Page last updated: 2024-12-09

2-(4-hydroxyphenyl)-5-methyl-1H-pyrazol-3-one

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

## 2-(4-hydroxyphenyl)-5-methyl-1H-pyrazol-3-one: A Versatile Molecule for Research

2-(4-hydroxyphenyl)-5-methyl-1H-pyrazol-3-one, often shortened to **4-HPP** or **4-hydroxyphenylpyrazolone**, is a versatile organic compound with a heterocyclic pyrazolone ring structure. It has garnered significant attention in research due to its diverse biological activities and potential applications in various fields.

**Key properties and characteristics:**

* **Versatile synthesis:** 4-HPP can be synthesized via various methods, making it a valuable starting material for further chemical modifications and derivative formation.
* **Strong UV absorbance:** Its chromophore group (the pyrazolone ring) exhibits strong UV absorption, making it suitable for spectrophotometric analysis and applications like analytical chemistry and drug development.
* **Metal complexation:** 4-HPP forms stable complexes with various metal ions, notably Fe(III), Cu(II), and Zn(II). This property makes it relevant in fields like coordination chemistry, analytical chemistry, and bioinorganic chemistry.

**Importance in Research:**

**1. Pharmaceutical Applications:**

* **Antioxidant and free radical scavenging:** 4-HPP exhibits antioxidant properties, making it a potential candidate for treating oxidative stress-related diseases like cancer, neurodegenerative disorders, and cardiovascular diseases.
* **Anti-inflammatory activity:** Studies suggest that 4-HPP has anti-inflammatory properties, potentially useful for treating inflammatory diseases like arthritis and inflammatory bowel disease.
* **Antimicrobial activity:** Research shows that 4-HPP possesses antimicrobial activity against various bacterial and fungal strains, making it a potential lead for developing new antimicrobial agents.
* **Analgesic activity:** Some studies indicate that 4-HPP might have analgesic properties, potentially useful for pain management.

**2. Analytical Applications:**

* **Spectrophotometric analysis:** 4-HPP's strong UV absorbance makes it a useful reagent for colorimetric analysis of various compounds, including metal ions.
* **Chemical sensing:** The ability of 4-HPP to form complexes with metal ions enables its use as a colorimetric sensor for detecting specific metal ions in environmental samples.

**3. Other Potential Applications:**

* **Dye synthesis:** 4-HPP can be used as a building block for synthesizing dyes and pigments with diverse applications.
* **Polymer chemistry:** 4-HPP can be incorporated into polymers to modify their properties and enhance their functionality.
* **Material science:** 4-HPP can be used to create new materials with specific properties like luminescence or conductivity.

**Current Research:**

Ongoing research focuses on:

* **Developing more potent and targeted derivatives of 4-HPP** for specific therapeutic applications.
* **Understanding the mechanisms of action** of 4-HPP in various biological systems.
* **Optimizing the synthesis and purification** of 4-HPP and its derivatives for commercial applications.

**Conclusion:**

2-(4-hydroxyphenyl)-5-methyl-1H-pyrazol-3-one is a promising molecule with significant potential for research in diverse fields, including pharmaceutical, analytical, and material science. Its versatile properties, coupled with ongoing research efforts, suggest that 4-HPP could contribute to significant advancements in medicine, industry, and scientific understanding.

Cross-References

ID SourceID
PubMed CID1279932
CHEMBL ID3145178
CHEBI ID112727

Synonyms (21)

Synonym
OPREA1_034201
smr000020389
MLS000085454 ,
2-(4-hydroxyphenyl)-5-methyl-1,2-dihydro-3h-pyrazol-3-one
CHEMDIV2_001618
CHEBI:112727
HMS1373J12
2-(4-hydroxyphenyl)-5-methyl-1h-pyrazol-3-one
mfcd01619014
AKOS001681780
HMS2177C13
CCG-116544
780806-23-7
bdbm70374
2-(4-hydroxyphenyl)-5-methyl-3-pyrazolin-3-one
cid_1279932
CHEMBL3145178
Q27192842
1-(4-hydroxyphenyl)-3-methyl-1h-pyrazol-5-ol
908230-35-3
EN300-1296663
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
ring assemblyTwo or more cyclic systems (single rings or fused systems) which are directly joined to each other by double or single bonds are named ring assemblies when the number of such direct ring junctions is one less than the number of cyclic systems involved.
pyrazoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency1.77830.177814.390939.8107AID2147
glp-1 receptor, partialHomo sapiens (human)Potency7.94330.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency11.65890.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency3.98110.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency0.79430.011212.4002100.0000AID1030
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency14.01750.036619.637650.1187AID2100
huntingtin isoform 2Homo sapiens (human)Potency14.12540.000618.41981,122.0200AID1688
VprHuman immunodeficiency virus 1Potency35.48131.584919.626463.0957AID651644
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
sentrin-specific protease 8Homo sapiens (human)IC50 (µMol)18.15000.040818.929294.8000AID624322; AID651559
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
recombinase AMycobacterium tuberculosis H37RvEC50 (µMol)1.49400.018023.2882287.6000AID434968; AID435010
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
replicative DNA helicaseMycobacterium tuberculosis H37RvAC504.87550.057030.7482325.3000AID449749; AID449750
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]