Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti‐Inflammatory Agents

Burguete, Asunción; Pontiki, Eleni; Hadjipavlou‐Litina, Dimitra; Ancizu, Saioa; Villar, Raquel; Solano, Beatriz; Moreno, Elsa Moreno; Torres, Enrique; Pérez, Silvia; Aldana, Ignacio; Monge, Antonio

doi:10.1111/j.1747-0285.2011.01076.x

Cited by 104 publications

(62 citation statements)

References 36 publications

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“…LOX is an enzyme essential to arachidonic acid (AA) metabolism, which leads to the formation of leukotrienes, a type of proinflammatory mediator involved in processes like fever, asthma and cardiovascular disease [52]. It was demonstrated that the incorporation of pyrimidine, thiazolopyrimidine, pyrazolopyridine, pyridopyridine, p-chlorophenyl, p-methoxyphenyl or pyridine nucleus to quinoxaline moiety cause significant anti-inflammatory activity, and also analgesic [50].…”

Section: Chronic Inflammationmentioning

confidence: 99%

Quinoxaline, its derivatives and applications: A State of the Art review

Pereira

Moura

Cordeiro

et al. 2015

European Journal of Medicinal Chemistry

380

124

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a b s t r a c tQuinoxaline derivatives are an important class of heterocycle compounds, where N replaces some carbon atoms in the ring of naphthalene. Its molecular formula is C 8 H 6 N 2 , formed by the fusion of two aromatic rings, benzene and pyrazine. It is rare in natural state, but their synthesis is easy to perform.In this review the State of the Art will be presented, which includes a summary of the progress made over the past years in the knowledge of the structure and mechanism of the quinoxaline and quinoxaline derivatives, associated medical and biomedical value as well as industrial value.Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.

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Section: Chronic Inflammationmentioning

confidence: 99%

Quinoxaline, its derivatives and applications: A State of the Art review

Pereira

Moura

Cordeiro

et al. 2015

European Journal of Medicinal Chemistry

380

124

View full text Add to dashboard Cite

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“…[14,15] Our group has vast experience in the synthesis and biological evaluation of multiple quinoxaline 1,4-di-Noxide derivatives, having identified a broad spectrum of anti-infective activities. [16][17][18][19][20][21][22][23][24][25][26] The evaluation of several libraries of compounds led us to find a series with high in vitro activity against T. cruzi. [27] This finding allowed us to establish structural features for maintaining high in vitro activity against the parasite (Scheme 1).…”

mentioning

confidence: 99%

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

Torres

Moreno‐Viguri

Galiano

et al. 2013

European Journal of Medicinal Chemistry

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ABSTRACT. As a continuation of our research and with the aim of obtaining new agents against Chagas disease, an extremely neglected disease which threatens 100 million people, eighteen new quinoxaline 1,4-di-N-oxide derivatives have been synthesized following the Beirut reaction. The synthesis of the new derivatives was optimized through the use of a new and more efficient microwave-assisted organic synthetic method. The new derivatives showed excellent in vitro biological activity against Trypanosoma cruzi. Compound 17, which was substituted with 2 fluoro groups at the 6-and 7-positions of the quinoxaline ring, was the most active and selective in the cytotoxicity assay. The electrochemical study showed that the most active compounds, which were substituted by electron-withdrawing groups, possessed a greater ease of reduction of the N-oxide groups.

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“…Several biological effects have been reported, including anticancer (14,16,17), antimicrobial (18)(19)(20)(21)(22), antiviral (23), and anti-inflammatory and antioxidant (24,25) effects.…”

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confidence: 99%

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

Kaplum

Cogo

Sangi

et al. 2016

Antimicrob Agents Chemother

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Leishmaniasis is endemic in 98 countries and territories worldwide. The therapies available for leishmaniasis have serious side effects, thus prompting the search for new therapies. The present study investigated the antileishmanial activities of 2,3-diarylsubstituted quinoxaline derivatives against Leishmania amazonensis. The antiproliferative activities of 6,7-dichloro-2,3-diphenylquinoxaline (LSPN329) and 2,3-di-(4-methoxyphenyl)-quinoxaline (LSPN331) against promastigotes and intracellular amastigotes were assessed, and the cytotoxicities of LSPN329 and LSPN331 were determined. Morphological and ultrastructural alterations were examined by electron microscopy, and biochemical alterations, reflected by the mitochondrial membrane potential (⌬⌿m), mitochondrial superoxide anion (O 2 · ؊ ) concentration, the intracellular ATP concentration, cell volume, the level of phosphatidylserine exposure on the cell membrane, cell membrane integrity, and lipid inclusions, were evaluated. In vivo antileishmanial activity was evaluated in a murine cutaneous leishmaniasis model. Compounds LSPN329 and LSPN331 showed significant selectivity for promastigotes and intracellular amastigotes and low cytotoxicity. In promastigotes, ultrastructural alterations were observed, including an increase in lipid inclusions, concentric membranes, and intense mitochondrial swelling, which were associated with hyperpolarization of ⌬⌿m, an increase in the O 2 · ؊ concentration, decreased intracellular ATP levels, and a decrease in cell volume. Phosphatidylserine exposure and DNA fragmentation were not observed. The cellular membrane remained intact after treatment. Thus, the multifactorial response that was responsible for the cellular collapse of promastigotes was based on intense mitochondrial alterations. BALB/c mice treated with LSPN329 or LSPN331 showed a significant decrease in lesion thickness in the infected footpad. Therefore, the antileishmanial activity and mitochondrial mechanism of action of LSPN329 and LSPN331 and the decrease in lesion thickness in vivo brought about by LSPN329 and LSPN331 make them potential candidates for new drug development for the treatment of leishmaniasis.

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Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti‐Inflammatory Agents

Cited by 104 publications

References 36 publications

Quinoxaline, its derivatives and applications: A State of the Art review

Quinoxaline, its derivatives and applications: A State of the Art review

Novel quinoxaline 1,4-di-N-oxide derivatives as new potential antichagasic agents

In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis

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