ChemInform Abstract: Synthesis of Acyclowyosine and Acyclo-3-methylguanosine, as Probes for Some Chemical and Biological Properties Resulting from the N-3 Substitution of Guanosine and Its Analogues.
Abstract
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ChemInform Abstract
The acetylation of compound (I), which is generated from acyclovir, followed by methylation and deacetylation yield the acyclowyosine (IV), which is transformed into the guanosine analogue (V). The direct coupling of 3-methylguanine with the appropriate chain component does not lead to the formation of (V), but its N-7 regioisomer is obtained instead. It is shown that electronic factors play an important role in the hydrolysis of 9-substituted 3-methylguanine derivatives. The compounds (IV) and (V) and their ribofuranosyl parents display no appreciable antiviral activity. This indicates the significance of the N-3 position in biological activity of acyclovir, which is a potent agent.
