Online citations, reference lists, and bibliographies.

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

Cite This
Download PDF
Analyze on Scholarcy
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
Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.
T. Mosmann (1983)
Neuere Entwicklungen in der Pteridin-Chemie
W. Pfleiderer (1963)
DNA and RNA synthesis: antifolates.
I. Kompiš (2005)
Degradation and interconversion of plant pteridines during sample preparation and ultra-high performance liquid chromatography-tandem mass spectrometry.
Jeroen Van Daele (2016)
Tetrahydrobiopterin biosynthesis, utilization and pharmacological effects.
G. Werner-felmayer (2002)
Oxidative Synthesis of Benzoylpteridines from Benzylpteridines by Potassium Permanganate.
Y. Kim (2001)
T. J. Mosmann (1983)
Systemic and Vascular Oxidation Limits the Efficacy of Oral Tetrahydrobiopterin Treatment in Patients With Coronary Artery Disease
C. Cunnington (2012)
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)
Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
Yasuhiro Kuroda (2012)
NMR spectroscopy explained : simplified theory, applications and examples for organic chemistry and structural biology
N. Jacobsen (2007)
Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives
M. S. Kazunin (2018)
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)
Determination of Xanthopterin in Patients with Renal Insufficiency
D. Qujeq (2001)
Vitro Toxicity Testing Protocols (Methods in Molecular Biology)
R. Supino (1995)
Tetrahydrobiopterin and Related Biologically Important Pterins
S. Murata (2007)
Bioactive Heterocycles II. Topics in Heterocyclic Chemistry
S. Murata (2007)
Amide bond formation: beyond the myth of coupling reagents.
Eric Valeur (2009)
Synthesis, DNA Binding and Antiviral Activity of New Uracil, Xanthine, and Pteridine Derivatives
O. I. El-Sabbagh (2007)

Semantic Scholar Logo Some data provided by SemanticScholar