title: Highly diastereoselective synthesis of enantiopure naphthylaminoalcohols with analgesic properties.
abstract: The diastereoselective synthesis via Grignard reaction of enantiopure analgesic naphthylaminoalcohols has been performed. The chiral racemic key intermediate 3-dimethylamino-2-methyl-1-(naphthalen-2-yl)propan-1-one and enantiomers were prepared and transformed into the desired compounds by addition of the organometallic reagent. The chemical characterization of all diastereoisomers was accomplished by 1H NMR and HPLC analyses and the absolute configuration assigned by CD spectroscopy. The in vitro and in vivo profile has also been evaluated.
authors.affiliation: Dipartimento di Chimica Farmaceutica, Università di Pavia, Viale Taramelli 12, I-27100, Pavia, Italy. ornella.azzolina@unipv.it
authors.forename: Ornella
authors.initials: O
authors.lastname: Azzolina
authors.forename: Simona
authors.initials: S
authors.lastname: Collina
authors.forename: Mariangela
authors.initials: M
authors.lastname: Urbano
authors.forename: Emilio
authors.initials: E
authors.lastname: Fata
authors.forename: Guya
authors.initials: G
authors.lastname: Loddo
authors.forename: Laura
authors.initials: L
authors.lastname: Linati
authors.forename: Enrica
authors.initials: E
authors.lastname: Lanza
authors.forename: Annalisa
authors.initials: A
authors.lastname: Barbieri
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000586:Amination; D000701:Analgesics, Opioid / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D002942:Circular Dichroism; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D015394:Molecular Structure; D010146:Pain / Q000517:prevention & control*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000701:Analgesics, Opioid