A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533

A 6-step synthesis of the antimalarial drug candidate MMV688533 is reported. Key transformations carried out under aqueous micellar conditions include two Sonogashira couplings and amide bond formation. Compared with the first-generation manufacturing process reported by Sanofi, the current route fe...

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Detalles Bibliográficos
Autores principales: Kavthe, Rahul D., Iyer, Karthik S., Caravez, Juan C., Lipshutz, Bruce H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10266478/
https://www.ncbi.nlm.nih.gov/pubmed/37325157
http://dx.doi.org/10.1039/d3sc01699d
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author Kavthe, Rahul D.
Iyer, Karthik S.
Caravez, Juan C.
Lipshutz, Bruce H.
author_facet Kavthe, Rahul D.
Iyer, Karthik S.
Caravez, Juan C.
Lipshutz, Bruce H.
author_sort Kavthe, Rahul D.
collection PubMed
description A 6-step synthesis of the antimalarial drug candidate MMV688533 is reported. Key transformations carried out under aqueous micellar conditions include two Sonogashira couplings and amide bond formation. Compared with the first-generation manufacturing process reported by Sanofi, the current route features ppm levels of palladium loading, less material input, less organic solvent, and no traditional amide coupling reagents. The overall yield is improved ten-fold, from 6.4% to 67%.
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spelling pubmed-102664782023-06-15 A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533 Kavthe, Rahul D. Iyer, Karthik S. Caravez, Juan C. Lipshutz, Bruce H. Chem Sci Chemistry A 6-step synthesis of the antimalarial drug candidate MMV688533 is reported. Key transformations carried out under aqueous micellar conditions include two Sonogashira couplings and amide bond formation. Compared with the first-generation manufacturing process reported by Sanofi, the current route features ppm levels of palladium loading, less material input, less organic solvent, and no traditional amide coupling reagents. The overall yield is improved ten-fold, from 6.4% to 67%. The Royal Society of Chemistry 2023-05-26 /pmc/articles/PMC10266478/ /pubmed/37325157 http://dx.doi.org/10.1039/d3sc01699d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Kavthe, Rahul D.
Iyer, Karthik S.
Caravez, Juan C.
Lipshutz, Bruce H.
A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533
title A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533
title_full A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533
title_fullStr A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533
title_full_unstemmed A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533
title_short A sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate MMV688533
title_sort sustainable, efficient, and potentially cost-effective approach to the antimalarial drug candidate mmv688533
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10266478/
https://www.ncbi.nlm.nih.gov/pubmed/37325157
http://dx.doi.org/10.1039/d3sc01699d
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