Cargando…

Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine

[Image: see text] Two routes to the antimalarial drug Pyronaridine are described. The first is a linear sequence that includes a two-step, one-pot transformation in an aqueous surfactant medium, leading to an overall yield of 87%. Alternatively, a convergent route utilizes a telescoped three-step se...

Descripción completa

Detalles Bibliográficos
Autores principales: Kincaid, Joseph R. A., Kavthe, Rahul D., Caravez, Juan C., Takale, Balaram S., Thakore, Ruchita R., Lipshutz, Bruce H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9112334/
https://www.ncbi.nlm.nih.gov/pubmed/35504038
http://dx.doi.org/10.1021/acs.orglett.2c00944
_version_ 1784709399970840576
author Kincaid, Joseph R. A.
Kavthe, Rahul D.
Caravez, Juan C.
Takale, Balaram S.
Thakore, Ruchita R.
Lipshutz, Bruce H.
author_facet Kincaid, Joseph R. A.
Kavthe, Rahul D.
Caravez, Juan C.
Takale, Balaram S.
Thakore, Ruchita R.
Lipshutz, Bruce H.
author_sort Kincaid, Joseph R. A.
collection PubMed
description [Image: see text] Two routes to the antimalarial drug Pyronaridine are described. The first is a linear sequence that includes a two-step, one-pot transformation in an aqueous surfactant medium, leading to an overall yield of 87%. Alternatively, a convergent route utilizes a telescoped three-step sequence involving an initial neat reaction, followed by two steps performed under aqueous micellar catalysis conditions affording Pyronaridine in 95% overall yield. Comparisons to existing literature performed exclusively in organic solvents reveal a 5-fold decrease in environmental impact as measured by E Factors.
format Online
Article
Text
id pubmed-9112334
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-91123342022-05-18 Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine Kincaid, Joseph R. A. Kavthe, Rahul D. Caravez, Juan C. Takale, Balaram S. Thakore, Ruchita R. Lipshutz, Bruce H. Org Lett [Image: see text] Two routes to the antimalarial drug Pyronaridine are described. The first is a linear sequence that includes a two-step, one-pot transformation in an aqueous surfactant medium, leading to an overall yield of 87%. Alternatively, a convergent route utilizes a telescoped three-step sequence involving an initial neat reaction, followed by two steps performed under aqueous micellar catalysis conditions affording Pyronaridine in 95% overall yield. Comparisons to existing literature performed exclusively in organic solvents reveal a 5-fold decrease in environmental impact as measured by E Factors. American Chemical Society 2022-05-03 2022-05-13 /pmc/articles/PMC9112334/ /pubmed/35504038 http://dx.doi.org/10.1021/acs.orglett.2c00944 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kincaid, Joseph R. A.
Kavthe, Rahul D.
Caravez, Juan C.
Takale, Balaram S.
Thakore, Ruchita R.
Lipshutz, Bruce H.
Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
title Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
title_full Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
title_fullStr Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
title_full_unstemmed Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
title_short Environmentally Responsible and Cost-Effective Synthesis of the Antimalarial Drug Pyronaridine
title_sort environmentally responsible and cost-effective synthesis of the antimalarial drug pyronaridine
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9112334/
https://www.ncbi.nlm.nih.gov/pubmed/35504038
http://dx.doi.org/10.1021/acs.orglett.2c00944
work_keys_str_mv AT kincaidjosephra environmentallyresponsibleandcosteffectivesynthesisoftheantimalarialdrugpyronaridine
AT kavtherahuld environmentallyresponsibleandcosteffectivesynthesisoftheantimalarialdrugpyronaridine
AT caravezjuanc environmentallyresponsibleandcosteffectivesynthesisoftheantimalarialdrugpyronaridine
AT takalebalarams environmentallyresponsibleandcosteffectivesynthesisoftheantimalarialdrugpyronaridine
AT thakoreruchitar environmentallyresponsibleandcosteffectivesynthesisoftheantimalarialdrugpyronaridine
AT lipshutzbruceh environmentallyresponsibleandcosteffectivesynthesisoftheantimalarialdrugpyronaridine