Synthesis of 7-(2-dimethylaminovinyl) derivatives of pyrazolo[1,5-a] pyrimidines, as precursors of new tricyclic series. Binding studies of BDZ receptor.
A series of 7-dimethylaminovinylpyrazolo[1,5-a]pyrimidines bearing an acetyl or an ethoxycarbonyl group at the 6-position turned out to be useful intermediates for the synthesis of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidines and 8H-pyrazolo[5',1':2,3]pyrimido[5,4-d][1,2]diazepines. These tricyclic derivatives were studied for their affinity for the central benzodiazepine receptor, and meaningful suggestions about the structure-affinity relationship were obtained. Some of the above intermediates were also reacted with S-methylthiourea, to give a mixture of pyrazolo[5',1':1,2]pyrimido[5,6-e][1,3]diazocines and pyrazolo[1,5-a]quinazolines.
Bruni
F
F
Dipartimento di Scienze Farmaceutiche, Università di Firenze, Italy.
Costanzo
A
A
Selleri
S
S
Guerrini
G
G
Giusti
L
L
Martini
C
C
Lucacchini
A
A
D001667:Binding, Competitive / Q000187:drug effects; D005445:Flunitrazepam / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000378:metabolism; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000378:metabolism; D011963:Receptors, GABA-A / Q000187:drug effects / Q000378:metabolism*; D013329:Structure-Activity Relationship
D011720:Pyrazoles; D011743:Pyrimidines; D011963:Receptors, GABA-A; D005445:Flunitrazepam