Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors
Joint Authors
Hawash, Mohammed
Abualhasan, Murad N.
Assali, Mohyeddin
Sawaftah, Hadeel
Mousa, Ahmed
Source
Issue
Vol. 2020, Issue 2020 (31 Dec. 2020), pp.1-14, 14 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2020-03-24
Country of Publication
Egypt
No. of Pages
14
Main Subjects
Abstract EN
Series of diaryl-based pyrazole and triazole derivatives were designed and synthesized in a facile synthetic approach in order to produce selective COX-2 inhibitor.
These series of derivatives were synthesized by different reactions like Vilsmeier–Haack reaction and click reaction.
In vitro COX-1 and COX-2 inhibition studies showed that five compounds were potent and selective inhibitors of the COX-2 isozyme with IC50 values in 0.551–0.002 μM range.
In the diarylpyrazole derivatives, compound 4b showed the best inhibitory activity against COX-2 with IC50 = 0.017 μM as one of the N-aromatic rings was substituted with sulfonamide and the other aromatic ring was unsubstituted.
However, when the N-aromatic ring was substituted with sulfonamide and the other aromatic ring was substituted with sulfone (compound 4d), best COX-2 selectivity was achieved (IC50 = 0.098 μM, SI = 54.847).
In the diaryltriazole derivatives, compound 15a showed the best inhibitory activity in comparison to all synthesized compounds including the reference celecoxib with IC50 = 0.002 μM and SI = 162.5 as it could better fit the extra hydrophobic pocket which is present in the COX-2 enzyme.
Moreover, the docking study supports the obtained SAR data and binding similarities and differences on both isozymes.
American Psychological Association (APA)
Assali, Mohyeddin& Abualhasan, Murad N.& Sawaftah, Hadeel& Hawash, Mohammed& Mousa, Ahmed. 2020. Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors. Journal of Chemistry،Vol. 2020, no. 2020, pp.1-14.
https://search.emarefa.net/detail/BIM-1182028
Modern Language Association (MLA)
Assali, Mohyeddin…[et al.]. Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors. Journal of Chemistry No. 2020 (2020), pp.1-14.
https://search.emarefa.net/detail/BIM-1182028
American Medical Association (AMA)
Assali, Mohyeddin& Abualhasan, Murad N.& Sawaftah, Hadeel& Hawash, Mohammed& Mousa, Ahmed. Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors. Journal of Chemistry. 2020. Vol. 2020, no. 2020, pp.1-14.
https://search.emarefa.net/detail/BIM-1182028
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1182028