2-hydroxy-1,4-naphthoquinones with 3-alkyldiarylether groups: synthesis and Plasmodium falciparum inhibitory activity
Abstract
Background: In 1948, the synthesis and Plasmodium lophurae activity of 2-hydroxy-1,4-naphthoquinones containing 3-alkyldiarylether side chains was reported. Method/results: The synthesis of five related compounds, designed to be more metabolically stable, was pursued. The compounds were synthesized using a radical alkylation reaction with naphthoquinones. One compound had a lower IC50 value against various strains of Plasmodium falciparum and assay data indicate that it binds to the Qo site of cytochrome bc1. With a low yield for the radical alkylation of the most active compound, a reductive alkylation method with used to improve reaction yields. Conclusion: Further synthetic knowledge was obtained, and the assay data indicate that there are sensitivity differences between avian and human malarial parasites for these molecules.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Nov 01, 2022
- Source ID
- 10.4155/fmc-2022-0127
Entities
People
- Aaron Nilsen
- Alyson N Sillin
- Amanda Berg
- Chelsea B. Swartchick
- Madeleine C Deem
- Matthew Chavarria
- Michael K. Riscoe
- Noah Forrest
- Teresa M. Riscoe
- Warren J. L. Wood
- Yuexin Li
Organizations
- M J Murdock Charitable Trust
- National Institute of Allergy and Infectious Diseases
- Oregon Health & Science University
- United States Department of Defense
- United States Department of Veterans Affairs
- University of Portland
- Veterans Affairs Medical Center (Oregon)