title: Synthesis, structural studies and pharmacological activity of novel bicyclic compounds derived from 3,4-dihydropyridones: 4-aryl-7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines.
abstract: The purpose of this research is to characterize the possible vascular selectivity of a series of novel bicyclic compounds derived from 3,4-dihydropyridones. We describe the synthesis, structural study by X-ray analysis and quantum chemical calculations at semiempirical (AMI) and ab initio (HF/321G) levels and pharmacological activity of these 4-aryl-7,7-dimethyl-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines. In addition, the more favoured conformation for compounds 4a-c in solution was determined from the calculated and experimental proton coupling constants. We report the first computational study on the structure of octahydroquinolines. The results of ab initio (HF/3-21G) and semiempirical molecular orbital calculations (AMI) are compared with the data obtained by X-ray crystallographic study for 4a.
authors.affiliation: Center of Pharmaceutical Chemistry, Havana, Cuba.
authors.forename: H
authors.initials: H
authors.lastname: Novoa de Armas
authors.forename: N
authors.initials: N
authors.lastname: Blaton
authors.forename: O M
authors.initials: OM
authors.lastname: Peeters
authors.forename: C
authors.initials: C
authors.lastname: De Ranter
authors.forename: M
authors.initials: M
authors.lastname: Suárez Navarro
authors.forename: Y
authors.initials: Y
authors.lastname: Verdecia Reyes
authors.forename: E
authors.initials: E
authors.lastname: Ochoa Rodriguez
authors.forename: L
authors.initials: L
authors.lastname: Morán del Prado
authors.forename: N
authors.initials: N
authors.lastname: Martin León
authors.forename: M
authors.initials: M
authors.lastname: Quinteiro Fernández
authors.forename: C
authors.initials: C
authors.lastname: Seoane Prado
authors.forename: J L
authors.initials: JL
authors.lastname: Soto Cámara
mesh_terms: D000818:Animals; D002121:Calcium Channel Blockers / Q000138:chemical synthesis* / Q000494:pharmacology; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D015394:Molecular Structure; D009119:Muscle Contraction / Q000187:drug effects; D009131:Muscle, Smooth, Vascular / Q000187:drug effects / Q000502:physiology; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D011817:Rabbits
chemical_list: D002121:Calcium Channel Blockers; D004095:Dihydropyridines; D011804:Quinolines