Synthesis, biological evaluation, molecular modeling, and structural analysis of new pyrazole and pyrazolone derivatives as N‐formyl peptide receptors agonists Article Swipe
Claudia Vergelli
,
Аndrei I. Khlebnikov
,
Letizia Crocetti
,
Gabriella Guerrini
,
Niccolò Cantini
,
Liliya N. Kirpotina
,
Igor A. Schepetkin
,
Agostino Cilibrizzi
,
Mark T. Quinn
,
Patrizia Rossi
,
Paola Paoli
,
Maria Paola Giovannoni
·
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1111/cbdd.13913
YOU?
·
· 2021
· Open Access
·
· DOI: https://doi.org/10.1111/cbdd.13913
N‐formyl peptide receptors (FPR1, FPR2, and FPR3) play key roles in the regulation of inflammatory processes, and recently, it was demonstrated that FPR1 and FPR2 have a dual role in the progression/suppression of some cancers. Therefore, FPRs represent an important therapeutic target for the treatment of both cancer and inflammatory diseases. Previously, we identified selective or mixed FPR agonists with pyridazinone or pyridinone scaffolds showing a common 4‐(bromophenyl)acetamide fragment, which was essential for activity. We report here new pyrazole and pyrazolone derivatives as restricted analogues of the above 6‐membered compounds, all exhibiting the same 4‐bromophenylacetamide side chain. Most new products had low or absent FPR agonist activity, suggesting that the pyrazole nucleus was not appropriate for FPR agonists. This hypothesis was confirmed by molecular modeling studies, which highlighted that the five‐membered scaffold was responsible for a worse arrangement of the molecules in the receptor binding site.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1111/cbdd.13913
- https://onlinelibrary.wiley.com/doi/pdfdirect/10.1111/cbdd.13913
- OA Status
- hybrid
- Cited By
- 8
- References
- 48
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W3173607987
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W3173607987Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1111/cbdd.13913Digital Object Identifier
- Title
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Synthesis, biological evaluation, molecular modeling, and structural analysis of new pyrazole and pyrazolone derivatives as N‐formyl peptide receptors agonistsWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2021Year of publication
- Publication date
-
2021-06-20Full publication date if available
- Authors
-
Claudia Vergelli, Аndrei I. Khlebnikov, Letizia Crocetti, Gabriella Guerrini, Niccolò Cantini, Liliya N. Kirpotina, Igor A. Schepetkin, Agostino Cilibrizzi, Mark T. Quinn, Patrizia Rossi, Paola Paoli, Maria Paola GiovannoniList of authors in order
- Landing page
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https://doi.org/10.1111/cbdd.13913Publisher landing page
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1111/cbdd.13913Direct link to full text PDF
- Open access
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YesWhether a free full text is available
- OA status
-
hybridOpen access status per OpenAlex
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https://onlinelibrary.wiley.com/doi/pdfdirect/10.1111/cbdd.13913Direct OA link when available
- Concepts
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Pyrazole, Pyrazolone, Receptor, Agonist, Chemistry, Acetamide, Peptide, Molecular model, Combinatorial chemistry, Stereochemistry, Biochemistry, Organic chemistryTop concepts (fields/topics) attached by OpenAlex
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8Total citation count in OpenAlex
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2025: 2, 2023: 2, 2022: 2, 2021: 2Per-year citation counts (last 5 years)
- References (count)
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48Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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| abstract_inverted_index.products | 100 |
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| abstract_inverted_index.receptor | 144 |
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| abstract_inverted_index.studies, | 126 |
| abstract_inverted_index.activity, | 107 |
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| abstract_inverted_index.diseases. | 51 |
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| abstract_inverted_index.scaffolds | 64 |
| abstract_inverted_index.selective | 55 |
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| abstract_inverted_index.N‐formyl | 1 |
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| abstract_inverted_index.compounds, | 90 |
| abstract_inverted_index.exhibiting | 92 |
| abstract_inverted_index.hypothesis | 120 |
| abstract_inverted_index.identified | 54 |
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| abstract_inverted_index.pyridinone | 63 |
| abstract_inverted_index.regulation | 13 |
| abstract_inverted_index.restricted | 84 |
| abstract_inverted_index.suggesting | 108 |
| abstract_inverted_index.Previously, | 52 |
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| abstract_inverted_index.highlighted | 128 |
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| abstract_inverted_index.4‐(bromophenyl)acetamide | 68 |
| cited_by_percentile_year.max | 97 |
| cited_by_percentile_year.min | 93 |
| corresponding_author_ids | https://openalex.org/A5019660090 |
| countries_distinct_count | 4 |
| institutions_distinct_count | 12 |
| corresponding_institution_ids | https://openalex.org/I45084792 |
| sustainable_development_goals[0].id | https://metadata.un.org/sdg/3 |
| sustainable_development_goals[0].score | 0.8100000023841858 |
| sustainable_development_goals[0].display_name | Good health and well-being |
| citation_normalized_percentile.value | 0.63811537 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |