Traceless synthesis of diketopiperazine fused tetrahydro-ß-carbolines on soluble polymer support.
Mol Divers
; 15(2): 569-81, 2011 May.
Article
en En
| MEDLINE
| ID: mdl-20936530
ABSTRACT
The Pictet-Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6-8 h to furnish soluble polymer-supported tetrahydro-ß-carboline in good yields. Further expansion at N-terminus of tetrahydro-ß-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a ß-carboline by amination of the resulting N-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Polímeros
/
Carbolinas
/
Técnicas Químicas Combinatorias
/
Dicetopiperazinas
Idioma:
En
Revista:
Mol Divers
Asunto de la revista:
BIOLOGIA MOLECULAR
Año:
2011
Tipo del documento:
Article