6325-94-6

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-HYDROXY-BENZYLIDENE)-THIAZOLIDINE-2,4-DIONE is used as an antidiabetic medication for the treatment of type 2 diabetes. It is utilized to increase insulin sensitivity, helping to lower blood glucose levels and manage the disease effectively.
Used in Diabetes Management:
5-(2-HYDROXY-BENZYLIDENE)-THIAZOLIDINE-2,4-DIONE is used as a therapeutic agent to improve the body's response to insulin, which is crucial for patients with type 2 diabetes to maintain healthy blood sugar levels and prevent complications associated with the disease.

InChI:InChI=1/C10H7NO3S/c12-7-4-2-1-3-6(7)5-8-9(13)11-10(14)15-8/h1-5,12H,(H,11,13,14)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 90-02-8 salicylaldehyde 
• 63671-19-2 chromeno[2,3-d]thiazol-2-one 
• 17356-08-0 thiourea 
• 79-11-8 chloroacetic acid 

Downstream Products

• 83749-88-6 5-(2-Hydroxybenzyliden)-3-hydroxymethylthiazolidinon-2,4 
• 1307299-61-1 (Z)-5-(2-hydroxybenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione 
• 1402084-13-2 (Z)-2'-(4-fluorobenzenesulfonyloxy)-5-benzylidenethiazolidine-2,4-dione 
• 1402084-14-3 (Z)-2'-(4-bromobenzenesulfonyloxy)-5-benzylidenethiazolidine-2,4-dione 
• 1402084-15-4 (Z)-2'-(3,4-dimethoxybenzenesulfonyloxy)-5-benzylidenethiazolidine-2,4-dione 
• 1402084-16-5 (Z)-2'-(4-isopropylbenzenesulfonyloxy)-5-benzylidenethiazolidine-2,4-dione 
• 1402084-17-6 (Z)-2'-(4-tert-butylbenzenesulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione 
• 1402084-18-7 (Z)-2'-(4-trifluoromethxybenzenesulfonyloxy)-5-benzylidenethiazolidine-2,4-dione 
• 1402084-19-8 (Z)-2'-(4-biphenylsulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione 
• 1402084-20-1 (Z)-2'-(1-naphthylsulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione 
• 1402084-21-2 (Z)-2'-(2-naphthylsulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione 
• 1020066-75-4 (Z)-5-(2-hydroxybenzylidene)-3-(1-methylcyclohexylmethyl)thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives

In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a

Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives

Derivatives of the thiazolidine-2,4-dione core represent a heterocyclic class with several correlated properties. In this context, the synthesis of structural analogues of these bioactive substances becomes attractive in the field of medicinal chemistry. These analogues act as antimicrobial agents against Gram-positives pathogens. The present work aimed to synthesize 10 different derivatives of 5-arylidene-thiazolidine-2,4-dione, employing urea as the catalyst in a solvent-free reaction medium, with yields that ranged from 45 to 99percent. The compounds obtained were submitted to an antimicrobial assay against S. aureus ATCC 29213. Two compounds presented minimum inhibitory concentration of 62.5 and 32.5 μg mL-1 and minimum bactericidal concentration -1, demonstrating their antibacterial potential. Principal component analysis was carried out to discriminate the compounds in active and inactive classes. Four geometric and electronic molecular descriptors were required to completely discriminate the compounds. The selected descriptors can guide us in designing new 5-arylidene-thiazolidine-2,4-dione derivatives with enhanced activity.

HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY

The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used

Tau-Centric Multitarget Approach for Alzheimer's Disease: Development of First-in-Class Dual Glycogen Synthase Kinase 3β and Tau-Aggregation Inhibitors

Several findings propose the altered tau protein network as an important target for Alzheimer's disease (AD). Particularly, two points of pharmacological intervention can be envisaged: inhibition of phosphorylating tau kinase GSK-3β and tau aggregation process. On the basis of this consideration and on our interest in multitarget paradigms in AD, we report on the discovery of 2,4-thiazolidinedione derivatives endowed with such a profile. 28 and 30 displayed micromolar IC50 values toward GSK-3β, together with the capacity of inhibiting AcPHF6 aggregation of 60% and 80% at 10 μM, respectively. In addition, they showed PAMPA-BBB permeability, together with a suitable cellular safety profile. 30 also displayed inhibition of both K18 and full-length tau aggregations. Finally, both compounds were able to improve cell viability in an okadaic acid-induced neurodegeneration cell model. To the best of our knowledge, 28 and 30 are the first balanced, nontoxic, dual-acting compounds hitting tau cascade at two different hubs.

New N-(oxazolylmethyl)-thiazolidinedione active against candida albicans biofilm: Potential Als proteins inhibitors

C. albicans is the most frequently occurring fungal pathogen, and is becoming an increasing public health problem, especially in the context of increased microbial resistance. This opportunistic pathogen is characterized by a versatility explained mainly

Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Abstract: The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure–activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-γ (PPARγ) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-γ (PPARγ) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor. Graphical abstract: [Figure not available: see fulltext.].

In silico design, chemical synthesis and toxicological evaluation of 1,3-thiazolidine-2,4-dione derivatives as PPARγ agonists

Peroxisome proliferator-activated receptors (PPARs) are nuclear receptors involved in the metabolism of lipids and carbohydrates. The exogenous ligands of these receptors are thiazolidinediones (TZDs), which are used to treat type 2 diabetes mellitus (DM2

One-Pot Synthesis of 5-Ene-4-aminothiazol-2(5H)-ones and Chromeno[2,3-d]thiazol-2-ones

Herein, we describe a one-pot, three-component method for the synthesis of 5-arylidene-4-aminothiazol-2(5H)-ones based on the reaction of isorhodanine, aromatic aldehydes, and ethanolamine. The one-pot procedure for chromeno[2,3-d]thiazol-2-one synthesis starting from 4-aminothiazol-2(5H)-one was proposed following the study of 5-(2-hydroxybenzylidene)-thiazolidinones. Structural features of the starting 4-thioxo-2-thiazolidinone, 4-aminothiazol-2(5H)-one, and target compounds are discussed.

New compounds having skin whitening, antioxidant and PPAR activity, and medical use thereof

PURPOSE: A novel compound with skin whitening, antioxidation, and PPAR activation effects, and a medical use thereof are provided to be used for a pharmaceutical composition or a cosmetic product. CONSTITUTION: A compound is denoted by chemical formula 1. A skin whitening composition contains the compound as an active ingredient. An antioxidative composition for preventing or treating oxidative diseases contains the compound of chemical formula 1 as an active ingredient. The oxidative diseases are selected among skin aging, pigmentation, wrinkling, psoriasis, or eczema. The composition prevents or treats diseases which are regulated by PPAR(peroxisome proliferator-activated receptor) activity. The PPAR includes PPAR alpha or PPAR gamma.

NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.