Access to the substituted benzyl-1,2,3-triazolyl hesperetin derivatives expressing antioxidant and anticancer effects

Abstract

Azide–alkyne cycloaddition was attempted to generate a flavanone hesperetin based phenyl substituted 1,2,3-triazolyls as semi-synthetic natural product derivatives utilizing copper-catalyzed click chemistry. All final compounds were analyzed for their in vitro antioxidant abilities using DPPH and ABTS bioassay. Moreover, cancerous cell inhibitory prospect of titled compounds was screened against cervical cancer cell lines, HeLa and CaSki and an ovarian cancer cell line SK-OV-3 implementing SRB assay. Bearable toxicity of 6a-s was examined employing Madin–Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-s indicated remarkable antioxidant power in scavenging DPPH and ABTS+; particularly, an analog 6o with meta-methoxy substituent showed most potent radical scavenging activity, whereas scaffolds 6d with para-fluoro, 6k with ortho-methyl, and 6o with meta-methoxy performed excellently in inhibiting both the cervical cancer cell lines and analog 6q with meta-trifluoromethyl substituent expressed excellent sensitivity toward ovarian cancer cell line. From the structure–activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the phenyl ring attached to the triazole core may contribute to the anticipated antioxidant and anticancer action. Structure of final compounds was adequately confirmed exploring different spectroscopic techniques and elemental analysis in addition to the measurements of some physical properties.