New 2-substituted 2,3,3a,4-tetrahydro-1H-imidazo[5,1-c] [1,4]benzoxazin-1-ones as alpha 2-adrenoceptor antagonists.
The synthesis of new 2-imidazol(in)yl-alkyl derivatives of 2,3,3a,4-tetrahydro-1H-imidazo[5,1-c][1,4]benzoxazin-1-one is reported. Some compounds of the series have shown high affinity for alpha 2 receptors, high alpha 2/alpha 1 selectivity and alpha 2 antagonism in vitro (vas deferens). Owing to their selective alpha 2-antagonism associated to a novel structure, compounds 8 and 20 have been selected for further biological investigation as potential antidepressants.
Melloni
P
P
Farmitalia Carlo Erba Research & Development, Erbamont Group, Milano, Italy.
Banzatti
C
C
Heidempergher
F
F
Marazzi
G
G
Ricciardi
S
S
Vaghi
F
F
Varasi
M
M
D000317:Adrenergic alpha-Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D009132:Muscles / Q000187:drug effects; D009638:Norepinephrine / Q000494:pharmacology; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D014649:Vas Deferens / Q000187:drug effects
D000317:Adrenergic alpha-Antagonists; D007093:Imidazoles; D010078:Oxazines; D009638:Norepinephrine