Some new isoxazole derivatives 3a-d were synthesized via the reaction of 3-(dimethylamino)-1-(5-methyl-1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one (1) with different hydroximoyl chlorides 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 structures of all 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.
This work concentrated on the utility of hydrazonoyl halides in synthesis of bioactive heterocycles like triazoles, pyrazoles, pyrimidines and their fused derivatives which have a wide spectrum of pharmaceutical value. Herein we discussed the synthesis of new heterocyclic compounds containing fused pyrimidine rings derived from hydrazonoyl halides and their significant pharmaceutical importance as anticancer agents. New fused pyrimidine derivatives bearing 1,2,3-triazole moiety were prepared via reaction of enaminone 2 with and 6-amino-2-thioxo-pyrimidin-4-one and then with hydrazonoyl chlorides 6a-h. In addition 3-amino-6-(2-oxo-2H-chromen-3-yl)pyridine-2-carbonitrile (12) was submitted to react with carbon dioxide to afford 3-(1,2,3,4-tetrahydro-2,4-dithioxopyrido[2,3-d]pyrimidin-7-yl)-2H-chromen-2-one (15), which act as key molecule for synthesis of new series of fused prymidinethione derivatives containing coumarine moiety via its reaction with different selected derivatives of hydrazonoyl halides 6a-h. Structures of the newly synthesized compounds were confirmed using spectral data (IR, H1NMR and Mass spectrometry) and microanalytical methods. Also, they screened for their anticancer activity.
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