RESUMEN
A series of novel polyacetylene substituted 2-hydroxy acids and derivatives were prepared and characterized. Alkylation of butane-2,3-diacetal (BDA) protected glycolic acid with iodoalkyl substituted polyacetylene compounds gave the corresponding diacetal protected polyacetylene substituted 2-hydroxy acids. Diacetal deprotection through acid mediated hydrolysis, transesterification or aminolysis afforded the 2-hydroxy-polyacetylenic acid, ester or amide derivatives. Twenty one of these novel compounds were tested against 10 microbes of clinical importance and several of them showed good antimicrobial activity, in particular against Pseudomonas aeruginosa.
Asunto(s)
Amidas/química , Antifúngicos/química , Hidroxiácidos/química , Poliinos/química , Antifúngicos/síntesis química , Antifúngicos/farmacología , Ésteres , Pruebas de Sensibilidad Microbiana , Poliinos/síntesis química , Poliinos/farmacología , Pseudomonas aeruginosa/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
A methodology for the enantioselective synthesis of alpha-fluorinated beta2-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective fluorination and alkylation gave 7 in high diastereomeric excess (>95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta2-amino acids.