184840-77-5

Usage

Molecular weight

295.37 g/mol

Chemical structure

2,4-thiazolidinedione ring with a 4-methoxyphenylmethyl group attached to the 5-position

Contains

Both thiazolidinedione and 4-methoxyphenyl group

Common use

As an antidiabetic drug

Mechanism of action

Improves insulin sensitivity in the body

Potential benefits

Specific pharmaceutical properties or binding affinities due to the presence of the 4-methoxyphenyl group

Intended use

As a pharmacological agent for addressing insulin resistance and related metabolic disorders.

Upstream product

• 6320-51-0 (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione 
• 74942-48-6 (5Z)-5-(4-methoxybenzylidene)-1,3-thiazolidine-2,4-dione 
• 123-11-5 4-methoxy-benzaldehyde 
• 73594-87-3 methyl 2-chloro-3-(4-methoxyphenyl)propionate 
• 17356-08-0 thiourea 
• 6320-51-0 5-(4-methoxybenzylidene)thiazolidine-2,4-dione 

Downstream Products

• 74772-78-4 5-(4-hydroxybenzyl)-2,4-thiazolidinedione 
• 371244-62-1 5-{4-[(S)-1-(2-benzoxazolyl)pyrrolidine-2-carboxy]benzyl}thiazolidine-2,4-dione 
• 494870-54-1 5-{4-[(R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxy]benzyl}thiazolidine-2,4-dione 
• 494870-55-2 C₂₄H₂₅NO₆S 
• 872979-81-2 [5-(4-methoxy-benzyl)-2,4-dioxo-thiazolidin-3-yl]-acetic acid methyl ester 

Relevant academic research and scientific papers

5-Benzylidene, 5-benzyl, and 3-benzylthiazolidine-2,4-diones as potential inhibitors of the mitochondrial pyruvate carrier: Effects on mitochondrial functions and survival in Drosophila melanogaster

A series of thiazolidinediones (TZDs) were synthesized and screened for their effect on the mitochondrial respiration as well as on several mitochondrial respiratory system components of Drosophila melanogaster. Substituted and non-substituted 5-benzylidene and 5-benzylthiazolidine-2,4-diones were investigated. The effect of a substitution in position 3, at the nitrogen atom, of the thiozolidine heterocycle was also investigated. The designed TZDs were compared to UK5099, the most potent mitochondrial pyruvate carrier (MPC) inhibitor, in in vitro and in vivo tests. Compared to 5-benzylthiazolidine-2,4-diones 6–7 and 3-benzylthiazolidine-2,4-dione 8, 5-benzylidenethiazolidine-2,4-diones 2–5 showed more inhibitory capacity on mitochondrial respiration. 5-(4-Hydroxybenzylidene)thiazolidine-2,4-dione (3) and 5-(3-hydroxy-4-methoxybenzylidene)thiazolidine-2,4-dione (5) were among the best compounds that compared well with UK5099. Additionally, TZDs 3 and 5, showed no effects on the non-coupled respiration and weak effects on pathways using substrates such as proline, succinate, and G3P. 5-Benzylidenethiazolidine-2,4-dione 3 showed a positive effect on survival and lifespan when added to Drosophila standard and high fat diet. Interestingly, analog 3 completely reversed the effects of high fat diet on Drosophila longevity and induced metabolic changes which suggests an in vivo inhibition of MPC at the mitochondrial level.

Hydrogenation of 5-alkylidene-2,4-thiazolidiones on Pd/C catalysts under mild conditions: An alternative synthesis route to pioglitazone

The hydrogenation of 5-alkylidene-2,4-thiazolidiones was studied using Pd/C to establish an alternative process for pioglitazone synthesis. The reportedly sluggish reactivity was due to the high reaction temperature in formic acid. The conditions were improved to 1 atm at 296 K, which results in a quantitative product with a smaller amount of the catalyst. Graphical Abstract: [Figure not available: see fulltext.]

In vitro aldose reductase inhibitory activity of 5-benzyl-2,4- thiazolidinediones

Several 5-benzyl-2,4-thiazolidinediones (5-7) were synthesised and tested as in vitro aldose reductase (ALR2) inhibitors. Most of them, particularly N-unsubstituted 5-benzyl-2,4-thiazolidinediones 5 and (5-benzyl-2,4- dioxothiazolidin-3-yl)acetic acids 7,

Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

MATERIALS AND METHODS FOR THE TREATMENT OF DIABETES, HYPERLIPIDEMIA, HYPERCHOLESTEROLEMIA, AND ATHEROSCLEROSIS

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities.

Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

SUBSTITUTED BENZYLTHIAZOLIDINE-2,4-DIONE DERIVATIVES

The invention provides novel substituted benzylthiazolidine-2,4-dione derivatives that bind to receptor to activate as ligands of human peroxisome proliferator-activated receptor (PPAR) and exhibit blood glucose-decreasing action and lipid-decreasing acti