74772-78-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Thiazolidinedione,5-[(4-hydroxyphenyl)methyl]is used as a metabolite of Pioglitazone for the treatment of type 2 diabetes. It plays a role in modulating insulin sensitivity and glucose metabolism in the body, helping to manage blood sugar levels in patients with diabetes.

InChI:InChI=1/C10H9NO3S/c12-7-3-1-6(2-4-7)5-8-9(13)11-10(14)15-8/h1-4,8,12H,5H2,(H,11,13,14)

Upstream product

• 17356-08-0 thiourea 
• 103788-60-9 (Z)-5-(4-hydroxyphenylmethylene)-2,4-thiazolidinedione 
• 100-02-7 4-nitro-phenol 
• 184840-77-5 5-[(4-methoxyphenyl)-methyl]thiazolidine-2,4-dione 
• 103788-60-9 5-[(4-hydroxyphenyl)methylene]-2,4-thiazolidinedione 
• 100126-02-1 methyl 2-bromo-3-(4-methoxyphenyl)propanoate 
• 73594-87-3 methyl 2-chloro-3-(4-methoxyphenyl)propionate 
• 104-94-9 4-methoxy-aniline 
• 101931-00-4 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione 
• 646519-84-8 5-{4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzylidene}-2,4-thiazolidene dione 
• 471295-98-4 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde 
• 646519-94-0 5-{4-[2-chloro-2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 123-08-0 4-hydroxy-benzaldehyde 
• 646519-89-3 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione hydrochloride 

Downstream Products

• 103787-88-8 5-[4-(2-Methyl-thiazol-4-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 107324-90-3 5-[4-(Benzothiazol-2-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 107324-89-0 5-[4-(Benzooxazol-2-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 85002-24-0 5-(4-geranyloxybenzyl)thiazolidine-2,4-dione 
• 103787-86-6 5-[4-(2-Phenyl-thiazol-4-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 107342-77-8 5-[4-(4-phenyl-2-thiazolylmethoxy)benzyl]-2,4-thiazolidinedione 
• 103787-90-2 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione 
• 103787-89-9 5-[4-(2-Methyl-oxazol-4-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 103787-91-3 5-[4-(2-Pyridin-3-yl-thiazol-4-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 1027242-96-1 5-[4-([1,3]dioxolan-2-ylmethoxy)-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 
• 150556-04-0 5-{4-[3-(2,5-dimethoxy-3,4,6-trimethylphenyl)propoxy]benzyl}thiazolidine-2,4-dione 
• 172648-12-3 5-[4-(2,2-diethoxyethoxy}benzyl]thiazolidine-2,4-dione 
• 691904-24-2 5-(4-([1,1'-biphenyl]-3-ylmethoxy)benzyl)thiazolidine-2,4-dione 

Relevant academic research and scientific papers

A novel chrysin thiazole derivative polarizes macrophages to an M1 phenotype via targeting TLR4

Tumor-associated macrophages (TAMs) are an important cause of tumorigenesis and tumor development. M2 macrophages can promote tumor growth while M1 macrophages kill tumor cells, therefore, polarizing macrophages to achieve a functional M1 phenotype could effectively play its anti-tumor role. In the current study, we synthesized a novel chrysin derivative which is termed as ChR-TD. And we found ChR-TD might be a ligand of TLR4 that polarized the TAMs towards M1 phenotype and played its anti-tumor role. Further study indicated that ChR-TD reprogrammed the macrophages into an M1 phenotype via TLR4 activation. Moreover, ChR-TD activated TLR4/NF-κB signaling pathway and promoted the NF-κB/p65 translocated into the nuclear, leading to the activation of NF-κB and proinflammatory cytokines release. In addition, type I interferon signaling was also activated by ChR-TD, leading to the expressions of IFN-α and IFN-β and its targeted genes NOS2, MCP-1 and IP-10 were significantly increased in macrophages. Importantly, these effects were disturbed in TLR4?/? macrophages, which are constructed by using CRISPR/Cas9 system. And the molecule docking simulation further indicated that ChR-TD could bind to TLR4 and might be a ligand of TLR4. Hence, these findings suggested that ChR-TD might be a ligand of TLR4 and can be used as a potential lead compound for tumors treatment.

The development of improved syntheses of PPARγ-sparing, insulin sensitizing thiazolidinedione-ketones

Ketones 2 (MSDC-0160) and 3 (MSDC-0602) had been selected for clinical development, however their initial syntheses were considered suboptimal for application deep into clinical trials. Difficulties ranging from the nature of the starting material, alcohol oxidation problems, epoxide opening regioisomeric issues, and endgame ketone redox problems had been encountered. Direct ketone introduction/maintenance was desired for maximum efficiency and convergence was found to be critically dependent upon the acidity of the nucleophilic species (13, 18) and the use of pre- or post-alkylative oximino-ether/oxime protection (vide infra). Improvements in overall yield for the syntheses of 2 (MSDC-0160) and 3 (MSDC-0602) from 20% (2) and 31% (3) respectively, to 44% (2) and 59% (3) were realized.

Whitening skin care productSkin-whitening cosmetic containing algae active extracts

The invention discloses a skin-whitening cosmetica whitening skin care product containing algae active extracts. The skin-whitening cosmetics iswhitening skin care product is prepared from the following raw materials in percentage by mass: 2 to 5 percent of hyaluronic acid, 0.5 to 1 percent of lecithin, 4 to 8 percent of glycerol, 1 to 5 percent of cetostearyl alcohol, 1 to 5.5 percent of glycerylstearate, 0.5 to 3 percent of polydimethylsiloxane, 0.5 to 1.5 percent of algal active extracts, 0.2 to 0.8 percent of whitening and anti-blackening agents, 2 to 6 percent of natural whitening grease, 0.5 to 1 percent of VC, 0.5 to 1 percent of VE, 0.1 to 0.35 percent of pH regulators, 1 to 5 percent of propanediol and the balance of deionized water. The raw material ingredients are scientifically proportioned; the activity of tyrosinase is inhibited internally in an inner aspect; the problem of melanin generation is fundamentally solved; in an outer aspectexternally, the active free radicalsare cleared through irideae extracts; the immunologic function of the skin is improved, so that the durable and continuous skin whitening effects can be achieved.

NOVEL PROCESS TO PREPARE PIOGLITAZONE VIA SEVERAL NOVEL INTERMEDIATES

A novel process for preparing thiazolidinediones, preferably Pioglitazone, as described. Also described are novel intermediates involved in its synthesis and process for their preparation and use in medicine.

SUBSTITUTED PIPERIDINE DERIVATIVES AND METHODS FOR PREPARING THE SAME

The present invention relates to a novel compound or a pharmaceutically acceptable salt thereof, a preparation method thereof and a pharmaceutical composition for treating metabolism-related disorder containing the same. Specifically, the present invention relates to a compound of the formula 1, which can activate GPR119 to treat metabolism-related disorders, including diabetes and related diseases, diabetes-related microvascular complications, diabetes-related macrovascular complications, cardiovascular abnormalities, metabolic syndrome and its constituent diseases, and obesity.

Design and synthesis of novel pyranone-based insulin sensitizers exhibiting in vivo hepatoprotective activity

Serious hepatic and cardiovascular complications after treatment with the thiazolidinedione (TZD) class of insulin sensitizers have significantly retarded the advancement of new TZD-based peroxisome proliferator-activated receptor agonists that bind with high affinity and selectivity. The aim of the present study is to design new antihyperglycemic agents that promote insulin sensitivity through partial adipogenesis as well as demonstrate beneficial hepatoprotective activity. The results indicated that among forty screened compounds, three of the novel pyranones at a dose of 10 μM increased the preadipocyte differentiation into adipocytes in 3T3-L1 cell lines. They showed an insulin-sensitizing effect by significantly increasing the glucose uptake and exhibited insulin resistance reversal. These compounds at a dose of 20 mg kg-1 significantly protected against thioacetamide-induced hepatotoxic changes in the serum biochemistry as compared to standard hepatoprotectant silymarin and also ameliorated the histopathological alterations in the liver tissues after acute liver injury in Swiss mice.

5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME

The present invention relates to 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by the following Chemical Formula [1], which is useful as an intermediate for synthesis of thiazolidinedione based compounds, a method for preparing the compound, and a method for preparing pioglitazone or pioglitazone hydrochloride, which is a thiazolidinedione based drug and useful in treating and preventing diabetes, using the 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by Chemical Formula [1] as an intermediate:

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.