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.
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.
Novoa de Armas
H
H
Center of Pharmaceutical Chemistry, Havana, Cuba.
Blaton
N
N
Peeters
O M
OM
De Ranter
C
C
Suárez Navarro
M
M
Verdecia Reyes
Y
Y
Ochoa Rodriguez
E
E
Morán del Prado
L
L
Martin León
N
N
Quinteiro Fernández
M
M
Seoane Prado
C
C
Soto Cámara
J L
JL
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
D002121:Calcium Channel Blockers; D004095:Dihydropyridines; D011804:Quinolines