The reaction of 4-azido-quinolin-2(1H)-ones 1a–e with the active methylene compounds
pentane-2,4-dione (2a), 1,3-diphenylpropane-1,3-dione (2b), and K2CO3 was investigated in this
study. This approach afforded 4-(1,2,3-triazol-1-yl)quinolin-2(1H)-ones 3a–j in high yields and
purity. All newly synthesized products’ structures were identified. Compounds 3a–j were tested
for antiproliferative activity against a panel of four cancer cell lines. In comparison to the reference
erlotinib (GI50 = 33), compounds 3f–j were the most potent derivatives, with GI50 values ranging
from 22 nM to 31 nM. The most effective antiproliferative derivatives, 3f–j, were subsequently
investigated as possible multi-target inhibitors of EGFR, BRAFV600E, and EGFRT790M. Compound 3h
was the most potent inhibitor of the studied molecular targets, with IC50 values of 57 nM, 68 nM, and
9.70 nM, respectively. The apoptotic assay results demonstrated that compounds 3g and 3h function
as caspase-3, 8, and Bax activators as well as down-regulators of the antiapoptotic Bcl2, and hence can
be classified as apoptotic inducers. Finally, compounds 3g and 3h displayed promising antioxidant
activity at 10 M, with DPPH radical scavenging of 70.6% and 73.5%, respectively, compared to
Trolox (77.6%)