Page last updated: 2024-11-13

2-(3-oxo-1,2-benzothiazol-2-yl)-N-phenylacetamide

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

2-(3-oxo-1,2-benzothiazol-2-yl)-N-phenylacetamide, also known as **thiazolidine-2,4-dione**, is a heterocyclic compound with a benzothiazole ring system.

**Structure and Properties:**

* **Benzothiazole ring:** This core structure contains a sulfur atom and a nitrogen atom within a six-membered ring.
* **3-oxo group:** A carbonyl group attached to the third position of the benzothiazole ring.
* **Acetamide group:** A carboxamide group attached to the second position of the benzothiazole ring, further connected to a phenyl group.

**Importance in Research:**

Thiazolidine-2,4-dione and its derivatives have shown promising biological activity and are actively researched for various applications:

* **Anti-inflammatory activity:** These compounds have been demonstrated to inhibit the production of inflammatory mediators like prostaglandins and leukotrienes, making them potential candidates for treating inflammatory conditions.
* **Antioxidant activity:** Thiazolidine-2,4-dione derivatives possess free radical scavenging properties, contributing to their potential role in protecting cells from oxidative damage.
* **Anti-cancer activity:** Some studies suggest that these compounds exhibit cytotoxic effects against various cancer cell lines, potentially through apoptosis induction and cell cycle arrest.
* **Antibacterial activity:** The heterocyclic nature of thiazolidine-2,4-dione derivatives has been linked to their potential antibacterial properties.
* **Anti-diabetic activity:** Some research indicates that these compounds might help regulate blood glucose levels and improve insulin sensitivity, making them promising for diabetes treatment.

**Current Research:**

Current research focuses on synthesizing new derivatives of thiazolidine-2,4-dione with improved pharmacological properties. Researchers are exploring different substituents on the phenyl group and the benzothiazole ring to enhance the desired biological activity and reduce potential side effects.

**Overall, 2-(3-oxo-1,2-benzothiazol-2-yl)-N-phenylacetamide and its derivatives are promising candidates for developing new drugs in various therapeutic areas, including inflammation, oxidative stress, cancer, and diabetes. Ongoing research aims to further elucidate their mechanisms of action and optimize their pharmacological profiles for clinical application.**

Cross-References

ID SourceID
PubMed CID44602374
CHEMBL ID1709906
CHEBI ID93426

Synonyms (13)

Synonym
ksc-4-244
KUC104122N ,
kuc104122
smr001831621
MLS003116067 ,
CHEMBL1709906
2-(3-oxidanylidene-1,2-benzothiazol-2-yl)-n-phenyl-ethanamide
2-(3-oxo-1,2-benzothiazol-2-yl)-n-phenylacetamide
2-(3-keto-1,2-benzothiazol-2-yl)-n-phenyl-acetamide
bdbm61925
cid_44602374
CHEBI:93426
Q27165128
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzothiazoles
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (19)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nrf2Homo sapiens (human)Potency12.58930.09208.222223.1093AID624171
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
GLS proteinHomo sapiens (human)Potency7.07950.35487.935539.8107AID624170
TDP1 proteinHomo sapiens (human)Potency2.18530.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency17.78280.00527.809829.0929AID588855
hypothetical protein, conservedTrypanosoma bruceiPotency3.98110.223911.245135.4813AID624173
67.9K proteinVaccinia virusPotency10.00000.00018.4406100.0000AID720579
IDH1Homo sapiens (human)Potency29.09290.005210.865235.4813AID686970
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency1.19170.168316.404067.0158AID720504
VprHuman immunodeficiency virus 1Potency56.23411.584919.626463.0957AID651644
Glycoprotein hormones alpha chainHomo sapiens (human)Potency10.00004.46688.344810.0000AID624291
Guanine nucleotide-binding protein GHomo sapiens (human)Potency44.66841.995325.532750.1187AID624287
[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)
glucose-6-phosphate dehydrogenase-6-phosphogluconolactonasePlasmodium bergheiIC50 (µMol)10.62330.889021.028671.5000AID504765; AID540252; AID540269
hexokinaseTrypanosoma brucei brucei TREU927IC50 (µMol)6.69000.20084.602422.3780AID2230
glucose-6-phosphate 1-dehydrogenase isoform bHomo sapiens (human)IC50 (µMol)12.70008.870012.851817.8000AID504792
rac GTPase-activating protein 1 isoform aHomo sapiens (human)IC50 (µMol)73.11007.390057.8904301.2400AID624330
Neutrophil elastaseHomo sapiens (human)IC50 (µMol)6.69000.00632.073422.3780AID2230
Replicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2IC50 (µMol)0.16520.00022.45859.9600AID1888964
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell population proliferationGlycoprotein hormones alpha chainHomo sapiens (human)
hormone-mediated signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
regulation of signaling receptor activityGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of steroid biosynthetic processGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of cell migrationGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid gland developmentGlycoprotein hormones alpha chainHomo sapiens (human)
luteinizing hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone signaling pathwayGlycoprotein hormones alpha chainHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIGlycoprotein hormones alpha chainHomo sapiens (human)
negative regulation of organ growthGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone secretionGlycoprotein hormones alpha chainHomo sapiens (human)
thyroid hormone generationGlycoprotein hormones alpha chainHomo sapiens (human)
proteolysisNeutrophil elastaseHomo sapiens (human)
negative regulation of transcription by RNA polymerase IINeutrophil elastaseHomo sapiens (human)
response to yeastNeutrophil elastaseHomo sapiens (human)
leukocyte migration involved in inflammatory responseNeutrophil elastaseHomo sapiens (human)
biosynthetic process of antibacterial peptides active against Gram-negative bacteriaNeutrophil elastaseHomo sapiens (human)
proteolysisNeutrophil elastaseHomo sapiens (human)
intracellular calcium ion homeostasisNeutrophil elastaseHomo sapiens (human)
response to UVNeutrophil elastaseHomo sapiens (human)
extracellular matrix disassemblyNeutrophil elastaseHomo sapiens (human)
protein catabolic processNeutrophil elastaseHomo sapiens (human)
response to lipopolysaccharideNeutrophil elastaseHomo sapiens (human)
negative regulation of chemokine productionNeutrophil elastaseHomo sapiens (human)
negative regulation of interleukin-8 productionNeutrophil elastaseHomo sapiens (human)
positive regulation of interleukin-8 productionNeutrophil elastaseHomo sapiens (human)
defense response to bacteriumNeutrophil elastaseHomo sapiens (human)
positive regulation of MAP kinase activityNeutrophil elastaseHomo sapiens (human)
positive regulation of smooth muscle cell proliferationNeutrophil elastaseHomo sapiens (human)
negative regulation of inflammatory responseNeutrophil elastaseHomo sapiens (human)
positive regulation of immune responseNeutrophil elastaseHomo sapiens (human)
negative regulation of chemotaxisNeutrophil elastaseHomo sapiens (human)
pyroptosisNeutrophil elastaseHomo sapiens (human)
neutrophil-mediated killing of gram-negative bacteriumNeutrophil elastaseHomo sapiens (human)
neutrophil-mediated killing of fungusNeutrophil elastaseHomo sapiens (human)
positive regulation of leukocyte tethering or rollingNeutrophil elastaseHomo sapiens (human)
phagocytosisNeutrophil elastaseHomo sapiens (human)
acute inflammatory response to antigenic stimulusNeutrophil elastaseHomo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protein bindingGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone activityGlycoprotein hormones alpha chainHomo sapiens (human)
protease bindingNeutrophil elastaseHomo sapiens (human)
transcription corepressor activityNeutrophil elastaseHomo sapiens (human)
endopeptidase activityNeutrophil elastaseHomo sapiens (human)
serine-type endopeptidase activityNeutrophil elastaseHomo sapiens (human)
protein bindingNeutrophil elastaseHomo sapiens (human)
heparin bindingNeutrophil elastaseHomo sapiens (human)
peptidase activityNeutrophil elastaseHomo sapiens (human)
cytokine bindingNeutrophil elastaseHomo sapiens (human)
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoestersReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
protein guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
extracellular regionGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
Golgi lumenGlycoprotein hormones alpha chainHomo sapiens (human)
follicle-stimulating hormone complexGlycoprotein hormones alpha chainHomo sapiens (human)
pituitary gonadotropin complexGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular spaceGlycoprotein hormones alpha chainHomo sapiens (human)
extracellular regionNeutrophil elastaseHomo sapiens (human)
extracellular spaceNeutrophil elastaseHomo sapiens (human)
cytoplasmNeutrophil elastaseHomo sapiens (human)
cytosolNeutrophil elastaseHomo sapiens (human)
cell surfaceNeutrophil elastaseHomo sapiens (human)
secretory granuleNeutrophil elastaseHomo sapiens (human)
azurophil granule lumenNeutrophil elastaseHomo sapiens (human)
specific granule lumenNeutrophil elastaseHomo sapiens (human)
phagocytic vesicleNeutrophil elastaseHomo sapiens (human)
collagen-containing extracellular matrixNeutrophil elastaseHomo sapiens (human)
extracellular exosomeNeutrophil elastaseHomo sapiens (human)
transcription repressor complexNeutrophil elastaseHomo sapiens (human)
extracellular spaceNeutrophil elastaseHomo sapiens (human)
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID619593Antifungal activity against Candida albicans RC-201 after 24 hrs by broth microdilution method2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Antifungal activity of a series of 1,2-benzisothiazol-3(2H)-one derivatives.
AID619592Antifungal activity against Candida albicans CAF-2 after 24 hrs by broth microdilution method2011Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19
Antifungal activity of a series of 1,2-benzisothiazol-3(2H)-one derivatives.
AID1888963Inhibition of SARS-CoV-2 main protease using Mca-AVLQSGFRK(Dnp)K as substrate at 40 uM preincubated with enzyme for 10 mins followed by substrate addition and measured every 30 secs for 10 mins by fluorescence based analysis2022Bioorganic & medicinal chemistry letters, 02-15, Volume: 58Discovery of highly potent SARS-CoV-2 M
AID1888964Inhibition of SARS-CoV-2 main protease using Mca-AVLQSGFRK(Dnp)K as substrate preincubated with enzyme for 10 mins followed by substrate addition and measured every 30 secs for 10 mins by fluorescence based analysis2022Bioorganic & medicinal chemistry letters, 02-15, Volume: 58Discovery of highly potent SARS-CoV-2 M
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]