Hydroxyl substituted anthraquinones are among the most important derivatives in organic synthesis. The attractive biological properties of these compounds are relevant to many therapeutic areas that are of use in clinical applications.In this present work, several amino-substituted anthraquinones were synthesized from 1,4-dihydroxyanthraquinone using a modified Marschalk reaction. Moreover, 1, 4, 5-trihydroxyanthraquinone was synthesized from anacardic acid, an agro-waste from the cashew industry. The in vitro screening of the compounds against Trypanosoma brucei parasites revealed noteworthy activity with reasonable selectivity against a human cell lines. A molecular docking study was performed to analyze the modes of interaction of the synthesized compounds to the active site of trypanothione reductase. The docked poses were examined by visual inspections, and test compounds displayed good binding affinity with the receptor protein. This in-vitro/ molecular docking evaluation suggest that substituted 1, 4-dihydroxyanthraquinone derivative can be promising starting structures in the search for active drugs against trypanosomiasis.