Page last updated: 2024-12-07

1-(4-nitrophenyl)piperazine

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Description

1-(4-nitrophenyl)piperazine is a chemical compound that has been studied for its potential as a pharmaceutical agent. It is a derivative of piperazine, a heterocyclic compound that is known to have a variety of pharmacological activities. 1-(4-nitrophenyl)piperazine has been shown to exhibit anti-inflammatory, analgesic, and anticonvulsant effects in animal models. The compound is typically synthesized through a multi-step process involving the reaction of 4-nitroaniline with piperazine. It is important to note that 1-(4-nitrophenyl)piperazine is not currently approved for use as a medication and is considered a research chemical. However, it is a promising candidate for the development of new therapeutic agents. It is studied because of its potential therapeutic applications. Further research is needed to fully understand its pharmacological properties and safety profile. The compound may be a useful lead for the development of new drugs for the treatment of inflammatory, pain, and neurological disorders.'

1-(4-nitrophenyl)piperazine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID80447
CHEMBL ID165012
SCHEMBL ID336262
MeSH IDM000602984

Synonyms (48)

Synonym
BB 0245817
nsc 33874
einecs 228-443-7
nsc33874
nsc-33874
OPREA1_305105
piperazine, 1-(4-nitrophenyl)-
inchi=1/c10h13n3o2/c14-13(15)10-3-1-9(2-4-10)12-7-5-11-6-8-12/h1-4,11h,5-8h
6269-89-2
1-(4-nitrophenyl)piperazine
1-(4-nitrophenyl)piperazine, 97%
1-(4-nitrophenyl)-piperazine
STK060571
1-nitro-4-(1-piperazinyl)benzene
N0694
bdbm50001908
CHEMBL165012 ,
1-(4-nitro-phenyl)-piperazine
AKOS000120835
A8666
FT-0602617
PS-5829
AM20060699
SCHEMBL336262
mfcd00005961
SY014764
4-nitrophenylpiperazine
1-(4nitrophenyl)piperazine
4-nitrophenyl piperazine
n-4-nitro-phenyl piperazine
4-(4-nitrophenyl)piperazine
4-(piperazin-1-yl)-nitrobenzene
4-nitro-1-(1-piperazinyl)benzene
1-(4-nitrophenyl) piperazine
4-nitro phenylpiperazine
n-(4-nitrophenyl)piperazine
n-p-nitrophenylpiperazine
n-(4-nitrophenyl)-piperazine
W-109010
AC-28094
SR-01000397548-1
sr-01000397548
F14874
DTXSID40978310
EN300-34183
STARBLD0013746
CS-W015268
SE8XST987K
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Replicase polyprotein 1abBetacoronavirus England 1IC50 (µMol)71.60000.00403.43889.5100AID1594515
Beta-1 adrenergic receptorHomo sapiens (human)IC50 (µMol)13.00000.00021.46819.0000AID42027
Beta-2 adrenergic receptorCanis lupus familiaris (dog)IC50 (µMol)56.00000.00012.45965.2000AID40701
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (67)

Processvia Protein(s)Taxonomy
positive regulation of heart rate by epinephrine-norepinephrineBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of the force of heart contraction by epinephrine-norepinephrineBeta-1 adrenergic receptorHomo sapiens (human)
diet induced thermogenesisBeta-1 adrenergic receptorHomo sapiens (human)
response to coldBeta-1 adrenergic receptorHomo sapiens (human)
heat generationBeta-1 adrenergic receptorHomo sapiens (human)
negative regulation of multicellular organism growthBeta-1 adrenergic receptorHomo sapiens (human)
fear responseBeta-1 adrenergic receptorHomo sapiens (human)
regulation of circadian sleep/wake cycle, sleepBeta-1 adrenergic receptorHomo sapiens (human)
brown fat cell differentiationBeta-1 adrenergic receptorHomo sapiens (human)
regulation of postsynaptic membrane potentialBeta-1 adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of cold-induced thermogenesisBeta-1 adrenergic receptorHomo sapiens (human)
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressureBeta-1 adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeBeta-1 adrenergic receptorHomo sapiens (human)
receptor-mediated endocytosisBeta-2 adrenergic receptorCanis lupus familiaris (dog)
regulation of smooth muscle contractionBeta-2 adrenergic receptorCanis lupus familiaris (dog)
positive regulation of MAPK cascadeBeta-2 adrenergic receptorCanis lupus familiaris (dog)
negative regulation of G protein-coupled receptor signaling pathwayBeta-2 adrenergic receptorCanis lupus familiaris (dog)
adenylate cyclase-activating adrenergic receptor signaling pathwayBeta-2 adrenergic receptorCanis lupus familiaris (dog)
positive regulation of autophagosome maturationBeta-2 adrenergic receptorCanis lupus familiaris (dog)
positive regulation of lipophagyBeta-2 adrenergic receptorCanis lupus familiaris (dog)
negative regulation of transcription by RNA polymerase IINAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
base-excision repairNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
double-strand break repairNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromatin remodelingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein deacetylationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of cell population proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
determination of adult lifespanNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
response to UVNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
retrotransposon silencingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of double-strand break repair via homologous recombinationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of lipid metabolic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
pericentric heterochromatin formationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
subtelomeric heterochromatin formationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein destabilizationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of insulin secretionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of telomere maintenanceNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of proteasomal ubiquitin-dependent protein catabolic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
circadian regulation of gene expressionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of transcription elongation by RNA polymerase IINAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
ketone biosynthetic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of protein import into nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
glucose homeostasisNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of circadian rhythmNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
post-translational protein modificationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of fat cell differentiationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of gluconeogenesisNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of gene expression, epigeneticNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of glycolytic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of glucose importNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of protein export from nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of fibroblast proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of protein secretionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of lipid catabolic processNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein delipidationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
cardiac muscle cell differentiationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of cold-induced thermogenesisNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of protein localization to chromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of protein localization to chromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
DNA repair-dependent chromatin remodelingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of stem cell population maintenanceNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of chondrocyte proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
regulation of protein localization to plasma membraneNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of blood vessel branchingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of vascular endothelial cell proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein localization to site of double-strand breakNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of stem cell proliferationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of stem cell differentiationNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
negative regulation of cellular senescenceNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
positive regulation of double-strand break repairNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (31)

Processvia Protein(s)Taxonomy
beta-adrenergic receptor activityBeta-1 adrenergic receptorHomo sapiens (human)
beta1-adrenergic receptor activityBeta-1 adrenergic receptorHomo sapiens (human)
protein bindingBeta-1 adrenergic receptorHomo sapiens (human)
PDZ domain bindingBeta-1 adrenergic receptorHomo sapiens (human)
alpha-2A adrenergic receptor bindingBeta-1 adrenergic receptorHomo sapiens (human)
protein heterodimerization activityBeta-1 adrenergic receptorHomo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic membrane potentialBeta-1 adrenergic receptorHomo sapiens (human)
beta2-adrenergic receptor activityBeta-2 adrenergic receptorCanis lupus familiaris (dog)
protein homodimerization activityBeta-2 adrenergic receptorCanis lupus familiaris (dog)
norepinephrine bindingBeta-2 adrenergic receptorCanis lupus familiaris (dog)
chromatin bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
damaged DNA bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+ ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
zinc ion bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleotidyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromatin DNA bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleosome bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent protein lysine deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
protein homodimerization activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone H3K9 deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+ bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone H3K18 deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+-protein-arginine ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
DNA damage sensor activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent histone H3K56 deacetylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent protein demyristoylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD-dependent protein depalmitoylase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+- protein-lysine ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
TORC2 complex bindingNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
NAD+-protein ADP-ribosyltransferase activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
transcription corepressor activityNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
early endosomeBeta-1 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-1 adrenergic receptorHomo sapiens (human)
Schaffer collateral - CA1 synapseBeta-1 adrenergic receptorHomo sapiens (human)
neuronal dense core vesicleBeta-1 adrenergic receptorHomo sapiens (human)
plasma membraneBeta-1 adrenergic receptorHomo sapiens (human)
early endosomeBeta-2 adrenergic receptorCanis lupus familiaris (dog)
Golgi apparatusBeta-2 adrenergic receptorCanis lupus familiaris (dog)
receptor complexBeta-2 adrenergic receptorCanis lupus familiaris (dog)
nucleolusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
pericentric heterochromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
endoplasmic reticulumNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
site of double-strand breakNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
site of DNA damageNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleusNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
nucleoplasmNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
intracellular membrane-bounded organelleNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromosome, subtelomeric regionNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
chromatinNAD-dependent protein deacetylase sirtuin-6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1664130Inhibition of SIRT6 (unknown origin) using Ac-RYQK(Ac)-AMC as substrate by Fluor de Lys assay2020Bioorganic & medicinal chemistry letters, 08-15, Volume: 30, Issue:16
Discovery of 5-(4-methylpiperazin-1-yl)-2-nitroaniline derivatives as a new class of SIRT6 inhibitors.
AID1594515Inhibition of MERS-CoV papain-like protease using Z-Arg-Leu-Arg-Gly-Gly-AMC as substrate preincubated for 5 mins followed by substrate addition and measured for 10 mins by fluorescence assay2019Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10
Identification and design of novel small molecule inhibitors against MERS-CoV papain-like protease via high-throughput screening and molecular modeling.
AID40701Binding affinity towards Beta-2 adrenergic receptor by displacing [3H]dihydroalprenolol, in partially purified membrane fractions from canine lung tissue in the presence of 0.1 uM metoprolol1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Synthesis, cardiac electrophysiology, and beta-blocking activity of novel arylpiperazines with potential as class II/III antiarrhythmic agents.
AID1664131Inhibition of SIRT6 (unknown origin) at 300 uM using Ac-RYQK(Ac)-AMC as substrate by Fluor de Lys assay relative to control2020Bioorganic & medicinal chemistry letters, 08-15, Volume: 30, Issue:16
Discovery of 5-(4-methylpiperazin-1-yl)-2-nitroaniline derivatives as a new class of SIRT6 inhibitors.
AID1524436Substrate activity at recombinant Haemophilus influenzae Chloramphenicol nitroreductase expressed in Escherichia coli assessed as initial rate of reaction at 150 uM measured at 30 sec interval for 5 mins in presence of NADPH at pH 8 under 37 degC by UV-vi2019Bioorganic & medicinal chemistry letters, 05-01, Volume: 29, Issue:9
Investigating the promiscuity of the chloramphenicol nitroreductase from Haemophilus influenzae towards the reduction of 4-nitrobenzene derivatives.
AID42027Binding affinity for Beta-1 adrenergic receptor by displacing [3H]dihydroalprenolol, in partially purified membrane fractions from canine ventricular muscle in the presence of 1 uM zinterol1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Synthesis, cardiac electrophysiology, and beta-blocking activity of novel arylpiperazines with potential as class II/III antiarrhythmic agents.
[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's1 (20.00)18.2507
2000's0 (0.00)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: 29.15

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.15 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.15)

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]