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-epoxypropyl ( 2a– 2c and 8a– 8c), 2,3-epoxypropyl ether ( 3), or 3-amino-2-hydroxypropyl ( 4a– 6c and 9a– 9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and...

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Bibliographic Details
Published in:European journal of medicinal chemistry 1999-05, Vol.34 (5), p.405-413
Main Authors: Raić-Malić, Silvana, Grdiša, Mira, Pavelic, Krešimir, Mintas, Mladen
Format: Article
Language:English
Subjects:
1H and 13C NMR
2D homo- and hetero-nuclear correlation spectroscopy
Antineoplastic agents
antitumour activity
antiviral activity
Biological and medical sciences
General aspects
Medical sciences
Pharmacology. Drug treatments
purine and pyrimidine nucleoside analogues
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Summary:The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl ( 2a– 2c and 8a– 8c), 2,3-epoxypropyl ether ( 3), or 3-amino-2-hydroxypropyl ( 4a– 6c and 9a– 9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and 8c showed marked inhibition of growth of human tumour cell lines (MiaPaCa2 and Raji), whilst the inhibitory effect of 6b was greater against Raji cells 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 active against the replication of HIV 1 (III B), while 2a- 2c and 8a- 8c were inactive.
ISSN:0223-5234
1768-3254
DOI:10.1016/S0223-5234(99)80090-7