Page last updated: 2024-12-09

1-(benzenesulfonyl)-3-pyrazolidinone

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

You're asking about **1-(benzenesulfonyl)-3-pyrazolidinone**, also known as **phenylsulfonylpyrazolidinone** or **PhSO2Pz**.

Here's a breakdown of its structure, properties, and significance in research:

**Structure:**

* **Pyrazolidinone:** This is a five-membered ring containing two nitrogen atoms and a carbonyl group (C=O).
* **Benzenesulfonyl:** A phenyl ring (C6H5) attached to a sulfonyl group (-SO2-).
* **1-(benzenesulfonyl)-3-pyrazolidinone:** The benzenesulfonyl group is attached to the nitrogen atom at position 1 of the pyrazolidinone ring.

**Properties:**

* **Solid:** PhSO2Pz is a white crystalline solid.
* **Solubility:** It's generally soluble in polar organic solvents like DMSO and DMF.
* **Acidity:** The pyrazolidinone ring contains an acidic hydrogen that can be deprotonated.

**Why it's important for research:**

PhSO2Pz is a versatile reagent used in various areas of chemistry, especially in **organic synthesis and medicinal chemistry**:

* **Protecting group:** PhSO2Pz can act as a protecting group for amines, protecting them from unwanted reactions. This is because the sulfonyl group can be easily removed under specific conditions.
* **Catalyst:** PhSO2Pz can catalyze a variety of reactions, including ring-opening reactions and cycloadditions.
* **Building block for heterocycles:** It's a key building block for synthesizing various heterocyclic compounds, which are important in drug discovery and materials science.
* **Precursor to pharmaceuticals:** PhSO2Pz has been used as a precursor to synthesize molecules with potential pharmacological activity.

**Examples of its use:**

* **Protecting group in peptide synthesis:** The sulfonyl group of PhSO2Pz can be used to protect amine groups during peptide synthesis, allowing for selective reactions at other sites of the molecule.
* **Catalyst in the synthesis of natural products:** PhSO2Pz has been employed in the synthesis of various natural products like alkaloids and terpenoids.
* **Precursor for anti-inflammatory drugs:** PhSO2Pz derivatives have been investigated for their anti-inflammatory properties, potentially leading to new drug candidates.

**Summary:**

1-(benzenesulfonyl)-3-pyrazolidinone is a valuable reagent in organic synthesis due to its versatility as a protecting group, catalyst, building block, and precursor for compounds with potential biological activity. Its importance stems from its ability to simplify complex reactions and facilitate the discovery of new and useful molecules.

Cross-References

ID SourceID
PubMed CID1487853
CHEMBL ID1517886
CHEBI ID116604

Synonyms (13)

Synonym
1-(phenylsulfonyl)tetrahydro-3h-pyrazol-3-one
smr000168416
MLS000327857
CHEBI:116604
1-(benzenesulfonyl)pyrazolidin-3-one
AKOS015991823
HMS2386J04
477850-49-0
11A-066
CHEMBL1517886
1-(benzenesulfonyl)-3-pyrazolidinone
Q27200241
mfcd00127085
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sulfonamideAn amide of a sulfonic acid RS(=O)2NR'2.
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Microtubule-associated protein tauHomo sapiens (human)Potency31.62280.180013.557439.8107AID1460
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency11.22020.035520.977089.1251AID504332
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
[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)18.24500.018023.2882287.6000AID434968; 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 H37RvAC50205.61000.057030.7482325.3000AID449749; AID449750
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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
AID1745845Primary 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]