Biological activity evaluation and computational study of novel triazene derivatives containing benzothiazole rings

Abstract

Three new triazene compounds namely, (E)-2-(3-(p-tolyl)triaz-1-en-1-yl)benzo[d]thiazole (L1), (E)-1-(4-(3-(benzo[d]thiazol-2-yl)triaz-2-en-1-yl)phenyl)ethan-1-one (L2), and (E)-2-(3-(4-nitrophenyl)triaz-1-en-1-yl)benzo[d]thiazole (L3) having the general structure R1-N=N-NH-R2 have been synthesized by diazo-coupling reaction. The synthesized compounds were characterized using different spectroscopic techniques such as FT-IR, 1HNMR and Uv-vis spectroscopy, and studied theoretically using DFT theory. Calf thymus-DNA binding activity of compounds were studied by UV–vis. absorption spectra and viscosity method. Intrinsic binding constant (Kb) of L1, L2 and L3 are 2.50 × 105, 6 × 105 and 8 × 105 M−1, respectively. Cytotoxic activity was tested against MCF-7 and HCT-116 cell lines. All compounds revealed a reasonable cytotoxic activity, where L2 illustrated maximum inhibition action against both cell lines compared to L1 and L3. Molecular docking used to envisage binding between compounds and 1hk7 breast cancer protein and 3ig7 colon cancer proteins. The results of molecular docking of the compounds disply good correlations with experimental cytotoxicity findings.