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Synthesis and Antiviral Activities of Novel Purinyl- and Pyrimidinylcarbanucleosides Derived from Indan
1 , 1 , 1 , * 1 , 1 , 2 , 3
1  Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain
2  CIQ, Departamento de Química, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal
3  Rega Institute for Medical Research, Katholieke Universiteit Leuven, 3000 Leuven, Belgium

Abstract: Starting from (±)-trans- and (±)-cis-3-hydroxymethyl-1-indanol, novel 6-substituted purinylcarbanucleoside derivatives of indan (5, 6, 9, 10, 15 and 17) were synthesized 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-arylpurinylcarbanucleoside derivatives. Finally, three new 5-halouracilcarbanucleosides (19, 20 and 21) were prepared by reaction of uracilcarbanucleoside 18 with different N-halosuccinimides. All of the new analogues were evaluated for antiviral activity against a wide variety of viruses.
Keywords: Synthesis; Indan carbanucleosides; Mitsunobu reaction; Suzuki–Miyaura reaction; Antiviral activity