Synthesis and antiviral activities of enantiomeric 1-[2-(hydroxymethyl)cyclopropyl] methyl nucleosides

Authors
Pierra, C Olgen, S Cavalcanti, SCH Cheng, YC Schinazi, RF Chu, CK
Citation
C. Pierra et al., Synthesis and antiviral activities of enantiomeric 1-[2-(hydroxymethyl)cyclopropyl] methyl nucleosides, NUCLEOS NUC, 19(1-2), 2000, pp. 253-268
Citations number
21
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
19
Issue
1-2
Year of publication
2000
Pages
253 - 268
Database
ISI
SICI code
1525-7770(2000)19:1-2<253:SAAAOE>2.0.ZU;2-7
Abstract
Cyclopropyl carbocyclic nucleosides have been synthesized from the key inte rmediate 2 which was converted to the mesylated cyclopropyl methyl alcohol 3. Condensation of compound 3 with various purine and pyrimidine bases gave the desired nucleosides. All synthesized nucleosides were evaluated for an tiviral activity and cellular toxicity. Among them adenine 22 and guanine 2 3 derivatives showed moderate antiviral activity against HIV-I and HBV. Non e of the other compounds showed any significant antiviral activities agains t HIV-1 HBV, HSV-1 and HSV-2 in vitro up to 100 mu M.