567. Quinoxaline N-oxides. Part I. The oxidation of quinoxaline and its Bz-substituted derivatives

Landquist, J. K.

doi:10.1039/jr9530002816

Cited by 49 publications

(13 citation statements)

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“…Subtherapeutic levels of antibacterial quinoxaline 1,4-dioxides (QdNO's), such as Quindoxin (QUIN; quinoxaline 1,4-dioxide [2][3]), Olaquindox (OLAQ; 2-(N-2'-hydroxyethyl-carbamoyl)-3-methyl quinoxaline 1,4-dioxide [4][5], e.g. BAY-O-NOX ® , Bayer), Carbadox (CARB; hydrazine carboxylic acid (2-quinoxalinyl-methylene) methyl ester 1,4-dioxide [6][7], e.g.…”

Section: Growth-promoting Properties and Toxicity Of Quinoxaline 14-mentioning

confidence: 99%

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Carta

Corona²,

Loriga

2005

CMC

137

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Since 1940s, Quinoxaline 1,4-dioxides (QdNO's) are known as potent antibacterial agents, and subtherapeutic levels have been used to promote growth and improve efficiency of feed conversion in animal feed. They have also shown a selective cytotoxicity against hypoxic cells present in solid tumours. Furthermore, recent studies have put in evidence that QdNO's are endowed with antitubercular, antiprotozoal and anticandida activities. On the other hand, several authors have reported about photoallergic and mutagenic effects of some derivatives. QdNO's may also cause the development of antibiotic-resistant bacteria and influence the horizontal transfer of virulence genes between bacteria. In this review article we report the biological properties, the mode of action and Structure Activity Relationship (SAR) studies of the QdNO derivatives. Furthermore, some cytogenetic and genotoxic effects, classical and more recent method of synthesis, the quinoxaline 1,4-dioxides, and some of their most important reactions, were also reported.

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Section: Growth-promoting Properties and Toxicity Of Quinoxaline 14-mentioning

confidence: 99%

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Carta

Corona²,

Loriga

2005

CMC

137

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“…Its formation from GS-7443 is metabolically reasonable, particularly since the corresponding mono-N-oxide is readily formed. (2). The limited analytical data on the acid are consistent with its formation.…”

Section: Discussionmentioning

confidence: 68%

“…2-Hydroxymethyl-3-methyl-was rapidly excreted and most of the dose was quinoxaline-di-N-oxide (GS-7443, 1) was first de-recovered during the 24 h period following adminscribed by Francis et al in 1956 (1) as one of istration of the drug (Table 1). In the rat and dog the metabolites of 2,3-dimethylquinoxaline-di-N-approximately two-thirds of the administered oxide (2) in sheep. The occurrence of further and radioactivity was recovered in urine and the readditional metabolic transformations was not mainder in the feces.…”

Section: Introductionmentioning

confidence: 99%

The metabolism of 2-hydroxymethyl-3-methylquinoxaline-di-N-oxide in the chicken, rat, and dog

Figdor¹,

Hobbs²

1980

Can. J. Chem.

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is rapldly metabolized in the chicken, rat, and dog to 3-carboxy-2-methylquinoxaline-1-oxide and a conjugate of 3-carboxy-2-methylquinoxaline-di-N-oxide. No appreciable amounts of other metabolites nor unchanged GS-7443 could be detected in the excreta from these anlmals. There were minor quantitative d~fferences in the relative amounts of the two metabolites; moreover, the conjugat~nggroup employed by the chicken is different from that of the dog but the material being conjugated is the same. Although measurable tissue levels of drug-related material were noted In several organs of the chicken 6 days after drug adm~nistration, all chicken tissues examined were cleared of radioactivity w~thin 21 days. Chem. 58, 1957Chem. 58, (1980. Le di-N-oxyde de I'hydroxymCthyl-2 methyl-3 quinoxaline (GS-7443) est metabolise rap~dement chez le poulet, le rat et le chien en oxyde-l de la carboxy-3 methyl-2 quinoxaline et en son espece conjugee, le di-N-oxyde de la carboxy-3 methyl-2quinoxaline. On n'a pas pu deceler des quant~tks apprkciables d'autres metabolites ou de GS-7443 de depart dans les excretions de ces animaux. Quantitativement il y a tres peu de differences entre les deux metabolites; de plus, le groupe conjugue employe par le poulet est different de celu~ employe par le chien mais c'est le mime produit qui dev~ent conjugue. Bien qu'on ait pu deceler des quantites mesurables des drogues mentionnees dans les tlssus de plus~eurs organes du poulet SIX jours apres que les drogues eurent ete administrees, toute la radioactivite des tissus examines disparait apres 21 jours. I [Traduit par le journal]Introduction ity extending to Terramycin resistant E. coli. In Quinoxaline-l,4-di-N-oxides were synthesized connection with its proposed use in food Proin the early 194OYs and evaluated as human ducing animals, the distribution and metabolism of chemotherapeutic agents. A variety of undesirable GS-7443 in the chicken and appropriate experiside effects rendered these compounds unsuitable mental animal species, such as the rat and dog, was for clinical therapy. However, as a result of the ofinteresteffective antibacterial activity shown by this group Results of chemicals, a renewed interest in quinoxalines Excretion of Radioactivity emerged for uses as antiinfective agents in foodIn the chicken, rat, and dog a dose of 30 mglkg producing animals. 2-Hydroxymethyl-3-methyl-was rapidly excreted and most of the dose was quinoxaline-di-N-oxide (GS-7443, 1) was first de-recovered during the 24 h period following adminscribed by Francis et al. in 1956 (1) as one of istration of the drug (Table 1). In the rat and dog the metabolites of 2,3-dimethylquinoxaline-di-N-approximately two-thirds of the administered oxide (2) in sheep. The occurrence of further and radioactivity was recovered in urine and the readditional metabolic transformations was not mainder in the feces. excluded since only a small percent of administered Paper chromatography indicated that the excreta 2 was recovered unchanged.of all animals contained two major metabol...

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“…Monitoring of the reaction course and the purity of the compounds prepared was performed by TLC on Silufol UV-254 plates with ethyl acetate eluent and revealed using UV light. Pyridine-1-oxide [19] and quinoxaline-1-oxide [20] were synthesized according to the literature methods.…”

Section: T-bulimentioning

confidence: 99%

Reaction of 2-pyridyllithium with azine N-oxides. Simple and convenient method for the synthesis of 2,2′-bipyridine 1-oxide and 2,2′:6′,2″:6″2′″-tetrapyridine 1′-oxide

Коvalev¹,

Русинов²,

Чупахин

2009

Chem Heterocycl Comp

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In the reaction of 2-pyridyllithium with quinoline 1-oxide and isoquinoline 2-oxide a nucleophilic substitution of hydrogen occurs to form the corresponding pyridin-2-ylquinolines. A dimerization of the substrate occurs with pyridine 1-oxide, 2,2'-bipyridine 1-oxide or quinoxaline N-oxide. A similar dimerization in good yield occurs when treating azine N-oxides with tert-butyllithium and this serves as a simple and convenient method for preparing bi-and tetrapyridines.

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567. Quinoxaline N-oxides. Part I. The oxidation of quinoxaline and its Bz-substituted derivatives

Cited by 49 publications

References 0 publications

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

Quinoxaline 1,4-Dioxide: A Versatile Scaffold Endowed With Manifold Activities

The metabolism of 2-hydroxymethyl-3-methylquinoxaline-di-N-oxide in the chicken, rat, and dog

Reaction of 2-pyridyllithium with azine N-oxides. Simple and convenient method for the synthesis of 2,2′-bipyridine 1-oxide and 2,2′:6′,2″:6″2′″-tetrapyridine 1′-oxide

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