SYNTHESIS OF CONFORMATIONALLY RESTRICTED ANALOGS OF KAINIC ACID - IS THE CONFORMATION OF THE C4-SUBSTITUENT OF KAINOID IMPORTANT TO ITS NEUROEXCITATORY ACTIVITY

被引：30

作者：

HASHIMOTO, K ^{[1
]}

OHFUNE, Y ^{[1
]}

SHIRAHAMA, H ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01094-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformationally restricted analogs of kainic acid, which have an azabicycto[3.3.0]octane system, were synthesized through the intramolecular addition reaction of trimethylenemethane to the alpha,beta-unsaturated ester. Every synthesized isomer showed very weak depolarizing activity. These results indicate that the plane of the isopropenyl group of kainic acid should be diagonal to the pyrrolidine ring to show potent activity.

引用

页码：6235 / 6238

页数：4

共 20 条

[1] SIMPLE ANALOGS OF ACROMELIC ACID, WHICH ARE HIGHLY-ACTIVE AGONISTS OF KAINATE TYPE NEUROEXCITANT
HASHIMOTO, K
HORIKAWA, M
SHIRAHAMA, H
[J]. TETRAHEDRON LETTERS, 1990, 31 (48) : 7047 - 7050
[2] SYNTHESIS OF NEW ACROMELIC ACID CONGENERS - NOVEL NEUROEXCITATORY AMINO-ACIDS ACTING ON GLUTAMATE RECEPTOR
HASHIMOTO, K
SHIRAHAMA, H
[J]. TETRAHEDRON LETTERS, 1991, 32 (23) : 2625 - 2628
[3] CONFIGURATIONAL VARIANTS OF HYDROXYPHENYLKAINOIDS - THEIR POTENT DEPOLARIZING ACTIVITIES IN THE RAT CENTRAL-NERVOUS-SYSTEM
HASHIMOTO, K
HORIKAWA, M
ISHIDA, M
SHINOZAKI, H
SHIRAHAMA, H
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (07) : 743 - 746
[4] Hashimoto K, 1991, TRENDS ORGANIC CHEM, V2, P1
[5] Heck R. F., 1985, PALLADIUM REAGENTS O
[6] SYNTHESIS OF 2-NORZIZAENE AND 9,10-DEHYDRO-2-NORZIZAENE "(7,7-DIMETHYL-6-METHYLIDENETRICYCLO [6.2.1.01,5]UNDEC-9-ENE) VIA INTRAMOLECULAR ALLYL CATION INDUCED CYCLOADDITION
HOFFMANN, HMR
HENNING, R
[J]. HELVETICA CHIMICA ACTA, 1983, 66 (03) : 828 - 841
[7] NOVEL KAINATE DERIVATIVES - POTENT DEPOLARIZING ACTIONS ON SPINAL MOTONEURONS AND DORSAL-ROOT FIBERS IN NEWBORN RATS
ISHIDA, M
SHINOZAKI, H
[J]. BRITISH JOURNAL OF PHARMACOLOGY, 1991, 104 (04) : 873 - 878
[8] PALLADIUM-CATALYZED REACTIONS OF ALLYLIC ELECTROPHILES WITH ORGANO-METALLIC REAGENTS - A REGIOSELECTIVE 1,4-ELIMINATION AND A REGIO- AND STEREOSELECTIVE REDUCTION OF ALLYLIC DERIVATIVES
MATSUSHITA, H
NEGISHI, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) : 4161 - 4165
[9] MCGEER E, 1978, KAINIC ACID AS TOOL
[10] A SELECTIVE 1,2-REDUCTION OF GAMMA-AMINO-ALPHA, BETA-UNSATURATED ESTERS BY MEANS OF BF3.OET2-DIBAL-H SYSTEM - HIGHLY VERSATILE CHIRAL BUILDING-BLOCKS FROM ALPHA-AMINO-ACIDS
MORIWAKE, T
HAMANO, S
MIKI, D
SAITO, S
TORII, S
[J]. CHEMISTRY LETTERS, 1986, (05) : 815 - 818

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