title: An improved synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT): a selective MT(2) melatonin receptor antagonist.
abstract: A novel, efficient and diastereoselective procedure was developed for the gram-scale synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT), a selective MT(2) melatonin receptor antagonist. The synthetic strategy involved the conversion of 4-phenyl-2-tetralone to enamide followed by diastereoselective reduction affording cis-4-P-PDOT in good yield. The mechanism of the reduction step was explored by employing deuterated reagents.
authors: Institute of Medicinal Chemistry, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors: Simone
authors: S
authors: Lucarini
authors: Annalida
authors: A
authors: Bedini
authors: Gilberto
authors: G
authors: Spadoni
authors: Giovanni
authors: G
authors: Piersanti
mesh_terms: D044123:Receptor, Melatonin, MT2 / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C114459:4-phenyl-2-propionamidotetraline; D044123:Receptor, Melatonin, MT2; D013764:Tetrahydronaphthalenes