5835-54-1

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 1307299-76-8 (Z)-5-[(E)-3-phenylallylidene]-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione 
• 42518-29-6 3-phenyl-5-cinnamylidene-2,4-thiazolidinedione 

Relevant academic research and scientific papers

Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging

A transition metal-free protocol for the preparation of fluorescent and non-fluoresent 3-methylthio-4-arylmaleimides in a single step through a new rearrangement from thiazolidine-2,4-diones is described. By employing the optimized reaction conditions, a broad scope of derivatives was prepared in ≤97% yield. The reaction tolerated several substituted aryl groups, including the challenging preparation of pyridyl-containing derivatives. A series of control experiments strongly suggested that the new rearrangement involves a key isocyanate intermediate and a further reaction with in situ-generated methylthiomethyl acetate. The photophysical properties of some of the synthesized derivatives as well as their use in live cell imaging were also investigated, revealing that some of the substituted maleimides are capable of selectively staining different regions of the cells.

ANTICANCER 1,3-DIOXANE-4,6-DIONE DERIVATIVES AND METHOD OF COMBINATORIAL SYNTHESIS THEREOF

Compounds, methods of synthesis, and methods of cancer treatment by arylidene-1,3-dioxane-4,6-diones. A Meldrum's acid-based chemistry and hybrid solid-liquid method. The method includes protection of ketone and aldehyde components and simultaneous immobilization on the solid phase, introduction of substituents, grafts and derivatives compatible with the protection, detachment and restoration of active carbonyl reactivity, reaction of ketone library with malonate, reacting of the products with the aldehyde library in liquid phase and separation of the products by preparative HPLC.

Tau-Centric Multitarget Approach for Alzheimer's Disease: Development of First-in-Class Dual Glycogen Synthase Kinase 3β and Tau-Aggregation Inhibitors

Several findings propose the altered tau protein network as an important target for Alzheimer's disease (AD). Particularly, two points of pharmacological intervention can be envisaged: inhibition of phosphorylating tau kinase GSK-3β and tau aggregation process. On the basis of this consideration and on our interest in multitarget paradigms in AD, we report on the discovery of 2,4-thiazolidinedione derivatives endowed with such a profile. 28 and 30 displayed micromolar IC50 values toward GSK-3β, together with the capacity of inhibiting AcPHF6 aggregation of 60% and 80% at 10 μM, respectively. In addition, they showed PAMPA-BBB permeability, together with a suitable cellular safety profile. 30 also displayed inhibition of both K18 and full-length tau aggregations. Finally, both compounds were able to improve cell viability in an okadaic acid-induced neurodegeneration cell model. To the best of our knowledge, 28 and 30 are the first balanced, nontoxic, dual-acting compounds hitting tau cascade at two different hubs.

Discovery of novel cinnamylidene-thiazolidinedione derivatives as PTP-1B inhibitors for the management of type 2 diabetes

Protein tyrosine phosphatase-1B (PTP-1B) inhibition is a legitimate approach to combat type 2 diabetes and obesity as it corrects the insulin and leptin signalling cascades. In pursuing this, our goal is to discover compounds bearing small molecular scaffolds, and able to inhibit PTP-1B in a selective manner. In the present work, we have synthesized N3-substituted cinnamylidene-thiazolidinediones (4p-4x), and evaluated in vitro PTP-1B inhibitory activity, and in vivo anti-hyperglycaemic potential in streptozotocin-nicotinamide induced diabetic mice. Among various synthesized compounds, 4w exhibited the most potent in vitro PTP-1B inhibitory activity (IC50 ～ 6.52 μM) along with excellent in vivo anti-hyperglycaemic activity. Furthermore, molecular docking assisted 3D-QSAR study was performed on the synthesized compounds (4p-4x) for the exploration of the binding mode of interactions, prediction of the binding affinity, and identification of 3D-pharmacophoric features (steric and electrostatic) responsible for inhibitory activity. The docking results were in agreement with the biological activity results i.e. compound 4w showed the highest binding affinity with PTP-1B (MolDock score -123.715), which is comparable with ertiprotafib (MolDock score -125.183). The lead discovered can be used for the further development of cinnamylidene-thiazolidinedione derivatives as antidiabetic agents.

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).

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.