Online citations, reference lists, and bibliographies.

Synthesis, Tautomerism, And Antiradical Activity Of Novel Pteridinetrione Derivatives

M. S. Kazunin, Oleksii Yu. Voskoboynik, Inna S. Nosulenko, Galina G. Berest, Tetiana Yu. Sergeieva, Sergiy I. Okovytyy, Olexandr Karpenko, B. O. Priimenko, Sergii Ivanovich Kovalenko
Published 2018 · Chemistry
Cite This
Download PDF
Analyze on Scholarcy
Share
Synthesis of 1-methyl-6-((2-(aryl-(heteryl-))-2-oxoethyl) pteridine-2,4,7(1H,3H,8H)-triones via [4 + 2]-cycloaddition of 1-methyl-5,6-diaminouracil with ethyl 4-aryl(heteryl)-2,4-dioxobutanoates is described in presented work. It was established that the reaction occurs regioselectively and proceeds under refluxing of starting compounds in acetic acid for 60 min. The structures of synthesized compounds were proven by complex of physicochemical methods including infrared, 1H-, 13C-NMR spectroscopy, liquid chromatography–mass spectrometry, and electron impact–mass spectrometry. Based on the detail analysis of the correlational NMR spectral data (correlation spectroscopy, heteronuclear single quantum coherence, heteronuclear multiple bond correlation, and Nuclear Overhauser effect spectroscopy), it was determined that in dimethyl sulfoxide solution, the 1-methyl-6-((2-(aryl-(heteryl-))-2-oxoethyl)pteridine-2,4,7(1H,3H,8H)-triones exist in two tautomeric forms: ketone (A) and enol (B). It was also found that tautomeric behavior of aforementioned compounds in hexadeuterated dimethyl sulfoxide is sensitive to the nature of the aryl or heteryl substituent at the position 6 of ring. The electron donating groups shift equilibrium to the tautomer A, while electron withdrawing – to the tautomer B. The synthesized compounds were tested on antiradical activity. It was found that obtained compounds reveal radical scavenging activity comparable or higher than ascorbic acid.
This paper references
10.1080/10715760310001623322
Modulation of LDL Oxidation by 7,8-Dihydroneopterin
Joachim Greilberger (2004)
10.1021/jm030931w
Folate-synthesizing enzyme system as target for development of inhibitors and inhibitor combinations against Candida albicans-synthesis and biological activity of new 2,4-diaminopyrimidines and 4'-substituted 4-aminodiphenyl sulfones.
Thomas Otzen (2004)
10.1016/J.MOLSTRUC.2016.11.023
Investigation of two o-hydroxy Schiff bases in terms of prototropy and radical scavenging activity
Çiğdem Albayrak Kaştaş (2017)
10.1007/978-1-4615-0945-5
Chemistry and Biology of Pteridines and Folates
Sheldon Milstien (2002)
10.1159/000328911
Trimethoprim, Creatinine and Creatinine-Based Equations
Pierre Delanaye (2011)
10.1166/JCTN.2010.1339
Tautomerism and Radical-Scavenging Activity of Edaravone by DFT Methods
Auriekson N. Queiroz (2010)
10.1016/S0306-9877(03)00002-1
Neopterin as a potential modulator of tumor cell growth and proliferation.
Josef Rieder (2003)
10.1016/j.jinorgbio.2008.09.014
Chloro-fac-tricarbonylrhenium(I) complexes of asymmetric azines derived from 6-acetyl-1,3,7-trimethylpteridine-2,4(1H,3H)-dione with hydrazine and aromatic aldehydes: preparation, structural characterization and biological activity against several human tumor cell lines.
Inmaculada Picón-Ferrer (2009)
10.2478/s11696-007-0022-7
Improved DPPH determination for antioxidant activity spectrophotometric assay
Maria-Raluca Szabo (2007)
10.1021/jm051056c
Discovery of 3,3'-(2,4-diaminopteridine-6,7-diyl)diphenol as an isozyme-selective inhibitor of PI3K for the treatment of ischemia reperfusion injury associated with myocardial infarction.
Moorthy S. S. Palanki (2007)
10.5012/bkcs.2002.23.3.374
A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines
Shaker Youssif (2002)
10.1007/s13197-011-0251-1
Genesis and development of DPPH method of antioxidant assay
Sagar B Kedare (2011)
10.1016/S1521-6616(03)00040-8
Induction of apoptosis in human blood T cells by 7,8-dihydroneopterin: the difference between healthy controls and patients with systemic lupus erythematosus.
Barbara Wirleitner (2003)
10.1016/j.bbrc.2004.06.157
Interference of 7,8-dihydroneopterin with peroxynitrite-mediated reactions.
Karl Oettl (2004)
10.1002/CHIN.201519330
Synthesis of Pteridines Derivatives from Different Heterocyclic Compounds
S. Ashraf Ahmed (2014)
10.1093/ajcn/77.6.1352
Riboflavin (vitamin B-2) and health.
Hilary J. Powers (2003)
10.1007/S00214-010-0737-3
Are pterins able to modulate oxidative stress?
Ana Martínez (2010)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar