Background:
A new series of 1,2,3-triazol-nitrostyrene derivatives was designed,
synthesized, and evaluated for cytotoxic activity against Hep-2 and L929 cell lines.
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Methods: The synthetic procedure started from the functionalization of 4-hydroxybenzaldehyde
with propargyl bromide and a subsequent click reaction to give 1,2,3-triazole derivatives. Then, the
reaction of the mentioned derivatives with nitromethane led to the formation of the title compounds
in excellent yields.
Results:
Most of the compounds exhibited better cytotoxic activity with respect to the standard drug
5-fluorouracil. Among them, (E)-1-(3,4-dichlorobenzyl)-4-((4-(2-nitrovinyl)phenoxy)methyl)-1H-
1,2,3-triazole 6i (IC50 = 4.66 ± 1.3 µM) against the Hep-2 cell line and (E)-1-(2,3-dichlorobenzoyl)-
4-((4-(2-nitrovinyl)phenoxy)methyl)-1H-1,2,3-triazole 6g (IC50 = 5.18 ± 0.8 µM) against the L929
cell line exhibited the best cytotoxic effects.
Conclusion:
Moreover, the acridine orange/ethidium bromide double staining technique showed
that the most potent compounds 6i and 6g could induce apoptosis in studied cancer cell lines.