RESUMEN
Surprisingly stable synperiplanar conformers of CFTA esters have led us to develop a new and very reliable method for assigning absolute configurations of even secondary alcohols having minimal structural differences, such as chiral benzhydrols and alpha-monodeuterated benzyl alcohols.
RESUMEN
We report the synthesis of optically active 2-aryl-2-fluoropropionic acids 2 as non-epimerizable mimics of 2-arylpropionic acids 1, a class of compounds which have been widely used as non-steroidal anti-inflammatory drugs (NSAIDs). This is a continuation of our research involving the design, synthesis, and evaluation of chiral fluorine-containing organic molecules as effective analogues of pharmacologically important compounds.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Propionatos/síntesis química , Propranolol/análogos & derivados , Conformación Molecular , Rotación Óptica , Propranolol/síntesis químicaRESUMEN
We investigated the cyclooxygenase (COX) inhibitory and anticancer activities of 2-aryl-2-fluoropropionic acids 1a-e. These fluorinated compounds showed lower inhibitory activity toward COX-1 than the corresponding non-fluorinated compounds 2a-e with retained inhibitory activity against COX-2 resulting in modification of the balance of COX-1/COX-2 inhibitions, and they showed little anticancer activity. Interesting differences of the activities between (S)- and (R)-enantiomers were observed in some cases.