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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 54, 2024 - Issue 1
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Articles

Design, synthesis, and antimicrobial evaluation of new antipyrine derivatives bearing thiazolopyridazine and pyrazolothiazole scaffolds

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Pages 22-40 | Received 16 Aug 2023, Published online: 07 Nov 2023

References

  • Durcik, M.; Lovison, D.; Skok, Ž.; Durante Cruz, C.; Tammela, P.; Tomašič, T.; Benedetto Tiz, D.; Draskovits, G.; Nyerges, Á.; Pál, C.; et al. New N-Phenylpyrrolamide DNA Gyrase B Inhibitors: Optimization of Efficacy and Antibacterial Activity. Eur. J. Med. Chem. 2018, 154, 117–132. DOI: 10.1016/j.ejmech.2018.05.011.
  • Yule, I. A.; Czaplewski, L. G.; Pommier, S.; Davies, D. T.; Narramore, S. K.; Fishwick, C. W. Pyridine-3-Carboxamide-6-yl-Ureas as Novel Inhibitors of Bacterial DNA Gyrase: Structure Based Design, Synthesis, SAR and Antimicrobial Activity. Eur. J. Med. Chem. 2014, 86, 31–38. DOI: 10.1016/j.ejmech.2014.08.025.
  • Leclercq, R. Epidemiological and Resistance Issues in Multidrug-Resistant Staphylococci and Enterococci. Clin. Microbiol. Infect. 2009, 15, 224–231. DOI: 10.1111/j.1469-0691.2009.02739.x.
  • Jaiswal, V.; Kalyani, K.; Rastogi, R. B.; Kumar, R. Tribological Studies of Some SAPS-Free Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes and Their Synergistic Interaction with Borate Ester. J. Mater. Chem. A 2014, 2, 10424–10434. DOI: 10.1039/C4TA01191K.
  • Abu-Melha, S. Molecular Modeling and Docking Studies of New Antimicrobial Antipyrine-Thiazole Hybrids. Arab. J. Chem. 2022, 15, 103898. DOI: 10.1016/j.arabjc.2022.103898.
  • Singh, G.; Satija, P.; Singh, B.; Sinha, S.; Sehgal, R.; Sahoo, S. C. Design, Crystal Structures and Sustainable Synthesis of Family of Antipyrine Derivatives: Abolish to Bacterial and Parasitic Infection. J. Mol. Struct. 2020, 1199, 127010. DOI: 10.1016/j.molstruc.2019.127010.
  • Mahle, F.; da Rosa Guimarães, T.; Meira, A. V.; Corrêa, R.; Cruz, R. C. B.; Cruz, A. B.; Nunes, R. J.; Cechinel-Filho, V.; de Campos-Buzzi, F. Synthesis and Biological Evaluation of N-Antipyrine-4-Substituted Amino-3-Chloromaleimide Derivatives. Eur. J. Med. Chem. 2010, 45, 4761–4768. DOI: 10.1016/j.ejmech.2010.07.040.
  • Remes, C.; Paun, A.; Zarafu, I.; Tudose, M.; Caproiu, M. T.; Ionita, G.; Bleotu, C.; Matei, L.; Ionita, P. Chemical and Biological Evaluation of Some New Antipyrine Derivatives with Particular Properties. Bioorg. Chem. 2012, 41-42, 6–12. DOI: 10.1016/j.bioorg.2011.12.003.
  • El Sayed, M. T.; El-Sharief, M. A. S.; Zarie, E. S.; Morsy, N. M.; Elsheakh, A. R.; Voronkov, A.; Berishvili, V.; Hassan, G. S. Design, Synthesis, anti-Inflammatory Activity and Molecular Docking of Potential Novel Antipyrine and Pyrazolone Analogs as Cyclooxygenase Enzyme (COX) Inhibitors. Bioorg. Med. Chem. Lett. 2018, 28, 952–957. DOI: 10.1016/j.bmcl.2018.01.043.
  • Othman, I. M.; Alamshany, Z. M.; Tashkandi, N. Y.; Gad-Elkareem, M. A.; Abd El-Karim, S. S.; Nossier, E. S. Synthesis and Biological Evaluation of New Derivatives of Thieno-Thiazole and Dihydrothiazolo-Thiazole Scaffolds Integrated with a Pyrazoline Nucleus as Anticancer and Multi-Targeting Kinase Inhibitors. RSC Adv. 2021, 12, 561–577. DOI: 10.1039/d1ra08055e.
  • 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.
  • Siddiqui, N.; Arshad, M. F.; Ahsan, W.; Alam, M. S. Thiazoles: a valuable insight into the recent advances and biological activities. Int. J. Pharm. Sci. Drug Res. 2009, 1, 136.
  • Hashem, H. E.; Amr, A. E. G. E.; Nossier, E. S.; Elsayed, E. A.; Azmy, E. M. Synthesis, Antimicrobial Activity and Molecular Docking of Novel Thiourea Derivatives Tagged with Thiadiazole, Imidazole and Triazine Moieties as Potential DNA Gyrase and Topoisomerase IV Inhibitors. Molecules 2020, 25, 2766. DOI: 10.3390/molecules25122766.
  • Mohi El-Deen, E. M.; Abd El-Meguid, E. A.; Hasabelnaby, S.; Karam, E. A.; Nossier, E. S. Synthesis, Docking Studies, and in Vitro Evaluation of Some Novel Thienopyridines and Fused Thienopyridine–Quinolines as Antibacterial Agents and DNA Gyrase Inhibitors. Molecules 2019, 24, 3650. DOI: 10.3390/molecules24203650.
  • Mohi El-Deen, E. M.; Abd El-Meguid, E. A.; Karam, E. A.; Nossier, E. S.; Ahmed, M. F. Synthesis and Biological Evaluation of New Pyridothienopyrimidine Derivatives as Antibacterial Agents and Escherichia coli Topoisomerase II Inhibitors. Antibiotics 2020, 9, 695. DOI: 10.3390/antibiotics9100695.
  • Mohi El-Deen, E. M.; Nossier, E. S.; Karam, E. A. New Quinazolin-4-(3H)-One Derivatives Incorporating Hydrazone and Pyrazole Scaffolds as Antimicrobial Agents Targeting DNA Gyrase Enzyme. Sci. Pharm. 2022, 90, 52. DOI: 10.3390/scipharm90030052.
  • El‐serwy, W. S.; Mohamed, H. S.; El‐serwy, W. S.; Mohamed, N. A.; Kassem, E. M.; Nossier, E. S.; Shalaby, A. S. G. Molecular Docking Study of Newly Synthesized Thiopyrimidines as Antimicrobial Agents Targeting DNA Gyrase Enzyme. J. Heterocyclic Chem. 2019, 56, 2027–2035. DOI: 10.1002/jhet.3583.
  • Brvar, M.; Perdih, A.; Renko, M.; Anderluh, G.; Turk, D.; Solmajer, T. Structure-Based Discovery of Substituted 4, 5′-Bithiazoles as Novel DNA Gyrase Inhibitors. J. Med. Chem. 2012, 55, 6413–6426. DOI: 10.1021/jm300395d.
  • Parks, W. M.; Bottrill, A. R.; Pierrat, O. A.; Durrant, M. C.; Maxwell, A. The Action of the Bacterial Toxin, Microcin B17, on DNA Gyrase. Biochimie 2007, 89, 500–507. DOI: 10.1016/j.biochi.2006.12.005.
  • Tanitame, A.; Oyamada, Y.; Ofuji, K.; Fujimoto, M.; Iwai, N.; Hiyama, Y.; Suzuki, K.; Ito, H.; Terauchi, H.; Kawasaki, M.; et al. Synthesis and Antibacterial Activity of a Novel Series of Potent DNA Gyrase Inhibitors. Pyrazole Derivatives. J. Med. Chem. 2004, 47, 3693–3696. DOI: 10.1021/jm030394f.
  • Chu, M. J.; Wang, W.; Ren, Z. L.; Liu, H.; Cheng, X.; Mo, K.; Wang, L.; Tang, F.; Lv, X. H. Discovery of Novel Triazole-Containing Pyrazole Ester Derivatives as Potential Antibacterial Agents. Molecules 2019, 24, 1311. DOI: 10.3390/molecules24071311.
  • Jakopin, Ž.; Ilaš, J.; Barančoková, M.; Brvar, M.; Tammela, P.; Dolenc, M. S.; Tomašič, T.; Kikelj, D. Discovery of Substituted Oxadiazoles as a Novel Scaffold for DNA Gyrase Inhibitors. Eur. J. Med. Chem. 2017, 130, 171–184. DOI: 10.1016/j.ejmech.2017.02.046.
  • Mesleh, M. F.; Cross, J. B.; Zhang, J.; Kahmann, J.; Andersen, O. A.; Barker, J.; Cheng, R. K.; Felicetti, B.; Wood, M.; Hadfield, A. T.; et al. Fragment-Based Discovery of DNA Gyrase Inhibitors Targeting the ATPase Subunit of GyrB. Bioorg. Med. Chem. Lett. 2016, 26, 1314–1318. DOI: 10.1016/j.bmcl.2016.01.009.
  • Dighe, S. N.; Collet, T. A. Recent Advances in DNA Gyrase-Targeted Antimicrobial Agents. Eur. J. Med. Chem. 2020, 199, 112326. DOI: 10.1016/j.ejmech.2020.112326.
  • Othman, I. M. M.; Mahross, M. H.; Gad-Elkareem, M. A. M.; Rudrapal, M.; Gogoi, N.; Chetia, D.; Aouadi, K.; Snoussi, M.; Kadri, A. Toward a Treatment of Antibacterial and Antifungal Infections: Design, Synthesis and in Vitro Activity of Novel Arylhydrazothiazolylsulfonamides Analogues and Their Insight of DFT, Docking and Molecular Dynamic Simulations. J. Mol. Struct. 2021, 1243, 130862. DOI: 10.1016/j.molstruc.2021.130862.
  • Othman, I. M. M.; Gad-Elkareem, M. A. M.; Amr, A. E.; Al-Omar, M. A.; Nossier, E. S.; Elsayed, E. A. Novel Heterocyclic Hybrids of Pyrazole Targeting Dihydrofolate Reductase: design, Biological Evaluation and in Silico Studies. J. Enzyme Inhib. Med. Chem. 2020, 35, 1491–1502. DOI: 10.1080/14756366.2020.1791842.
  • Othman, I. M. M.; Alamshany, Z. M.; Tashkandi, N. Y.; Nossier, E. S.; Anwar, M. M.; Radwan, H. A. Chemical Synthesis and Molecular Docking Study of New Thiazole, Thiophene, and Thieno [2, 3-d] Pyrimidine Derivatives as Potential Antiproliferative and Antimicrobial Agents. J. Mol. Struct. 2022, 1270, 133926. DOI: 10.1016/j.molstruc.2022.133926.
  • El‐Zahabi, H. S.; Nossier, E. S.; Mousa, S. M.; Hassan, H.; Shalaby, A. S. G.; Arafa, R. K. Antibacterial and Anticancer Profiling of New Benzocaine Derivatives: Design, Synthesis, and Molecular Mechanism of Action. Arch. Pharm. 2022, 355, 2100451. DOI: 10.1002/ardp.202100451.
  • Moustafa, G. O.; Shalaby, A.; Naglah, A. M.; Mounier, M. M.; El-Sayed, H.; Anwar, M. M.; Nossier, E. S. Synthesis, Characterization, in Vitro Anticancer Potentiality, and Antimicrobial Activities of Novel Peptide–Glycyrrhetinic-Acid-Based Derivatives. Molecules 2021, 26, 4573. DOI: 10.3390/molecules26154573.
  • Hussein, M. E.; Mohamed, O. G.; El-Fishawy, A. M.; El-Askary, H. I.; El-Senousy, A. S.; El-Beih, A. A.; Nossier, E. S.; Naglah, A. M.; Almehizia, A. A.; Tripathi, A.; Hamed, A. A. Identification of Antibacterial Metabolites from Endophytic Fungus Aspergillus fumigatus, Isolated from Albizia Lucidior Leaves (Fabaceae), Utilizing Metabolomic and Molecular Docking Techniques. Molecules 2022, 27, 1117. DOI: 10.3390/molecules27031117.
  • Abd El-Meguid, E. A.; Moustafa, G. O.; Awad, H. M.; Zaki, E. R.; Nossier, E. S. Novel Benzothiazole Hybrids Targeting EGFR: Design, Synthesis, Biological Evaluation and Molecular Docking Studies. J. Mol. Struct. 2021, 1240, 130595. DOI: 10.1016/j.molstruc.2021.130595.
  • Amr, A. E. G. E.; Elsayed, E. A.; Al-Omar, M. A.; Badr Eldin, H. O.; Nossier, E. S.; Abdallah, M. M. Design, Synthesis, Anticancer Evaluation and Molecular Modeling of Novel Estrogen Derivatives. Molecules 2019, 24, 416. DOI: 10.3390/molecules24030416.
  • Nossier, E. S.; El-Hallouty, S. M.; Zaki, E. R. Synthesis, Anticancer Evaluation and Molecular Modeling of Some Substituted Thiazolidinonyl and Thiazolyl Pyrazole Derivatives. Int. J. Pharm. Pharm. Sci. 2015, 7, 353–359.
  • Bax, B. D.; Chan, P. F.; Eggleston, D. S.; Fosberry, A.; Gentry, D. R.; Gorrec, F.; Giordano, I.; Hann, M. M.; Hennessy, A.; Hibbs, M.; et al. Type IIA Topoisomerase Inhibition by a New Class of Antibacterial Agents. Nature 2010, 466, 935–940. DOI: 10.1038/nature09197.
  • Alamshany, Z. M.; Algamdi, E. M.; Othman, I. M.; Anwar, M. M.; Nossier, E. S. New Pyrazolopyridine and Pyrazolothiazole-Based Compounds as anti-Proliferative Agents Targeting c-Met Kinase Inhibition: design, Synthesis, Biological Evaluation, and Computational Studies. RSC Adv. 2023, 13, 12889–12905. DOI: 10.1039/d3ra01931d.

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