1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione, CAS No. 3083-77-0

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3083-77-0

Catalog No. EBD143169

CAS 3083-77-0

Name 1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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Basic Information

Synonyms: uracil-1-beta-D-arabinofuranoside 1-?Arabinofuranosyluracil 1-β-D-Arabinofuranosyluracil ara-U Arabinfuranosyluracil 1-pentofuranosylpyrimidine-2,4(1H,3H)-dione 1-(beta-D-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione Spongouridine Arabinofuranosyluracil 1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Molecular Formula: C9H12N2O6

Molecular Weight: 244.2

MDL Number: MFCD00065998

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

Product Description:

6-Azauridine is a synthetic nucleoside analog, specifically a triazine nucleoside. Its chemical structure features a uracil base where one of the carbon atoms in the pyrimidine ring is replaced by a nitrogen atom, forming a 1,2,4-triazine ring, which is linked to a ribose sugar moiety. This structural modification is key to its biological activity. The primary application of 6-Azauridine is in biochemical and pharmacological research. It acts as a competitive inhibitor of orotidine-5'-monophosphate decarboxylase (OMP decarboxylase), a key enzyme in the *de novo* pyrimidine biosynthesis pathway. By inhibiting this enzyme, it disrupts the production of uridine monophosphate (UMP) and subsequently other pyrimidine nucleotides, leading to cytotoxic effects. Historically, it has been investigated for its potential as an antineoplastic (anti-cancer) and antiviral agent. It serves as an important research tool for studying pyrimidine metabolism and for the development of related nucleoside-based therapeutics. As a modified nucleoside, it is also utilized as a specialized building block (synthetic intermediate) in the synthesis of more complex nucleoside analogs and probes for life science research. Its handling requires standard laboratory precautions for biochemical reagents.

Physical Properties

Melting Point: 220-222°C

Density: 1.674 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: white to off-white solid