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

被引：27

作者：

Oliviero, Giorgia ^{[1
]}

Amato, Jussara ^{[1
]}

Borbone, Nicola ^{[2
]}

D'Errico, Stefano ^{[1
]}

Piccialli, Gennaro ^{[1
]}

Bucci, Enrico ^{[3
]}

Piccialli, Vincenzo ^{[4
]}

Mayol, Luciano ^{[2
]}

机构：

[1] Univ Naples Federico 2, Dipartimento Chim Sostanze Nat, Fac Sci Biotecnol, I-80131 Naples, Italy

[2] Univ Naples Federico 2, Dipartimento Chim Sostanze Nat, Fac Farm, I-80131 Naples, Italy

[3] Bioind Pk Canavese SpA, I-10010 Turin, Italy

[4] Univ Naples Federico 2, Dipartimento Chim Organ & Biochim, Fac Sci MMFFNN, I-80126 Naples, Italy

来源：

TETRAHEDRON | 2008年 / 64卷 / 27期

关键词：

AICAR; nucleoside analogues; solid-phase synthesis; combinatorial chemistry;

D O I：

10.1016/j.tet.2008.04.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6475 / 6481

页数：7

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