877681-24-8

Upstream product

• 186581-53-3 diazomethane 
• 877932-06-4 (2R)-2-hydroxy-2-(3-methylphenyl)propanoic acid 
• 136125-68-3 methyl 3-methylphenylglyoxylate 
• 544-97-8 dimethyl zinc(II) 
• 585-74-0 3-Methylacetophenone 
• 1124-20-5 2-(3-methylphenyl)propene 
• 875542-01-1 (2R)-2-(3-methylphenyl)propane-1,2-diol 

Downstream Products

• 875542-02-2 (5R)-5-methyl-5-(3-methylphenyl)oxazolidine-2,4-dione 
• 877681-25-9 (5R)-5-methyl-5-(3-methylphenyl)-N-trityl-oxazolidine-2,4-dione 
• 875542-03-3 (5R)-5-(3-bromomethylphenyl)-5-methyl-N-trityl-oxazolidine-2,4-dione 

Relevant academic research and scientific papers

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Benzimidazolones: A new class of selective peroxisome proliferator- activated receptor γ (PPARγ) modulators

A series of benzimidazolone carboxylic acids and oxazolidinediones were designed and synthesized in search of selective PPARγ modulators (SPPARγMs) as potential therapeutic agents for the treatment of type II diabetes mellitus (T2DM) with improved safety profiles relative to rosiglitazone and pioglitazone, the currently marketed PPARγ full agonist drugs. Structure-activity relationships of these potent and highly selective SPPARγMs were studied with a focus on their unique profiles as partial agonists or modulators. A variety of methods, such as X-ray crystallographic analysis, PPARγ transactivation coactivator profiling, gene expression profiling, and mutagenesis studies, were employed to reveal the differential interactions of these new analogues with PPARγ receptor in comparison to full agonists. In rodent models of T2DM, benzimidazolone analogues such as (5R)-5-(3-{[3-(5-methoxybenzisoxazol-3-yl)benzimidazol-1-yl]methyl}phenyl) -5-methylox-azolidinedione (51) demonstrated efficacy equivalent to that of rosiglitazone. Side effects, such as fluid retention and heart weight gain associated with PPARγ full agonists, were diminished with 51 in comparison to rosiglitazone based on studies in two independent animal models. (Figure presented)

Asymmetric addition of dimethylzinc to α-ketoesters catalyzed by (-)-MITH

(Chemical Equation Presented) This investigation describes the catalytic asymmetric addition of dimethylzinc to α-ketoesters in the presence of (-)-MITH (5) and triethyl borate as an additive to give the corresponding chiral α-hydroxy esters with good yie

INDOLES HAVING ANTI-DIABETIC ACTIVITY

Indoles of Formula (I) having -X-aryl-(CH2)x#191-oxazolidinedione and -X-heteroaryl-(CH2)X-oxazolidinedione substituents on the N atom of the indole ring, where x is 0 or 1, and -X-is a bond or -CH2-, and their thiazolidinedione analogs, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.

BENZOUREAS HAVING ANTI-DIABETIC ACTIVITY

Benzourea compounds of Formula I having aryl-(CH2)x-oxazolidinedione or aryl-(CH2)x-thiazolidinedione substituents on one of the N atoms of the benzourea ring, wherein x is 0 or 1, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia and other symptoms such as dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity, that are often associated with type 2 diabetes. I