6320-51-0

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Thiazolidinedione, 5-p-methoxybenzylideneis used as an antidiabetic medication for the treatment of type 2 diabetes. It is employed to improve the body's cells' responsiveness to insulin, which helps in maintaining a stable blood sugar level. However, it is important to note that the use of pioglitazone may be accompanied by several side effects, such as an increased risk of heart failure, bladder cancer, and bone fractures in females.

InChI:InChI=1/C11H9NO3S/c1-15-8-4-2-7(3-5-8)6-9-10(13)12-11(14)16-9/h2-6H,1H3,(H,12,13,14)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 123-11-5 4-methoxy-benzaldehyde 
• 4334-74-1 4-methoxybenzylidene thiosemicarbazone 
• 79-11-8 chloroacetic acid 
• 99819-42-8 3-allyl-5-(4-methoxybenzylidene)thiazolidine-2,4-dione 
• 67-56-1 methanol 
• 151-50-8 potassium cyanide 
• 292871-31-9 C₂₄H₂₂N₂O₄S 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 33402-67-4 sodium hydroxy(4-methoxyphenyl)methanesulfonate 
• 459-57-4 4-fluorobenzaldehyde 
• 5462-97-5 5-(4-methoxybenzylidene)-2-thioxo-4-thiazolidinone 
• 716336-73-1 1-benzylideneurea 
• 55111-58-5 5-(4-Methoxyphenylmethylene)-4-oxo-2-piperidino-2-thiazoline 

Downstream Products

• 83749-89-7 5-(4-Methoxybenzyliden)-3-hydroxymethylthiazolidinon-2,4 
• 74942-61-3 2-mercapto-3-(4-methoxyphenyl)-N-(N-methyl-N-phenylhydrazinocarbonyl)propenamide 
• 74948-39-3 3-hydrazino-6-(4-methoxybenzyl)-1,2,4-triazin-5(2H)-one 
• 74942-51-1 N-(hydrazinocarbonyl)-2-hydrazono-3-(4-methoxyphenyl)propanamide 
• 99819-42-8 3-allyl-5-(4-methoxybenzylidene)thiazolidine-2,4-dione 
• 1119274-20-2 7-(4-methoxyphenyl)-5-thioxo-4,5,6,7-tetrahydro-3H-thiazolo[4,5-d]pyrimidin-2-one 
• 464882-41-5 2-{[5-(4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]methyl}-1H-benzimidazole 

Relevant academic research and scientific papers

Multicomponent assembling of imidazole N-oxides, aldehydes and CH-acids: A simple and efficient approach to newly functionalized imidazole derivatives

An efficient and simple method for C2-functionalization of 2-unsubstituted imidazole N-oxides has been developed. It consists at the condensation of 2-unsubstituted imidazole N-oxides with aldehydes and CH-acids. This method permits broad variations in th

Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms

Different 2,4-thiazolidinedione-tethered coumarins 5a–b, 10a–n and 11a–d were synthesised and evaluated for their inhibitory action against the cancer-associated hCAs IX and XII, as well as the physiologically dominant hCAs I and II to explore their selec

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

Biological Prediction from Computational Approach, Synthesis, and Biological Evaluations of Newer Thiazolidine-2,4-dione Conjugates

Thiazolidine-2,4-dione is a toxophoric unit and its derivatives act as antimicrobial and antitubercular agents. Computational approach two-dimensional quantitative structure-activity relationship (2D-QSAR) was used to predict antitubercular activity of the thizolidine-2,4-dione derivatives. 2D-QSARS generated model using partial least squares regression method which predicted the statistically significant r2 = 0.3868, q2= 0.0193, pred_r2 = 0.5240, and F test = 3.7855. 2D-QSAR model equation denoted log(1/MIC) of the antitubercular activity correlated with thermodynamic descriptor SAMost Hydrophobic Hydrophilic Distance. Biological predicted derivatives of thiazolidine-2,4-dione (Z)-N-(2-(2,4-dichlorophenoxy)phenyl)-2-(5-substitutidene-2,4-dioxothiazolidin-3-yl)acetamide (C1-C10) were synthesized and spectrally evicted from IR, 1H NMR, 13C NMR and Mass spectral data analysis as well as biologically evaluated against antitubercular and antimicrobial activities. From the biologically evaluated derivatives, compounds C1, C2, C3 and C6 were found to be active against the different antimicrobial species. Compounds C1, C3 and C10 are more progressive than others against antitubercular species.

Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase

Dihydrodipicolinate synthase (DHDPS), responsible for the first committed step of the diaminopimelate pathway for lysine biosynthesis, has become an attractive target for the development of new antibacterial and herbicidal agents. Herein, we report the di

Synthesis and antimicrobial activity of a new series of thiazolidine-2,4-diones carboxamide and amino acid derivatives

Novel thiazolidine-2,4-dione carboxamide and amino acid derivatives were synthesized in excellent yield using OxymaPure/N,N'-diisopropylcarbodimide coupling methodology and were characterized by chromatographic and spectrometric methods, and elemental ana

A class of carbonic anhydrase IX/XII–selective carboxylate inhibitors

A small series of 2,4-dioxothiazolidinyl acetic acids was prepared from thiourea, chloroacetic acid, aromatic aldehydes, and ethyl-2-bromoacetate. They were assayed for the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isoforms of human (h) origin, the cytosolic hCA I and II, and the transmembrane hCA IX and XII, involved among others in tumorigenesis (hCA IX and XII) and glaucoma (hCA II and XII). The two cytosolic isoforms were not inhibited by these carboxylates, which were also rather ineffective as hCA IX inhibitors. On the other hand, they showed submicromolar hCA XII inhibition, with KIs in the range of 0.30–0.93 μM, making them highly CA XII-selective inhibitors.

Synthesis and anti-diabetic activity evaluation of phosphonates containing thiazolidinedione moiety

A sequence of substituted phosphonates containing the thiazolidinedione moiety was synthesized with good yields. The structures of all the synthesized compounds were confirmed by NMR (31P, 1H and 13C) and IR spectroscopy, mass spectrometry and C, H, N elemental analyses. In silico molecular docking study was also carried out to evaluate their interaction and binding modes on ligands against human PPAR γ protein for their anti-diabetic activity. From the docking results, it was determined that the compounds (Z)-dimethyl 5-(3-nitrobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7a), (Z)-dimethyl 5-(3-chloro-4-fluorobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7f), (Z)-dimethyl 5-(2,4-dichlorobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7e) and (Z)-dimethyl 5-((5-methoxypyridin-2-yl)methylene)?2,4-dioxothiazolidin-3-ylphosphonate (7j) have shown better binding energies (?7.8, ?7.6, ?7.5 and ?7.6 Kcal/mol) with the target gene, PPAR γ than the reference drug, Rosiglitazone (?7.4 Kcal/mol). In vitro anti-diabetic activity of the title compounds was also screened by standard α-amylase inhibition assay. Some of the tested compounds proved to possess promising activity when compared with the reference drug.

Design, synthesis and in vitro antiproliferative activity of new thiazolidinedione-1,3,4-oxadiazole hybrids as thymidylate synthase inhibitors

Thymidylate synthase (TS) has been an attention-grabbing area of research for the treatment of cancers due to their role in DNA biosynthesis. In the present study, we have synthesised a library of thiazolidinedione-1,3,4-oxadiazole hybrids as TS inhibitors. All the synthesised hybrids followed Lipinski and Veber rules which indicated good drug likeness properties upon oral administration. Among the synthesised hybrids, compound 9 and 10 displayed 4.5 and 4.4 folds activity of 5-Fluorouracil, respectively against MCF-7 cell line whereas 3.1 and 2.5 folds cytotoxicity against HCT-116 cell line. Furthermore, compound 9 and 10 also inhibited TS enzyme with IC50 = 1.67 and 2.21 μM, respectively. Finally, the docking studies of 9 and 10 were found to be consistent with in vitro TS results. From these studies, compound 9 and 10 has the potential to be developed as TS inhibitors.

5-(4-Methoxybenzylidene)thiazolidine-2,4-dione-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations

A novel series of 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives, 5a–g and 7a–f, was designed, synthesized, and evaluated for their anticancer activity against HepG2, HCT116, and MCF-7 cells. HepG2 and HCT116 were the most sensitive cell lines to the influence of the new derivatives. In particular, compounds 7f, 7e, 7d, and 7c were found to be the most potent derivatives of all the tested compounds against the HepG2, HCT116, and MCF-7 cancer cell lines. Compound 7f (IC50 = 6.19 ± 0.5, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively) exhibited a higher activity than sorafenib (IC50 = 9.18 ± 0.6, 8.37 ± 0.7, and 5.10 ± 0.4 μM, respectively) against HepG2 and MCF-7, cells but a lower activity against HCT116 cancer cells, respectively. Also, this compound displayed a higher activity than doxorubicin (IC50 = 7.94 ± 0.6, 8.07 ± 0.8, and 6.75 ± 0.4 μM, respectively) against HepG2 and MCF-7 cells, but nearly the same activity against HCT116 cells, respectively. All derivatives, 5a–g and 7a–f, were evaluated for their inhibitory activities against vascular endothelial growth factor receptor-2 (VEGFR-2). Among them, compound 7f was found to be the most potent derivative that inhibited VEGFR-2 at an IC50 value of 0.12 ± 0.02 μM, which is nearly the same as that of sorafenib (IC50 = 0.10 ± 0.02 μM). Compounds 7e, 7d, 7c, and 7b exhibited the highest activity, with IC50 values of 0.13 ± 0.02, 0.14 ± 0.02, 0.14 ± 0.02, and 0.18 ± 0.03 μM, respectively, which are more than the half of that of sorafenib. Furthermore, molecular docking was performed to investigate their binding mode and affinities toward the VEGFR-2 receptor. The data obtained from the docking studies highly correlated with those obtained from the biological screening.