New Generation of Hybrid Pyrazole–Tetrazole Tetrapodal Compounds: Synthesis and Biological Activities
Malika Amanchar, Tarik Harit, Mounir Cherfi, Meryem Idrissi Yahyaoui, Nour Elhouda Daoudi, Abderrahmane Yahyi, Abdeslam Asehraou, Fouad Malek
Organics · pp. 290–297 · Published 4 Sep 2024
10.3390/org5030016Abstract
The elaboration of a new family of tetrapodal molecules L1–L3 bearing two pyrazole–tetrazole units is presented. The structure assigned to such molecules was verified by various techniques, including FTIR, NMR, HRMS and elemental analysis. The ability of these tetrapods to inhibit the growth of four fungal strains was examined, and the obtained results showed that they have some antifungal potency in the range of 12–16 mm. The alpha-amylase inhibition activity of these molecules was also evaluated. The obtained IC50 values (1.34 × 10−1–1.2 × 10−2 mg/mL) demonstrated that all compounds are potent enough to inhibit this enzyme much better than the positive control acarbose (2.6 × 10−1 mg/mL). A docking study on the porcine alpha-amylase was performed, and the results were in good correlation with the experimental results.
References (31)
- 1 Kaur, 2023, Pyrazole as an anti-microbial scaffold: A comprehensive review [DOI]
- 2 Malek, F., Harit, T., Cherfi, M., and Kim, B. (2022). Insights on the synthesis of n-heterocycles containing macrocycles and their complexion and biological properties. Molecules, 27. [DOI]
- 3 Harit, 2018, New copper complexes with bipyrazolic ligands: Synthesis, characterization and evaluation of the antibacterial and catalytic propertie [DOI]
- 4 Kumar, 2020, Synthetic methods and antimicrobial perspective of pyrazole derivatives: An insight [DOI]
- 5 Reddy, 2020, Design, synthesis of tri-substituted pyrazole derivatives as promising antimicrobial agents and investigation of structure activity relationships [DOI]
- 6 Wu, Z., Yang, W., Hou, S., Xie, D., Yang, J., Liu, L., and Yang, S. (2021). In vivo antiviral activity and disassembly mechanism of novel 1-phenyl-5-amine-4-pyrazole thioether derivatives against Tobacco mosaic virus. Pestic. Biochem. Physioly., 173. [DOI]
- 7 Pastorino, 2015, Identification of pyrazole derivative as an antiviral agent against Chikungunya through HTVS [DOI]
- 8 Kumar, 2022, Pyrazole containing anti-HIV agents: An update [DOI]
- 9 Kumar, 2016, Anti-inflammatory and antimicrobial activities of novel pyrazole analogues [DOI]
- 10 Hassan, 2019, New pyrazole derivatives: Synthesis, anti-inflammatory activity, cycloxygenase inhibition assay and evaluation of mPGES [DOI]
- 11 Mantzanidou, M., Pontiki, E., and Hadjipavlou-Litina, D. (2021). Pyrazoles and pyrazolines as anti-inflammatory agents. Molecules, 26. [DOI]
- 12 Kodadi, 2007, New synthesis of two tridentate bipyrazolic compounds and their cytotoxic activity tumor cell lines [DOI]
- 13 Zhang, Y., Wu, C., Zhang, N., Fan, R., Ye, Y., and Xu, J. (2023). Recent advances in the development of pyrazole derivatives as anticancer agents. Int. J. Mol. Sci., 24. [DOI]
- 14 Mor, 2022, Recent progress in anticancer agents incorporating pyrazole scaffold [DOI]
- 15 Malek, 2014, Tridentate bipyrazole compounds with a side-arm as a new class of antitumor agents [DOI]
- 16 2021, Recent developments in the synthesis of tetrazoles and their pharmacological relevance [DOI]
- 17 Allen, 2012, The hydrogen bond environments of 1 H-tetrazole and tetrazolate rings: The structural basis for tetrazole–carboxylic acid bioisosterism [DOI]
- 18 Wei, 2015, Tetrazolium compounds: Synthesis and applications in medicine [DOI]
- 19 Zou, 2020, Bioisosteres in drug discovery: Focus on tetrazole [DOI]
- 20 Hall, A., Chatzopoulou, M., and Frost, J. (2024). Bioisoteres for carboxylic acids: From ionized isosteres to novel unionized replacements. Bioorg. Med. Chem., 104. [DOI]
- 21 Faria, 2013, Synthesis and activity of novel tetrazole compounds and their pyrazole-4-carbonitrile precursors against Leishmania spp [DOI]
- 22 Chi, 2023, Discovery of novel tetrazoles featuring a pyrazole moiety as potent and highly selective antifungal agents [DOI]
- 23 Metre, 2024, Design, Synthesis and Characterization of novel 1, 5-and 2, 5-coumarin-4-yl-methyl regioisomers of 5-pyrazol-3-yl-tetrazoles as promising anticancer and antifungal agents [DOI]
- 24 Cherfi, 2023, Pyrazole-tetrazole hybrid compounds: Synthesis, characterization and their biological activities
- 25 Harit, 2022, Hybrid pyrazole-tetrazole derivatives with high α-amylase inhibition activity: Synthesis, biological evaluation and docking study [DOI]
- 26 Cherfi, 2022, Synthesis, antimicrobial activity and in-silico docking of two macrocycles based on pyrazole-tetrazole subunit [DOI]
- 27 Oulous, A., Daoudi, N.E., Harit, T., Cherfi, M., Bnouham, M., and Malek, F. (2022). New pyrazole-tetrazole hybrid compounds as potent α-amylase and non-enzymatic glycation inhibitors. Bioorg. Med. Chem. Lett., 69. [DOI]
- 28 Cherfi, 2021, Synthesis and characterization of new pyrazole–tetrazole derivatives as new vasorelaxant agents [DOI]
- 29 Tundis, 2010, Natural products as α-amylase and α-glucosidase inhibitors and their hypoglycaemic potential in the treatment of diabetes: An update [DOI]
- 30 Yang, 2004, GEMDOCK: A generic evolutionary method for molecular docking [DOI]
- 31 Larson, 2010, X-ray crystallographic analyses of pig pancreatic α-amylase with limit dextrin, oligosaccharide, and α-cyclodextrin [DOI]
Cited by 8
Nour Elhouda Daoudi, Nadia Houmy, Reda Melhaoui · Tropical Journal of Natural Product Research · 2025
Bhupender Nehra, Manoj Kumar, Pooja A Chawla · Future Medicinal Chemistry · 2026
Oumaima Boulehya, Tarik Harit, Mounir Cherfi · ChemistrySelect · 2025
Ahlam Oulous, Ikram Dib, Tarik Harit · Chemical Biology & Drug Design · 2025
Showing 4 of 8 known citations — external sources report more than can currently be individually listed.
Related research
- A Novel Catalytic Synthesis of Flavones under Autoclave Conditions and Comparative Study of Anti-cancer Activity — shares topic coverage
- Thermostability and in-vitro Antibacterial Activity of Aqueous Extracts of Tetrapleura tetraptera Pods on Multidrug Resistant Clinical Isolates — shares topic coverage
- Acute Toxicity, Phytochemistry and Anti-diarrheal Effects of Celtis integrifolia Lam. Aqueous Leaf Extract in Wistar Albino Rats — shares topic coverage
- Understanding the Reactivity of Trimethylsilyldiazoalkanes Participating in [3+2] Cycloaddition Reactions towards Diethylfumarate with a Molecular Electron Density Theory Perspective — shares topic coverage
- Understanding the Origin of the Regioselectivity in Non-Polar [3+2] Cycloaddition Reactions through the Molecular Electron Density Theory — shares topic coverage
Article metrics
Real usage data collected on this platform.
0
Page views
0
PDF downloads
0
Outbound clicks
8
Citations
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
No views recorded yet.
Traffic sources
Referring site, by host.
No traffic recorded yet.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.