Collect. Czech. Chem. Commun. 2006, 71, 1122-1129

The 3-Deaza and 7-Deaza Derivatives of 5'-Amino-5'-deoxy-5'-noraristeromycin

Minmin Yang, Tesfaye Serbessa and Stewart W. Schneller*

Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849, U.S.A.


The 3-deaza and 7-deaza derivatives of 5'-amino-5'-deoxy-5'-noraristeromycin (6 and 7, respectively) have been prepared from the common starting material (+)-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate (8). Two Pd(0)-catalyzed allylic substitution reactions afforded the desired azide intermediates, 12 and 16, which were transformed to target compounds by standard procedures. These compounds were evaluated against a large number of viruses and found to be inactive except for weak effect against hepatitis B virus: 6, EC50 4.7 μM (3TC EC50 0.056 μM); 7, EC50 4.8 μM (3TC EC50 0.063 μM).

Keywords: Deazapurines; Carbanucleosides; Imidazo[4,5-c]pyridines; Allylic substitution; Pyrrolo[2,3-d]pyrimidines; Carbocyclic nucleosides; Antivirals.

References: 17 live references.