3,5-Diphenyl-1H-pyrazole derivatives. III--Esters from 1-(2-hydroxyethyl)-3,5-diphenyl-1H-pyrazole and its 4-bromo derivative with hypotensive, depressant, antiarrhythmic and analgesic activities.
The synthesis of dialkylaminoalkyl ethers (III a-g) by reaction of 1-(2-hydroxyethyl)-3,5-diphenyl-1H-pyrazole (I) sodium salt with a series of omega-chloroalkyldialkylamines is described. Cyanoethylation of alcohol (I) and its 4-bromo derivative (II) gave 2-cyanoethyl ethers (III h, i), one of which (III h) was hydrolyzed to the corresponding carboxylic acid. Cyanoethylation of 3,5-diphenylpyrazole (IV) and its 4-bromo derivative (V) yielded nitriles (VI) and (VII), respectively, which were hydrolyzed to the corresponding carboxylic acids (VIII) and (IX). Some of the above compounds showed considerable hypotensive, depressant, antiarrhythmic and analgesic activities in mice and rats, as well as a remarkable platelet antiaggregating activity in vitro. Moreover, the above compounds usually exhibited a moderate antiinflammatory activity in rats and infiltration anesthesia in mice.
Bondavalli
F
F
Istituto di Scienze Farmaceutiche, Università di Genova, Italy.
Bruno
O
O
Ranise
A
A
Schenone
P
P
Donnoli
D
D
Cenicola
M L
ML
Matera
C
C
Russo
S
S
Marmo
E
E
D000700:Analgesics / Q000138:chemical synthesis*; D000779:Anesthetics, Local / Q000138:chemical synthesis; D000818:Animals; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis; D000959:Antihypertensive Agents / Q000138:chemical synthesis*; D001794:Blood Pressure / Q000187:drug effects; D002492:Central Nervous System Depressants / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006339:Heart Rate / Q000187:drug effects; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D009043:Motor Activity / Q000187:drug effects; D010974:Platelet Aggregation / Q000187:drug effects; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats
D000700:Analgesics; D000779:Anesthetics, Local; D000889:Anti-Arrhythmia Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000959:Antihypertensive Agents; D002492:Central Nervous System Depressants; D010975:Platelet Aggregation Inhibitors; D011720:Pyrazoles; C058759:1-(2-hydroxyethyl)-3,5-diphenyl-4-bromo-1H-pyrazole; C058758:1-(2-hydroxyethyl)-3,5-diphenyl-1H-pyrazole