142649-87-4

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 142649-86-3 methanesulfonic acid 2-(benzyloxycarbonyl-methyl-amino)-ethyl ester 
• 67580-96-5 benzyl (2-hydroxyethyl)methylcarbamate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 901120-42-1 (Z)-phenylmethyl <2-<4-<(2,4-dioxo-5-thiazolidinylidene)methyl>phenoxy>ethyl>methylcarbamate 
• 158562-98-2 5-[4-(2-methylamino-ethoxy)-benzyl]-thiazolidine-2,4-dione 
• 142649-75-0 phenylmethyl <2-<4-<(2,4-dioxo-5-thiazolidinyl)methyl>phenoxy>ethyl>methylcarbamate 
• 122320-46-1 5-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]benzyl]-2,4-thiazolidinedione 
• 901120-46-5 C₁₈H₁₉N₃O₄S 

Relevant academic research and scientific papers

The synthesis of tethered ligand dimers for PPARγ-RXR protein heterodimers

The synthesis of heterodimeric compounds based on tethering the peroxisome proliferator-activated receptors (PPAR)γ agonist, Rosiglitazone and the RXR ligand Targetin is investigated. The synthesis of these compounds was accomplished via a convergent strategy, employed for preparing the appropriately-functionalized subunits of Rosiglitazone and Targetin and then attaching them to opposite ends of the tether. It was observed that a Mitsunobu reaction between the alcohol 5 and 4-hydroxy-benzaldehyde produced the ether 6 in a yield of 80%. It was concluded that the convergent strategy for the synthesis of these compounds could be easily adaptable to a larger and more diverse set of compounds as ligands for the PPARγ-RXR protein heterodimer.

benzyl>-2,4-thiazolidinediones as Potent Antihyperglycemic Agents

A series of -2,4-thiazolidinediones and benzyl>-2,4-thiazolidinediones was synthesized from the corresponding aldehydes.Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045).The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies.Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 BI/6 ob/ob mice.From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.