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Highly Regioselective Protecting-Group-Free Synthesis of the Antimalarial Drug MMV693183.

Pankaj V KhairnarSarah L BlieseRavi Kumar OngoluLi-Mei JinMichael G LaidlawKai O DonsbachB Frank GuptonRyan C NelsonCharles S Shanahan
Published in: Organic process research & development (2023)
MMV693183 is a promising antimalarial drug candidate that works for uncomplicated malaria treatment and resistance management. Herein, we report an efficient and highly regioselective synthesis of MMV693183. This novel synthetic method highlights a three-step route with an overall yield of 46% from readily available starting materials. The key to the success lies in (1) utilizing the subtle difference of the two amino groups in the starting material ( S )-propane-1,2-diamine dihydrochloride without amino protection and (2) identifying the L -(+)-tartaric acid as the counter acid for the organic salt formation, yielding the desired regioisomer up to 100:0. The efficient and scalable three-step protocol operates under mild conditions with a high chemo/regioselectivity, providing effective access to MMV693183.
Keyphrases
  • plasmodium falciparum
  • randomized controlled trial
  • photodynamic therapy
  • combination therapy
  • adverse drug
  • emergency department
  • squamous cell carcinoma
  • cancer therapy
  • urinary tract infection
  • rectal cancer