17056-99-4Relevant articles and documents
Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases
Thinnes,Tumber,Yapp,Scozzafava,Yeh,Chan,Tran,Hsu,Tarhonskaya,Walport,Wilkins,Martinez,Müller,Pugh,Ratcliffe,Brennan,Kawamura,Schofield
supporting information, p. 15458 - 15461 (2015/10/20)
There is interest in developing potent, selective, and cell-permeable inhibitors of human ferrous iron and 2-oxoglutarate (2OG) oxygenases for use in functional and target validation studies. The 3-component Betti reaction enables efficient one-step C-7 functionalisation of modified 8-hydroxyquinolines (8HQs) to produce cell-active inhibitors of KDM4 histone demethylases and other 2OG oxygenases; the work exemplifies how a template-based metallo-enzyme inhibitor approach can be used to give biologically active compounds.
Computational design, synthesis and biological evaluation of para-quinone-based inhibitors for redox regulation of the dual-specificity phosphatase Cdc25B
Keinan, Shahar,Paquette, William D.,Skoko, John J.,Beratan, David N.,Yang, Weitao,Shinde, Sunita,Johnston, Paul A.,Lazo, John S.,Wipf, Peter
experimental part, p. 3256 - 3263 (2009/02/05)
Quinoid inhibitors of Cdc25B were designed based on the Linear Combination of Atomic Potentials (LCAP) methodology. In contrast to a published hypothesis, the biological activities and hydrogen peroxide generation in reducing media of three synthetic models did not correlate with the quinone half-wave potential, E1/2.
Phototransformations of 6-X-5-nitroquinoxalines
Rtishchev,Selitrennikov
, p. 428 - 437 (2007/10/03)
Photophysical properties and photochemical activity of 6-X-5- nitroquinoxalines with electron-donor substituents (X = H, CH3, Cl, OC2H5, NH2) ortho to the nitro group were studied. The quantum yield of the formation of 5-hydroxyquinoxaline from the corresponding nitro derivative depends on the nature of the substituent and irradiation conditions. Phototransformations can go through nitro-nitrite rearrangement with the participation of two alternative T(nπ*) levels, depending on the size and electronic effects of the substituent. The latter factor is largely determined by the population on excitation of different charge-transfer states involving the nitro group.
Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4
Boyd, Derek R.,Sharma, Narain D.,Dorrity, Michael R. J.,Hand, Mark V.,McMordie, R. Austin S.,et al.
, p. 1065 - 1072 (2007/10/02)
Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.
Metabolism of Bicyclic Aza-arenes by Pseudomonas putida to Yield Vicinal cis-Dihydrodiols and Phenols
Boyd, Derek R.,McMordie, R. Austin S.,Porter, H. Patricia,Dalton, Howard,Jenkins, Richard O.,Howarth, Oliver W.
, p. 1722 - 1724 (2007/10/02)
Metabolism of the aza-arenes quinoline, isoquinoline, quinazoline, and quinoxaline by a mutant strain of the bacterium Pseudomonas putida resulted in attack at the carbocyclic ring (to yield stable cis-dihydrodiols and phenols) and at the heterocyclic ring (to yield phenols and ring cleavage products).
