187142-96-7

Upstream product

• 262844-52-0 5-(4-(benzyloxy)benzylidene)thiazolidine-2,4-dione 
• 103788-60-9 5-[(4-hydroxyphenyl)methylene]-2,4-thiazolidinedione 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 291536-40-8 (Z)-5-(4-benzyloxyphenylmethylene)-2,4-thiazolidinedione 

Downstream Products

• 872979-78-7 [5-(4-benzyloxy-benzyl)-2,4-dioxo-thiazolidin-3-yl]-acetic acid methyl ester 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel thiazolidinediones as PPAR3/FFAR1 dual agonists

Diabetes mellitus is a chronic metabolic disorder that affects more than 180 million people worldwide. Peroxisome proliferator activated receptors (PPARs) are a group of nuclear receptors that have been targeted by the thiazolidinedione (TZD) class of compounds for the management of type II diabetes. PPAR3 is known to regulate adipogenesis and glucose metabolism. Another emerging target for the design of antidiabetic agents is the free fatty acid receptor 1 (FFAR1), previously known as GPR40. Agonists of this receptor were found to enhance insulin secretion in diabetic patients. It has been reported that some thiazolidinediones (TZDs) activate FFAR1 with micromolar potency. In this study, based on docking studies into the crystal structure of PPAR3 and a homology model of FFAR1, nineteen compounds were designed, synthesized, and biologically tested for agonistic activity on both receptors. Nine compounds showed promising dual activity, with two compounds, 11a and 5b, having affinities in the low micromolar range on both targets. These molecules represent the first antidiabetic agents that could act as insulin sensitizers as well as insulin secretagogues.

NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF

The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.

In vitro aldose reductase inhibitory activity of 5-benzyl-2,4- thiazolidinediones

Several 5-benzyl-2,4-thiazolidinediones (5-7) were synthesised and tested as in vitro aldose reductase (ALR2) inhibitors. Most of them, particularly N-unsubstituted 5-benzyl-2,4-thiazolidinediones 5 and (5-benzyl-2,4- dioxothiazolidin-3-yl)acetic acids 7,

Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities.

Regiospecific reduction of 5-benzylidene-2,4-thiazolidinediones and 4- oxo-2-thiazolidinethiones using lithium borohydride in pyridine and tetrahydrofuran

The novel regiospecific and general reduction of 5-benzylidene-2,4- thiazolidinediones and 5-benzylidene-4-oxo-2-thiazolidinethiones to the corresponding 5-benzyl derivatives has been accomplished using lithium borohydride in pyridine and tetrahydrofuran. Sodium borohydride and lithium chloride can also be used under these conditions, which represents a cheaper alternative to lithium borohydride. (C) 2000 Elsevier Science Ltd.