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Formation of Spirolactams for Trichomoniasis Vaginalis

  • Goal: To synthesize novel spirolactams via hypervalent iodine dearomatization for testing to obtain IC50 of the enzymes used by the parasite, Trichomoniasis vaginalis.
  • Summary: A common example of a non-viral sexually transmitted disease that affects people worldwide is Trichomoniasis vaginalis. Current treatments involving metronidazole and tinidazole antibiotics are unable to treat the parasite due to drug resistance. Such antibiotics that exhibit high inhibition of the enzymes used by Trichomoniasis vaginalis involve molecules containing core structures of spirolactams. Due to the underlying issue of antibiotic resistance of the parasite, a novel method involving hypervalent iodine dearomatization is utilized for the formation of spirolactams for the treatment of Trichomoniasis vaginalis. The use of hypervalent iodine reactions were employed for quick assemblance of the active core structure and evaluated in collaboration with the Stockman Research Group and AstraZeneca to test for inhibition of enzymes necessary for Trichomoniasis vaginalis reproduction.