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 from which a small library of 4-N-alkyl AICAR derivatives has been synthesized. A set of new 4-N-alkyl AICA-2′,3′-secoriboside derivatives have also been obtained in high yields by solid-phase cleavage of the 2′,3′-ribose bond.
Synthesis of 4-N-alkyl and ribose-modified AICAR analogs on solid support / Oliviero, Giorgia; Amato, Jussara; Borbone, Nicola; D'Errico, Stefano; Piccialli, Gennaro; Bucci, Enrico; Piccialli, Vincenzo; Mayol, Luciano. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 64:27(2008), pp. 6475-6481. [10.1016/j.tet.2008.04.071]
Synthesis of 4-N-alkyl and ribose-modified AICAR analogs on solid support
OLIVIERO, GIORGIA;AMATO, JUSSARA;BORBONE, NICOLA;D'ERRICO, STEFANO;PICCIALLI, GENNARO;BUCCI, ENRICO;PICCIALLI, VINCENZO;MAYOL, LUCIANO
2008
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 from which a small library of 4-N-alkyl AICAR derivatives has been synthesized. A set of new 4-N-alkyl AICA-2′,3′-secoriboside derivatives have also been obtained in high yields by solid-phase cleavage of the 2′,3′-ribose bond.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.