Synthesis of Guanine α-Carboxy Nucleoside Phosphonate (G-α-CNP), a Direct Inhibitor of Multiple Viral DNA Polymerases.
J Org Chem
; 83(17): 10510-10517, 2018 09 07.
Article
em En
| MEDLINE
| ID: mdl-30084243
ABSTRACT
The synthesis of guanine α-carboxy nucleoside phosphonate (G-α-CNP) is described. Two routes provide access to racemic G-α-CNP 9, one via base construction and the other utilizing Tsuji-Trost allylic substitution. The latter methodology was also applied to the enantiopure synthesis of both antipodes of G-α-CNP, each of which showing interesting antiviral DNA polymerase activity. Additionally, we report an improved multigram scale preparation of the cyclopentene building block 10, starting material for the preferred Tsuji-Trost route to 9.
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Base de dados:
MEDLINE
Assunto principal:
Nucleosídeos de Purina
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Inibidores da Síntese de Ácido Nucleico
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DNA Polimerase Dirigida por DNA
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Organofosfonatos
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Guanina
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article