American trypanosomiasis, or Chagas disease, is a neglected tropical disease caused by the parasite Trypanosoma cruzi. This illness is known to affect over one sixth of the world’s population, most prevalently in Central and South America. The two current treatments for Chagas disease utilize the drugs Nifurtimox and Benznidazole, potent anti-parasitic medications that eliminate T. cruzi. Though effective drugs, their side effects are extremely harsh. Some of these effects include difficulty eating, passing stool, and cardiac complications which could result in sudden death. Our research project focuses on the production of a library of drug candidates that are inexpensive yet innocuous to treat Chagas disease. Squaramide-based drug derivatives synthesized from 3,4-dihydroxycyclobut-3-ene-1,2-dione (squaric acid) have shown to have anti-parasitic properties against T. cruzi. Our target compounds are synthesized in three short synthethic steps. Squaric acid is first converted to the squaric ester diethyl squarate via condensation with ethanol. Diethyl squarate is subsequently converted to the targeted squaramides when reacted with a variety of amines. This class of compounds have demonstrated low toxicity in humans and high affinity for the T. cruzi parasite. Through a series of condensation reactions, potential drugs are being created from alkyl and aryl amines. The availability of these compounds will enhance the chances of discovering a novel and safer remedy for Chagas disease. Currently, significant progress has been made in the synthesis of a diverse drug library. Future research involves testing the potency of these drug candidates and synthesizing a new generation of drug derivatives.

Squaramide-based anti-parasitic drugs toward the discovery of novel treatments for American trypanosomiasis

2019 Spring National Meeting

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