Optimization of pyrazolo[1,5-a]pyrimidine based compounds with pyridine scaffold: Synthesis, biological evaluation and molecular modeling study Article Swipe
Mohamed A. Abdelgawad
,
Nadia A. A. Elkanzi
,
Arafa Musa
,
Mohammed M. Ghoneim
,
Waqas Ahmad
,
Mohammed Elmowafy
,
Ahmed Mahmoud Abdelhaleem Ali
,
Ahmed H. Abdelazeem
,
Syed Nasir Abbas Bukhari
,
Mohamed El-Sherbiny
,
Mohammed A. S. Abourehab
,
Rania B. Bakr
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1016/j.arabjc.2022.104015
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1016/j.arabjc.2022.104015
Background: Pyrazolopyrimidine heterocycle and its isosteres represent the main scaffold for many pharmacologically active drugs including anti-inflammatory agents. The COX-2 inhibitors are the principal gate for the design of new safe and potent anti-inflammatory agents. Methods: Novel derivatives of pyrazolo[1,5-a] pyrimidines were synthesized and screened in vivo and in vitro for their anti-inflammatory potential. Results: Within the constructed compounds, compound 11 was the most active compound on IL-6 and TNF-α (percentage inhibition = 80 and 89%, respectively). In addition, compound 12 displayed the most inhibitory effect towards COX-2 (IC50 = 1.11 µM), whereas compound 11 recorded the highest COX-2 selectivity (S.I = 8.97). The target derivatives 11–14 displayed good edema inhibitory potential (46–68%) and compound 11 was the most potent candidate (ED50 = 35 mg/kg). Additionally, the most potent sPLA2-V inhibitors were compounds 11 and 13 (IC50 = 1 and 1.7 µM respectively). Regarding activity towards 15-LOX, derivative 12 was the most active compound with IC50 = 5.6 µM revealing higher inhibitory activity than nor-dihydroguaiaretic acid (IC50 = 8.5 µM). To confirm the anti-inflammatory potential of the target derivatives, molecular modeling was performed inside COX-2 and 15-LOX active sites. Conclusion: Display discoveries increment the plausibility that these pyrazolo[1,5-a]pyrimidines might act as a beginning point for the improvement of anti-inflammatory agents.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1016/j.arabjc.2022.104015
- OA Status
- gold
- Cited By
- 23
- References
- 69
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4281623828
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4281623828Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1016/j.arabjc.2022.104015Digital Object Identifier
- Title
-
Optimization of pyrazolo[1,5-a]pyrimidine based compounds with pyridine scaffold: Synthesis, biological evaluation and molecular modeling studyWork title
- Type
-
articleOpenAlex work type
- Language
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enPrimary language
- Publication year
-
2022Year of publication
- Publication date
-
2022-05-30Full publication date if available
- Authors
-
Mohamed A. Abdelgawad, Nadia A. A. Elkanzi, Arafa Musa, Mohammed M. Ghoneim, Waqas Ahmad, Mohammed Elmowafy, Ahmed Mahmoud Abdelhaleem Ali, Ahmed H. Abdelazeem, Syed Nasir Abbas Bukhari, Mohamed El-Sherbiny, Mohammed A. S. Abourehab, Rania B. BakrList of authors in order
- Landing page
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https://doi.org/10.1016/j.arabjc.2022.104015Publisher landing page
- Open access
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YesWhether a free full text is available
- OA status
-
goldOpen access status per OpenAlex
- OA URL
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https://doi.org/10.1016/j.arabjc.2022.104015Direct OA link when available
- Concepts
-
Chemistry, Pyrimidine, IC50, Lead compound, Stereochemistry, In vivo, Anti-inflammatory, Active site, Combinatorial chemistry, Pyridine, In vitro, Molecular model, Pharmacology, Biochemistry, Enzyme, Medicinal chemistry, Biotechnology, Medicine, BiologyTop concepts (fields/topics) attached by OpenAlex
- Cited by
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23Total citation count in OpenAlex
- Citations by year (recent)
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2025: 3, 2024: 7, 2023: 11, 2022: 2Per-year citation counts (last 5 years)
- References (count)
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69Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.anti-inflammatory | 16, 33, 52, 173, 208 |
| abstract_inverted_index.pharmacologically | 12 |
| abstract_inverted_index.Pyrazolopyrimidine | 1 |
| abstract_inverted_index.nor-dihydroguaiaretic | 164 |
| abstract_inverted_index.pyrazolo[1,5-a]pyrimidines | 197 |
| cited_by_percentile_year.max | 99 |
| cited_by_percentile_year.min | 94 |
| corresponding_author_ids | https://openalex.org/A5059969073 |
| countries_distinct_count | 3 |
| institutions_distinct_count | 12 |
| corresponding_institution_ids | https://openalex.org/I199702508 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/3 |
| sustainable_development_goals[0].score | 0.49000000953674316 |
| sustainable_development_goals[0].display_name | Good health and well-being |
| citation_normalized_percentile.value | 0.90109184 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | True |