title: Structural Analogues of Selfotel.
abstract: A small library of phosphonopiperidylcarboxylic acids, analogues of NMDA antagonist selfotel (CGS 19755), was synthesized. First, the series of aromatic esters was obtained via a palladium-catalyzed cross-coupling reaction (Hirao coupling) of dialkyl phosphites with bromopyridinecarboxylates, followed by their hydrolysis. Then, hydrogenation of the resulting phosphonopyridylcarboxylic acids over PtO2 yielded the desired phosphonopiperidylcarboxylic acids. NMR studies indicated that the hydrogenation reaction proceeds predominantly by cis addition. Several compounds were obtained as monocrystal structures. Preliminary biological studies performed on cultures of neurons suggest that the obtained compounds possess promising activity toward NMDA receptors.
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology , Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Zofia A
authors.initials: ZA
authors.lastname: Dziuganowska
authors.affiliation: Faculty of Chemistry, Wrocław University , 14. F. Joliot-Curie Street, 50-383 Wrocław, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Ślepokura
authors.affiliation: AM2N, UMR 5253, ICGM, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
authors.forename: Jean-Noël
authors.initials: JN
authors.lastname: Volle
authors.affiliation: AM2N, UMR 5253, ICGM, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
authors.forename: David
authors.initials: D
authors.lastname: Virieux
authors.affiliation: AM2N, UMR 5253, ICGM, ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
authors.forename: Jean-Luc
authors.initials: JL
authors.lastname: Pirat
authors.affiliation: Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology , Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.
authors.forename: Paweł
authors.initials: P
authors.lastname: Kafarski