The chemistry of aspirin and azo derivatives has been widely studied for pharmaceutical
purposes. In this study, a series of halogenated azo derivatives 47-49(a-d) and aspirinhalogenated azo derivatives 50-52(a-d) were successfully synthesised. Halogenated azo
derivatives 47-49(a-d) were synthesized via coupling reaction while aspirin-halogenated
azo derivatives 50-52(a-d) were synthesised via esterification reaction of aspirin with 47-
49(a-d). The structures of all the synthesized compounds were characterized by using
elemental analysis (CHNS), nuclear magnetic resonance (1H NMR and 13C NMR) and
Fourier Transform infrared (FTIR) spectroscopies. All compounds were evaluated for
antibacterial activities against Escherichia coli ATCC 25922 and Staphylococcus aureus
S48/81 via turbidimetric kinetic method. Compounds 47-49(a-d) showed good
antibacterial activity against E. coli and S. aureus due to the presence of halogen
substituents and -N=N- groups, which played significant role in antibacterial activities. The
synthesised aspirin–halogenated azo derivatives 50-52(a-d) showed weak antibacterial
activity against tested bacteria due to bulky molecular structure thus hindered the
penetration into bacterial cell wall. All compounds were also further screened for their
anticancer activities against nasopharyngeal cancer cell lines HK-1 using MTS [3-(4,5-
dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide]-based colorimetric assay.
Among 47-49(a-d), compound 47a and 49a showed good cell inhibition against HK-1.
Aspirin–halogenated azo derivatives 50-52(a-d), on the other hand, exhibited weak cancer
cells inhibition due to possible weak binding into EGFR tyrosine kinase
