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- Title
SYNTHESIS OF β-D-RIBONUCLEOSIDES DERIVED FROM DIPYRAZOLO[3,4-b:3',4'-d]PYRIDIN- 3-ONE SYSTEM.
- Authors
Bernardino, Alice M. R.; Nogueira, Christiane M.; de O. Lepesch, Carla M.; Gomes, Claudia R. B.; Schmitz, Francis J.; Romeiro, Gilberto A.; de S. Pereira, Helena; de P. P. Frughlhetti, Isabel C.; de Oliveira, Mara R. P.; de Souza, Maria C. B. V.; Leed, Marietta Y. W. T.; Chaves, Salma A.; Ferreira, Vitor F.
- Abstract
The new ribonucleosides 8-methyl-2,6-diphenyl-5-(2,3,5-tri-O-benzoyl-s-D-ribofuranosyl)-2.H,6H-dipyrazolo[3,4-b:3',4'-d]pyridin-3(5H)-one (la) and 8-methyl-2-(p-nitrophenyl)-6-phenyl-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H,6H-dipyrazolo[3,4-b:3',4'-d]pyridin-3(5H)-one (lb) were prepared from stannic chloride-catalyzed ribosylations of the corresponding heterocycles 6a and 6b. Attempts of dec-O-benzoylation of la and lb failed to give the free ribosides lc and Id. The effect of compounds la, lb, 6a and 6b on the catalytic activities of reverse transcriptase from recombinant immunodeficiency virus type 1 was evaluated. Compounds lb and 6b inhibited the RNA dependent DNA polymerase activity of the enzyme by more than 50% at a concentration of 70 μm. In contrast, human placental DNA polymerase activities 1D and 2D were unaffected by this concentration. The structures of the nucleosides are supported by ID and 2D-nmr techniques (nOdes, HMBC and HMQC experiments).
- Publication
Heterocyclic Communications, 1997, Vol 3, Issue 6, p527
- ISSN
0793-0283
- Publication type
Article