Synthesis and alpha4beta2 nicotinic affinity of 2-pyrrolidinylmethoxyimines and prolinal oxime ethers
Articolo
Data di Pubblicazione:
2004
Citazione:
Synthesis and alpha4beta2 nicotinic affinity of 2-pyrrolidinylmethoxyimines and prolinal oxime ethers / M. Pallavicini, B. Moroni, C. Bolchi, F. Clementi, L. Fumagalli, C. Gotti, S. Vailati, E. Valoti, L. Villa. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - 14:23(2004), pp. 5827-5830.
Abstract:
Homochiral E and Z isomers of N -methylprolinal O -isopropyloxime and (1-methyl-2-pyrrolidinyl)methoxyimines were synthesized as candidate bioisosteres of nicotine and its isoxazolic analogue ABT 418. Two of them, namely (S)-2-isopropylideneaminooxymethyl- and (Z)-(S)-2-ethylideneaminooxymethyl-1-methylpyrrolidine, proved to bind at α4β2 nicotinic acetylcholine receptor with submicromolar affinity and remarkable selectivity over α7 and muscarinic receptors thus supporting the hypothesized bioisosteric relationship between their methyloxyimino group and the aromatic heterocycles of the reference ligands.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Affinity; Bioisostere; Ligand; nAChR; Neuronal nicotinic acetylcholine receptor; Nicotine; Oxime ether
Elenco autori:
M. Pallavicini, B. Moroni, C. Bolchi, F. Clementi, L. Fumagalli, C. Gotti, S. Vailati, E. Valoti, L. Villa
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