Design, synthesis, molecular docking, and biological evaluation of new emodin anthraquinone derivatives as potential antitumor substances.

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized among which 1,3-Dimethoxy-6,8-dihydroxy-anthraquinone ( 11b ) is a natural compound that has been synthesized for the very first time, and 1,3-Dimethoxy-5,8-dimethyl-anthraquinone ( 11c ) is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50%, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 11c showed the best anticancer activity among all the as synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 11c with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.