Page last updated: 2024-11-12

a 304121

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Description

4-((3-(4-(2-aminopropanoyl)-1-piperazinyl)propoxy)phenyl)cyclopropylmethanone: InChIKey: GTMGELLVPUSBMG-UHFFFAOYSA-N [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9906860
CHEMBL ID302196
SCHEMBL ID7244264
MeSH IDM0451217

Synonyms (20)

Synonym
(2r)-2-amino-1-[4-[3-[4-(cyclopropanecarbonyl)phenoxy]propyl]piperazin-1-yl]propan-1-one
gtpl1258
bdbm50139308
(r)-2-amino-1-{4-[3-(4-cyclopropanecarbonyl-phenoxy)-propyl]-piperazin-1-yl}-propan-1-one
CHEMBL302196 ,
a-304121
4-((3-(4-(2-aminopropanoyl)-1-piperazinyl)propoxy)phenyl)cyclopropylmethanone
1039lg569y ,
unii-1039lg569y
piperazine, 1-((2r)-2-amino-1-oxopropyl)-4-(3-(4-(cyclopropylcarbonyl)phenoxy)propyl)-
a 304121
360551-71-9
a304121
1-propanone, 2-amino-1-(4-(3-(4-(cyclopropylcarbonyl)phenoxy)propyl)-1-piperazinyl)-, (2r)-
SCHEMBL7244264
DTXSID60189623
KPXVCGPCRXEDLT-OAHLLOKOSA-N ,
(4-(3-(4-((2r)-2-aminopropanoyl)-1-piperazinyl)propoxy)phenyl)(cyclopropyl)methanone
Q27074062
AKOS040750018
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H2 receptorHomo sapiens (human)Ki70.79460.00062.197310.0000AID88470
Histamine H1 receptorCavia porcellus (domestic guinea pig)Ki69.18310.00261.783210.0000AID87367
Histamine H1 receptorRattus norvegicus (Norway rat)Ki69.18310.00071.54406.5000AID87367
Histamine H1 receptorHomo sapiens (human)Ki69.18310.00000.511010.0000AID87367
Histamine H3 receptorRattus norvegicus (Norway rat)Ki0.00220.00010.29638.5110AID239562; AID239987; AID692493; AID89741
Histamine H3 receptorHomo sapiens (human)Ki0.76820.00010.33998.5110AID239591; AID239988; AID692494; AID86460
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
gastric acid secretionHistamine H2 receptorHomo sapiens (human)
immune responseHistamine H2 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H2 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H2 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H2 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H2 receptorHomo sapiens (human)
inflammatory responseHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
memoryHistamine H1 receptorHomo sapiens (human)
visual learningHistamine H1 receptorHomo sapiens (human)
regulation of vascular permeabilityHistamine H1 receptorHomo sapiens (human)
positive regulation of vasoconstrictionHistamine H1 receptorHomo sapiens (human)
regulation of synaptic plasticityHistamine H1 receptorHomo sapiens (human)
cellular response to histamineHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H1 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H1 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H1 receptorHomo sapiens (human)
neurotransmitter secretionHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerHistamine H3 receptorHomo sapiens (human)
chemical synaptic transmissionHistamine H3 receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
histamine receptor activityHistamine H2 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H2 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H2 receptorHomo sapiens (human)
histamine receptor activityHistamine H1 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H1 receptorHomo sapiens (human)
neurotransmitter receptor activityHistamine H1 receptorHomo sapiens (human)
histamine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled acetylcholine receptor activityHistamine H3 receptorHomo sapiens (human)
G protein-coupled serotonin receptor activityHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneHistamine H2 receptorHomo sapiens (human)
synapseHistamine H2 receptorHomo sapiens (human)
plasma membraneHistamine H2 receptorHomo sapiens (human)
dendriteHistamine H2 receptorHomo sapiens (human)
cytosolHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
synapseHistamine H1 receptorHomo sapiens (human)
dendriteHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H1 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
presynapseHistamine H3 receptorHomo sapiens (human)
plasma membraneHistamine H3 receptorHomo sapiens (human)
synapseHistamine H3 receptorHomo sapiens (human)
dendriteHistamine H3 receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID246007Tested for their ability to enhance memory in the adult rats using social recognition memory test2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID237820Concentration in brain of rats after 1 hr of intravenous administration2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID692494Binding affinity to human histamine H3 receptor2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Histamine H3 receptor as a drug discovery target.
AID237554Volume of distribution was observed in rat after intravenous administration of 1-5 mg/kg2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID239893Tested for its ability to block human histamine H3 receptor activation by the agonist R-alpha-methyl histamine in a [Ca2+] flux assay2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID239988In vitro binding affinity was determined as displacement of [3H]N-R-methylhistamine from C6 cell membranes expressing human histamine H3 receptor2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID89733In vitro histamine H3 receptor antagonist activity was determined by K+-evoked depolarization- induced release of [3H]histamine from rat synaptosomes2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 2: binding preference for D-amino acids motifs.
AID13000Oral bioavailability in rat (dose 5 mg/kg p.o.)2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 2: binding preference for D-amino acids motifs.
AID87367Binding affinity towards Histamine H1 receptor of human membranes.2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 2: binding preference for D-amino acids motifs.
AID236100Oral bioavailability in rat (dose 1-5 mg/kg i.v.)2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID86460Binding affinity for human histamine H3 receptor on human colon cells2004Bioorganic & medicinal chemistry letters, Feb-09, Volume: 14, Issue:3
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 3: 5-Substituted 3-phenyl-1,2,4-oxadiazoles as potent antagonists.
AID239591In vitro binding affinity was determined as displacement of [3H]N-R-methylhistamine from C6 cell membranes expressing human histamine H3 receptor2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID86298Tested in vitro for histamine H3 receptor mediate inhibition of neurogenic contractions in guinea pig isolated ileum assay2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 2: binding preference for D-amino acids motifs.
AID89741Binding affinity towards Histamine H3 receptor of rat cortical membranes.2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 2: binding preference for D-amino acids motifs.
AID239562In vitro binding affinity was determined as displacement of [3H]N-R-methylhistamine from C6 cell membranes expressing rat histamine H3 receptor2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID692493Binding affinity to rat cortical histamine H3 receptor2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Histamine H3 receptor as a drug discovery target.
AID246006Lowest dose to induce CNS side effects was assessed in a general behavioral screen in rats2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID88470Binding affinity towards Histamine H2 receptor from human membranes2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Structure-activity relationships of non-imidazole H(3) receptor ligands. Part 2: binding preference for D-amino acids motifs.
AID237264Half life was observed in rat after intravenous administration of 3-5 mg/kg; (n=3)2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID236517Clearance was observed in rat after intravenous administration of 1-5 mg/kg2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID239987In vitro binding affinity was determined as displacement of [3H]N-R-methylhistamine from C6 cell membranes expressing rat histamine H3 receptor2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID246008Tested for their ability to enhance learning in the rat pups using inhibitory avoidance acquisition model2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention.
AID1346017Rat H3 receptor (Histamine receptors)2004Biochemical pharmacology, Sep-01, Volume: 68, Issue:5
Pharmacological and behavioral properties of A-349821, a selective and potent human histamine H3 receptor antagonist.
AID1346107Human H3 receptor (Histamine receptors)2003The Journal of pharmacology and experimental therapeutics, Jun, Volume: 305, Issue:3
Two novel and selective nonimidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects.
AID1346107Human H3 receptor (Histamine receptors)2004Biochemical pharmacology, Sep-01, Volume: 68, Issue:5
Pharmacological and behavioral properties of A-349821, a selective and potent human histamine H3 receptor antagonist.
AID1346017Rat H3 receptor (Histamine receptors)2003The Journal of pharmacology and experimental therapeutics, Jun, Volume: 305, Issue:3
Two novel and selective nonimidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's10 (90.91)29.6817
2010's1 (9.09)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.76

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 Index11.76 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]