Cas no 27921-78-4 (2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl-)

4-Amino-1-β-L-arabinofuranosyl-2(1H)-pyrimidinone is a nucleoside analog with significant potential in biochemical and pharmaceutical research. Its structure, featuring an arabinofuranosyl sugar moiety linked to a 4-aminopyrimidinone base, confers unique properties for studying nucleic acid interactions and enzyme inhibition. This compound is particularly relevant in antiviral and anticancer research due to its ability to mimic natural nucleosides, potentially interfering with DNA/RNA synthesis. Its stereospecific β-L-configuration enhances selectivity, reducing off-target effects. The 4-amino group further allows for functionalization, enabling tailored modifications for specific applications. This makes it a valuable intermediate for developing novel therapeutics or probes in molecular biology. High purity and well-characterized synthesis pathways ensure reproducibility for research use.
2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl- structure
27921-78-4 structure
Product Name:2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl-
CAS No:27921-78-4
MF:C9H13N3O5
MW:243.216622114182
CID:251593
PubChem ID:6476646
Update Time:2025-06-08

2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl- Chemical and Physical Properties

Names and Identifiers

    • 2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl-
    • 1-β-L-Arabinofuranosylcytosine
    • 1-b-L-Arabinofuranosylcytosine
    • Cytosine,1-b-L-arabinofuranosyl- (8CI)
    • 2(1H)-Pyrimidinone, 4-amino-1-β-L-arabinofuranosyl-
    • Cytosine, 1-β-L-arabinofuranosyl- (8CI)
    • Inchi: 1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m0/s1
    • InChI Key: UHDGCWIWMRVCDJ-JPCMASIJSA-N
    • SMILES: O[C@@H]1[C@H]([C@H](CO)O[C@@H]1N1C=CC(N)=NC1=O)O

Computed Properties

  • Exact Mass: 243.08552052g/mol
  • Monoisotopic Mass: 243.08552052g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 2
  • Complexity: 383
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.1
  • Topological Polar Surface Area: 129?2

2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl- Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Enamine
EN300-37158622-0.05g
4-amino-1-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
27921-78-4 95.0%
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Additional information on 2(1H)-Pyrimidinone,4-amino-1-b-L-arabinofuranosyl-

Introduction to 2(1H)-Pyrimidinone, 4-amino-1-b-L-arabinofuranosyl- (CAS No. 27921-78-4)

2(1H)-Pyrimidinone, 4-amino-1-b-L-arabinofuranosyl-, also known as Ara-A or Vidarabine, is a nucleoside analog with significant antiviral properties. This compound, identified by the CAS number 27921-78-4, has been extensively studied for its therapeutic potential in treating various viral infections, particularly those caused by herpesviruses and adenoviruses. The unique structure of Ara-A, characterized by the presence of a modified pyrimidine base and an L-arabinose sugar, confers it with high specificity and efficacy against these pathogens.

The molecular formula of 2(1H)-Pyrimidinone, 4-amino-1-b-L-arabinofuranosyl- is C10H13N5O4, and its molecular weight is approximately 255.23 g/mol. The compound is a white to off-white crystalline powder that is soluble in water and slightly soluble in ethanol. Its chemical structure allows it to mimic natural nucleosides, thereby interfering with viral DNA synthesis and replication.

In clinical settings, Ara-A has been used primarily for the treatment of severe herpes simplex virus (HSV) infections, particularly in immunocompromised patients such as those with AIDS or undergoing organ transplantation. It has also shown efficacy against adenovirus infections, which can be particularly problematic in neonates and immunocompromised individuals. The mechanism of action of Ara-A involves its phosphorylation by cellular kinases to form the active triphosphate form, which then competes with natural deoxyadenosine triphosphate (dATP) for incorporation into viral DNA. Once incorporated, it causes chain termination, effectively halting viral replication.

Recent research has further elucidated the pharmacokinetics and pharmacodynamics of Ara-A. Studies have shown that the compound has a relatively short half-life in vivo, necessitating frequent dosing to maintain therapeutic levels. However, its high selectivity for viral DNA polymerases over human DNA polymerases minimizes toxicity to host cells. This selectivity is crucial for its safety profile and effectiveness as an antiviral agent.

In addition to its established use in treating viral infections, there is growing interest in exploring the broader therapeutic applications of Ara-A. For instance, preclinical studies have investigated its potential as an antitumor agent due to its ability to inhibit DNA synthesis in rapidly dividing cells. While more research is needed to fully understand its anticancer properties, preliminary findings are promising and warrant further investigation.

The development of novel delivery systems for Ara-A has also been a focus of recent research. Nanoparticle-based formulations have shown promise in enhancing the bioavailability and reducing the toxicity of the compound. These advanced delivery systems aim to optimize drug distribution and target specific tissues or cells, thereby improving treatment outcomes and patient compliance.

In conclusion, 2(1H)-Pyrimidinone, 4-amino-1-b-L-arabinofuranosyl- (CAS No. 27921-78-4) remains a valuable compound in the arsenal of antiviral therapies. Its unique chemical structure and mechanism of action make it an effective treatment option for severe viral infections. Ongoing research continues to expand our understanding of its potential applications and improve its delivery methods, ensuring that it remains a relevant and important molecule in the field of medicinal chemistry.

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