Cas no 131346-22-0 (N-hydroxypyrimidine-4-carboxamide)

N-Hydroxypyrimidine-4-carboxamide is a versatile heterocyclic compound characterized by its hydroxamic acid functional group and pyrimidine core. This structure imparts notable reactivity, making it valuable as a synthetic intermediate in medicinal chemistry and organic synthesis. Its hydroxamic acid moiety enables chelation with metal ions, facilitating applications in catalysis and metalloenzyme inhibition studies. The pyrimidine scaffold further enhances its utility in designing pharmacologically active molecules, particularly in kinase and protease inhibitor development. The compound’s balanced solubility in polar and semi-polar solvents allows for flexible use in diverse reaction conditions. Its stability under standard laboratory conditions ensures reliable handling and storage.
N-hydroxypyrimidine-4-carboxamide structure
131346-22-0 structure
Product Name:N-hydroxypyrimidine-4-carboxamide
CAS No:131346-22-0
MF:C5H5N3O2
MW:139.112100362778
CID:102351
PubChem ID:45080175
Update Time:2025-06-14

N-hydroxypyrimidine-4-carboxamide Chemical and Physical Properties

Names and Identifiers

    • 4-Pyrimidinecarboxamide,N-hydroxy-
    • 4-Pyrimidinecarboxamide, N-hydroxy- (9CI)
    • N-hydroxypyrimidine-4-carboxamide
    • N-Hydroxy-4-pyrimidinecarboxamide
    • DTXSID201300750
    • EN300-1294334
    • 131346-22-0
    • SCHEMBL37633
    • Inchi: 1S/C5H5N3O2/c9-5(8-10)4-1-2-6-3-7-4/h1-3,10H,(H,8,9)
    • InChI Key: ZOCWDWMASUCTTI-UHFFFAOYSA-N
    • SMILES: O=C(C1C=CN=CN=1)NO

Computed Properties

  • Exact Mass: 139.03825
  • Monoisotopic Mass: 139.038176411g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 128
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.8
  • Topological Polar Surface Area: 75.1?2

Experimental Properties

  • PSA: 75.11

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Additional information on N-hydroxypyrimidine-4-carboxamide

Recent Advances in the Study of N-hydroxypyrimidine-4-carboxamide (CAS: 131346-22-0) in Chemical Biology and Pharmaceutical Research

N-hydroxypyrimidine-4-carboxamide (CAS: 131346-22-0) has emerged as a compound of significant interest in chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. Recent studies have focused on its role as a versatile scaffold in drug discovery, particularly in the development of enzyme inhibitors and modulators of biological pathways. This research brief synthesizes the latest findings on this compound, highlighting its mechanisms of action, synthetic routes, and applications in medicinal chemistry.

A key area of investigation has been the compound's ability to act as a selective inhibitor of metalloenzymes, such as histone deacetylases (HDACs) and matrix metalloproteinases (MMPs). Studies published in the past year demonstrate that N-hydroxypyrimidine-4-carboxamide derivatives exhibit potent inhibitory activity against HDAC isoforms, with promising implications for cancer therapy. The hydroxamic acid moiety in its structure is particularly noteworthy, as it enables chelation of zinc ions in the active sites of these enzymes, thereby blocking their catalytic activity.

Recent synthetic chemistry advancements have expanded the toolbox for creating diverse derivatives of 131346-22-0. A 2023 study in the Journal of Medicinal Chemistry reported an efficient three-step synthesis protocol that improves yield and purity while allowing for extensive structural modifications at the pyrimidine ring. This development has facilitated structure-activity relationship (SAR) studies, leading to the identification of analogs with enhanced pharmacokinetic properties and target specificity.

In the realm of drug discovery, computational modeling studies have provided valuable insights into the binding modes of N-hydroxypyrimidine-4-carboxamide derivatives with their biological targets. Molecular dynamics simulations have revealed that subtle modifications to the carboxamide group can significantly influence binding affinity and selectivity. These findings are guiding the rational design of next-generation inhibitors with improved therapeutic profiles.

Emerging preclinical data suggest potential applications beyond oncology. Recent investigations have explored the compound's anti-inflammatory properties through its modulation of NF-κB signaling pathways. Additionally, its ability to cross the blood-brain barrier has sparked interest in neurological disorders, with preliminary studies showing neuroprotective effects in models of neurodegenerative diseases.

The pharmaceutical industry has taken notice of these developments, with several companies filing patents for novel N-hydroxypyrimidine-4-carboxamide derivatives in 2022-2023. These patents cover compositions ranging from standalone therapeutic agents to combination therapies with existing drugs, reflecting the compound's versatility in treatment strategies.

While the research landscape is promising, challenges remain in optimizing the pharmacological properties of 131346-22-0 derivatives. Current efforts focus on addressing issues related to metabolic stability and off-target effects. The development of prodrug strategies and targeted delivery systems represents an active area of investigation that may overcome these limitations.

In conclusion, N-hydroxypyrimidine-4-carboxamide (131346-22-0) continues to demonstrate significant potential in chemical biology and drug discovery. The convergence of synthetic chemistry, computational modeling, and biological evaluation is driving the development of novel therapeutic agents based on this scaffold. As research progresses, this compound class may yield important clinical candidates for multiple disease indications.

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