An improved synthesis of cis-4-phenyl-2-propionamidotetralin (4-P-PDOT): a selective MT(2) melatonin receptor antagonist.
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.
Lucarini
Simone
S
Institute of Medicinal Chemistry, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
Bedini
Annalida
A
Spadoni
Gilberto
G
Piersanti
Giovanni
G
D044123:Receptor, Melatonin, MT2 / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C114459:4-phenyl-2-propionamidotetraline; D044123:Receptor, Melatonin, MT2; D013764:Tetrahydronaphthalenes