J. L. Kelley, Carl A. Miller, J. Selway
Jul 1, 1988
Citations
0
Influential Citations
6
Citations
Journal
European Journal of Medicinal Chemistry
Abstract
Abstract Several aminoacylamido derivatives of 9-benzyladenine and of 9-benzyl-6-dimethylaminopurine were synthesized for evaluation in anti-viral and anti-bacterial screens and in tests for inhibition of protein synthesis. The 9-(aminoacylamidobenzyl)purines were synthesized in two steps from the appropriate 9-(aminobenzyl)adenine 3 or 9-(aminobenzyl)-6-dimethylaminopurine 4 . Amines 3 and 4 were acylated with an N -carbobenzoxyamino acid via the mixed anhydride method to give the 9-( N -carbobenzoxyaminoacylamidobenzyl)purines 5–10 . The N -carbobenzoxy groups were removed by catalytic hydrogenolysis or with hydrogen bromide in acetic acid to give 9-(aminoacylamidobenzyl)purines 11–16 . Against rhinovirus serotype 1B, 6-dimethylamino-9-(3-phenylalanylamidobenzyl)-9 H -purine 16b had in vitro activity with an IC 50 = 17 μM.