Synthesis of mannich bases of arylidenepyridazinones as analgesic agents

✍ Scribed by Catherine Rubat; Pascal Coudert; Eliane Albuisson; Janine Bastide; Joele Couquelet; Pierre Tronche

• Book ID: 102410381
• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 392 KB
• Volume: 81
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600811108

✦ Synopsis

A series of 5-arylidenepyridazin-3-ones substituted in the 2-position by an arylpiperazinoalkyl moiety (2-16) was synthesized and evaluated for analgesic activity. In the phenylbenzoquinone-induced writhing test, Mannich bases 2-14 were the most active compounds (6.1 < or = ED50 < or = 43.0 mg/kg, orally; ED50 is the half-maximal effective dose). Pyridazinones 8 and 9, with a 3-chlorophenylpiperazinomethyl substituent, also exhibited significant anti-inflammatory and antipyretic effects. The activities in the phenylbenzoquinone-induced writhing test were subjected to a Hansch analysis, and a significant correlation with lipophilicity and Hammett's constants was obtained.