Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors

被引：38

作者：

Boyer, Nicolas ^{[1
,2
]}

Gloanec, Philippe ^{[3
]}

De Nanteuil, Guillaume ^{[3
]}

Jubault, Philippe ^{[1
,2
]}

Quirion, Jean-Charles ^{[1
,2
]}

机构：

[1] INSA, CNRS, Inst Rech Chim Organ Fine, UMR 6014, F-76131 Mont St Aignan, France

[2] Univ Rouen, F-76131 Mont St Aignan, France

[3] Inst Rech Servier, Div D Med Chem, F-92150 Suresnes, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 25期

关键词：

beta-lactams; fluorinated building blocks; 3,3-difluoroazetidin-2-ones; alpha; alpha-difluoro-beta-amino acids; reformatsky reaction;

D O I：

10.1002/ejoc.200800363

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of gem-difluorinated beta-lactams and gem-difluorinated beta-amino acids, each possessing a potential basic functional group, from ethyl bromodifluoroacetate and either imines (for beta-lactams) or N-(alpha-aminoalkyl) benzotriazoles (for beta-amino esters) was investigated. A series of these compounds were used for the design of novel metallocarboxy-peptidase inhibitors. N-Alkylation and N-acylation of these two versatile scaffolds were carried out, leading to the expected targets in moderate to good yields. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：4277 / 4295

页数：19

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