Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides.
Bioorg Med Chem
; 23(23): 7422-38, 2015 Dec 01.
Article
em En
| MEDLINE
| ID: mdl-26558518
ABSTRACT
The synthesis and biological activity profiling of a large series of diverse pyrrolo[2,3-d]pyrimidine 4'-C-methylribonucleosides bearing an (het)aryl group at position 4 or 5 is reported as well as the synthesis of several phosphoramidate prodrugs. These compounds are 4'-C-methyl derivatives of previously reported cytostatic hetaryl-7-deazapurine ribonucleosides. The synthesis is based on glycosylation of halogenated 7-deazapurine bases with 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-methyl-ß-d-ribofuranose followed by cross-coupling and nucleophilic substitution reactions. The final compounds showed low cytotoxicity and several derivatives exerted antiviral activity against HCV or Dengue viruses at micromolar concentrations.
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MEDLINE
Assunto principal:
Antivirais
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Nucleosídeos de Purina
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Nucleotídeos de Purina
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Pró-Fármacos
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Antineoplásicos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article