Synthesis and Evaluation of 3‐Anilino‐quinoxalinones as Glycogen Phosphorylase Inhibitors.

Dudash, Joseph; Zhang, Yongzheng; Moore, John B.; Look, Richard; Liang, Yin; Beavers, Mary Pat; Conway, Bruce R.; Rybczynski, Philip J.; Demarest, Keith T.

doi:10.1002/chin.200605234

Cited by 8 publications

(10 citation statements)

References 1 publication

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“…(3), or initiate the chain propagation reactions of Eqs. (7) and (8). The consumption of two PhNHCH 2 • by reactant 1, would terminate the radical propagation leading to product 3, Eq.…”

Section: Laser Flash Photolysismentioning

confidence: 99%

“…In the last few decades, many studies on the biological properties of quinoxalin-2-one derivatives have been published because of their several pharmacological properties such as: antimicrobial, antifungal, anxiolytic, analgesic, antithrombotic, antitumoral and due to their capacity as inhibitors of the activity of certain enzymes involved in HIV-1 (1)(2)(3)(4)(5)(6)(7)(8).…”

Section: Introductionmentioning

confidence: 99%

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Unexpected Imidazoquinoxalinone Annulation Products in the Photoinitiated Reaction of Substituted‐3‐Methyl‐Quinoxalin‐2‐Ones with N‐Phenylglycine

Fuente

Cañete

Jullian

et al. 2013

Photochem & Photobiology

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Photoinduced electron transfer between N-phenylglycine (NPG) and electronically excited triplets of 7-substituted-3-methyl-quinoxalin-2-ones in acetonitrile generate the respective ion radical pair, where by decarboxylation the phenyl-amino-alkyl radical, PhNHCH2•, is generated. This radical reacts with the 3-methyl-quinoxalin-2-ones ground states, leading to the product 2. Other, unexpected, 7-substituted-1,2,3,3a-tetrahydro-3a-methyl-2-phenylimidazo[1,5-a]quinoxalin-4(5H)-ones, annulation products, 3a-f, were generated; likely by the addition of two PhNHCH2• radicals, to positions 3 and 4 of the quinoxalin-2-ones. The reaction mechanism includes a photoinduced one electron transfer initiation step, propagation steps involving radical intermediates and NPG with radical chain termination steps that lead to the respective products 2a-f and 3a-f and NPG by-products. The proposed mechanism accounts for the strong dependency found for the initial photoconsumption quantum yields on the electron-withdrawing power of the substituent. Therefore, photolysis of common reactants widely used such as NPG and substituted quinoxalin-2-ones may provide a simple synthetic way to the unusual, unreported tetrahydro-imidazoquinoxalinones 3a-f.

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“…(3), or initiate the chain propagation reactions of Eqs. (7) and (8). The consumption of two PhNHCH 2 • by reactant 1, would terminate the radical propagation leading to product 3, Eq.…”

Section: Laser Flash Photolysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Unexpected Imidazoquinoxalinone Annulation Products in the Photoinitiated Reaction of Substituted‐3‐Methyl‐Quinoxalin‐2‐Ones with N‐Phenylglycine

Fuente

Cañete

Jullian

et al. 2013

Photochem & Photobiology

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“…Substituted quinoxalin-2(1 H )-ones represent an important class of fused heterocyclic compounds due to their diverse pharmacological properties and have been synthesized through diverse chemical routes. , 3-Aminoquinoxalin-2(1 H )-one, in particular, is an important subfamily known to possess potent biological activities such as antimicrobial, antiviral, antihypertensive, anticancer, antidiabetic, and anti-inflammatory . A wide variety of 3-aminoquinoxalinone derivatives have recently been explored for their therapeutic applications such as calcium channel blockers, aldose reductase inhibitors, modulators of PAS kinase, and histamine receptor antagonists (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Iodine-Catalyzed C–N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions

2017

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A metal-free cross-dehydrogenative coupling between quinoxalinones (sp C-H) and amines (N-H) in the presence of catalytic iodine is reported. The reaction yields 3-aminoquinoxalinones in moderate to high yields under ambient conditions in dioxane as solvent and aqueous tert-butyl hydroperoxide (TBHP) as the terminal oxidant. The reaction is highly versatile and exhibits good functional group tolerance with a range of primary and secondary amines. It provides a practical access to pharmaceutically active 3-aminoquinoxalinone derivatives. Preliminary mechanistic studies reveal in situ iodination of the amine as the putative mode of activation.

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“…Mayer and Taberner (2002) reported the utility of quinoxaline derivatives as blood glucose level reducing agents and insulinomimetic agent in mice. A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors by Dudash et al (2005). They have made some incorporation to the quinoxaline scaffold with various aliphatic and aromatic compounds to produce novel analogues, some of which are 25 times more potent than the lead compound.…”

Section: Introductionmentioning

confidence: 99%

Transition metal complexes of thiosemicarbazones with quinoxaline hub: an emphasis on antidiabetic property

Kulkarni

Revankar

Kirasur³

et al. 2011

Med Chem Res

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New transition metal complexes of quinoxaline-thiosemicarbazone ligands were prepared and characterised by spectroanalytical techniques. The ligands L 1 H 2 and L 2 H 2 were obtained by the reaction of quinoxaline-2.3(1,4H)-dione with methyl and phenyl thiosemicarbazide, respectively. All the complexes are found to be monomeric in nature and have tetrahedral geometry. The copper complexes have shown redox responses in the applied voltage range, whereas the ligands and other complexes are electrochemically innocent. The ligands, copper and zinc complexes are explored for antidiabetic activity in the diabetes-induced Wister rats. Evaluation of antidiabetic activity was done by blood-glucose test and oral glucose tolerance test; few compounds have exhibited significant antidiabetic activity and posses low toxicity with a high safety profile.

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Synthesis and Evaluation of 3‐Anilino‐quinoxalinones as Glycogen Phosphorylase Inhibitors.

Cited by 8 publications

References 1 publication

Unexpected Imidazoquinoxalinone Annulation Products in the Photoinitiated Reaction of Substituted‐3‐Methyl‐Quinoxalin‐2‐Ones with N‐Phenylglycine

Unexpected Imidazoquinoxalinone Annulation Products in the Photoinitiated Reaction of Substituted‐3‐Methyl‐Quinoxalin‐2‐Ones with N‐Phenylglycine

Iodine-Catalyzed C–N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions

Transition metal complexes of thiosemicarbazones with quinoxaline hub: an emphasis on antidiabetic property

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