by Faville SC, Harris-Hamdscomb K, Harker O, Mattison S, Tamorite H, Bristowe J, Daly D, Ege R, He H, Jones J, McCorkindale A, Mei K, Monson A, Moree L, Perkovic F, Rickerby G, Robinson J, Rudkin F, Whibley L, Worthington R, Ennis C, de la Harpe S, Brind T, Hopkins A, Winefield K, Hendrickx S, Caljon G, Perry B, Vernall AJ. Journal of Chemical Education 2022, 99(4); 1682–1690. doi: 10.1021/acs.jchemed.1c01213
Summary: An undergraduate laboratory at University of Otago, New Zealand was developed as part of the Drugs for Neglected Diseases initiative’s Open Synthesis Network. Students successfully synthesized, purified, and characterized ten different benzoxazole amides that were sent for biological testing against several protozoan parasites, three of which showed moderate activity against T. cruzi, T. b. rhodesiense, and T. b. brucei and had low cell cytotoxicity. This drug discovery laboratory activity made a measurable contribution to neglected tropical disease research and was an engaging and rewarding experience for the students. From an environmental perspective, it was a better use of organic solvents and reagents than synthesizing the same “model” compound as every other year, which ultimately is discarded.