Synthesis and in vitro anticancer activity assessment of bis-1,3,4-thiadiazol-2-amino flavone derivatives
DOI:
https://doi.org/10.60988/p.v37i2S.237Keywords:
bis-thiadiazol-2-amino flavone; imine flavone ethyl acetate; FT-IR; 1HNMR; MCF-7Abstract
2-Amino-1,3,4-thiadiazole is a heterocyclic scaffold associated with a wide range of pharmacological activities, including anticancer, antibacterial, antifungal, antiviral, antiparasitic, anticonvulsant, anticoagulant, antidiabetic, and antitumor effects. This structural motif has attracted considerable interest due to its therapeutic potential. Although several synthetic approaches have been proposed for this class of compounds, most are neither straightforward, economical, nor environmentally friendly. Given the established biosynthetic pathway of pyrimidines, it is reasonable to hypothesize that thiadiazoles may possess significant therapeutic value. The presence of a sulfur atom in the thiadiazole ring enhances liposolubility, while the mesoionic nature of these compounds facilitates cellular membrane penetration. In this study, novel 1,3,4-thiadiazole derivatives of bis-flavone imine were synthesized from bis-flavone imine ethyl acetate derivatives using a convergent synthetic strategy, yielding satisfactory product quantities. The chemical structures of the synthesized compounds were characterized using Fourier-transform infrared (FT-IR) spectroscopy and proton nuclear magnetic resonance (1H-NMR) spectroscopy. In vitro anticancer assays on MCF-7 human breast cancer cells have revealed that compound T8 can achieve a 50% inhibition of cell viability (IC50) at a concentration of 29.23 µg/mL. Compound T4 has exhibited a comparable anticancer effect, with an IC50 value of 30.02 µg/mL.
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