Studies of Nucleosides and Nucleotides. LII. Purine Cyclonucleosides. (17). Synthesis and Properties of Cyclonucleosides derived from Inosine and Thioinosine
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概要
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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.
- 公益社団法人日本薬学会の論文
- 1972-03-25
著者
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池原 森男
Faculty of Pharmaceutical Sciences, Osaka University(Present address)
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村岡 全子
Department Of Chemistry Japan Women's University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
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