Abstract
8, 2'-Anhydro-8-mercapto- 9-β-D-arabinofuranosyladenine (I), 8, 3'-anhydro-8-mercapto-9-β-D-xylofuranosyladenine (II) and 8, 5'-anhydro-8-mercapto-9-β-D-ribofuranosyladenine (III) were deaminated with barium nitrite in acetic acid to give the corresponding S-cycloinosines (IV-VI). These cyclonucleosides had characteristic properties in ultraviolet (UV), nuclear magnetic resonance (NMR), circular dichroism (CD) and mass spectra, which were as expected from those of adenosine cyclonucleosides. Compounds IV-VI were benzoylated on sugar OH groups and subjected to thiolation reaction using phosphorus pentasulfide in pyridine containing water. Deprotection either with sodium methoxide or ammonia in methanol gave 8, 2'-anhydro-6, 8-dimercapto-9-β-D-arabinofuranosylpurine (XVI), 8, 3'-anhydro-6, 8-dimercapto-9-β-D-xylofuranosylpurine (XVII) and 8, 5'-anhydro-6, 8-dimercapto-9-β-D-ribofuranosylpurine (XVIII), respectively. The structure of these cyclonucleosides was confirmed by their characteristic UV, CD, NMR and mass spectra. 6-Mercaptopurine cyclonucleosides were easily oxidized to form disulfides by air oxidation or iodine treatment.
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