Synthesis and antiviral activities of novel purinyl- and pyrimidinyl-carbanucleosides derived from indan

Abstract

Starting from (±)-trans- and (±)-ew-3-hydroxymethyl-l- indanol, novel 6-substituted purinylcarbanucleoside derivatives of indan were synthesised through a key coupling reaction with 6-chloropurine under Mitsunobu conditions. Suzuki-Miyaura reactions of the protected 6-chloropurine derivative with different arylboronic acids afforded the corresponding 6-arylpurinylcarba- nucleoside derivatives. Finally, three new 5-halouracilcarbanucleo-sides were prepared by the reaction of a uracilcarbanucleoside with different N-halosuccinimides. All of the new analogues were evaluated for antiviral activity against a wide variety of viruses.