A solid-phase approach to the synthesis of N-1-alkyl analogues of cyclic inosine-diphosphate-ribose (cIDPR)

被引：27

作者：

Oliviero, Giorgia ^{[1
]}

D'Errico, Stefano ^{[1
]}

Borbone, Nicola ^{[1
]}

Amato, Jussara ^{[1
]}

Piccialli, Vincenzo ^{[2
]}

Varra, Michela ^{[1
]}

Piccialli, Gennaro ^{[1
]}

Mayol, Luciano ^{[1
]}

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

来源：

TETRAHEDRON | 2010年 / 66卷 / 10期

关键词：

CALCIUM-RELEASE ACTIVITY; ADP-RIBOSE; CARBOCYCLIC-RIBOSE; CHEMICAL-SYNTHESIS; SUBSTITUTION; DERIVATIVES; MIMICS; N-1;

D O I：

10.1016/j.tet.2010.01.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here an efficient solid-phase synthesis of N-1-alkyl-substituted analogues of cyclic inosine-diphosphate-ribose (cIDPR), a mimic of cyclic ADP-ribose (cADPR). Our synthetic strategy makes use of a polystyrene support to which inosine was bonded through a 2',3'-acetal linkage. Insertion of a ea-hydroxy-polymethylene chain of variable length on N-1, followed by conversion into N-1-alkylinosine-bisphosphate derivatives and cyclization, allowed to obtain analogues of cIDPR of various ring size. The cyclization step was carried out both in solid-phase and in solution by pyrophosphate bond formation. The effect of the N-1-polymethylene chain length on the cyclization yields as well as the reaction conditions, which led to the solid-phase pyrophosphate bond formation, were thoroughly investigated. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1931 / 1936

页数：6

共 22 条

[11] Substitution at the 8-position of 3"-deoxy-cyclic ADP-carbocyclic-ribose, a highly potent Ca2+-mobilizing agent, provides partial agonists [J].