438190-27-3

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 39515-51-0 3-Phenoxybenzaldehyde 

Downstream Products

• 438190-36-4 {2,4-Dioxo-5-[1-(3-phenoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-3-yl}-acetic acid methyl ester 
• 262844-57-5 5-(3-phenoxy-benzyl)-thiazolidine-2,4-dione 
• 872979-76-5 [2,4-dioxo-5-(3-phenoxy-benzyl)-thiazolidin-3-yl]-acetic acid methyl ester 
• 438190-43-3 {2,4-Dioxo-5-[1-(3-phenoxy-phenyl)-meth-(Z)-ylidene]-thiazolidin-3-yl}-acetic acid 
• 1039558-78-5 C₁₈H₁₄N₂O₄S 
• 1307299-73-5 (Z)-5-(3-phenoxybenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones

Several (Z)-5-arylidene-2,4- hiazolidinediones were synthesized and tested as aldose reductase inhibitors (ARIs). The most active of the N-unsubstituted derivatives (2) exerted the same inhibitory activity of Sorbinil. The introduction of an acetic side chain on N-3 of the thiazolidinedione moiety led to a marked increase in lending inhibitory activi y, conducting to the discovery of a very potent ARI (4c), whose activity level (IC50 =0.1 μM) was in the same range of Tolrestat . Moreover, the corresponding methyl esters (3), devoid of any acidic functionality, showed appreciable inhibitory activity similar to that of the N-unsubstituted compounds. It was also found that the substitution pattern on the 5-benzylidene moiety markedly influenced the activity of N-unsubstituted 2,4-thiazolidinediones 2, compounds with substituents at the meta position being generally more effective than the para-substituted ones; however, this SAR was not evidenced in acetates 3 and acids 4. Copyright

In search for multi-target ligands as potential agents for diabetes mellitus and its complications—a structure-activity relationship study on inhibitors of aldose reductase and protein tyrosine phosphatase 1b

Diabetes mellitus (DM) is a complex disease which currently affects more than 460 million people and is one of the leading cause of death worldwide. Its development implies numerous metabolic dysfunctions and the onset of hyperglycaemia-induced chronic complications. Multiple ligands can be rationally designed for the treatment of multifactorial diseases, such as DM, with the precise aim of simultaneously controlling multiple pathogenic mechanisms related to the disease and providing a more effective and safer therapeutic treatment compared to combinations of selective drugs. Starting from our previous findings that highlighted the possibility to target both aldose reductase (AR) and protein tyrosine phosphatase 1B (PTP1B), two enzymes strictly implicated in the development of DM and its complications, we synthesised 3-(5-arylidene-4-oxothiazolidin-3-yl)propanoic acids and analogous 2-butenoic acid derivatives, with the aim of balancing the effectiveness of dual AR/PTP1B inhibitors which we had identified as designed multiple ligands (DMLs). Out of the tested compounds, 4f exhibited well-balanced AR/PTP1B inhibitory effects at low micromolar concentrations, along with interesting insulin-sensitizing activity in murine C2C12 cell cultures. The SARs here highlighted along with their rationalization by in silico docking experiments into both target enzymes provide further insights into this class of inhibitors for their development as potential DML antidiabetic candidates.

5-Arylidene-4-thiazolidinone derivatives active as antidegenerative agents on human chondrocyte cultures

5-Arylidene-2-oxo-4-thiazolidinones and 2-phenylimino analogues were evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1β and for their inhibitory capability against matrix metalloproteinase- 13. Our results indicated that 5-arylidene-4-thiazolidinone derivatives 1-9 exhibit antidegenerative activity and could block multiple cartilage destruction during the osteoarthritic process. Out of the selected compounds, (5-arylidene- 2,4-dioxothiazolidin-3-yl)acetic acids 7-9 showed significant effectiveness in reducing NO release and restoring normal levels of GAGs in chondrocytes treated with IL-1β. Moreover, benzoic acids 1, 5 and 6 proved to be effective MMP-13 inhibitors and were able to restore normal levels of GAGs.

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).

Identification of new non-carboxylic acid containing inhibitors of aldose reductase

Non-carboxylic acid containing bioisosteres of (5-arylidene-2,4-dioxothiazolidin-3-yl)acetic acids, which are active as aldose reductase (ALR2) inhibitors, were designed by replacing the carboxylic group with the trifluoromethyl ketone moiety. The in vitr

Synthesis, induced-fit docking investigations, and in vitro aldose reductase inhibitory activity of non-carboxylic acid containing 2,4-thiazolidinedione derivatives

In continuation of our studies, we here report a series of non-carboxylic acid containing 2,4-thiazolidinedione derivatives, analogues of previously synthesized carboxylic acids which we had found to be very active in vitro aldose reductase (ALR2) inhibit

5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases

4-(5-Arylidene-2,4-dioxothiazolidin-3-yl)methylbenzoic acids (2) were synthesized and evaluated in vitro as inhibitors of PTP1B and LMW-PTP, two protein tyrosine phosphatases (PTPs) which act as negative regulators of the metabolic and mitotic signalling

PHARMACEUTICAL PREPARATIONS COMPRISING INSULIN, ZINC IONS AND A ZINC-BINDING LIGAND

Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.

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.

PHARMACEUTICAL PREPARATIONS COMPRISING ACID-STABILISED INSULIN

Novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.