EXCITATORY AMINO-ACID RECEPTOR LIGANDS - ASYMMETRIC-SYNTHESIS, ABSOLUTE STEREOCHEMISTRY AND PHARMACOLOGY OF (R)AND (S)-HOMOIBOTENIC ACID

被引：18

作者：

BISCHOFF, F ^{[1
]}

JOHANSEN, TN ^{[1
]}

EBERT, B ^{[1
]}

KROGSGAARDLARSEN, P ^{[1
]}

MADSEN, U ^{[1
]}

机构：

[1] ROYAL DANISH SCH PHARM,PHARMABIOTEC RES CTR,DEPT MED CHEM,DK-2100 COPENHAGEN,DENMARK

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1995年 / 3卷 / 05期

关键词：

D O I：

10.1016/0968-0896(95)00044-H

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The (R) and (S)-forms of 2-amino-3-(3-hydroxyisoxazol-5-yl)propio acid (homoibotenic acid, HIBO) were synthesized, using (S)-BOC-phenylalanine as a chiral auxiliary and their absolute stereochemistry correlated with that of (R)-Br-HIBO. The enantiomeric excesses for (R)-HIBO (1) (> 99.5%) and (S)-HIBO (2) (99.5%) were determined using chiral HPLC. Whereas compounds 1 and 2 were equipotent inhibitors of the binding of [H-3]glutamic acid in the presence of calcium chloride, 2 showed AMPA agonist activity and 1 very weak NMDA agonist activity.

引用

页码：553 / 558

页数：6

共 20 条

[1] INHIBITION OF [H-3] KAINIC ACID RECEPTOR-BINDING BY DIVALENT-CATIONS CORRELATES WITH ION AFFINITY FOR THE CALCIUM-CHANNEL [J].

BRAITMAN, DJ ;

COYLE, JT .

NEUROPHARMACOLOGY, 1987, 26 (09) :1247-1251

[2] RESOLUTION, ABSOLUTE STEREOCHEMISTRY, AND PHARMACOLOGY OF THE S-(+)-ISOMERS AND R-(-)-ISOMERS OF THE APPARENT PARTIAL AMPA RECEPTOR AGONIST (R,S)-2-AMINO-3-(3-HYDROXY-5-PHENYLISOXAZOL-4-YL)PROPIONIC ACID [(R,S)-APPA] [J].

EBERT, B ;

LENZ, S ;

BREHM, L ;

BREGNEDAL, P ;

HANSEN, JJ ;

FREDERIKSEN, K ;

BOGESO, KP ;

KROGSGAARDLARSEN, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (07) :878-884

[3] ISOXAZOLE AMINO-ACIDS AS GLUTAMIC-ACID AGONISTS - SYNTHESIS OF SOME ANALOGS AND HOMOLOGS OF IBOTENIC ACID [J].

HANSEN, JJ ;

KROGSGAARDLARSEN, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (08) :1826-1833

[4] STRUCTURAL, CONFORMATIONAL, AND STEREOCHEMICAL REQUIREMENTS OF CENTRAL EXCITATORY AMINO-ACID RECEPTORS [J].

HANSEN, JJ ;

KROGSGAARDLARSEN, P .

MEDICINAL RESEARCH REVIEWS, 1990, 10 (01) :55-94

[5] EXCITATORY AMINO-ACID AGONISTS - ENZYMIC RESOLUTION, X-RAY STRUCTURE, AND ENANTIOSELECTIVE ACTIVITIES OF (R)-BROMOHOMOIBOTENIC AND (S)-BROMOHOMOIBOTENIC ACID [J].

HANSEN, JJ ;

NIELSEN, B ;

KROGSGAARDLARSEN, P ;

BREHM, L ;

NIELSEN, EO ;

CURTIS, DR .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2254-2260

[6] ENZYMIC RESOLUTION AND BINDING TO RAT-BRAIN MEMBRANES OF THE GLUTAMIC-ACID AGONIST ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID [J].

HANSEN, JJ ;

LAURIDSEN, J ;

NIELSEN, E ;

KROGSGAARDLARSEN, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) :901-903

[7] QUANTITATIVE STUDIES ON SOME ANTAGONISTS OF N-METHYL D-ASPARTATE IN SLICES OF RAT CEREBRAL-CORTEX [J].

HARRISON, NL ;

SIMMONDS, MA .

BRITISH JOURNAL OF PHARMACOLOGY, 1985, 84 (02) :381-391

[8] CLONED GLUTAMATE RECEPTORS [J].

HOLLMANN, M ;

HEINEMANN, S .

ANNUAL REVIEW OF NEUROSCIENCE, 1994, 17 :31-108

[9] DIFFERENTIATION OF CL-/CA-2+-DEPENDENT AND SODIUM-DEPENDENT GLUTAMATE H-3 BINDING TO CORTICAL MEMBRANES FROM RAT-BRAIN BY HIGH-ENERGY RADIATION INACTIVATION ANALYSIS [J].

HONORE, T ;

DREJER, J ;

NIELSEN, M ;

BRAESTRUP, C .

JOURNAL OF NEURAL TRANSMISSION, 1986, 65 (02) :93-101

[10] COMPLEX STRUCTURE OF QUISQUALATE-SENSITIVE GLUTAMATE RECEPTORS IN RAT CORTEX [J].

HONORE, T ;

NIELSEN, M .

NEUROSCIENCE LETTERS, 1985, 54 (01) :27-32

← 1 2 →