Premium
Synthesis of Acyclic Nucleosides with N ‐[(Benzyloxy)(aryl)methyl] Substituents as Potential HEPT, EBPU, and TNK‐651 Analogues
Author(s) -
KhalafiNezhad Ali,
Rad Mohammad Navid Soltani,
MoosaviMovahedi A. A.,
Kosari M.
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790073
Subject(s) - chemistry , electrophile , aryl , nucleobase , pyrimidine , reactivity (psychology) , stereochemistry , ab initio , silylation , imidazole , medicinal chemistry , computational chemistry , organic chemistry , catalysis , medicine , dna , biochemistry , alkyl , alternative medicine , pathology
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.