SYNTHESIS, AND BIOLOGICAL EVALUATION OF NEWLY SUNTHESIZED TRIAZOLOTRIAZINES AND TRIAZOLOTRAIZINES DERIVATIVES

Novel 8-(4-fluorophenyl)-6,6-diphenyl-3-(pyrimidin-4-yl) -5,6,7,8-tetrahydro-6l5-[1,2,4]triazolo [4,3-a][1,3,5]diazaphosphinin-6-ol(5),8-(4-fluorophenyl)-6-phenyl-3-(pyrimidin-4-yl)-7,8-dihydro [1,2,4]triazolo [4,3-b][1,2,4]triazine (6), 8-(4-fluorophenyl)-6-methyl-3-(pyrimidin-4-yl)-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7(8H)-one (7) and 8-(4-fluorophenyl)-3-(pyrimidin-4-yl)-[1,2,4]triazolo[4,3-b][1,2,4]triazine-6,7(5H,8H)-dione (8) and 7-(pyrimidin-4-yl)-3,4-dihydro-[1,2,4]triazolo[4,e][1,2,4,5,3]tetrazaphosphinine (10), 3-(pyrimidin-4-yl)-1,7-dihydro-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine (11), 6-(2-chloro-6-fluorophenyl)-3-(pyrimidin-4-yl)-1,5,6,7,8,8a-hexahydro-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine (12), 3-(pyrimidin-4-yl)-1,7,8,8a-tetrahydro-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine-6(5H)-thione (13) and 3-(pyrimidin-4-yl)-1,7,8,8a-tetrahydro-[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazin-6(5H)-one (14) have been synthesized via heterocyclization of 3-(pyridin-4yl)-4-amino-5-substituted amino-1,2,4-triazole (3) and 3-(pyridin-4yl)-4-amino-5-hydrazino-1,2,4-triazole (9) with α,β-bifunctional reagents such as chloromethyldiphenyl-phosphanoxide, phenacyl bromide, pyruvic acid, diethyl oxalate, triethylphosphite, triethyl orthoformate, fluorinated benzaldehydes, ethyl chloroformate and carbon disulfide in different experimental conditions. The molecular structures of the synthesized target molecules were elucidated by FT-IR, 1H NMR, 13C NMR and mass spectral data, in addition to the fine elements analysis C.H.N.% data. The antimicrobial and anti-inflammatory effects of the obtained derivatives were evaluated and compared with that of the standard Indomethacin, Nalidixic acid and Nystatin.