Synthesis and metabotropic glutamate receptor activity of a 2-aminobicyclo[3.2.0]heptane-2,5-dicarboxylic acid, a molecule possessing an extended glutamate conformation

被引：7

作者：

Kozikowski, AP

Araldi, GL

Flippen-Anderson, J

George, C

Pshenichkin, S

Surina, E

Wroblewski, J

机构：

[1] Georgetown Univ, Med Ctr, Inst Cognit & Computat Sci, Drug Discovery Program, Washington, DC 20007 USA

[2] USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA

[3] Georgetown Univ, Med Ctr, Dept Pharmacol, Washington, DC 20007 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0960-894X(98)00146-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A photochemical approach to the synthesis of the aminobicycloheptane 6a is reported. This compound assumes an extended glutamate conformation, and for this reason was created to further probe the structural features relevant to achieving selectivity for the subtypes of the metabotropic glutamate family of receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：925 / 930

页数：6

相关论文

共 20 条

[1] Pharmacology and functions of metabotropic glutamate receptors [J].

Conn, PJ ;

Pin, JP .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1997, 37 :205-237

[2] PHOTOCHEMICAL REACTIONS OF SIMPLE ALICYCLIC ENONES [J].

EATON, PE .

ACCOUNTS OF CHEMICAL RESEARCH, 1968, 1 (02) :50-&

[3] A GENERAL MECHANISTIC SCHEME FOR INTRAMOLECULAR ELECTROCHEMICAL HYDROCYCLIZATIONS - MECHANISM OF THE ELECTROREDUCTIVE CYCLIZATION OF OMEGA-KETO-ALPHA,BETA-UNSATURATED ESTERS [J].

FRY, AJ ;

LITTLE, RD ;

LEONETTI, J .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :5017-5026

[4]

JOLY C, 1995, J NEUROSCI, V15, P3970

[5] METABOTROPIC GLUTAMATE RECEPTORS : NOVEL TARGETS FOR DRUG DEVELOPMENT [J].

KNOEPFEL, T ;

KUHN, R ;

ALLGEIER, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (09) :1417-1426

[6]

KOZIKOWSKI AP, IN PRESS J MED CHEM

[7]

LARUE V, 1995, J CHEM SOC P2, P111

[8] EXCITATORY AMINO-ACID NEUROTOXICITY AND NEURODEGENERATIVE DISEASE [J].

MELDRUM, B ;

GARTHWAITE, J .

TRENDS IN PHARMACOLOGICAL SCIENCES, 1990, 11 (09) :379-387

[9] SNB - CRYSTAL-STRUCTURE DETERMINATION VIA SHAKE-AND-BAKE [J].

MILLER, R ;

GALLO, SM ;

KHALAK, HG ;

WEEKS, CM .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :613-621

[10] Design, synthesis, and pharmacological characterization of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740): A potent, selective, and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties [J].

Monn, JA ;

Valli, MJ ;

Massey, SM ;

Wright, RA ;

Salhoff, CR ;

Johnson, BG ;

Howe, T ;

Alt, CA ;

Rhodes, GA ;

Robey, RL ;

Griffey, KR ;

Tizzano, JP ;

Kallman, MJ ;

Helton, DR ;

Schoepp, DD .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (04) :528-537