Page last updated: 2024-11-11

5-(4-methoxybenzylidene)thiazolidine-2,4-dione

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

Description

5-(4-methoxybenzylidene)thiazolidine-2,4-dione: used to treat concanavalin A-induced liver injury; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5373936
CHEMBL ID85496
SCHEMBL ID1247705
MeSH IDM0543213

Synonyms (28)

Synonym
5-(4-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
CHEMBL85496
thiazolidine-2,4-dione, 5-(4-methoxyphenyl)methylene-
2,4-thiazolidinedione, 5-[(4-methoxyphenyl)methylene]-
nsc-31205
nsc31205
STK338390
(5z)-5-(4-methoxybenzylidene)-1,3-thiazolidine-2,4-dione
bdbm26632
thiazolidine-2,4-dione, 10a
(5z)-5-[(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
AKOS000270995
HMS1414C03
CS-004/03872062
2,4-thiazolidinedione, 5-[(4-methoxyphenyl)methylene]-, (z)-
74942-63-5
(z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione
F0207-0891
SCHEMBL1247705
nsc 31205
VRUKGUBMRBLJJW-TWGQIWQCSA-N
2,4-thiazolidinedione, 5-p-methoxybenzylidene-
dihydro-5-(4-methoxybenzylidene)thiazole-2,4-dione
sklb-010
5-(4-methoxybenzylidene)thiazolidine-2,4-dione
5-[(z)-1-(4-methoxyphenyl)methylidene]-1,3-thiazolane-2,4-dione
MS-23358
EN300-21037531

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The method described above was successfully applied to reveal the single- and multi-pharmacokinetic profiles of SKLB010 in beagle dogs and should be extendable to pharmacokinetic studies in other species as well."( Development and validation of a UPLC-MS/MS method for quantification of SKLB010, an investigational anti-inflammatory compound, and its application to pharmacokinetic studies in beagle dogs.
Chen, L; Chen, X; Duan, X; Hu, J; Liu, J; Ma, L; Tang, M; Wang, X; Ye, X; Zheng, H, 2011
)
0.37
[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)
Serine/threonine-protein kinase pim-1Homo sapiens (human)IC50 (µMol)3.50000.00040.887110.0000AID1798713; AID410272
Aldo-keto reductase family 1 member B1Homo sapiens (human)IC50 (µMol)40.83000.00101.191310.0000AID549698
Serine/threonine-protein kinase pim-2Homo sapiens (human)IC50 (µMol)1.90000.00470.52145.1000AID1798713; AID410273
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
protein phosphorylationSerine/threonine-protein kinase pim-1Homo sapiens (human)
apoptotic processSerine/threonine-protein kinase pim-1Homo sapiens (human)
regulation of transmembrane transporter activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of apoptotic processSerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of DNA-binding transcription factor activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of innate immune responseSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of DNA-templated transcriptionSerine/threonine-protein kinase pim-1Homo sapiens (human)
protein autophosphorylationSerine/threonine-protein kinase pim-1Homo sapiens (human)
protein stabilizationSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of cardiac muscle cell proliferationSerine/threonine-protein kinase pim-1Homo sapiens (human)
vitamin D receptor signaling pathwaySerine/threonine-protein kinase pim-1Homo sapiens (human)
cellular response to type II interferonSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of brown fat cell differentiationSerine/threonine-protein kinase pim-1Homo sapiens (human)
regulation of hematopoietic stem cell proliferationSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of TORC1 signalingSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of cardioblast proliferationSerine/threonine-protein kinase pim-1Homo sapiens (human)
cellular detoxificationSerine/threonine-protein kinase pim-1Homo sapiens (human)
retinoid metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
epithelial cell maturationAldo-keto reductase family 1 member B1Homo sapiens (human)
renal water homeostasisAldo-keto reductase family 1 member B1Homo sapiens (human)
carbohydrate metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
C21-steroid hormone biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
L-ascorbic acid biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
regulation of urine volumeAldo-keto reductase family 1 member B1Homo sapiens (human)
retinol metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
negative regulation of apoptotic processAldo-keto reductase family 1 member B1Homo sapiens (human)
daunorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
doxorubicin metabolic processAldo-keto reductase family 1 member B1Homo sapiens (human)
fructose biosynthetic processAldo-keto reductase family 1 member B1Homo sapiens (human)
cellular hyperosmotic salinity responseAldo-keto reductase family 1 member B1Homo sapiens (human)
metanephric collecting duct developmentAldo-keto reductase family 1 member B1Homo sapiens (human)
G1/S transition of mitotic cell cycleSerine/threonine-protein kinase pim-2Homo sapiens (human)
protein phosphorylationSerine/threonine-protein kinase pim-2Homo sapiens (human)
negative regulation of cell population proliferationSerine/threonine-protein kinase pim-2Homo sapiens (human)
apoptotic mitochondrial changesSerine/threonine-protein kinase pim-2Homo sapiens (human)
response to virusSerine/threonine-protein kinase pim-2Homo sapiens (human)
positive regulation of autophagySerine/threonine-protein kinase pim-2Homo sapiens (human)
macroautophagySerine/threonine-protein kinase pim-2Homo sapiens (human)
positive regulation of macroautophagySerine/threonine-protein kinase pim-2Homo sapiens (human)
negative regulation of apoptotic processSerine/threonine-protein kinase pim-2Homo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionSerine/threonine-protein kinase pim-2Homo sapiens (human)
positive regulation of DNA-templated transcriptionSerine/threonine-protein kinase pim-2Homo sapiens (human)
protein stabilizationSerine/threonine-protein kinase pim-2Homo sapiens (human)
protein autophosphorylationSerine/threonine-protein kinase pim-2Homo sapiens (human)
regulation of mitotic cell cycleSerine/threonine-protein kinase pim-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
protein serine/threonine kinase activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
protein bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
ATP bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
transcription factor bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
manganese ion bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
ribosomal small subunit bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
protein serine kinase activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
retinal dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
aldose reductase (NADPH) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
protein bindingAldo-keto reductase family 1 member B1Homo sapiens (human)
electron transfer activityAldo-keto reductase family 1 member B1Homo sapiens (human)
prostaglandin H2 endoperoxidase reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glyceraldehyde oxidoreductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
allyl-alcohol dehydrogenase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
L-glucuronate reductase activityAldo-keto reductase family 1 member B1Homo sapiens (human)
glycerol dehydrogenase [NADP+] activityAldo-keto reductase family 1 member B1Homo sapiens (human)
all-trans-retinol dehydrogenase (NADP+) activityAldo-keto reductase family 1 member B1Homo sapiens (human)
protein serine/threonine kinase activitySerine/threonine-protein kinase pim-2Homo sapiens (human)
protein bindingSerine/threonine-protein kinase pim-2Homo sapiens (human)
ATP bindingSerine/threonine-protein kinase pim-2Homo sapiens (human)
protein serine kinase activitySerine/threonine-protein kinase pim-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
nucleusSerine/threonine-protein kinase pim-1Homo sapiens (human)
nucleoplasmSerine/threonine-protein kinase pim-1Homo sapiens (human)
nucleolusSerine/threonine-protein kinase pim-1Homo sapiens (human)
cytoplasmSerine/threonine-protein kinase pim-1Homo sapiens (human)
cytosolSerine/threonine-protein kinase pim-1Homo sapiens (human)
plasma membraneSerine/threonine-protein kinase pim-1Homo sapiens (human)
cytoplasmSerine/threonine-protein kinase pim-1Homo sapiens (human)
extracellular spaceAldo-keto reductase family 1 member B1Homo sapiens (human)
nucleoplasmAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
extracellular exosomeAldo-keto reductase family 1 member B1Homo sapiens (human)
cytosolAldo-keto reductase family 1 member B1Homo sapiens (human)
cytoplasmSerine/threonine-protein kinase pim-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID670040Inhibition of mushroom tyrosinase activity using L-tyrosine as substrate at 20 uM after 30 mins by spectrophotometric analysis2012European journal of medicinal chemistry, Mar, Volume: 49Design and synthesis of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as novel tyrosinase inhibitors.
AID648277Inhibition of Dengue virus NS2B-NS3 protease using Abz-NleKRRS-3-(NO2)Y as substrate at 50 uM preincubated for 15 mins measured every sec for 15 mins by fluorimetric analysis2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID155860Concentration required for 50% inhibition of cell proliferation in PC12 cells using sulforhodamine B assay2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium.
AID444574Toxicity in BALB/c mouse assessed as pathological changes in spleen at 50 mg/kg, ig after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444576Toxicity in BALB/c mouse assessed as pathological changes in kidney at 50 mg/kg, ig after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID1782519Cytotoxicity against HEK293 cells assessed as reduction in cell viability measured after 48 hrs by MTT assay2021Bioorganic & medicinal chemistry, 12-15, Volume: 52Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase.
AID1782516Inhibition of Escherichia coli recombinant his-tagged DHDPS using (S)-aspartate-semialdehyde as a substrate preincubated for 12 mins followed by substrate addition by UV-Vis spectrophotometer based coupled DHDPS-DHDPR assay2021Bioorganic & medicinal chemistry, 12-15, Volume: 52Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase.
AID19643Partition coefficient (logP)2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium.
AID155855Tested for the intracellular Ca+2 release in PC12 cells; - = No release2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium.
AID1782518Cytotoxicity against human HepG2 cells assessed as reduction in cell viability measured after 48 hrs by MTT assay2021Bioorganic & medicinal chemistry, 12-15, Volume: 52Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase.
AID444567Inhibition of MCP1-induced chemotaxis in mouse RAW264.7 cells at 25 ug/mL relative to control2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444580Half life in BALB/c mouse at 30 mg/kg, po2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444581Oral bioavailability in BALB/c mouse at 30 mg/kg2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444573Toxicity in BALB/c mouse assessed as pathological changes in liver at 50 mg/kg, ig after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID410273Inhibition of human recombinant Pim2 by ATP depletion assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and evaluation of novel inhibitors of Pim-1 and Pim-2 protein kinases.
AID444568Inhibition of MCP1-induced chemotaxis in mouse RAW264.7 cells2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444570Effect on serum aspartate aminotransaminase level in concanavalin A-induced acute hepatitis model of BALB/c mouse at 50 mg/kg, po treated 0.5 hrs after concanavalin A challenge measured after 20 hrs (Rvb= 4997.9 +/- 2619.6)2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID155858Phosphorylation of eukaryotic initiation factor 2 alpha (eIF2alpha) in PC12 cells, - = No phosphorylation2004Bioorganic & medicinal chemistry letters, May-17, Volume: 14, Issue:10
Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium.
AID410272Inhibition of human recombinant Pim1 by ATP depletion assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and evaluation of novel inhibitors of Pim-1 and Pim-2 protein kinases.
AID549698Inhibition of aldose reductase2011Bioorganic & medicinal chemistry letters, Jan-01, Volume: 21, Issue:1
In vitro evaluation of 5-arylidene-2-thioxo-4-thiazolidinones active as aldose reductase inhibitors.
AID444571Decrease in concanavalin A-induced hepatic cell necrosis in acute hepatitis model of BALB/c mouse at 50 mg/kg, ig treated 0.5 hrs after concanavalin A challenge measured after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID410274Antiproliferative activity against human PC3 cells after 48 hrs by MTS assay2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and evaluation of novel inhibitors of Pim-1 and Pim-2 protein kinases.
AID444575Toxicity in BALB/c mouse assessed as pathological changes in lung at 50 mg/kg, ig after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID648280Inhibition of Escherichia coli MetAP at 10 uM after 15 mins by fluorescence analysis2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID648278Inhibition of bovine plasma thrombin using Boc-Val-Pro-Arg-AMC as substrate at 25 uM preincubated for 15 mins measured after 10 mins by fluorimetric assay2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID444577Toxicity in BALB/c mouse liver assessed as change in transaminase level at 50 mg/kg, ig after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444569Effect on serum alanine aminotransaminase level in concanavalin A-induced acute hepatitis model of BALB/c mouse at 50 mg/kg, po treated 0.5 hrs after concanavalin A challenge measured after 20 hrs (Rvb= 5734.5 +/- 2599.5)2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444572Toxicity in BALB/c mouse assessed as pathological changes in heart at 50 mg/kg, ig after 20 hrs by H and E staining based histopathology study2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID444579Plasma concentration in BALB/c mouse at 30 mg/kg, po2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID648279Inhibition of Escherichia coli MurA using PEP as substrate assessed as inorganic phosphate release at 25 uM preincubated for 10 mins measured after 60 mins by fluorimetric assay2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID444578Tmax in BALB/c mouse at 30 mg/kg, po2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID1798713Pim Kinase Assay from Article 10.1021/jm800937p: \\Synthesis and evaluation of novel inhibitors of Pim-1 and Pim-2 protein kinases.\\2009Journal of medicinal chemistry, Jan-08, Volume: 52, Issue:1
Synthesis and evaluation of novel inhibitors of Pim-1 and Pim-2 protein kinases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (21.43)29.6817
2010's9 (64.29)24.3611
2020's2 (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: 11.98

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 Index11.98 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.69 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.98)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]