Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

摘要

2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-l,2,4-triazole with 2,3-dibromo-l,3-diarylpropan-1-ones,and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with a-bromopropenones in the presence of a base.The structure of the 7-arylidenetriazolothia-diazines was confirmed by an alternative synthesis.A plausible mechanism for the formation of 7-arylidene-triazolothiadiazines is proposed.All newly synthesized compounds were screened for their analgesic and antimicrobial activities.Compounds bearing 4-chlorophenyl or 3,4-mefhylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity.Arylidenetriazolothiadiazines carrying a phenyl,4-chlorophenyl,4-methylphenyl,3,4-dimethoxyphenyl,and 2,4-di-chlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.