Tricyclic heteroaromatic systems. Synthesis of 1,3 and 1,2 disubstituted [1]benzopyrano[4,3-b]pyrrol-4-ones and structure-activity relationships as benzodiazepine receptor ligands.
The synthesis of some 1,3- and 1,2- disubstituted [1]benzopyrano-pyrrol-4-ones is reported as well as their benzodiazepine receptor affinity, as measured by the ability to displace [3H]flunitrazepam from its specific central binding. The structure-activity relationships on the whole series of disubstituted [1]benzopyrano-pyrrol-4-ones show the importance of the presence of the 1-aryl substituent and the size limitation of the 3-substituent. The size of the latter seems also to be important for the "in vitro" efficacy.
Colotta
V
V
Dipartimento di Scienze Farmaceutiche, Università di Firenze, Italy.
Cecchi
L
L
Melani
F
F
Filacchioni
G
G
Martini
C
C
Gelli
S
S
Lucacchini
A
A
D000818:Animals; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D001667:Binding, Competitive / Q000187:drug effects; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D002417:Cattle; D002540:Cerebral Cortex / Q000187:drug effects / Q000378:metabolism; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005445:Flunitrazepam / Q000378:metabolism; D066298:In Vitro Techniques; D008024:Ligands; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D011963:Receptors, GABA-A / Q000187:drug effects*; D013329:Structure-Activity Relationship; D005680:gamma-Aminobutyric Acid / Q000378:metabolism
D001578:Benzopyrans; D008024:Ligands; D011758:Pyrroles; D011963:Receptors, GABA-A; D005680:gamma-Aminobutyric Acid; D005445:Flunitrazepam