[4-(3-Oxo-1,2-benzisothiazolin-2-yl)alkanoic, phenyl and phenoxyalkanoic acids: synthesis and anti-inflammatory, analgesic, and antipyretic properties].
Based on previous observations, the preparation, some physicochemical (partition coefficient, pKa) and pharmacological properties of 4-(3-oxo-1,2-benzisothiazolin-2-yl)alkanoic, benzoic, phenyl, phenoxyalkanoic acids and of some of their functional derivatives are reported. All new compounds were biologically examined for their antiphlogistic, analgesic and antipiretic actions, in comparison with those of 1,2-benzisothiazolin-2-one and with those of ibuprofen as the antiphlogistic, analgesic, antipyretic arylalkanoic prototype. Structure-activity relationships showed that the 1,2-benzisothiazolin-2-one and its new alkanoic and arylalkanoic derivatives have strong actions which are however specific for some of the tested pharmacological properties. From this point of view, the synthesized substances have a narrow spectrum of activity, if compared with ibuprofen which is at the same time an antiphlogistic, analgesic and antipiretic substance. The antiphlogistic and antipyretic activities of 4-(3-oxo-1,2-benzisothiazolin-2-yl)benzoic, phenylacetic and phenylmethylacetic acids and the antipyretic and analgesic actions of 3-oxo-1,2-benzisothiazolin-2-ylacetic acid, which are comparable or higher in "potency" than those of ibuprofen, are noteworthy.
Bordi
F
F
Istituti di Chimica Farmaceutica e Tecnica Farmaceutica, Facoltà di Farmacia, Università di Parma.
Catellani
P L
PL
Morini
G
G
Plazzi
P V
PV
Silva
C
C
Barocelli
E
E
Chiavarini
M
M
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D008297:Male; D051381:Rats; D011919:Rats, Inbred Strains; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000894:Anti-Inflammatory Agents, Non-Steroidal; D002264:Carboxylic Acids; D013844:Thiazoles
Acidi 4-(3-oxo-1,2-benzisotiazolin-2-il)alcanoici, fenil e fenossialcanoici: sintesi, proprietà antiflogistiche, analgesiche ed antipiretiche.