Synthesis of Vitamin E Novel Analogues as Anti-Cancer Compounds

Antioxidant compounds have been shown to slow down the development of chemically induced tumors. It has been estimated that most of human cancer cases are due to environmental factors and would be preventable if the main risks could be identified. The potential of vitamin E as a cancer preventive agent has been studied and individuals whose intake of vitamin E was above average showed a low risk of lung cancer. Vitamin E is a mixture of four lipid soluble phenols including α-, β-, γ-, and δ-tocopherol.
In our study, to investigate the antioxidant activity of α-tocopherol-derived radicals in comparison with other phenoxyl radicals, a number of substituted phenols were synthesized, most of which contained t-butyl groups in the 2- and 6-positions.
All the synthesized compounds were recrystallized and the nuclear magnetic resonance (NMR) spectra were run on Bruker GRYOSPES WM 360 machine; the IR spectra were also run on a Perkin Elmer 1430 ratio recording infrared spectrophotometer. Microanalyses were carried out on a Perkin Elmer 4000 CHN analyzer; all the melting points were measured by an electrothermal melting point apparatus, which were uncorrected.
Five synthesized vitamin E analogues, including 2, 6-di-t-butyl-4-nitrophenol, 2, 6-di-t-butyl-4-formylphenol, 2, 6-di-t-butyl-4aldoximephenol, 2, 6-di-t-butyl-4-cyanophenol, and 2, 4, 6-trimethoxyphenol, were analyzed by NMR, infrared (IR), and microanalysis, and their melting point were measured by the electrothermal melting point apparatus.
In this study, five vitamin E analogues were synthesized to compare their efficiencies with vitamin E as an antioxidant to be able to interfere in free radical chain reactions and terminate the propagation of free radicals. The efficacies of all five synthesized vitamin E analogues in terms of antioxidant activity and their kinetic study will be investigated in our other study.