Synthesis of 2-(aminocarbonylmethylthio)-1H-imidazoles as novel Capravirine analogues.
Bioorg Med Chem
; 13(13): 4209-20, 2005 Jul 01.
Article
en En
| MEDLINE
| ID: mdl-15896963
ABSTRACT
Different analogues of Capravirine (AG-1549) or S-1153 were prepared by synthesis of 2-(5-benzyl-4-isopropyl-1-methyl-2,3-dihydro-1H-imidazol-2-ylthio)acetamide (3a-c), ethyl [5-benzyl-1-(ethoxymethyl)-4-ethyl-1H-imidazol-2-ylthio]acetate (10), 2-[5-alkyl-4-substituted 1-(pyridin-4-ylmethyl)-1H-imidazol-2-ylthio]acetamides (12a-f), and 2-[5-benzyl-1-(benzyloxymethyl)-4-isopropyl-1H-imidazol-2-ylthio]acetamides (14a-l) from their corresponding amino acids through a sequence of reactions Dakin-West reaction, hydrolysis, condensation with thiocyanate derivatives, alkylation with 2-iodoacetamide and ethyl chloroacetate, and coupling with 4-pyridylmethyl chloride, ethoxymethyl chloride and benzyloxymethyl chloride. All the synthesized compounds were screened for their activity against HIV-1 (wild type) and some of them (especially Capravirine like structures) were found active.
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Banco de datos:
MEDLINE
Asunto principal:
Replicación Viral
/
VIH-1
/
Inhibidores de la Transcriptasa Inversa
/
Fármacos Anti-VIH
/
Imidazoles
Límite:
Humans
Idioma:
En
Año:
2005
Tipo del documento:
Article