Page last updated: 2024-12-09

(z)-5-(2'-hydroxybenzylidene)-2-thioxothiazolidin-4-one

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

Description

**(z)-5-(2'-hydroxybenzylidene)-2-thioxothiazolidin-4-one** is a chemical compound, also known as **2-(2-hydroxybenzylidene)-4-oxothiazolidine-2-thione**, that belongs to the **thiazolidin-4-one** class of compounds.

Here's a breakdown of its structure and potential importance in research:

**Structure:**

* **Thiazolidin-4-one:** A heterocyclic ring system containing sulfur, nitrogen, and oxygen atoms.
* **2-thioxo:** Indicates a sulfur atom double-bonded to a carbon atom in the thiazolidin-4-one ring.
* **Benzylidene:** A phenyl ring (benzene) attached to a methylene group (CH2).
* **2'-hydroxy:** A hydroxyl group (OH) attached to the benzene ring, in the 2' position.
* **(z):** The (z) designation indicates the *cis* isomer, where the hydroxyl group and the thiazolidin-4-one ring are on the same side of the double bond.

**Why it's important for research:**

This compound and its derivatives have shown potential in a variety of research areas due to their diverse pharmacological properties:

* **Anti-inflammatory:** Studies suggest these compounds may have anti-inflammatory effects by inhibiting the production of pro-inflammatory mediators.
* **Antioxidant:** Their ability to scavenge free radicals could contribute to antioxidant activity.
* **Antimicrobial:** Some derivatives exhibit antimicrobial activity against bacteria and fungi.
* **Anti-cancer:** Research is ongoing to investigate their potential for treating cancer by inducing cell death in cancer cells.
* **Cardiovascular:** Potential to modulate blood pressure and other cardiovascular parameters.

**Current Research:**

* Synthesis: Researchers are developing efficient and sustainable synthetic methods to produce these compounds.
* Structure-Activity Relationship (SAR): Studying how structural modifications affect their pharmacological properties to design even more potent and selective drugs.
* In vivo Studies: Testing these compounds in animal models to assess their efficacy and safety before potential clinical trials.

**Overall, (z)-5-(2'-hydroxybenzylidene)-2-thioxothiazolidin-4-one and its derivatives offer promising potential for therapeutic development in several disease areas.** However, further research is necessary to fully understand their mechanisms of action and to develop safe and effective drugs for clinical use.

(Z)-5-(2'-hydroxybenzylidene)-2-thioxothiazolidin-4-one: arylamine N-acetyltransferase 1inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1270513
CHEMBL ID431550
SCHEMBL ID3425968
MeSH IDM0544448

Synonyms (18)

Synonym
nsc31202
34709-44-9
nsc-31202
STK397032
(5z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
bdbm50092273
5-[1-(2-hydroxy-phenyl)-meth-(z)-ylidene]-2-thioxo-thiazolidin-4-one
(z)-5-(2''-hydroxybenzylidene)-2-thioxothiazolidin-4-one
(z)-5-(2-hydroxybenzylidene)-2-thioxothiazolidin-4-one
AKOS001451805
CHEMBL431550 ,
(5z)-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
SCHEMBL3425968
ZROKEZLWNZKNSJ-YVMONPNESA-N
DTXSID00361522
81154-12-3
(z)-5-(2'-hydroxybenzylidene)-2-thioxothiazolidin-4-one
Z44301451
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)9,550.00000.03403.987110.0000AID589733
Beta-lactamaseEnterobacter cloacaeIC50 (µMol)335.00000.10001.87457.7000AID43281
Arylamine N-acetyltransferase 1Homo sapiens (human)IC50 (µMol)1.10001.10001.10001.1000AID346066
Beta-lactamase Enterobacter cloacaeIC50 (µMol)700.00000.06000.19000.3200AID44222
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (1)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processArylamine N-acetyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
arylamine N-acetyltransferase activityArylamine N-acetyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolArylamine N-acetyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID346072Inhibition of Mycobacterium marinum recombinant NAT using isoniazid as substrate at 30 uM2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2.
AID589733Inhibition of diphenolase activity of mushroom tyrosinase preincubated with compound for 10 mins before addition of L-DOPA as substrate by spectrophotometric analysis2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Evaluation of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives as tyrosinase inhibitors.
AID1756844Antimycobacterial activity against Mycobacterium tuberculosis H37Ra2021European journal of medicinal chemistry, Apr-05, Volume: 215Antitubercular properties of thiazolidin-4-ones - A review.
AID44222Inhibitory activity against class A Beta-lactamase TEM isolated from Enterobacter coli2000Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19
The synthesis and SAR of rhodanines as novel class C beta-lactamase inhibitors.
AID346069Cytotoxicity against mouse macrophage at 10 ug/ml after 72 hrs by trypan blue exclusion method2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2.
AID462262Inhibition of Arabidopsis thaliana LL-DAP-AT expressed in Escherichia coli by aminobenzaldehyde-based assay2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Exploration of inhibitors for diaminopimelate aminotransferase.
AID43281Inhibitory activity against class C Beta-lactamase isolated from Enterobacter cloacae2000Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19
The synthesis and SAR of rhodanines as novel class C beta-lactamase inhibitors.
AID346066Inhibition of human recombinant NAT1 assessed as hydrolysis of acetyl coA using PABA as substrate by Ellman's method2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2.
AID346073Inhibition of Pseudomonas aeruginosa recombinant NAT using isoniazid as substrate at 30 uM2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2.
[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's2 (33.33)29.6817
2010's3 (50.00)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.97

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 Index12.97 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.97)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]