Design of novel conformationally restricted analogues of glutamic acid

被引：13

作者：

Conti, P

De Amici, M

Roda, G

Vistoli, G

Stensbol, TB

Bräuner-Osborne, H

Madsen, U

Toma, L

De Micheli, C

机构：

[1] Univ Milan, Ist Chim Farmaceut, I-20131 Milan, Italy

[2] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark

[3] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 09期

关键词：

1,3-dipolar cycloaddition; bicyclic amino acids; glutamic acid analogues; ionotropic glutamate receptors; metabotropic glutamate receptors;

D O I：

10.1016/S0040-4020(03)00079-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereomeric 3-carboxy-Delta(2)-isoxazoline-cyclopentane amino acids, which represent restricted conformations of glutamic acid, have been prepared through a strategy based on the 1,3-dipolar cycloaddition of ethoxycarbonylformonitrile oxide to a suitably protected 1-amino-cyclopent-2-enecarboxylic acid. These amino acids, assayed at iGluRs and mGluRs, proved to be inactive. The biological data have been accounted for through the comparison of their conformational. profile with that of a 3-carboxy-Delta(2)-isoxazolinyl proline (CIP-A) and (+/-)-1-aminocyclopentane-1,3-dicarboxylic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1443 / 1452

页数：10

共 36 条

[11] Synthesis and pharmacology of a new AMPA-kainate receptor agonist with potent convulsant activity [J].