Page last updated: 2024-12-08

1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole

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

1-Acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole, also known as **1-acetyl-3,5-diphenylpyrazoline**, is an organic compound with the chemical formula C17H16N2O. It's a derivative of pyrazoline, a five-membered heterocyclic ring containing two nitrogen atoms.

**Structure and Properties:**

* **Structure:** The molecule consists of a pyrazoline ring with an acetyl group at the 1-position and phenyl groups at the 3 and 5 positions.
* **Appearance:** It is a white to off-white solid.
* **Melting Point:** Approximately 120-122°C.

**Importance in Research:**

While 1-acetyl-3,5-diphenylpyrazoline itself might not have widespread direct applications, its significance lies in its potential as a **synthetic precursor or intermediate** in research involving various fields, such as:

* **Pharmaceutical Chemistry:** Pyrazoline derivatives are known for their pharmacological activities, including anti-inflammatory, analgesic, and antimicrobial properties. This specific compound could be used as a starting material to synthesize new and potentially beneficial drugs.
* **Organic Synthesis:** Pyrazoline derivatives are valuable building blocks for various organic transformations. Their reactivity allows for the creation of diverse structures and functionalities.
* **Materials Science:** Pyrazoline derivatives can exhibit interesting optical properties and can be explored for potential applications in polymers, dyes, or sensors.

**Specific Applications:**

While specific studies are limited, the compound's structure suggests potential applications in:

* **Antioxidant Research:** The presence of phenyl rings and the pyrazoline scaffold could contribute to antioxidant activity, which could be explored for its protective effects against oxidative stress.
* **Photochemistry:** The presence of aromatic rings might lead to interesting photochemical properties, potentially making it useful for the development of photoactive materials.

**Research Directions:**

Further research involving 1-acetyl-3,5-diphenylpyrazoline could focus on:

* **Synthesis of new derivatives with diverse functionalities:** Modifying the structure through different substituents could lead to compounds with different pharmacological or chemical properties.
* **Exploration of its biological activity:** Detailed studies could investigate its potential as an antioxidant, anti-inflammatory, or antimicrobial agent.
* **Investigating its optical properties:** Exploring its potential applications in materials science, such as organic electronics or sensors.

In summary, while 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole itself may not have immediate practical applications, its importance lies in its potential as a synthetic precursor and its intriguing chemical structure, opening doors for future research in diverse fields.

Cross-References

ID SourceID
PubMed CID207753
CHEMBL ID193585
SCHEMBL ID1658926
MeSH IDM0483156

Synonyms (28)

Synonym
HMS1681E17
1-acetyl-4,5-dihydro-3,5-diphenyl-1h-pyrazole
1h-pyrazole, 4,5-dihydro-1-acetyl-3,5-diphenyl-
brn 0221183
1-acetyl-3,5-diphenyl-4,5-dihydropyrazole
1-(3,5-diphenyl-4,5-dihydro-pyrazol-1-yl)-ethanone
smr000514781
MLS001212267
1-(3,5-diphenyl-4,5-dihydro-1h-pyrazol-1-yl)ethanone
STK050480
bstjkgvhqltine-uhfffaoysa-
inchi=1/c17h16n2o/c1-13(20)19-17(15-10-6-3-7-11-15)12-16(18-19)14-8-4-2-5-9-14/h2-11,17h,12h2,1h3
AKOS000520661
bdbm50164871
4,5-dihydro-(1h)-pyrazole derivative, 1a
CHEMBL193585 ,
1-(3,5-diphenyl-3,4-dihydropyrazol-2-yl)ethanone
NCGC00245163-01
30693-34-6
5-23-09-00010 (beilstein handbook reference)
HMS2849L05
AKOS016038525
SCHEMBL1658926
1-acetyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazole
1-(3,5-diphenyl-4,5-dihydro-1h-pyrazol-1-yl)ethan-1-one
DTXSID20952936
PD081949
ethanone, 1-(4,5-dihydro-3,5-diphenyl-1h-pyrazol-1-yl)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency1.00000.044717.8581100.0000AID485294
TDP1 proteinHomo sapiens (human)Potency25.92900.000811.382244.6684AID686978
chromobox protein homolog 1Homo sapiens (human)Potency79.43280.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency29.09290.00419.984825.9290AID504444
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]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cathepsin HCapra hircus (goat)Ki17.54008.20008.20008.2000AID1179617
Cathepsin B Capra hircus (goat)Ki17.67000.00000.63811.9000AID1179616
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)20.50450.00002.37899.7700AID1799567
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)20.50450.00001.89149.5700AID1799567
Kinesin-like protein KIF11Homo sapiens (human)IC50 (µMol)50.00000.00011.405710.0000AID242686
Xanthine dehydrogenase/oxidaseBos taurus (cattle)IC50 (µMol)61.40000.00303.10159.8000AID578685
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
response to xenobiotic stimulusAmine oxidase [flavin-containing] BHomo sapiens (human)
response to toxic substanceAmine oxidase [flavin-containing] BHomo sapiens (human)
response to aluminum ionAmine oxidase [flavin-containing] BHomo sapiens (human)
response to selenium ionAmine oxidase [flavin-containing] BHomo sapiens (human)
negative regulation of serotonin secretionAmine oxidase [flavin-containing] BHomo sapiens (human)
phenylethylamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
substantia nigra developmentAmine oxidase [flavin-containing] BHomo sapiens (human)
response to lipopolysaccharideAmine oxidase [flavin-containing] BHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to ethanolAmine oxidase [flavin-containing] BHomo sapiens (human)
positive regulation of dopamine metabolic processAmine oxidase [flavin-containing] BHomo sapiens (human)
hydrogen peroxide biosynthetic processAmine oxidase [flavin-containing] BHomo sapiens (human)
response to corticosteroneAmine oxidase [flavin-containing] BHomo sapiens (human)
mitotic cell cycleKinesin-like protein KIF11Homo sapiens (human)
microtubule-based movementKinesin-like protein KIF11Homo sapiens (human)
spindle organizationKinesin-like protein KIF11Homo sapiens (human)
mitotic spindle organizationKinesin-like protein KIF11Homo sapiens (human)
mitotic centrosome separationKinesin-like protein KIF11Homo sapiens (human)
regulation of mitotic centrosome separationKinesin-like protein KIF11Homo sapiens (human)
cell divisionKinesin-like protein KIF11Homo sapiens (human)
mitotic spindle assemblyKinesin-like protein KIF11Homo sapiens (human)
spindle elongationKinesin-like protein KIF11Homo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
electron transfer activityAmine oxidase [flavin-containing] BHomo sapiens (human)
identical protein bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] BHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] BHomo sapiens (human)
microtubule motor activityKinesin-like protein KIF11Homo sapiens (human)
protein bindingKinesin-like protein KIF11Homo sapiens (human)
ATP bindingKinesin-like protein KIF11Homo sapiens (human)
microtubule bindingKinesin-like protein KIF11Homo sapiens (human)
protein kinase bindingKinesin-like protein KIF11Homo sapiens (human)
plus-end-directed microtubule motor activityKinesin-like protein KIF11Homo sapiens (human)
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
xanthine oxidase activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
iron ion bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
molybdenum ion bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
protein homodimerization activityXanthine dehydrogenase/oxidaseBos taurus (cattle)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
FAD bindingXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial envelopeAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] BHomo sapiens (human)
dendriteAmine oxidase [flavin-containing] BHomo sapiens (human)
neuronal cell bodyAmine oxidase [flavin-containing] BHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BHomo sapiens (human)
spindle poleKinesin-like protein KIF11Homo sapiens (human)
spindle microtubuleKinesin-like protein KIF11Homo sapiens (human)
spindleKinesin-like protein KIF11Homo sapiens (human)
cytosolKinesin-like protein KIF11Homo sapiens (human)
microtubuleKinesin-like protein KIF11Homo sapiens (human)
membraneKinesin-like protein KIF11Homo sapiens (human)
mitotic spindleKinesin-like protein KIF11Homo sapiens (human)
kinesin complexKinesin-like protein KIF11Homo sapiens (human)
protein-containing complexKinesin-like protein KIF11Homo sapiens (human)
nucleusKinesin-like protein KIF11Homo sapiens (human)
mitotic spindleKinesin-like protein KIF11Homo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseBos taurus (cattle)
peroxisomeXanthine dehydrogenase/oxidaseBos taurus (cattle)
xanthine dehydrogenase complexXanthine dehydrogenase/oxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID1179621Inhibition of goat liver cathepsin B assessed as enzyme activity at 10 uM using BANA substrate pre-incubated 30 mins before substrate addition by colorimetry (Rvb = 5.65 +/- 0.0276 nmol/min/ml)2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H.
AID1179622Inhibition of goat liver cathepsin H assessed as enzyme activity at 10 uM using BANA substrate pre-incubated 30 mins before substrate addition by colorimetry (Rvb = 3.70 +/- 0.0387 nmol/min/ml)2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H.
AID493654Antimicrobial activity against Staphylococcus aureus ATCC 6538 by MTT assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors.
AID493658Antimicrobial activity against Enterobacter cloacae ATCC 13047 by MTT assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors.
AID493656Antimicrobial activity against Pseudomonas aeruginosa ATCC 13525 by MTT assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors.
AID1179617Non-competitive inhibition of goat liver cathepsin H using Leu-betaNA substrate by Lineweaver-Burk plot analysis2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H.
AID493655Antimicrobial activity against Streptococcus faecalis ATCC 9790 by MTT assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors.
AID578685Inhibition of bovine Xanthine oxidase assessed as decrease in uric acid production preincubated at 293 nM of compound for 5 mins by spectrophotometry2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors.
AID242686In vitro inhibitory concentration towards kinesin spindle protein activity of ATP hydrolysis in the presence of microtubules measured by ATPase assay (n=3)2005Bioorganic & medicinal chemistry letters, Apr-15, Volume: 15, Issue:8
Kinesin spindle protein (KSP) inhibitors. Part 1: The discovery of 3,5-diaryl-4,5-dihydropyrazoles as potent and selective inhibitors of the mitotic kinesin KSP.
AID1179616Non-competitive inhibition of goat liver cathepsin B using BANA substrate by Lineweaver-Burk plot analysis2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H.
AID493653Antimicrobial activity against Bacillus subtilis ATCC 6633 by MTT assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH inhibitors.
AID493657Antimicrobial activity against Escherichia coli ATCC 35218 by MTT assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Design, synthesis, and structure-activity relationships of pyrazole derivatives as potential FabH 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.
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1799567Inhibition Assay from Article 10.1111/j.1747-0285.2006.00367.x: \\Synthesis and molecular modelling of novel substituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase-A inhibitors.\\2006Chemical biology & drug design, Mar, Volume: 67, Issue:3
Synthesis and molecular modelling of novel substituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase-A inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (30.77)29.6817
2010's8 (61.54)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.68

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 Index11.68 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.68)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]