Page last updated: 2024-11-09

3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

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Description

3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione: inhibits ERK1 and ERK2; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1249836
CHEMBL ID363555
SCHEMBL ID12652927
MeSH IDM0542431

Synonyms (10)

Synonym
CHEMBL363555 ,
bdbm50169955
3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione
3-(2-amino-ethyl)-5-[1-(4-ethoxy-phenyl)-meth-(z)-ylidene]-thiazolidine-2,4-dione
AKOS008967393
NBJOUCGADPALIB-XFXZXTDPSA-N
(z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione
SCHEMBL12652927
3-(2-aminoethyl)-5-(4-ethoxybenzylidene)-1,3-thiazolidine-2,4-dione
NCGC00387760-03

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)1.04000.00002.37899.7700AID612542
Amine oxidase [flavin-containing] BHomo sapiens (human)IC50 (µMol)0.08200.00001.89149.5700AID1917380; AID501302; AID612541
[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)
Mitogen-activated protein kinase 1Homo sapiens (human)Kd5.00000.00012.74417.3000AID238115
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (75)

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)
positive regulation of macrophage chemotaxisMitogen-activated protein kinase 1Homo sapiens (human)
positive regulation of macrophage proliferationMitogen-activated protein kinase 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIMitogen-activated protein kinase 1Homo sapiens (human)
protein phosphorylationMitogen-activated protein kinase 1Homo sapiens (human)
apoptotic processMitogen-activated protein kinase 1Homo sapiens (human)
chemotaxisMitogen-activated protein kinase 1Homo sapiens (human)
DNA damage responseMitogen-activated protein kinase 1Homo sapiens (human)
signal transductionMitogen-activated protein kinase 1Homo sapiens (human)
chemical synaptic transmissionMitogen-activated protein kinase 1Homo sapiens (human)
learning or memoryMitogen-activated protein kinase 1Homo sapiens (human)
insulin receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
positive regulation of peptidyl-threonine phosphorylationMitogen-activated protein kinase 1Homo sapiens (human)
Schwann cell developmentMitogen-activated protein kinase 1Homo sapiens (human)
peptidyl-serine phosphorylationMitogen-activated protein kinase 1Homo sapiens (human)
peptidyl-threonine phosphorylationMitogen-activated protein kinase 1Homo sapiens (human)
cytosine metabolic processMitogen-activated protein kinase 1Homo sapiens (human)
regulation of ossificationMitogen-activated protein kinase 1Homo sapiens (human)
androgen receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
regulation of cellular pHMitogen-activated protein kinase 1Homo sapiens (human)
thyroid gland developmentMitogen-activated protein kinase 1Homo sapiens (human)
regulation of protein stabilityMitogen-activated protein kinase 1Homo sapiens (human)
lipopolysaccharide-mediated signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
positive regulation of telomere maintenance via telomeraseMitogen-activated protein kinase 1Homo sapiens (human)
regulation of stress-activated MAPK cascadeMitogen-activated protein kinase 1Homo sapiens (human)
mammary gland epithelial cell proliferationMitogen-activated protein kinase 1Homo sapiens (human)
cellular response to amino acid starvationMitogen-activated protein kinase 1Homo sapiens (human)
cellular response to reactive oxygen speciesMitogen-activated protein kinase 1Homo sapiens (human)
response to nicotineMitogen-activated protein kinase 1Homo sapiens (human)
ERBB signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
ERBB2-ERBB3 signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
outer ear morphogenesisMitogen-activated protein kinase 1Homo sapiens (human)
myelinationMitogen-activated protein kinase 1Homo sapiens (human)
response to exogenous dsRNAMitogen-activated protein kinase 1Homo sapiens (human)
steroid hormone mediated signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
negative regulation of cell differentiationMitogen-activated protein kinase 1Homo sapiens (human)
insulin-like growth factor receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
thymus developmentMitogen-activated protein kinase 1Homo sapiens (human)
progesterone receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
T cell receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
B cell receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
stress-activated MAPK cascadeMitogen-activated protein kinase 1Homo sapiens (human)
regulation of cytoskeleton organizationMitogen-activated protein kinase 1Homo sapiens (human)
positive regulation of telomerase activityMitogen-activated protein kinase 1Homo sapiens (human)
Bergmann glial cell differentiationMitogen-activated protein kinase 1Homo sapiens (human)
long-term synaptic potentiationMitogen-activated protein kinase 1Homo sapiens (human)
face developmentMitogen-activated protein kinase 1Homo sapiens (human)
lung morphogenesisMitogen-activated protein kinase 1Homo sapiens (human)
trachea formationMitogen-activated protein kinase 1Homo sapiens (human)
labyrinthine layer blood vessel developmentMitogen-activated protein kinase 1Homo sapiens (human)
cardiac neural crest cell development involved in heart developmentMitogen-activated protein kinase 1Homo sapiens (human)
ERK1 and ERK2 cascadeMitogen-activated protein kinase 1Homo sapiens (human)
response to epidermal growth factorMitogen-activated protein kinase 1Homo sapiens (human)
cellular response to cadmium ionMitogen-activated protein kinase 1Homo sapiens (human)
cellular response to tumor necrosis factorMitogen-activated protein kinase 1Homo sapiens (human)
caveolin-mediated endocytosisMitogen-activated protein kinase 1Homo sapiens (human)
regulation of Golgi inheritanceMitogen-activated protein kinase 1Homo sapiens (human)
positive regulation of telomere cappingMitogen-activated protein kinase 1Homo sapiens (human)
regulation of early endosome to late endosome transportMitogen-activated protein kinase 1Homo sapiens (human)
cell surface receptor signaling pathwayMitogen-activated protein kinase 1Homo sapiens (human)
intracellular signal transductionMitogen-activated protein kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

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)
phosphotyrosine residue bindingMitogen-activated protein kinase 1Homo sapiens (human)
DNA bindingMitogen-activated protein kinase 1Homo sapiens (human)
protein serine/threonine kinase activityMitogen-activated protein kinase 1Homo sapiens (human)
MAP kinase activityMitogen-activated protein kinase 1Homo sapiens (human)
protein bindingMitogen-activated protein kinase 1Homo sapiens (human)
ATP bindingMitogen-activated protein kinase 1Homo sapiens (human)
RNA polymerase II CTD heptapeptide repeat kinase activityMitogen-activated protein kinase 1Homo sapiens (human)
phosphatase bindingMitogen-activated protein kinase 1Homo sapiens (human)
identical protein bindingMitogen-activated protein kinase 1Homo sapiens (human)
protein serine kinase activityMitogen-activated protein kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (24)

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)
extracellular regionMitogen-activated protein kinase 1Homo sapiens (human)
nucleusMitogen-activated protein kinase 1Homo sapiens (human)
nucleoplasmMitogen-activated protein kinase 1Homo sapiens (human)
cytoplasmMitogen-activated protein kinase 1Homo sapiens (human)
mitochondrionMitogen-activated protein kinase 1Homo sapiens (human)
early endosomeMitogen-activated protein kinase 1Homo sapiens (human)
late endosomeMitogen-activated protein kinase 1Homo sapiens (human)
endoplasmic reticulum lumenMitogen-activated protein kinase 1Homo sapiens (human)
Golgi apparatusMitogen-activated protein kinase 1Homo sapiens (human)
centrosomeMitogen-activated protein kinase 1Homo sapiens (human)
cytosolMitogen-activated protein kinase 1Homo sapiens (human)
cytoskeletonMitogen-activated protein kinase 1Homo sapiens (human)
plasma membraneMitogen-activated protein kinase 1Homo sapiens (human)
caveolaMitogen-activated protein kinase 1Homo sapiens (human)
focal adhesionMitogen-activated protein kinase 1Homo sapiens (human)
pseudopodiumMitogen-activated protein kinase 1Homo sapiens (human)
azurophil granule lumenMitogen-activated protein kinase 1Homo sapiens (human)
synapseMitogen-activated protein kinase 1Homo sapiens (human)
mitotic spindleMitogen-activated protein kinase 1Homo sapiens (human)
ficolin-1-rich granule lumenMitogen-activated protein kinase 1Homo sapiens (human)
cytoplasmMitogen-activated protein kinase 1Homo sapiens (human)
nucleusMitogen-activated protein kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID443876Inhibition of ERK1/2 phosphorylation in PMA-stimulated human U937 cells at 50 uM after 3 hrs by Western blotting2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID248093Inhibitory concentration against HeLa cell colony formation; Range is 15-20 uM2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Identification of novel extracellular signal-regulated kinase docking domain inhibitors.
AID443877Inhibition of Rsk1 phosphorylation in PMA-stimulated human U937 cells at 50 uM after 3 hrs by Western blotting2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID612541Inhibition of human recombinant MAOB by amplex red assay2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Structure-activity relationship and docking studies of thiazolidinedione-type compounds with monoamine oxidase B.
AID443884Inhibition of JNK phosphorylation2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID1917380Inhibition of recombinant human MAO-B2022Bioorganic & medicinal chemistry letters, 11-15, Volume: 76Design, synthesis, in-vitro, in-vivo and ex-vivo pharmacology of thiazolidine-2,4-dione derivatives as selective and reversible monoamine oxidase-B inhibitors.
AID443887Inhibition of recombinant ERK2-mediated myelin basic protein phosphorylation at 50 uM after 30 mins by SDS-PAGE2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID443888Cytotoxicity against human U937 cells assessed as cell viability up to 30 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID247896Inhibitory concentration against growth of A549 lung carcinoma cell2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Identification of novel extracellular signal-regulated kinase docking domain inhibitors.
AID612542Inhibition of human recombinant MAOA assessed as inhibition of kynuramine conversion to fluorescent metabolite 4-hydroxyquinoline by fluorimetry2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Structure-activity relationship and docking studies of thiazolidinedione-type compounds with monoamine oxidase B.
AID443882Inhibition of p38 phosphorylation in PMA-stimulated human U937 cells at 50 uM after 3 hrs by Western blotting2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID238115Dissociation constant for ERK2 kinase2005Journal of medicinal chemistry, Jul-14, Volume: 48, Issue:14
Identification of novel extracellular signal-regulated kinase docking domain inhibitors.
AID501302Inhibition of human recombinant MAO-B after 15 mins2010Bioorganic & medicinal chemistry letters, Sep-01, Volume: 20, Issue:17
Identification of novel monoamine oxidase B inhibitors by structure-based virtual screening.
AID443886Inhibition of ERK1/2 phosphorylation in EGF-stimulated human SKOV3 cells2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID501303Inhibition of ERK in human HeLa cells2010Bioorganic & medicinal chemistry letters, Sep-01, Volume: 20, Issue:17
Identification of novel monoamine oxidase B inhibitors by structure-based virtual screening.
AID443883Inhibition of MEK phosphorylation2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
AID443885Inhibition of ERK1/2 phosphorylation in EGF-stimulated human OVCAR5 cells2009Bioorganic & medicinal chemistry letters, Nov-01, Volume: 19, Issue:21
Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (28.57)29.6817
2010's4 (57.14)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.54

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 Index12.54 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.54)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]