Design, synthesis, and AMPA receptor antagonistic activity of a novel 6-nitro-3-oxoquinoxaline-2-carboxylic acid with a substituted phenyl group at the 7 position

Takano, Yasuo; Shiga, Futoshi; Asano, Jun; Ando, Naoki; Uchiki, Hideharu; Fukuchi, Kazunori; Anraku, Tsuyosi

doi:10.1016/j.bmc.2005.05.030

Cited by 16 publications

(13 citation statements)

References 29 publications

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“…This explains why the proportions of products containing these fragments are close to 1:1 (e.g., 9e and 9e’ , 9f and 9f’ , 10e and 10e’ , 10f and 10f’ , and 11e and 11e’ ). As can be seen in the literature, the use of 8e [29] and 8f [30] in the synthesis of quinoxalinones leads to the formation of isomeric mixtures.…”

Section: Resultsmentioning

confidence: 99%

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

Campos¹,

Rodrigues²,

Belladona³

et al. 2017

Beilstein J. Org. Chem.

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The syntheses of several polyazaheterocycles are demonstrated. The cyclocondensation reactions between β-enaminodiketones [CCl3C(O)C(=CNMe2)C(O)-CO2Et] and aromatic amidines resulted in glyoxalate-substituted pyrido[1,2-a]pyrimidinone, thiazolo[3,2-a]pyrimidinone and pyrimido[1,2-a]benzimidazole. Pyrazinones and quinoxalinones were obtained through the reaction of these glyoxalates with ethylenediamine and 1,2-phenylenediamine derivatives. On the other hand, the reaction of glyoxalates with amidines did not lead to the formation of imidazolones, but rather N-acylated products were obtained. All the products were isolated in good yields. DFT-B3LYP calculations provided HOMO/LUMO coefficients, charge densities, and the stability energies of the intermediates, and from these data it was possible to explain the regiochemistry of the products obtained. Additionally, the data were a useful tool for elucidating the reaction mechanisms.

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Section: Resultsmentioning

confidence: 99%

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

Campos¹,

Rodrigues²,

Belladona³

et al. 2017

Beilstein J. Org. Chem.

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“…Simple method modifications were required to generate 20 – 23 . The synthesis of 20 and 21 involved: 1) oxidizing (4-chloropyridin-3-yl)methanol 34 into an aldehyde intermediate and 2) coupling with the 4,7-ACQ component via reductive amination (Scheme 2). Methoxy substituted derivatives 22 and 23 were obtained in high yield following substitution of the chlorine atom at the aromatic C(4) position of 20 and 21 , respectively.…”

Section: Resultsmentioning

confidence: 99%

4-Amino-7-chloroquinolines: Probing Ligand Efficiency Provides Botulinum Neurotoxin Serotype A Light Chain Inhibitors with Significant Antiprotozoal Activity

et al. 2013

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Structurally simplified analogs of dual antimalarial and botulinum neurotoxin serotype A light chain (BoNT/A LC) inhibitor bis-aminoquinoline (1) were prepared. New compounds were designed to improve ligand efficiency while maintaining or exceeding the inhibitory potency of 1. Three of the new compounds are more active than 1 against both indications. Metabolically, the new inhibitors are relatively stable and non-toxic. Twelve, 14, and 15 are more potent BoNT/A LC inhibitors than 1. Additionally, 15 has excellent in vitro antimalarial efficacy, with IC90 values ranging from 4.45-12.11 nM against five Plasmodium falciparum (P.f.) strains: W2, D6, C235, C2A, C2B. The results indicate that the same level of inhibitory efficacy provided by 1 can be retained/exceeded with less structural complexity. Twelve, 14, and 15 provide new platforms for the development of more potent dual BoNT/A LC and P.f. inhibitors adhering to generally accepted chemical properties associated with the druggability of synthetic molecules.

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“…Among the glutamate receptor antagonists, AMPA-R antagonists appear to be free from side effects such as schizophrenia and have shown effectiveness against neuronal death, even if administered after-ischemia. In consequence, AMPA-R antagonists have been reported to be effective in the therapy of neurodegenerative disorders such as ischemic stroke, epilepsy, head trauma, and Alzheimer's disease [6, 7]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Neuropharmacological Evaluation of Some Novel Quinoxaline 2, 3-Dione Derivatives

Selvaraj

Rajamanickam

Rajagopal

2012

The Scientific World Journal

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Quinoxaline-2, 3-dione obtained from cyclocondensation reaction of o-phenylene diamine with oxalic acid was reacted with three different ketones and formaldehyde to give the corresponding Mannich bases in satisfactory yield. Their structures were confirmed by using 1H NMR, IR, and mass analysis. In pharmacological evaluation, the synthesized compounds showed its curative effect against ethidium-bromide-induced demyelination in rats. For the purpose, different screening methods such as open field exploratory behavior test, rota rod test, grip strength test, beam walk test, and photo actometer test were performed. Ethidium bromide induction showed muscle weakness; muscle discoordination; loss of locomotor activity, and so forth, the synthesized drugs reversed all the above-mentioned neuromuscular disorders caused by ethidium bromide administration.

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Design, synthesis, and AMPA receptor antagonistic activity of a novel 6-nitro-3-oxoquinoxaline-2-carboxylic acid with a substituted phenyl group at the 7 position

Cited by 16 publications

References 29 publications

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

4-Amino-7-chloroquinolines: Probing Ligand Efficiency Provides Botulinum Neurotoxin Serotype A Light Chain Inhibitors with Significant Antiprotozoal Activity

Synthesis and Neuropharmacological Evaluation of Some Novel Quinoxaline 2, 3-Dione Derivatives

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