title: omega-Dialkylaminoalkyl ethers of 6-(benzyl or phenyl)-1,3,3-trimethyl-2-oxabicyclo [2.2.2]octan-6-ol with platelet antiaggregating and local anesthetic activities.
abstract: The synthesis of 1,3,3-trimethyl-6-phenyl-2-oxabicyclo[2.2.2]octan-6-ol 2 and 6-benzyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol 3 starting from (+)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one and phenylmagnesium bromide or benzylmagnesium chloride, respectively, is described. Alcohols 2 and 3 gave a series of omega-dialkylaminoalkyl ethers 4 by reaction as sodium salts with omega-chloroalkyldialkylamines in toluene solution. Some compounds 4, in particular those derived from alcohol 2, showed a strong platelet antiaggregating activity in vitro, superior to that of acetylsalicylic acid, as well as in general an appreciable local anesthetic activity and a weak sedative effect in mice.
authors.affiliation: Istituto di Scienze Farmaceutiche dell'Università Viale Benedetto XV, Genova, Italy.
authors.forename: S
authors.initials: S
authors.lastname: Schenone
authors.forename: O
authors.initials: O
authors.lastname: Bruno
authors.forename: A
authors.initials: A
authors.lastname: Ranise
authors.forename: F
authors.initials: F
authors.lastname: Bondavalli
authors.forename: M L
authors.initials: ML
authors.lastname: Cenicola
authors.forename: C
authors.initials: C
authors.lastname: Losasso
authors.forename: M
authors.initials: M
authors.lastname: Carnevale
authors.forename: R
authors.initials: R
authors.lastname: Ottavo
authors.forename: M
authors.initials: M
authors.lastname: D'Antonio
mesh_terms: D000758:Anesthesia; D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D002725:Chloroform; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D010974:Platelet Aggregation / Q000187:drug effects; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013055:Spectrophotometry, Infrared; D014693:Ventricular Fibrillation / Q000139:chemically induced / Q000517:prevention & control
chemical_list: D000779:Anesthetics, Local; D001643:Bridged Bicyclo Compounds; D010975:Platelet Aggregation Inhibitors; D002725:Chloroform