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Usage

Uses

Used in Pharmaceutical Industry:
2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-, (5Z)is used as an insulin sensitizer for the treatment of type 2 diabetes. It increases the body's sensitivity to insulin, helping to regulate blood sugar levels and manage the symptoms associated with the condition. This application is particularly beneficial for patients who have developed resistance to insulin or have difficulty controlling their blood glucose levels through diet and exercise alone.
Additionally, pioglitazone may also be used in combination with other diabetes medications to enhance their effectiveness and provide a more comprehensive approach to managing type 2 diabetes. Its role in improving insulin sensitivity makes it a valuable component in the treatment regimen for many individuals with this chronic condition.

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 123-08-0 4-hydroxy-benzaldehyde 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 79-11-8 chloroacetic acid 
• 327055-07-2 ethyl 5-phenyl-2-(4-hydroxyphenylmethylene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 
• 123-11-5 4-methoxy-benzaldehyde 
• 110-89-4 piperidine 

Downstream Products

• 123021-85-2 2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetic acid 
• 199114-66-4 ethyl 2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetate 
• 146062-49-9 rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Tetrabutylammonium bromide and K 2CO 3: An eco-benign catalyst for the synthesis of 5-Arylidene-1,3-Thiazolidine-2,4-diones via Knoevenagel condensation

Phase-Transfer catalyzed, energy-efficient and facile synthesis of 5-Arylidene-1,3-Thiazolidine-2,4-diones was developed. Three independent variables (temperature, bases and phase-Transfer catalyst (PTC)) were screened through one-factor-At-A time (OFAT) study. The optimum reaction conditions suggested by the OFAT analysis were the use of tetrabutylammonium bromide (8mol%) and potassium carbonate (1mmol) for the reaction at 100°C. The nitrogen of PTC stabilizes carbonyl groups of thiazolidine-2,4-dione (TZD). The active methylene hydrogen of TZD forms potassium salt with potassium carbonate and generates 5-Arylidene-1,3-Thiazolidine-2,4-diones (1-16) through nucleophilic attack on the carbonyl carbon of arylaldehydes. The prominent advantages of this new process are economic viability, shorter reaction time (15min), simple product isolation (non-chromatographic method), good to excellent yields (78-96%) and solvent-free conditions.

Experimental and theoretical study of substituent effect on 13C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones

The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidin-ediones have been performed by the use of quantum chemical methods. The calculated 13C NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their 13C NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with σ using SSP (single substituent parameter), field (σF) and resonance (σR) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at Cβ and C7 carbons, while reverse substituent effect was found for C α. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at Cβ carbon causes increased sensitivity of SCS C β to the resonance effect with increasing of electron-accepting capabilities of the group present at Cβ.

Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 μM).

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

Multi-target weapons: diaryl-pyrazoline thiazolidinediones simultaneously targeting VEGFR-2 and HDAC cancer hallmarks

In anticancer drug discovery, multi-targeting compounds have been beneficial due to their advantages over single-targeting compounds. For instance, VEGFR-2 has a crucial role in angiogenesis and cancer management, whereas HDACs are well-known regulators o

Synthesis and biological evaluation of thiazolidinedione derivatives of chalcones and flavones as antihyperglycemic and antidyslipidemic agents

A series of chalcone and flavone derivatives (6a-d, 9a-f) based on 2,4-thiazolidinedione have been synthesized and evaluated for in vivo antihyperglycemic activity in sucrose loaded (SLM) and streptozotocin (STZ) induced diabetic animal models and also fo

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.

Regioselectivity evaluation of the (Z)-5-(4-hydroxybenzylidene)-thiazolidine-2,4?dione alkylation in alkaline environment

Thiazolidine-2,4?dione represents a key heterocyclic core in medicinal chemistry because it has the ability to bind to a wide variety of protein targets and has been intensively studied for developing bioactive multitargeting agents. The N-alkylation of i

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.

De-novo design and synthesis of conformationally restricted thiazolidine-2,4-dione analogues: highly selective PPAR-γ agonist in search of anti-diabetic agent

In the present investigation, design, molecular docking simulations, and synthesis of few 2,4-thiazolidinedione for selective modulation of PPAR-gamma are reported. Further evaluation of anti-diabetic activity of few thiazolidine-2,4-diones is assessed using cell line analysis. The structures of the synthesized compounds were confirmed on the basis of FT-IR, 1H-NMR, and mass analyses. Acute toxicity study was done to by using Trypan blue assay and MTT assay of the synthesized compounds. Synthesized compounds were evaluated for their antihyperglycemic effect by glucose absorption assay. The compound code TZD4 showed highest percentage of glucose absorption by 3T3-L1 cells compared with control.