Despite the progress in antibacterial therapy, the infectious diseases caused by widespread prevalence of different types of bacteria and the randomly usage of antibiotics are still one of the greatest threats to human health globally. At this regard, Novel N',N''-(1,2-diphenylethane1,2-diylidene)bis(2-cyanoacetohydrazide) (3), derived from benzil and 2-cyanoacetohydrazide, was condensed with benzaldehyde to afford N',N''-(1,2-diphenylethane-1,2-diylidene)bis(2-cyano-3-phenylacrylohydrazide) (4) as a key intermediate. Bis-pyrazoles 8a, b containing hydrazone moiety were synthesized through the reaction of compound 4 with hydrazines. Also, N-bridged bis-fused azoles such as: bis([1,2,4]triazolo[1,5-a]pyrimidine) 11, bis(tetrazolo[1,5-a]pyrimidine) 14, bis(benzimidazo[1,2-a]pyrimidine) 16, bis(pyrido[2`,3`:3,4]pyrazolo[1,5-a] pyrimidine) 18, bis(thiazolo [3,2-a]pyrimidine) 20, bis(benzothiazolo[3,2-a]pyrimidine) 22, bis(pyrido[1,2-a]pyrimidine) 24, and bis(pyrimido[1,2-a]pyrimidine) 26 were synthesized by reaction of compound 4 with respective heterocyclic amines. Moreover, the molecular docking study of the compounds was carried out with the active site of Staphylococcus aureus tyrosyl-tRNA synthetase, to understand their binding mode of interactions. In silico ADMET properties of new azole analogues were also calculated.