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Synthesis of 3‐Hydroxy‐ and 3‐Carboxy‐Δ 2 ‐isoxazoline Amino Acids and Evaluation of Their Interaction with GABA Receptors and Transporters
Author(s) -
Conti Paola,
De Amici Marco,
Pinto Andrea,
Tamborini Lucia,
Grazioso Giovanni,
Frølund Bente,
Nielsen Birgitte,
Thomsen Christian,
Ebert Bjarke,
De Micheli Carlo
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600628
Subject(s) - chemistry , nitrile , amino acid , receptor , stereochemistry , agonist , transporter , cycloaddition , biochemistry , organic chemistry , catalysis , gene
Abstract A series of 3‐hydroxy‐ and 3‐carboxy‐Δ 2 ‐isoxazoline amino acids, structurally related to the GABA A agonist THIP and to the GABA uptake inhibitors THPO and exo ‐THPO, was prepared by means of synthetic strategies involving the 1,3‐dipolar cycloaddition of nitrile oxides. All derivatives were submitted to a pharmacological investigation at both GABA receptors and transporters. Unfortunately, all amino acids were devoid of activity except for a very low affinity at GABA A receptors, displayed by compounds 8 and 17 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)