Solid-phase synthesis of benzoxazoles from 3-nitrotyrosine.

Beebe, X; Wodka, D; Sowin, T J

Beebe, X; Wodka, D; Sowin, T J.

Afiliación

Beebe X; D4CP, Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, Illinois 60064, USA.

J Comb Chem ; 3(4): 360-6, 2001.

Article en En | MEDLINE | ID: mdl-11442393

RESUMEN

A method to synthesize benzoxazoles on solid phase using 3-nitrotyrosine as a scaffold has been developed. The synthesis couples N-protected 3-nitrotyrosine to polystyrene via a Wang-type linker. The polymer-supported 3-nitrotyrosine is deprotected and the resultant primary amine converted to a tertiary amine via sequential reductive alkylation using aromatic followed by unhindered aliphatic aldehydes. The phenol is acylated, and the nitro group is reduced using SnCl(2). The resulting amino ester is then dehydratively cyclized to a benzoxazole. The synthesis was developed for a large mix and split (50 x 50 x 50) combinatorial library. The single compounds presented herein represent a diverse array of the types of monomers amenable to the chemistry developed.

Asunto(s)

Benzoxazoles/síntesis química; Tirosina/análogos & derivados; Tirosina/síntesis química; Alquilación; Técnicas Químicas Combinatorias; Ciclización; Evaluación Preclínica de Medicamentos; Espectroscopía de Resonancia Magnética

Buscar en Google

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Tirosina / Benzoxazoles Idioma: En Revista: J Comb Chem Asunto de la revista: QUIMICA Año: 2001 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

Buscar en Google

Añadir a Mi BVS

Imprimir

XML

PubMed Links