D-3,4-CYCLOPROPYLGLUTAMATE ISOMERS AS NMDA RECEPTOR LIGANDS - SYNTHESIS AND ENANTIOSELECTIVE ACTIVITY

被引:56
作者
PELLICCIARI, R
NATALINI, B
MARINOZZI, M
MONAHAN, JB
SNYDER, JP
机构
[1] GD SEARLE & CO,SEARLE R&D DIV,ST LOUIS,MO
[2] GD SEARLE & CO,SEARLE R&D DIV,SKOKIE,IL 60077
关键词
D O I
10.1016/S0040-4039(00)94355-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dirhodium(II) tetraacetate catalyzed decomposition of ethyl diazoacetate in the presence of D-Cbz-vinylglycine methyl ester (11) afforded a mixture of the cyclopropyl esters D-CGA A-D (13) from which the corresponding 2R-acids 7-10 were obtained and their absolute configurations assigned. The (2R,3S,4R) α-(carboxycyclopropyl)glycine (D-CGA C, 9 resulted to be the most potent and selective among the NMDA receptor ligands yet reported. © 1990.
引用
收藏
页码:139 / 142
页数:4
相关论文
共 12 条
[1]   A NOVEL AND EFFICIENT SYNTHESIS OF L-VINYLGLYCINE [J].
HANESSIAN, S ;
SAHOO, SP .
TETRAHEDRON LETTERS, 1984, 25 (14) :1425-1428
[2]   DIRECTED RESOLUTION OF ENANTIOMERS VIA LIQUID-CHROMATOGRAPHY OF DIASTEREOMERIC DERIVATIVES .4. EXTREME LIQUID-CHROMATOGRAPHIC SEPARATION EFFECTS IN THE CASE OF DIASTEREOMERIC AMIDES CONTAINING POLAR SUBSTITUENTS [J].
HELMCHEN, G ;
NILL, G ;
FLOCKERZI, D ;
SCHUHLE, W ;
YOUSSEF, MSK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :62-63
[3]  
HELMCHEN G, 1979, ANGEW CHEM, V91, P65
[4]   EXCITATORY AMINO-ACID NEUROTRANSMISSION [J].
JOHNSON, RL ;
KOERNER, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2057-2066
[5]  
PELLICCIARI R, 1987, 6 CAM NOORDW S REC A, P73
[6]  
PELLICCIARI R, 1988, NEUROCHEM INT S1, V12, P26
[7]  
PELLICCIARI R, 1988, NEUROL NEUR, V46, P67
[8]  
PELLICCIARI R, 1986, 9 INT S MED CHEM BER, P118
[9]  
SHIMAMOTO K, 1989, TETRAHEDRON LETT, V30, P3803
[10]   A CONFORMATIONALLY RESTRICTED ANALOG OF L-GLUTAMATE, THE (2S,3R,4S) ISOMER OF L-ALPHA-(CARBOXYCYCLOPROPYL)GLYCINE, ACTIVATES THE NMDA-TYPE RECEPTOR MORE MARKEDLY THAN NMDA IN THE ISOLATED RAT SPINAL-CORD [J].
SHINOZAKI, H ;
ISHIDA, M ;
SHIMAMOTO, K ;
OHFUNE, Y .
BRAIN RESEARCH, 1989, 480 (1-2) :355-359