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Synthesis of Chalcones: Starting Materials for the Synthesis Of Parasite-targeted Compounds. Sarah Canch é Lee Lab Group. Malaria, Leishmaniasis, and Trypanosomiasis. Diseases caused by protozoan parasites transmitted by mosquitoes, sand flies, and tsetse flies. Some Symptoms. Malaria:

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synthesis of chalcones starting materials for the synthesis of parasite targeted compounds

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

Sarah Canché

Lee Lab Group

malaria leishmaniasis and trypanosomiasis
Malaria, Leishmaniasis, and Trypanosomiasis
  • Diseases caused by protozoan parasites transmitted by mosquitoes, sand flies, and tsetse flies
some symptoms
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
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
pentamidine and furamidine
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
Synthetic Pathways

Diarylpyrazolediamidine Synthesis

Thioxopyrimidine Synthesis

how to synthesize chalcones method 1
How to synthesize chalcones: Method 1

To make…

86% yield

94% yield

method 2
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
what i learned
What I learned
  • Run an NMR
  • Run an IR
  • Perform TLC analysis
  • ChemDraw
  • Rotovap
acknowledgements
Acknowledgements
  • Dr. Moses Lee
  • Drs. Toni Brown & Hilary Mackay
  • Kristin Dittenhafer
  • Lee Lab Group
  • REACH
  • Hope College Chemistry Department
  • Conjura Pharmaceuticals, LLC
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