Synthesis And Biological Activity Of Imine Resveratrol Analogues

Resveratrol, a well-known natural stilbene polyphenol, has attracted a great deal of attention in the past decades. Its simple structure and diverse biological activities encouraged researchers to synthesize new resveratrol analogues with more powerful biological activities. In this research, imine resveratrol analogues (IRAs) were synthesized and their biological activities were evaluated as follows:1.25imine resveratrol analogues (IRAs) were synthesized, replacing the C=C bond in resveratrol with C=N bond, as well as substitution modifications on aromatic rings. Radical scavenging activities against DPPH were evaluated. It was found that IRAs bearing ortho-OH on B ring (the phenyl ring attached to N atom) have better radical scavenging activities against DPPH than resveratrol.2. The singlet oxygen quenching capacities of IRAs bearing ortho-OH on B ring were further evaluated by ESR, and theoretically confirmed using density functional theory calculations (DFT). It was found that these compounds were effective1O2quenchers. Theoretical studies on the reaction mechanism of these compounds with1O2suggest that the1,3-addition to a double bond with a-OH group with the formation of allylic hydroperoxide is the most probable route. Furthermore, ARE-driven luciferase activities of all IRAs together with2new analogues were also evaluated. IRAs bearing ortho-OH on B ring can also increase the luciferase activity. This phenomenon reveals that these analogues can not only scavenge ROS, but also improve chemopreventive activity.3. The antitumor activity and synergitic effect with traditional cancer drugs were also evaluated using MTT method. The results show that IRAs have no effective antitumor and synergitic activity. It is indicated that IRAs have potential to developed as new antioxidants and cancer chemoproventive drugs with low toxicities.