Current status of quinoxaline and quinoxaline 1,4‐di‐N‐oxides derivatives as potential antiparasitic agents

Abstract

Parasitic diseases are a public health problem, especially in developing countries where millions of people are affected every year. Current treatments have several drawbacks: emerging resistance to the existing drugs, lack of efficacy, and toxic side effects. Therefore, new antiparasitic drugs are urgently needed to treat and control diseases that affect human health, such as malaria, Chagas disease, leishmaniasis, amebiasis, giardiasis schistosomiasis, and filariasis, among others. Quinoxaline is a compound containing a benzene ring and a pyrazine ring. The oxidation of both pyrazine ring nitrogens allows the obtention of quinoxaline 1,4-di-N-oxides (QdNOs) derivatives. By modifying the chemical structure of these compounds, it is possible to obtain a wide variety of biological properties. This review investigated the activity of quinoxaline derivatives and QdNOs against different protozoan parasites and helminths. We also cover the structure-activity relationship (SAR) and summarize the main findings related to their mechanisms of action from published works in recent years. However, further studies are needed to determine specific molecular targets. This review aims to highlight the new development of antiparasitic drugs with better pharmacological profiles than current treatments.

Recent Advances in Anti-Schistosomiasis Drug Discovery

“…Recent Advances in Anti-Schistosomiasis Drug Discovery DOI: http://dx.doi.org/10.5772/intechopen.103056 as malaria, Chagas disease, leishmaniasis, amebiasis, giardiasis, and filariasis [66]. Analogs of quinoxaline 27 (47, including 12 triazoloquinoxalines) were screened as above; three nitroquinoxalines (33)(34)(35) showed IC 50 's of under 0.31 μM against adult S. mansoni worms.…”

“…Leads resulting from a high throughput screen using ATP quantitation (60)(61)(62)(63)(64)(65)(66)(67).…”

Visible light sensing of ions by a cyanoquinoxaline 1,4-dioxide-based probe and its applications

“…Column chromatography was performed on silica gel (Merck 100-200 mesh). For the synthesised probes, 1 H NMR and 13 C NMR studies were conducted in CDCl 3 and DMSO-d 6 solutions with tetramethyl silane (TMS) as the internal standard using a Bruker AV 400 spectrometer at 400 MHz and 101 MHz, respectively. Analytical grade solvents were used for absorption and fluorescence experiments.…”

“…This heterocyclic system is well known, but most available literature studies focus on biological activities. [11][12][13][14][15] No reports on its application in ion sensing are known. However, fluorescence-based sensors relying on other heterocyclic and aliphatic N-oxide systems are available in the literature.…”

An appraisal on synthetic and pharmaceutical perspectives of quinoxaline 1,4‐di‐N‐oxide scaffold

“…Quinoxaline is a heterocyclic molecule with benzene and pyrazine rings (Landquist, 1953; Silk, 1956). When the two nitrogens in the pyrazine ring are oxidized, QdNO (Figure 1) is synthesized which exhibits multifaceted biological properties, wherein antimicrobial, anticancer, antitrypanosomal, and anti‐inflammatory properties are included (Husain & Madhesia, 2011; Soto‐Sánchez & Ospina‐Villa, 2021). QdNOs' diverse actions have piqued curiosity around the world, and they have the potential to be utilized in human and veterinary medicine.…”