1,8-Naphthyridines VI. Synthesis and anti-inflammatory activity of 5-(alkylamino)-N,N-diethyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides with a new substitution pattern on the triazole ring.
On the basis of the good anti-inflammatory properties shown by the 9-alkyl-N,N-dialkyl-5-(alkylamino)[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides 1, a series of analogues of such compounds, in which the 9-alkyl substituent was replaced by an ester or amide group (compounds 3a-i), was prepared and tested (inhibition of carrageenan-induced paw edema in the rat). Also two 5-(N-alkyl,N-acylamino) derivatives (compounds 4a,b) were synthesized and evaluated for the same purpose. Even though the general trend for these new [1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives was a decrease in activity compared with compounds 1, some of the new synthesized compounds exhibited still good anti-inflammatory properties.
Di Braccio
Mario
M
Dipartimento di Scienze Farmaceutiche, Università di Genova, Viale Benedetto XV, 3, 16132 Genova, Italy. dbraccio@unige.it
Grossi
Giancarlo
G
Roma
Giorgio
G
Piras
Daniela
D
Mattioli
Francesca
F
Gosmar
Marzia
M
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D002351:Carrageenan / Q000633:toxicity; D015195:Drug Design; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D007249:Inflammation / Q000188:drug therapy; D008297:Male; D009287:Naphthyridines / Q000737:chemistry*; D051381:Rats; D017207:Rats, Sprague-Dawley; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use
D000893:Anti-Inflammatory Agents; D009287:Naphthyridines; D014230:Triazoles; D002351:Carrageenan