3,5-Diphenyl-1H-pyrazole derivatives. IX. 2-substituted 4-phenyl-5-(3,5-diphenyl-1H-pyrazol-1-yl) pyrimidines with platelet antiaggregating and other activities.
The synthesis of 2-substituted 4-phenyl-5-(3,5-diphenyl-1H-pyrazol-1-yl)pyrimidines 4 a-e by reaction of 1-(1-dimethylaminomethylene-2-oxo-2-phenylethyl)-3,5-diphenyl-1H-pyrazol e with acetamidine, benzamidine, guanidine, guanidinaecetic acid and creatine, respectively, is described. The alpha-aminoacid derivatives 4 d and 4 e gave a series of amides 7 by coupling with primary or secondary amines in dimethylformamide (DMF) solution in the presence of diphenyl-phosphorylazide (DPPA) and triethylamine. Some compounds 4 and 7 showed a platelet antiaggregating activity in vitro superior or comparable to that of acetyl-salicylic acid, as well as moderate antihypertensive, local anesthetic, analgesic and antiinflammatory activities in rats and mice.
Bondavalli
F
F
Istituto di Scienze Farmaceutiche Dell'Università, Genova, Italy.
Bruno
O
O
Ranise
A
A
Schenone
P
P
D'Amico
M
M
Parrillo
C
C
Filippelli
W
W
Rossi
F
F
D000779:Anesthetics, Local / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology; D000959:Antihypertensive Agents / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010147:Pain Measurement; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011918:Rats, Inbred SHR
D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000959:Antihypertensive Agents; D010975:Platelet Aggregation Inhibitors; D011720:Pyrazoles; D011743:Pyrimidines