Tetrahedron

Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support

G Oliviero, J Amato, N Borbone, S D'Errico, G Piccialli…

Index: Oliviero, Giorgia; Amato, Jussara; Borbone, Nicola; D'Errico, Stefano; Piccialli, Gennaro; Bucci, Enrico; Piccialli, Vincenzo; Mayol, Luciano Tetrahedron, 2008 , vol. 64, # 27 p. 6475 - 6481

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Citation Number: 15

Abstract

Herein, we report the solid-phase synthesis of several 5-aminoimidazole-4-(N-alkyl) carboxamide-1-ribosides (4-N-alkyl AICARs) and the corresponding 2′, 3′-secoriboside derivatives. The method uses the N-1-dinitrophenyl-inosine 5′-bonded to a solid support. This inosine derivative has the C-2 of the purine base strongly activated towards the attack of N-nucleophiles thus allowing the preparation of several N-1 alkylated inosine supports ...