Synthesis of Acyclic Nucleosides with N‐[(Benzyloxy)(aryl)methyl] Substituents as Potential HEPT,EBPU, and TNK‐651 Analogues |
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| Authors: | Ali Khalafi‐Nezhad Mohammad Navid Soltani Rad A. A. Moosavi‐Movahedi M. Kosari |
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| Affiliation: | 1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran, (phone: +98‐711‐2284822;2. fax: +98‐711‐2280926);3. Department of Chemistry, Faculty of Basic Sciences, Shiraz University of Technology, Shiraz 71555‐313, Iran, (phone: +98‐711‐7261392;4. fax: +98‐711‐7354523);5. Institute of Biophysics‐Biochemistry, Tehran University, Tehran, Iran |
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| Abstract: | The syntheses of the novel acyclic nucleosides 5a – 5m , carrying different N‐[(benzyloxy)(aryl)methyl] substituents, are described (Scheme). These compounds could be prepared in medium‐to‐good yields by either direct or silyl‐assisted coupling of the electrophiles 6 with either purine or pyrimidine nucleobases, or with different imidazole derivatives. The reactivity of the positively charged electrophilic intermediates derived from 6 upon Cl? abstraction was rationalized by ab initio HF/6‐311G quantum‐mechanic calculations. The positive charge was found to be dispersed differently, depending on the electronic properties of the aryl substituents. |
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