Synthesis and anti-inflammatory properties of 1,2-dialkoxy-4-(3-dimethylaminopropionyl)benzenes and their 5-halogeno derivatives.
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A series of new 1,2-dialkoxy-4-(3-dimethylaminopropionyl)benzene hydrochlorides and their 5-halogeno derivatives were synthesized and studied for anti-inflammatory properties. The diethoxy and dipropoxy derivatives were more active than the dimethoxy derivative and previously reported heterocyclic analogues. The introduction of a halogeno substituent at the 5-position of the dimethoxy derivative aromatic ring potentiated the activity. The 5-bromo derivative was more active than 5-chloro and 5-fluoro derivatives. Anti-inflammatory and analgesic effects of the 5-bromo derivative were less pronounced than those of indomethacin but greater than those of lysine acetylsalicylate (LAS). The 5-bromo derivative was more toxic than LAS but possessed similar gastrotoxicity. This compound was significantly less toxic and significantly less gastrotoxic than indomethacin++. Therapeutic indices of the 5-bromo derivative were significantly greater than those of LAS and indomethacin.