Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties

The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxy propyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypr opyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted p urine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluat ed on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cell s than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly ac tive against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were in active. (C) Elsevier, Paris.