Chiral 3,3′-(1,2-Ethanediyl)-bis[2-(3,4-dimethoxyphenyl)-4-thiazolidinones] with anti-inflammatory activity. Part 11: Evaluation of COX-2 selectivity and modelling

Add time:07/15/2019    Source:sciencedirect.com

Anti-inflammatory/analgesic 3,3′-(1,2-ethanediyl)-bis[2-(3,4-dimethoxyphenyl)-4-thiazolidinones] 1, obtained as racemic mixtures (a) and mesoforms (b), have two equivalent stereogenic centres (C-2 and C-2′) and exist as RR, SS and RS isomers. The enantioseparation of 1a provided the single enantiomers that displayed different in vitro cyclooxygenase-1/cyclooxygenase-2 selectivity ratios. In particular the dextrorotatory compound is a highly selective COX-2 inhibitor and the levorotatory one is moderately selective. Instead, RS-meso isomer (1b) exhibited similar levels of inhibitory activity on both COX isozymes. The diastereo- and enantioselectivity has been explained by molecular modelling of RR, SS and RS compounds into COX-1 and COX-2 binding sites. Theoretical results indicated SS>RS>RR affinity order towards COX-2 isoenzyme, in agreement with in vitro and previous in vivo pharmacological results.

We also recommend Trading Suppliers and Manufacturers of (2S)-2-Amino-3-(3,4-dimethoxyphenyl)-2-methyl-propanoic acid (cas 10128-06-0). Pls Click Website Link as below: cas 10128-06-0 suppliers

Prev:Dependence of enantioseparation performance on structure of chiral selectors derived from N-cycloalkylcarbonyl chitosan
Next:Ammonolysis of (5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2-pyrroline with immobilized Candida antarctica lipase B (CAL B) in a packed bed reactor)