Epoxide and Hydroperoxide Derived from Naturally Cinnamaldehyde and its Schiff Base Derivatives

摘要

Thermal and photo epoxidation. photooxygenation reactions of cinnamaldehyde may be useful tool for the design of drugs to act as potent chemopreventation and anticancer agents. trans-Cinnamaldehyde was isolated from essential oil of cinnamon (Cinnamonum verum). It was subjected to oxidation reactions either photochemically with hydrogen peroxide or thermally with 3-chloro-peroxybenzoic acid. Schiff base derivative was synthesized through condensation reaction with aniline. It subjected to photooxidation reaction in the presence of tetraphenylporphin as singlet oxygen sensitizer, photochemically oxidation reaction gave the corresponding epoxy derivative together with cis-isomerisation. Whereas, thermally oxidation reaction resulted the corresponding epoxy derivative together with einnamic acid. In addition, photooxidation reaction of Schiff base derivative led to 1-phenyl-3-phenyliminopropen-1-yl hydroperoxide through endoperoxide derivative. The primary tested of hydroperoxide derivative showed a moderate degree of DNA degradation. trans-Cinnamaldehyde and its derivatives can act as antioxidants. They were trapped the reactive oxygen species (ROS) to give the intermediated epoxides and hydroperoxide derivatives, which could be alkylated or damage DNA, proteins and other biological species