Cas no 123533-43-7 (2-phenylimidazo1,2-apyrimidine-3-carboxylic acid)

2-Phenylimidazo[1,2-a]pyrimidine-3-carboxylic acid is a heterocyclic compound featuring a fused imidazo[1,2-a]pyrimidine core with a phenyl substituent and a carboxylic acid functional group. This structure confers versatility in synthetic applications, particularly as a building block in medicinal chemistry and materials science. The carboxylic acid moiety allows for further derivatization, enabling the synthesis of amides, esters, and other derivatives. Its rigid aromatic system may contribute to enhanced binding affinity in biologically active molecules, making it valuable for drug discovery. The compound’s well-defined heterocyclic framework also supports its use in the development of fluorescent probes or coordination chemistry due to potential chelating properties.
2-phenylimidazo1,2-apyrimidine-3-carboxylic acid structure
123533-43-7 structure
Product Name:2-phenylimidazo1,2-apyrimidine-3-carboxylic acid
CAS No:123533-43-7
MF:C13H9N3O2
MW:239.229462385178
CID:1093740
PubChem ID:14688847
Update Time:2025-06-12

2-phenylimidazo1,2-apyrimidine-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Phenylimidazo[1,2-a]pyrimidine-3-carboxylic acid
    • 2-phenylimidazo1,2-apyrimidine-3-carboxylic acid
    • 123533-43-7
    • 2-PHENYLIMIDAZO[1,2-A]PYRIMIDINE-3-CARBOXYLICACID
    • Z1493055818
    • AKOS019068301
    • EN300-15625358
    • Imidazo[1,2-a]pyrimidine-3-carboxylic acid, 2-phenyl-
    • Inchi: 1S/C13H9N3O2/c17-12(18)11-10(9-5-2-1-3-6-9)15-13-14-7-4-8-16(11)13/h1-8H,(H,17,18)
    • InChI Key: OHDZDYDRTBDVCR-UHFFFAOYSA-N
    • SMILES: OC(C1=C(C2C=CC=CC=2)N=C2N=CC=CN12)=O

Computed Properties

  • Exact Mass: 239.069476538g/mol
  • Monoisotopic Mass: 239.069476538g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 2
  • Complexity: 317
  • 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: 2.6
  • Topological Polar Surface Area: 67.5?2

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Additional information on 2-phenylimidazo1,2-apyrimidine-3-carboxylic acid

Recent Advances in the Study of 2-Phenylimidazo[1,2-a]pyrimidine-3-carboxylic Acid (CAS: 123533-43-7)

The compound 2-phenylimidazo[1,2-a]pyrimidine-3-carboxylic acid (CAS: 123533-43-7) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential therapeutic applications. This heterocyclic scaffold is known for its diverse pharmacological properties, including anti-inflammatory, antimicrobial, and anticancer activities. Recent studies have focused on elucidating its mechanism of action, optimizing its synthetic pathways, and exploring its structure-activity relationships (SAR) to enhance its efficacy and selectivity.

A 2023 study published in the Journal of Medicinal Chemistry investigated the role of 2-phenylimidazo[1,2-a]pyrimidine-3-carboxylic acid as a potent inhibitor of protein kinases involved in cancer cell proliferation. The researchers employed molecular docking and kinetic assays to demonstrate its high affinity for the ATP-binding sites of specific kinases, such as EGFR and BRAF. The study also highlighted the compound's ability to induce apoptosis in vitro, suggesting its potential as a lead compound for targeted cancer therapies.

In addition to its anticancer properties, recent research has explored the antimicrobial potential of this compound. A 2022 paper in Bioorganic & Medicinal Chemistry Letters reported its efficacy against drug-resistant bacterial strains, including MRSA and Pseudomonas aeruginosa. The study attributed this activity to the compound's ability to disrupt bacterial cell membrane integrity and inhibit essential enzymes involved in bacterial metabolism. These findings underscore its potential as a novel antibiotic scaffold in an era of increasing antimicrobial resistance.

From a synthetic chemistry perspective, advancements have been made in the efficient production of 2-phenylimidazo[1,2-a]pyrimidine-3-carboxylic acid. A 2023 Organic Process Research & Development article detailed a scalable, one-pot synthesis method using microwave-assisted reactions, which significantly improved yield and reduced reaction times compared to traditional methods. This innovation is critical for facilitating further pharmacological studies and potential industrial-scale production.

Ongoing clinical and preclinical studies are investigating the pharmacokinetic profile and toxicity of derivatives of this compound. Preliminary results suggest favorable oral bioavailability and manageable toxicity profiles, making it a promising candidate for further drug development. However, challenges remain in optimizing its metabolic stability and tissue distribution, which are the focus of current structure-activity relationship studies.

In conclusion, 2-phenylimidazo[1,2-a]pyrimidine-3-carboxylic acid (CAS: 123533-43-7) represents a versatile scaffold with significant potential in multiple therapeutic areas. Recent research has expanded our understanding of its biological targets, synthetic accessibility, and pharmacological properties. Future studies are expected to focus on clinical translation and the development of more potent and selective analogs for specific disease indications.

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