1934, 2, 782–793. DOI: 10.1063/1.1749394.
  • Świsłocka, R.; Regulska, E.; Karpińska, J.; Świderski, G.; Lewandowski, W. Molecular Structure and Antioxidant Properties of Alkali Metal Salts of Rosmarinic Acid. Experimental and DFT Studies. Molecules 2019, 24, 2645. DOI: 10.3390/molecules24142645.
  • Alasmi, A.; Merza, J. Synthesis and Characterization of Novel Dialdehydes Based on SN2 Reaction of Aromatic Aldehyde. Inorg. Chem. Ind. J. 2017, 12, 111. https://www.tsijournals.com/articles/synthesis-and-characterization-of-novel-dialdehydes-based-on-sn2-reaction-of-aromatic-aldehyde-13306.html
  • Scott, A. C. Laboratory Control of Antimicrobial Therapy. In Mackie & McCartney-Practical Medical Microbiology, 13th ed.; Collee, J. G., Duguid, J. P., Fraser, A. G., Marmion, B. P. Eds.; Churchill Livingstone: London, 1989; pp. 161–181.
  • Mohamed, H. A.; Ammar, Y. A.; Elhagali, G. A. M.; Eyada, H. A.; Aboul-Magd, D. S.; Ragab, A. Discovery a Novel of Thiazolo[3,2-a]Pyridine and Pyrazolo[3,4-d]Thiazole Derivatives as DNA Gyrase Inhibitors; Design, Synthesis, Antimicrobial Activity, and Some in-Silico ADMET with Molecular Docking Study. J. Mol. Struct. 2023, 1287, 135671. DOI: 10.1016/j.molstruc.2023.135671.

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.