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The phenoxazine core has been explored in the development of chromophoric systems that have seen use as fluorescent probes and therapeutic agents in combating illnesses of many forms. This thesis reports the synthesis and evaluation of some novel phenoxazine and benzo[a]phenoxazine analogs. Phenoxazinium are charged lipophilic molecules and the recent resurgence of π-Delocalized Lipophilic Cations (DLC) hypothesis in the combat against protozoan illnesses has prompted focus on the synthetic exploration of the derivatization of their architectures in medicinal chemistry. The principle aim of these modifications were to synthesize a focused library of systematically modified analogs catering to the enhancement of related “drug like” properties found throughout the literature of their development as antimalarials.