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

Uses

6-Methyluridine exhibited weak antimalarial activity against P. falciparum 3D7 isolate. It is a weak substrate of Escherichia coli pyrimidine nucleoside phosphorylase.

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

• 64898-15-3 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine 
• 74-88-4 methyl iodide 
• 23316-76-9 6-methyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione 
• 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 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 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 

Downstream Products

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