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Quinoxaline 1,4-di-N-oxides: a review of the importance of their structure in the development of drugs against infectious diseases and cancer

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Abstract

Quinoxaline 1,4-di-N-oxides (QdNO’s) are potent drugs used since the middle of the last century as food additives to improve animal growth; however, their use as antibacterial agents led to an interest in investigating their mechanism of action, discovering that this heterocycle can cause DNA damage. Consequently, many molecules with different applications have been developed, with most of the research focused on studying their action as antibiotics, antifungals, antiparasitics, antituberculous, and anticancer agents. This review aims to present a condensate of the leading QdNO’s derivatives, as well as a description of the biological activities finding the importance of the nature and type of substituents present in positions R2, R3, R6, and R7 when they are biologically evaluated.

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Abbreviations

3D-QSAR:

Three-Dimensional Quantitative Structure–Activity Relationships

CQ:

Chloroquine

HAPs:

Hypoxia-Activated Prodrugs

INH:

Isonicotinic Acid Hydrazide

MIC:

Minimum Inhibitory Concentration

MDR-TB:

Multidrug-Resistant Tuberculosis

PQ:

Primaquine

QdNO’s:

Quinoxaline 1,4-di-N-oxides

QSAR:

Quantitative Structure–Activity Relationship

ROS:

Reactive Oxygen Species

SAR:

Structure–Activity Relationship

TC:

anti-Trypanosoma cruzi

TPZ:

Tirapazamine

ZOI:

Zone of Inhibition

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Acknowledgements

We are grateful to the Consejo Nacional de Ciencia y Tecnología (CONACYT) for the scholarship awarded with No. 291197.

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  1. These authors contributed equally: Socorro Leyva-Ramos, Alberto Pedraza-Alvarez

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  1. Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Av. Manuel Nava 6, Zona Universitaria, CP 78210, San Luis Potosí, SLP, México

    Socorro Leyva-Ramos & Alberto Pedraza-Alvarez

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  1. Socorro Leyva-Ramos
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  2. Alberto Pedraza-Alvarez
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Correspondence to Socorro Leyva-Ramos or Alberto Pedraza-Alvarez.

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Leyva-Ramos, S., Pedraza-Alvarez, A. Quinoxaline 1,4-di-N-oxides: a review of the importance of their structure in the development of drugs against infectious diseases and cancer. Med Chem Res 30, 1175–1184 (2021). https://doi.org/10.1007/s00044-021-02731-8

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