1-Aminocyclopropane-1-carboxylic acid derivatives: a new, general synthesis and NMDA receptor complex binding affinity study.
A new synthesis of 1-aminocyclopropane-1-carboxylic acid and of its (E)- and (Z)-2-substituted analogues (R = CH3;i-Pr;C6H5) has been performed by means of the "diazo-addition" method, starting from N-(diphenylmethylene)-2,3-dehydro-1-amino-1-carboxylate precursors. The (E)- and (Z)-2-phenyl and the (Z)-2-methylcyclopropaneamino acids have been obtained with high diastereospecificity. All the cyclopropaneamino acids prepared were tested for their affinity for some glutamate receptors and resulted inactive, with the exception of compounds (E)-1b and (Z)-1c which showed a shallow displacement of [3H]-glycine binding.
Spadoni
G
G
Istituto di Chimica Farmaceutica, Università Degli Studi, Urbino, Italia.
Balsamini
C
C
Bedini
A
A
Mugnaini
M
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D001665:Binding Sites; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D005998:Glycine / Q000378:metabolism; D008297:Male; D051381:Rats; D017207:Rats, Sprague-Dawley; D016194:Receptors, N-Methyl-D-Aspartate / Q000378:metabolism; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D003521:Cyclopropanes; D016194:Receptors, N-Methyl-D-Aspartate; D005998:Glycine