Synthesis and Biological Evaluation of Some New Pyridines, Isoxazoles and Isoxazolopyridazines Bearing 1,2,3-Triazole Moiety

Abstract

Some new isoxazole derivatives 3a-d were synthesized via the reaction of 3-(dimethylamino)-1-(5methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one (1) with different hydroximoyl chloride derivatives 2a-d. From these new isoxazoles 3a-d a new series of isoxazolopyridazines 4a-d was derived using hydrazine hydrate. In addition, enaminone 1 was reacted with ethyl acetoacetate to afford the corresponding ester derivative 6, the latter was submitted to react with different chemical reagents to obtain a variety of bioactive substituted pyridine derivatives. The azido derivative 14, was used as the key molecule for the synthesis of new urea and aryl carbamate derivatives upon its reaction with different amines and phenol through Curtius rearrangement. The chemical compositions of all the new compounds were investigated from their spectral and microanalytical data. The synthesized compounds were tested for their pharmacological potency as, anti-hepatic cancer and anti-microbial agents. Most of the tested compounds showed good anti-hepatic cancer results comparing with the standard drug doxorubicin especially when their toxic effects on the normal cell lines were studied. Referring to the anti-microbial test most of the compounds showed strong effects.