Synthesis and anti-inflammatory properties of 1,2-dialkoxy-4- (3-dimethylaminopropionyl) benzenes and their 5-halogeno derivatives
Dauksas, V.; Gaidelis, P.; Udrènaitè, E.; Kuliesius, V.; Labanauskas, L.
Arzneimittel-Forschung 44(7): 835-839
1994
ISSN/ISBN: 0004-4172 PMID: 7945518 Document Number: 437027
A series of new 1,2-dialkoxy-4-(3-dimethylaminopropionyl) benzene hydochlorides 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.