Probing the reactivity of nebularine N1-oxide. A novel approach to C-6 C-substituted purine nucleosides

被引：15

作者：

D'Errico, Stefano ^{[1
]}

Piccialli, Vincenzo ^{[2
]}

Oliviero, Giorgia ^{[1
,3
]}

Borbone, Nicola ^{[1
]}

Amato, Jussara ^{[1
]}

D'Atri, Valentina ^{[1
]}

Piccialli, Gennaro ^{[1
,3
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

[2] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

[3] Univ Naples Federico II, Fac Sci Biotecnol, I-80131 Naples, Italy

来源：

TETRAHEDRON | 2011年 / 67卷 / 34期

关键词：

N-OXIDES; 1,3-DIPOLAR CYCLOADDITION; ORGANOMETALLIC REAGENTS; NUCLEOPHILIC ADDITIONS; NITRONES; ANALOGS; DESIGN; NUCLEOTIDES; OLIGONUCLEOTIDES; SHOWDOMYCIN;

D O I：

10.1016/j.tet.2011.06.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to the synthesis of purine nucleoside analogues, featuring the reaction of the C6-N1-O(-)aldonitrone moiety of 9-ribosyl-purine (nebularine) N1-oxide with some representative dipolarophiles, as well as Grignard reagents, is reported. Addition of Grignard reagents to the electrophilic C-6 carbon of the substrate allows a facile access to C-6 C-substituted purine nucleosides without using metal catalysts. 1.3-Dipolar cycloaddition processes lead to novel nucleoside analogues via opening, degradation or ring-enlargement of the pyrimidine ring of the base system of the first-formed isoxazoline or isoxazolidine cycloadduct. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6138 / 6144

页数：7

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