Fluoro carbocyclic nucleosides: synthesis and antiviral activity of 2'- and 6'-fluoro carbocyclic pyrimidine nucleosides including carbocyclic 1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)-5-methyluracil and carbocyclic 1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)-5-iodouracil
- 1 January 1990
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 33 (1) , 179-186
- https://doi.org/10.1021/jm00163a030
Abstract
The racemic carbocyclic 2''-fluoroarabinosyl pyrimidine nucleosides, 8, 9 (C-FIAU), 12, and 13 (C-FMAU) and the 2''-fluororibosyl pyrimidine nucleosides 17, 20, and 21 were prepared from their respective protected 2''-fluoro amino diols 5 and 14. The carbocyclic 2'',2''-difluorothymidine analogue 27 was obtained from the protected difluoro amino diol 24 which was prepared from the ketone 23 and (diethylamino)sulfur trifluoride (DAST). The chiral carbocyclic 2''-deoxy-6''-fluorouridines 33, 34, 38, and 39 were synthesized from the protected 6-fluoro amino diols 30 and 36, which were prepared by reduction of the azides 28 and 35. C-FMAU (13) and C-FIAU (9) were active in vitro against HSV-1 with ID50 values of 4.4 and 11 .mu.g/mL, respectively, but they were inactive against HSV-2. The cytidine analogues 12 and 20 displayed modest activity in vitro against HSV-1 and HSV-2 but were inactive against human influenza A virus.This publication has 13 references indexed in Scilit:
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