A new, high yield regioselective reaction affording racemic and enantiomeric 1,2-dimethyl-3-[2-(6-substituted naphthyl)]-2H,5H-pyrrolines is reported. Compounds were provided by dehydration of the corresponding 1,2-dimethyl-3-[2-(6-substitutednaphthyl)]-3-hydroxypyrrolidines under microwave irradiation and solvent-free conditions. Pharmacological properties of enantiomeric compounds are also described; the analgesic activity was investigated by the hot plate test. A conformational analysis of the compounds was carried out by molecular modeling techniques with the aim to get information about the fitting to known analgesic pharmacophore models.
Microwave assisted synthesis of chiral pyrrolines with biological activity
COLLINA, SIMONA;LODDO, GUYA;BARBIERI, ANNALISA;LINATI, LAURA;AZZOLINA, ORNELLA
2004-01-01
Abstract
A new, high yield regioselective reaction affording racemic and enantiomeric 1,2-dimethyl-3-[2-(6-substituted naphthyl)]-2H,5H-pyrrolines is reported. Compounds were provided by dehydration of the corresponding 1,2-dimethyl-3-[2-(6-substitutednaphthyl)]-3-hydroxypyrrolidines under microwave irradiation and solvent-free conditions. Pharmacological properties of enantiomeric compounds are also described; the analgesic activity was investigated by the hot plate test. A conformational analysis of the compounds was carried out by molecular modeling techniques with the aim to get information about the fitting to known analgesic pharmacophore models.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
