Synthesis and structure–activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents

Vicente, Esther, Lima, Lidia M., Bongard, Emily ORCID: https://orcid.org/0000-0001-5957-6280, Charnaud, Sarah, Villar, Raquel, Solano, Beatriz, Burguete, Asunción, Perez-Silanes, Silvia, Aldana, Ignacio and Vivas, Livia 2008. Synthesis and structure–activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents. European Journal of Medicinal Chemistry 43 (9) , pp. 1903-1910. 10.1016/j.ejmech.2007.11.024

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Abstract

As a continuation of our research and with the aim of obtaining new antimalarial agents, new series of 3-phenylquinoxaline 1,4-di-N-oxide derivatives have been synthesized following the classical Beirut reaction. Antiplasmodial activity was evaluated in vitro against Plasmodium falciparum by the incorporation of [3H]-hypoxanthine. Cytotoxicity was tested in KB cells by AlamarBlue assay. Twenty-one of the 60 compounds that were assayed against 3D7 (CQ-sensitive) showed enough activity to be also evaluated against K1 (CQ-resistant) strain. Ten of them were shown to be more active than chloroquine in the resistant strain. The most interesting compounds are 7-(methyl or methoxy)-3-(4′-fluoro or chloro)phenylquinoxaline-2-carbonitrile 1,4-di-N-oxides because of their low IC50 and their high SI shown for the K1 strain, making them valid new leads.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Medicine
Subjects:	R Medicine > R Medicine (General) R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords:	Quinoxaline; N-Oxide; Beirut reaction; Antiplasmodial; Malaria; Plasmodium falciparum
Publisher:	Elsevier
ISSN:	0223-5234
Last Modified:	19 Oct 2022 10:33
URI:	https://orca.cardiff.ac.uk/id/eprint/24760

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