Oxidative stress results from excess reactive oxygen species (ROS) in the body. ROS can cause damage to cellular macromolecules, which over time can result in cancer, neurodegeneration and cardiovascular disease. Antioxidants play a role in mitigating or preventing these diseases. The trimethoxyphenyl and thiosemicarbazide moieties are present in many compounds that show antioxidant activity. In the current study, twelve trimethoxyphenyl aryl thiosemicarbazide hybrid derivatives containing various electron-donating and electron-withdrawing substituents were synthesized in four steps. The derivatives were evaluated for antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, with ascorbic acid and trolox as positive controls. Derivatives containing pi donating substituents (SCH3, OCH3, F) were most effective at scavenging DPPH radicals (IC50 = 20-25 microM), while derivatives with strong electron withdrawing groups such as NO2 and OCF3 were least effective (IC50 = 47-54 microM). Eleven of the twelve trimethoxyphenyl aryl thiosemicarbazide hybrid derivatives were more effective at scavenging the DPPH radical than trolox (IC50 = 53 microM), while all derivatives were less effective than ascorbic acid (IC50 = 14 microM).

Synthesis and radical scavenging activity of trimethoxyphenyl-aryl thiosemicarbazide derivatives

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