5835-46-1

Usage

Chemical Class

Thiazolidinedione

Therapeutic Properties

Potential anti-inflammatory and antidiabetic effects

Chemical Structure

Contains a thiazolidinedione ring and a methoxyphenyl group

Mode of Action

Activates peroxisome proliferator-activated receptors (PPARs)

Biological Activity

Likely contributes to its pharmacological effects

Regulation Targets

Involved in the regulation of glucose and lipid metabolism

Potential Applications

Treatment of type 2 diabetes and inflammation-related diseases

Research Status

Further investigation required to elucidate pharmacological properties and therapeutic uses

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 135-02-4 ortho-anisaldehyde 

Downstream Products

• 1119274-21-3 7-(2-methoxyphenyl)-5-thioxo-4,5,6,7-tetrahydro-3H-thiazolo[4,5-d]pyrimidin-2-one 
• 398130-18-2 3-(2-methoxyphenyl)-4-(methylthio)-1H-pyrrole-2,5-dione 
• 1307299-64-4 (Z)-5-(2-methoxybenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents

Thalidomide and its analogs are immunomodulatory drugs that inhibit the production of certain inflammatory mediators associated with cancer. In the present work, a new series of thalidomide analogs was designed and synthesized to obtain new effective antitumor immunomodulatory agents. The synthesized compounds were evaluated for their cytotoxic activities against a panel of four cancer cell lines (HepG-2, HCT-116, PC3 and MCF-7). Compounds 33h, 33i, 42f and 42h showed strong potencies against all tested cell lines with IC50 values ranging from 14.63 to 49.90 μM comparable to that of thalidomide (IC50 values ranging from 32.12 to 76.91 μM). The most active compounds were further evaluated for their in vitro immunomodulatory activities via estimation of human tumor necrosis factor alpha (TNF-α), human caspase-8 (CASP8), human vascular endothelial growth factor (VEGF), and nuclear factor kappa-B P65 (NF-κB P65) in HCT-116 cells. Thalidomide was used as a positive control. Compounds 33h and 42f showed a significant reduction in TNF-α. Furthermore, compounds 33i and 42f exhibited significant elevation in CASP8 levels. Compounds 33i and 42f inhibited VEGF. In addition, compound 42f showed significant decrease in levels of NF-κB p65. Moreover, apoptosis and cell cycle tests of the most active compound 42f, were performed. The results indicated that compound 42f significantly induce apoptosis in HCT-116 cells and arrest cell cycle at the G2/M phase.

Microwave assisted urea-acetic acid catalyzed knoevenagel condensation of ethyl cyanoacetate and 1,3-Thiazolidine-2,4-dione with aromatic aldehydes under solvent free condition

Knoevengel condensation reaction of various aromatic aldehydes with ethyl cyanoacetate and 1,3-thiazolidinone-2,4-diones catalyzed by urea-acetic acid under solvent free condition where olefinic products were obtained in high yield within short reaction time.

New Route for the Synthesis of Thiazolidine 2,4dione Azepine Derivatives

A new facile ionic liquid mediated proficient method is developed for the synthesis of structurally new thiazepine and oxazepine derivatives of thiazolidine 2,4-dione. This protocol proceeds through, one-pot three component reaction between fused cyclic k

Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound

The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.

Sonochemistry: A good, fast and clean method to promote the synthesis of 5-arylidene-2,4-thiazolidinediones

The efficient synthesis of sixteen 5-arylidene-2,4-thiazolidinediones by aldol condensation reaction of 2,4-thiazolidinedione, mono- and di-substituted arenealdehydes and KOH using ultrasound irradiation is reported. The desired compounds were obtained in

Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry

Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.

Design, synthesis and characterization of some novel 3-coumarinyl- 5-aryliden-1,3-thiazolidine-2,4-diones and their antioxidant activity

In our effort to obtain biologically active compounds, new 3,5-disubstituted 1,3-thiazolidine-2,4- diones (5a - r) were synthesized. A series of 5-arylmethylidene-1,3-thiazolidine-2,4-diones (3a - r) were prepared by Knoevenagel reaction from 1,3-thiazolidine-2,4-dione (2) and appropriate aromatic aldehydes. Condensation of 3a - r with 7-hydroxy-4-bromomethyl-2-oxo- 2H-chromene (1) afforded novel 3-(7-hydroxy-2-oxo-2H-chromen-4-ylmethyl)-5- arylidene-1,3-thiazolidine-2,4-diones 5a - r. Compounds 3a - r and 5a - r were evaluated for their antioxidant activity (DPPH free radical scavenging activity).

Synthesis of some new pyrazolo[3,4-d]pyrimidines and thiazolo [4,5-d]pyrimidines and evaluation of their antimicrobial activities

The desired fused ring system 3-isopropyl-4-aryl-1,4,5,7-tetrahydro- pyrazolo[3,4-d]pyrimidine-6-thiones 4a-d were synthesized by the reaction of 5-isopropyl-2,4-dihydro-3-pyrazolone 1, thiourea and different aromatic aldehydes, while 7-aryl-5-thioxo-4,5,

PHAMACEUTICAL PREPARATIONS COMPRISING INSULIN

Novel preparations comprising ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer wherein the ligand is extended by protamine that are capable of prolonging the ac-tion of insulin preparations.

Stabilised insulin compositions

The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.