Regiospecific Oxidative Nitration of 3,4-Dihydro-6,7-disubstituted Quinoxaline-2(1H)-ones Gives 1,4-Dihydro-5-nitro-6,7-disubstituted Quinoxaline-2,3-diones, Potent Antagonists at the NMDA/Glycine Site

Kher, S. M.; Cai, Sui Xiong; Weber, Eckard; Keana, John F. W.

doi:10.1021/jo00123a020

Cited by 21 publications

(17 citation statements)

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“…Quinoxaline (1) and quinoxalin-2-one (2) were oxidized by treatment with ammonium peroxodisulfate [(NH 4 ) 2 S 2 O 8 ] and potassium permanganate (KMnO 4 ) respectively, to obtain quinoxalin-2,3-dione (3) [174][175]. Furthermore, oxidative nitration of substituted quinoxalin-2-ones (4), in THF and f HNO 3 , affords the corresponding 5-nitroquinoxalin-2,3-dione derivatives (5) [176]. Hydrolysis of 2,3-dichloro-6-methoxyquinoxaline (6) with 48% HBr aqueous solution and acetic anhydride gives 6-hydroxyquinoxalin-2,3-dione (7) [177].…”

Section: Preparation Of Quinoxalin-23-dionesmentioning

confidence: 99%

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Carta

Piras²,

Loriga

et al. 2006

MRMC

229

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Quinoxaline derivatives have received much attention in recent years owing to their both biological properties and pharmaceutical applications. In this review we focus the attention on quinoxalin-2(3)-ones and quinoxalin-2,3-diones. These derivatives are particularly interesting since some of them showed antimicrobial (against several bacteria, viruses, fungi, etc), or anticancer activities. Furthermore, others are reported to be potent no-NMDA glutamate receptor antagonists, endowed with anxiolytic, deconditioning, analgesic, antispastic, antiallergic, antithrombotic activities. In this article we also report SAR studies and the most important methods of synthesis of the quinoxalin-2(3)-(di)ones.

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Section: Preparation Of Quinoxalin-23-dionesmentioning

confidence: 99%

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Carta

Piras²,

Loriga

et al. 2006

MRMC

229

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“…The quinoxaline system, (I), and its derivatives have been successfully used in medicinal chemistry, particularly as synthetic precursors of antihypertensives, analgesics and neurotransmitter antagonists (Fuente et al, 2000;Kher et al, 1995;Manca et al, 1992). Many of these compounds also exhibit in vitro anticancer activity (Loriga et al, 1995).…”

Section: Commentmentioning

confidence: 99%

A series of three (E)-2-alkylidene-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline compounds

et al. 2001

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The three title quinoxaline derivatives, (E)-2-(4-methylbenzylidene)-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline, C30H28N2O4S2, (II), (E)-2-(4-methoxybenzylidene)-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline, C30H28N2O5S2, (III), and (E)-2-(3-chlorobenzylidene)-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline, C29H25ClN2O4S2, (IV), were synthesized by palladium-catalyzed hetero-annulation. The E configuration of the exocyclic double bond in the three compounds has been established by the present X-ray study. The saturated part of the quinoxaline moiety in all three compounds assumes a distorted chair conformation. The numerical descriptors indicate a high degree of isostructurality between compounds (II) and (III), but no isostructurality with compound (IV).

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“…The quinoxaline heterocycle, (I), has been an integral part in many natural products (Dell et al, 1975). Several quinoxaline derivatives have been successfully used in the pharmaceutical industry as synthetic precursors of antihypertensives, analgesics and neurotransmitter antagonists (Fuente et al, 2000;Kher et al, 1995). Furthermore, the in vitro anticancer activity of quinoxaline compounds has recently emerged as a promising modality against cancer and allied diseases (Lorgia et al, 1995;Bonnett, 1995).…”

Section: Commentmentioning

confidence: 99%

Two (E)-2-arylidene-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline compounds: supramolecular frameworks built with C—H...O and C—H...π(arene) hydrogen bonds and π–π stacking interactions

2007

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The pyrazine ring in two N-substituted quinoxaline derivatives, namely (E)-2-(2-methoxybenzylidene)-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline, C(30)H(28)N(2)S(2)O(5), (II), and (E)-methyl 2-[(1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxalin-2-ylidene)methyl]benzoate, C(31)H(28)N(2)S(2)O(6), (III), assumes a half-chair conformation and is shielded by the terminal tosyl groups. In the molecular packing of the compounds, intermolecular C-H...O hydrogen bonds between centrosymmetrically related molecules generate dimeric rings, viz. R(2)(2)(22) in (II) and R(2)(2)(26) in (III), which are further connected through C-H...pi(arene) hydrogen bonds and pi-pi stacking interactions into novel supramolecular frameworks.

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Regiospecific Oxidative Nitration of 3,4-Dihydro-6,7-disubstituted Quinoxaline-2(1H)-ones Gives 1,4-Dihydro-5-nitro-6,7-disubstituted Quinoxaline-2,3-diones, Potent Antagonists at the NMDA/Glycine Site

Cited by 21 publications

References 0 publications

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

Chemistry, Biological Properties and SAR Analysis of Quinoxalinones

A series of three (E)-2-alkylidene-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline compounds

Two (E)-2-arylidene-1,4-di-p-tosyl-1,2,3,4-tetrahydroquinoxaline compounds: supramolecular frameworks built with C—H...O and C—H...π(arene) hydrogen bonds and π–π stacking interactions

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