Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties

被引：44

作者：

Adamczyk, M ^{[1
]}

Akireddy, SR ^{[1
]}

Johnson, DD ^{[1
]}

Mattingly, PG ^{[1
]}

Pan, Y ^{[1
]}

Reddy, RE ^{[1
]}

机构：

[1] Abbott Labs, Diagnost Div, Dept Chem, Abbott Pk, IL 60064 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 41期

关键词：

chemiluminescence; bioluminescence; coelenterazine; peroxymonocarbonate; assays; HYDROGEN-PEROXIDE; BIOLUMINESCENCE IMMUNOASSAY; WATASENIA PRELUCIFERIN; COELENTERAZINE ANALOGS; SQUID BIOLUMINESCENCE; ORGANOZINC REAGENTS; LUCIFERIN; MECHANISM; PYRAZINES; PEROXYMONOCARBONATE;

D O I：

10.1016/j.tet.2003.08.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8129 / 8142

页数：14

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