Synthesis and Characterization of 2‐(2‐((1‐Aryl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)benzoxazoles: Evaluation of Cytotoxicity and Antioxidant Activity

Abstract

A series of twenty 2‐(2‐((1‐aryl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl) benzoxazoles were synthesized from different aryl azides by copper catalyzed [3+2] cycloaddition reaction in 78–88 % yield. The structure of products was elucidated using spectroscopic techniques. These compounds were tested for cytotoxicity against five cancer cell lines [MCF‐7 (Breast), HT‐29 (Colon), Hep‐G2 (Liver), A549 (Lung) and PC‐3 (Prostate)] using the standard drug Adriamycin. It was found that 2‐(2‐((1‐(3,4‐dichlorophenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)benzoxazole (6 g) was active against all the above cancer cell lines with good activity against PC‐3 cancer cell line (GI50 value 60 μM) comparative to Adriamycin (GI50 value 0.3 μM). Compound 6 g also displayed significant antioxidant activity (IC50 value 4.56 μM) as compared to standard ascorbic acid (IC50 value 9.10 μM).

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

“…The majority of 1,2,3‐triazole‐benzoxazole hybrids only showed weak to moderate antiproliferative activity against breast cancer cell lines, [ 44,45 ] whereas 1,2,3‐triazole‐pyrimidine‐oxazolo[4,5‐ b ]pyridine hybrids 23 (IC 50 : 0.045–13.2 µM, MTT assay) exhibited promising activity against MCF‐7 breast cancer cells. [ 46 ] The SAR illustrated that electron‐donating group especially methoxy group was beneficial for the activity.…”