79137-59-0Relevant academic research and scientific papers
Novel 2,7-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids: Peroxisome proliferator-activated receptor γ partial agonists with protein-tyrosine phosphatase 1B inhibition
Otake, Kazuya,Azukizawa, Satoru,Takeda, Shigemitsu,Fukui, Masaki,Kawahara, Arisa,Kitao, Tatsuya,Shirahase, Hiroaki
, p. 998 - 1014 (2016/02/03)
A novel series of 2,7-substituted 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and biologically evaluated. (S)-2-(2-Furylacryloyl)-7-[2-(2-methylindane-2-yl)-5-methyloxazol-4-yl] methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid tert-butylamine salt (13jE) was identified as a potent human peroxisome proliferator-activated receptor γ (PPARγ)-selective agonist (EC50=85 nM) and human protein-tyrosine phosphatase 1B (PTP-1B) inhibitor (IC50=1.0 μM). Compound 13jE partially activated PPARγ, but not PPARα or PPARδ, and antagonized farglitazar, a full PPARγ agonist. Cmax after the oral administration of 13jE at 10 mg/kg was 28.6 μg/mL (53 μM) in male Sprague-Dawley (SD) rats. Repeated administration of 13jE and rosiglitazone for 14 d at 10 mg/kg/d decreased plasma glucose and triglyceride levels significantly in male KK-Ay mice. Rosiglitazone, but not 13jE, significantly increased the plasma volume and liver weight. In conclusion, 13jE showed stronger hypoglycemic and hypolipidemic effects and weaker hemodilution and hepatotoxic effects than rosiglitazone, suggesting that its safer efficacy may be due to its partial PPARγ agonism and PTP-1B inhibition.
α-Aminosaeuren als nucleophile Acylaequivalente, V. Sterisch gelenkte Michael-Addition von Oxazolin-5-on-Anionen an aktivierte Doppelbindungen; Synthese von 1,4-Dicarbonylverbindungen und γ-Oxonitrilen
Wegmann, Helmut,Steglich, Wolfgang
, p. 2580 - 2594 (2007/10/02)
Oxazolin-5-ones with bulky substituents like mesityl or 1-butylcyclohexyl at C-2 undergo triethylamine catalyzed addition to activated olefins exclusively at C-4.Hydrolysis of the derived 4,4-disubstituted 2-mesityl-2-oxazolin-5-ones 9 leads to N-mesitoyl
