16710-13-7

Basic information

• Product Name: NSC 112513
• Synonyms: NSC 112513;6-methyluridine;Uridine, 6-methyl-;1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 16710-13-7
• Molecular Formula: C₁₀H₁₄N₂O₆
• Molecular Weight: 258.228
• Mol File: 16710-13-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.576g/cm³
• Refractive Index: 1.618
• CAS DataBase Reference: NSC 112513(CAS DataBase Reference)
• NIST Chemistry Reference: NSC 112513(16710-13-7)
• EPA Substance Registry System: NSC 112513(16710-13-7)

Safety Data

• Hazardous Substances Data: 16710-13-7(Hazardous Substances Data)

Usage

Description

NSC 112513, also known as 6-Methyluridine, is a compound that has been identified for its potential applications in various fields. It is a derivative of uridine, a pyrimidine nucleoside, and features a methyl group at the 6-position of the sugar moiety. This modification influences its interactions and properties, making it a compound of interest for research and development.

Uses

Used in Pharmaceutical Industry:
NSC 112513 is used as a research compound for studying its potential antimalarial properties. It has demonstrated weak antimalarial activity against the P. falciparum 3D7 isolate, which is a strain of the Plasmodium falciparum parasite responsible for causing malaria in humans. This activity suggests that further research and development could lead to the enhancement of its efficacy as an antimalarial agent.
Additionally, NSC 112513 is used as a weak substrate for Escherichia coli pyrimidine nucleoside phosphorylase. This application is valuable in biochemical and enzymatic studies, as it helps researchers understand the enzyme's substrate specificity and its role in metabolic pathways. The use of NSC 112513 in this context contributes to the broader understanding of nucleoside metabolism and the development of potential therapeutic agents targeting these pathways.

InChI:InChI=1/C10H14N2O6/c1-4-2-6(14)11-10(17)12(4)9-8(16)7(15)5(3-13)18-9/h2,5,7-9,13,15-16H,3H2,1H3,(H,11,14,17)

Upstream product

• 58-96-8 uridine 
• 102147-76-2 5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 626-48-2 6-Methyluracil 
• 36807-62-2 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-6-methyluracil 
• 869880-90-0 6-cyano-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene uridine 
• 869880-87-5 5-bromo-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene uridine 
• 142682-83-5 2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-methyluridine 
• 1070994-34-1 3-Benzyl-6-methyl-2-trimethylsilanyloxy-3H-pyrimidin-4-one 
• 99284-28-3 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-(methylthio)-6-methyluracil 
• 25589-18-8 3-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione 
• 638-13-1 6-methyl-4-sulfanylidene-1,2,3,4-tetrahydropyrimidin-2-one 
• 6328-58-1 6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one 
• 944317-12-8 C₃₂H₂₈N₂O₈S 

Downstream Products

• 626-48-2 6-Methyluracil 
• 50-69-1 D-ribose 
• 169886-85-5 5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-6-methyluridine 
• 169886-81-1 5'-O-4,4'-dimethoxytrityl-6-methyluridine 

Relevant articles and documents

Structure-activity relationships of C6-uridine derivatives targeting Plasmodia orotidine monophosphate decarboxylase

Malaria, caused by Plasmodia parasites, has re-emerged as a major problem, imposing its fatal effects on human health, especially due to multidrug resistance. In Plasmodia, orotidine 5′-monophosphate decarboxylase (ODCase) is an essential enzyme for the de novo synthesis of uridine 5′-monophosphate. Impairing ODCase in these pathogens is a promising strategy to develop novel classes of therapeutics. Encouraged by our recent discovery that 6-iodo uridine is a potent inhibitor of P. falciparum, we investigated the structure-activity relationships of various C6 derivatives of UMP. 6-Cyano, 6-azido, 6-amino, 6-methyl, 6-N-methylamino, and 6-N,N-dimethylamino derivatives of uridine were evaluated against P. falciparum. The mononucleotides of 6-cyano, 6-azido, 6-amino, and 6-methyl uridine derivatives were studied as inhibitors of plasmodial ODCase. 6-Azidouridine 5′-monophosphate is a potent covalent inhibitor of P. falciparum ODCase. 6-Methyluridine exhibited weak antimalarial activity against P. falciparum 3D7 isolate. 6-N-Methylamino and 6-N,N-dimethylamino uridine derivatives exhibited moderate antimalarial activities.

NMR-based conformational analysis of 2′,6-disubstituted uridines and antiviral evaluation of new phosphoramidate prodrugs

Six novel phosphoramidate prodrugs of uridine analogues, with structural modifications introduced at the 6- and 2′,6-positions, have been prepared and evaluated for selective antiviral activity against hepatitis C virus, as well as other positive-stranded RNA viruses. An analysis of the conformational properties of the parent nucleosides was carried out using two-dimensional NMR spectroscopy based experiments, highlighting a 3′-endo (North) sugar puckering preference and syn orientation.

PYRIMIDINE DERIVATIVES AS ANTICANCER AGENTS

The present invention includes methods of treating or preventing cancer by administering an effective amount of 6-substituted pyrimidine derivatives of the Formula I to a subject need thereof: