Synthesis of Chalcones: Starting Materials for the Synthesis Of Parasite-targeted Compounds

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Synthesis of Chalcones Starting Materials for
the Synthesis Of Parasite-targeted Compounds

• Sarah Canché
• Lee Lab Group

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Malaria, Leishmaniasis, and Trypanosomiasis

• Diseases caused by protozoan parasites
  transmitted by mosquitoes, sand flies, and tsetse
  flies

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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

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Widespread Problem

• Malaria
• 1-3 million deaths per year
• Trypanosomiasis
• 50,000 to 70,000 cases per year
• Leishmaniasis
• 10-15 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

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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
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Synthetic Pathways
Diarylpyrazolediamidine Synthesis
Thioxopyrimidine Synthesis
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How to synthesize chalcones Method 1
To make
86 yield
94 yield
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Method 2
65 yield
6 M NaOH
MeOH Reflux
94 yield

• Methanol added to flask
• Reaction mixture heated to reflux
• 1 M NaOH added to the mixture
• Solid forms
• Solid collected by vacuum filtration

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What I learned

• Run an NMR
• Run an IR
• Perform TLC analysis
• ChemDraw
• Rotovap

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Acknowledgements

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