16710-16-0

Usage

Uses

Used in Pharmaceutical Research:
5,6-dimethyl-1-pentofuranosylpyrimidine-2,4(1H,3H)-dione is used as a research compound for its potential biological activity, which may be attributed to its distinctive structural features. It is employed in the exploration of new drug candidates and the understanding of its interactions with biological systems.
Used in Chemical Synthesis:
In the chemical industry, 5,6-dimethyl-1-pentofuranosylpyrimidine-2,4(1H,3H)-dione is used as a building block for the synthesis of other complex organic compounds. Its unique structure makes it a valuable intermediate in the creation of pharmaceuticals, agrochemicals, or other specialty chemicals that require its specific functional groups and ring systems.

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 175354-50-4 4-Ethylsulfanyl-5,6-dimethyl-1H-pyrimidin-2-one 

Downstream Products

• 268745-98-8 5'-O-4,4'-dimethoxytrityl-5,6-dimethyluridine 
• 268745-99-9 5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-5,6-dimethyluridine 

Relevant academic research and scientific papers

6-Substituted and 5,6-disubstituted derivatives of uridine: Stereoselective synthesis, interaction with uridine phosphorylase, and in vitro antitumor activity

Stereoselective procedures are described for the synthesis of 6- alkyluridines by Lewis acid-catalyzed condensation of (a) trimethylsilylated 6-alkyl-4-alkylthiouracils with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D- ribofuranose (ABR) and (b) trimethylsilylated 6-alkyl-3-benzyluracils with ABR. The 4-methylthio group was subsequently removed with the use of 1 N trifluoroacetic acid and the 3-benzyl group by a new modified procedure with the use of the complex BBr3-THF. Furthermore, 6-(hydroxymethyl)uridine (39) and 5-fluoro-6-(hydroxymethyl)uridine (40) were obtained by sequential oxidation with SeO2 and reduction with tetrabutylammonium borohydride of the 6-methyl group of 6-methyluridine (5) and 5-fluoro-6-methyluridine (35), and their corresponding 6-fluoromethyl congeners 41 and 42 were obtained by DAST treatment of 39 and 40, respectively. For all the foregoing nucleosides in the fixed syn conformation about the glycosyl bond, 1H NMR spectroscopy further demonstrated that the pentose rings exist predominantly in the conformation N (3'-endo). Most of the nucleosides were weak substrates of Escherichia coli pyrimidine nucleoside phosphorylase. Enhanced susceptibility to phosphorolysis was exhibited by two of them, 39 and 41, with 6-CH2OH and 6-CH2F substituents capable of formation of an additional hydrogen bond with the enzyme. The 5-fluoro-6-substituted uridines were the poorest substrates. Cytotoxicities of the nucleosides were examined vs the human tumor cell lines MOLT-3, U-937, K-562, and IM-9, as well as PHA-stimulated human lymphocytes. Two of the analogues, 5-fluoro-6-(fluoromethyl)uridine (42) and 5-fluoro-6- (hydroxymethyl)uridine (40), exhibited cytotoxicities comparable to that of 5-fluorouracil.