Synthesis of Chalcones: Starting Materials for the Synthesis Of Parasite-targeted Compounds Sarah Canché Lee Lab Group

Malaria, Leishmaniasis, and Trypanosomiasis  Diseases caused by protozoan parasites transmitted by mosquitoes, sand flies, and tsetse flies

Some Symptoms Malaria:  Dry cough, fever, headache, fatigue, body aches Leishmaniasis:  Skin sores, fever, visceral swelling Trypanosomiasis:  Muscle and joint aches, fever, confusion, slurred speech

Widespread Problem: Malaria:  1-3 million deaths per year Trypanosomiasis:  50,000 to 70,000 cases per year Leishmaniasis:  million have it, with 1.5 to 2 million new cases per year  Treatment for these diseases is expensive and not always effective  Parasites can develop resistance  Need to make treatments that are more affordable and effective

Pentamidine and Furamidine  Molecule currently being used to fight parasitic diseases  Destroys parasite DNA  Molecule that has been proven to help fight parasitic diseases.  Goal: Make a molecule similar to this  Increase potency  Cheaper to produce Pentamidine Furamidine

Synthetic Pathways Thioxopyrimidine Synthesis Diarylpyrazolediamidine Synthesis

How to synthesize chalcones: Method 1 To make… 86% yield 94% yield

Method 2 Methanol added to flask Reaction mixture heated to reflux 1 M NaOH added to the mixture Solid forms Solid collected by vacuum filtration 65% yield 94% yield 6 M NaOH MeOH Reflux

What I learned  Run an NMR  Run an IR  Perform TLC analysis  ChemDraw  Rotovap

Acknowledgements  Dr. Moses Lee  Drs. Toni Brown & Hilary Mackay  Kristin Dittenhafer  Lee Lab Group  REACH  Hope College Chemistry Department  Conjura Pharmaceuticals, LLC