81797-05-9

Basic information

• Product Name: 1-[(2-hydroxyethoxy)methyl]-5-nitropyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-[(2-Hydroxyethoxy)methyl]-5-nitropyrimidine-2,4(1H,3H)-dione; 2,4(1H,3H)-pyrimidinedione, 1-[(2-hydroxyethoxy)methyl]-5-nitro-
• CAS NO: 81797-05-9
• Molecular Formula: C₇H₉N₃O₆
• Molecular Weight: 231.1629
• Mol File: 81797-05-9.mol
• Article Data: 3

Chemical Properties

• Density: 1.6g/cm³
• Refractive Index: 1.599
• CAS DataBase Reference: 1-[(2-hydroxyethoxy)methyl]-5-nitropyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2-hydroxyethoxy)methyl]-5-nitropyrimidine-2,4(1H,3H)-dione(81797-05-9)
• EPA Substance Registry System: 1-[(2-hydroxyethoxy)methyl]-5-nitropyrimidine-2,4(1H,3H)-dione(81797-05-9)

Safety Data

• Hazardous Substances Data: 81797-05-9(Hazardous Substances Data)

Usage

Functional groups

Nitro group (-NO2), Hydroxyethyl group (-CH2CH2OH), Pyrimidine ring, Carbonyl groups (C=O)

Nitro-substituted pyrimidine derivative

The presence of a nitro group (-NO2) attached to the pyrimidine ring

Hydroxyethyl group attachment

A hydroxyethyl group (-CH2CH2OH) is attached to the nitrogen atom of the pyrimidine ring

Application in synthesis

Used in the synthesis of pharmaceuticals and agrochemicals

Building block in organic synthesis

Can be used as a building block to create more complex molecules

Potential precursor

The nitro group makes it a potential precursor for the production of various nitro-containing compounds

Interactions with biological systems

The presence of the hydroxyethyl group adds potential for interactions with biological systems

Interest for medicinal and biological research

Due to its potential interactions with biological systems, the compound is of interest for research in medicine and biology

Upstream product

• 611-08-5 5-nitrobarbituric acid 
• 58305-05-8 (2-benzoyloxyethyl)oxymethyl chloride 
• 646-06-0 1,3-DIOXOLANE 
• 52522-97-1 5-nitro-2,4-bis-trimethylsilanyloxy-pyrimidine 
• 81777-44-8 Acetic acid 2-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethoxy)-ethyl ester 

Relevant articles and documents

Inhibition of hepatitis B virus (HBV) replication by pyrimidines bearing an acyclic moiety: Effect on wild-type and mutant HBV

Chronic hepatitis B virus (HBV) infection remains a major health problem worldwide. The main clinical limitation of a current antiviral drug for HBV, lamivudine, is the emergence of drug-resistant viral strains upon prolonged therapy. A group of 5-, 6-, or 5,6-substituted acyclic pyrimidine nucleosides with a 1-[(2-hydroxyethoxy)methyl] moiety were synthesized and evaluated for antiviral activities. The target compounds were prepared by the reaction of silylated uracils possessing a variety of substituents at the C-5 or C-6 positions or both with 1,3-dioxolane in the presence of potassium iodide and chlorotrimethylsilane by a convenient and single-step synthesis. Among the compounds tested, 5-chloro and 5-bromo analogues possessing an acyclic glycosyl moiety were the most effective and selective antiviral agents in the in vitro assays against wild-type duck HBV (EC50 = 0.4-2.2 and 3.7-18.5 μM, respectively) and human HBV-containing 2.2.15 cells (EC50 = 4.5-45.4 and 18.5-37.7 μM, respectively). These compounds were also found to retain sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and double mutations (L180M/M204V). The compounds investigated did not show cytotoxicity to host HepG2 and Vero cells, up to the highest concentration tested. The results presented here confirm and accentuate the potential of acyclic pyrimidine nucleosides as anti-HBV agents and extend our previous observations. We herein report the capability of acyclic pyrimidine nucleosides to inhibit the replication of both wild-type and drug-resistant mutant HBV.

Nucleic acid related compounds. 37. Convenient and high-yield syntheses of N-[(2-hydroxyethoxy)methyl] heterocycles as 'acyclic nucleoside' analogues

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