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Amides Of Substituted 3-(pteridin-6-yl)propanoic Acids: Synthesis, Spectral Characteristics, And Cytotoxic Activity

M. S. Kazunin, Oleksii Yu. Voskoboynik, Oksana M. Shatalova, Ludmila N. Maloshtan, Sergiy Kovalenko
Published 2019 · Chemistry

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A heterocyclization reaction of 5,6-diamino-1-methyluracil and 2-oxopentanedioic acid was used in this study to synthesize 3-(1-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropteridin-6-yl)propanoic acid, intramolecular cyclization of which led to the formation of a tricyclic lactone, namely, 1-methyl-6,7-dihydro-2H-pyrano[3,2-g]pteridine-2,4,8-(1H,3H)-trione. Reactions of the latter with N-nucleophiles gave a series of amides – structural analogs of antifolates. The structure and identity of the synthesized compounds were confirmed by IR spectroscopy, 1H and 13C NMR spectroscopy, LC-MS analysis, and mass spectrometry. It was established that the synthesized compounds showed cytotoxic effects against human hepatocellular carcinoma (HepG2) cells and may be of interest for further studies of their antitumor activity against other cell lines.
This paper references
10.1016/0022-1759(83)90303-4
Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.
T. Mosmann (1983)
10.1002/ange.19630752102
Neuere Entwicklungen in der Pteridin-Chemie
W. Pfleiderer (1963)
10.1021/CR0301144
DNA and RNA synthesis: antifolates.
I. Kompiš (2005)
10.1016/j.foodchem.2015.08.098
Degradation and interconversion of plant pteridines during sample preparation and ultra-high performance liquid chromatography-tandem mass spectrometry.
Jeroen Van Daele (2016)
10.2174/1389200024605073
Tetrahydrobiopterin biosynthesis, utilization and pharmacological effects.
G. Werner-felmayer (2002)
10.1002/CHIN.200215168
Oxidative Synthesis of Benzoylpteridines from Benzylpteridines by Potassium Permanganate.
Y. Kim (2001)
Immunol
T. J. Mosmann (1983)
10.1161/CIRCULATIONAHA.111.038919
Systemic and Vascular Oxidation Limits the Efficacy of Oral Tetrahydrobiopterin Treatment in Patients With Coronary Artery Disease
C. Cunnington (2012)
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.
M. Palanki (2007)
10.1515/hc-2012-0046
Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
Yasuhiro Kuroda (2012)
10.5860/choice.46-0294
NMR spectroscopy explained : simplified theory, applications and examples for organic chemistry and structural biology
N. Jacobsen (2007)
10.1002/JHET.3135
Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives
M. S. Kazunin (2018)
10.1039/B211564F
Syntheses of highly functionalised 6-substituted pteridines.
D. Guiney (2003)
Determination of Cell Culture Viability: a Study Aid [in Russian]; Nizhegorod Lobachevsky State University
E. V. Mitroshina (2015)
10.1159/000046271
Determination of Xanthopterin in Patients with Renal Insufficiency
D. Qujeq (2001)
Vitro Toxicity Testing Protocols (Methods in Molecular Biology)
R. Supino (1995)
10.1007/7081_2007_061
Tetrahydrobiopterin and Related Biologically Important Pterins
S. Murata (2007)
Bioactive Heterocycles II. Topics in Heterocyclic Chemistry
S. Murata (2007)
10.1039/b701677h
Amide bond formation: beyond the myth of coupling reagents.
Eric Valeur (2009)
10.1002/ARDP.200600149
Synthesis, DNA Binding and Antiviral Activity of New Uracil, Xanthine, and Pteridine Derivatives
O. I. El-Sabbagh (2007)



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