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Pure Appl. Chem. Vol. 73, No. 9, pp. 1499-1509 (2001)

Pure and Applied Chemistry

Vol. 73, Issue 9


Opioid and sigma receptor studies. New developments in the design of selective sigma ligands*

Giuseppe Ronsisvalle1,#, Agostino Marrazzo1, Orazio Prezzavento1, Alfredo Cagnotto2, Tiziana Mennini2, Carmela Parenti1, and Giovanna M. Scoto1

1Department of Pharmaceutical Sciences, University of Catania, Viale Andrea Doria, 6, 95125 Catania; 2Department of Molecular Biochemistry and Pharmacology, Istituto di Ricerche Farmacologiche Mario Negri, Via Eritrea 62, 20157 Milano, Italy

Abstract: New racemic and chiral methyl 2-{[4-(4-chlorophenyl)-4-hydroxypiperi-din-1-yl]methyl}-1-phenylcyclopropanecarboxylate derivatives were synthesized in order to obtain sigma ligands with increased affinity and selectivity compared to (+)-MPCB and haloperidol. The cis-(±)-7 racemic mixture showed a better binding affinity and selectivity than the (±)-8 trans isomers. Between the two cis enantiomers, (+)-7, with configuration (1R,2S), showed a very high affinity and the best selectivity for s1. All compounds synthesized (7­9) showed a reduced or negligible affinity for opioid and dopaminergic D1 and D2 receptors. Nociceptive in vivo test confirms that (+)-7 (namely MR200), such as non-selective antagonist haloperidol, increased the analgesic effect induced by the k opioid selective ligand U50,488H and reversed the inhibiting effect of (+)-pentazocine on analgesia.

*Plenary lecture presented at the Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry, Budapest, Hungary, 2 –6 September 2001. Other presentations are published in this issue, pp. 1387-1509.
# Corresponding author.

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