Abstract
8,2′-Anhydro-8-hydroxy-9-β-D-arabinofuranosylpurine cyclic 3′,5′-phosphates (Va,b) have been synthesized by intramolecular cyclization of the corresponding 8-hydroxy-2′-O-tosyl-9-β-D-ribofuranosylpurine cyclic 3′,5′-phosphates (IVa.b). A reductive cleavage of anhydro derivatives Va,b with H2S followed by Raney nickel desulfurization provided 9-β-D-arabinofuranosyladenine cyclic 3′,5′- (VIIa, c-ara-AMP) and 9-β-D-arabinofuranosylguanine cyclic 3′,5′-phosphate (VIIb, c-ara-GMP). c-Ara-AMP is cytotoxic to KB and HeLa cells in culture and exhibits significant antiviral activity against herpes simplex type 1 and type 2 infections. c-Ara-GMP is cytotoxic to KB, Sarcoma 180, and HeLa cells. Unlike c-ara-AMP, c-ara-GMP did not exhibit any significant antiviral activity.
Original language | English (US) |
---|---|
Pages (from-to) | 259-263 |
Number of pages | 5 |
Journal | Journal of Medicinal Chemistry |
Volume | 17 |
Issue number | 3 |
DOIs | |
State | Published - Mar 1 1974 |
ASJC Scopus subject areas
- Molecular Medicine
- Drug Discovery