178610-75-8

Upstream product

• 178610-70-3 ethyl (E)-4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxycinnamate 
• 178610-74-7 4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]butyronitrile 

Downstream Products

• 178610-77-0 isopropyl 5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-hydroxyvalerate 
• 207728-19-6 5-[4-(2-furan-2-yl-5-methyl-oxazol-4-ylmethoxy)-3-methoxy-phenyl]-2-oxo-pentanoic acid isopropyl ester 
• 1027493-60-2 2-{2-[4-(2-furan-2-yl-5-methyl-oxazol-4-ylmethoxy)-3-methoxy-phenyl]-ethyl}-3-oxo-succinic acid diisopropyl ester 
• 178610-76-9 isopropyl 4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]butyrate 

Relevant academic research and scientific papers

Novel 5-substituted 2,4-thiazolidinedione and 2,4-oxazolidinedione derivatives as insulin sensitizers with antidiabetic activities

Two novel classes of 2,4-thiazolidinediones and 2,4-oxazolidinediones with an ω-(azolylalkoxyphenyl)alkyl substituent at the 5-position were prepared and their antidiabetic effects were evaluated in two genetically obese and diabetic animal models, KKAy mice and Wistar fatty rats. A large number of the 2,4-thia(oxa)zolidinediones showed potent glucose- and lipid-lowering activities. The antidiabetic activities of the 2,4-oxazolidinediones were superior to those of the 2,4-thiazolidinediones. Among the compounds, both enantiomers of 5-[3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3- methoxyphenyl]propyl]-2,4-oxazolidinedione (64), one of the most interesting compounds in terms of activity, were synthesized by using an asymmetric O-acetylation of the corresponding α-hydroxyvalerate (26) with immobilized lipase, followed by cyclization of the oxazolidinedione ring. (R)-(+)-64 showed more potent glucose-lowering activity (effective dose (ED)25 = 0.561 mg/kg/d) than (S)-(-)-64 (ED25 > 1.5 mg/kg/d) or pioglitazone (ED25 = 6 mg/kg/d) in KKAy mice. It also exhibited a 10-fold more potent antidiabetic activity (ED25 = 0.05 mg/kg/d) than pioglitazone (ED25 = 0.5 mg/kg/d) in Wistar fatty rats. The antidiabetic effects of this compound are considered to be due to its potent agonistic activity for peroxisome proliferator-activated receptor γ (EC50 = 8.87 nM).

Oxazolidinedione derivatives, their production and use

2,4-Oxazolidinedione derivative represented by the formula: STR1 wherein R stands for an optionally substituted hydrocarbon residue or heterocyclic group; Y stands for a group represented by --CO--, --CH(OH)-- or --NR3 -- (wherein R3 stands for an optionally substituted alkyl group); m is 0 or 1; n is 0, 1 or 2; A stands for a C1-7 divalent aliphatic hydrocarbon group; R1 stands for hydrogen or an alkyl group; ring E stands for a benzene ring having 1 or 2 substituents; L and M respectively stand for hydrogen, or L and M may optionally be combined with each other to form a bond; with a proviso that the partial formula: STR2 does not include the formula: STR3 wherein R' stands for an alkyl group; or a salt thereof, which has excellent actions of lowering blood sugar and lipid in blood.