Cas no 1053164-76-3 (5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid)

5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid is a heterocyclic compound featuring a pyrazole core substituted with an amino group at the 5-position and a phenyl ring at the 1-position. The carboxylic acid functionality at the 3-position enhances its utility as a versatile building block in organic synthesis and pharmaceutical research. This compound is particularly valued for its role in the development of biologically active molecules, including potential drug candidates, due to its ability to participate in diverse chemical transformations such as amide coupling and cyclization reactions. Its structural features make it a useful intermediate for designing compounds with tailored properties in medicinal and agrochemical applications.
5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid structure
1053164-76-3 structure
Product Name:5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid
CAS No:1053164-76-3
MF:C10H9N3O2
MW:203.197361707687
CID:833251
Update Time:2026-04-29

5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid
    • 1H-Pyrazole-3-carboxylic acid, 5-amino-1-phenyl-
    • 5-amino-1-phenylpyrazole-3-carboxylic acid
    • AC 010220 dihydrochloride
    • MOUMWCTZFHYCJY-UHFFFAOYSA-N
    • Inchi: InChI=1S/C10H9N3O2/c11-9-6-8(10(14)15)12-13(9)7-4-2-1-3-5-7/h1-6H,11H2,(H,14,15)
    • InChI Key: MOUMWCTZFHYCJY-UHFFFAOYSA-N
    • SMILES: C1=CC=C(C=C1)N2C(=CC(=N2)C(=O)O)N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2

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Additional information on 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid

Introduction to 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid (CAS No. 1053164-76-3) and Its Emerging Applications in Chemical Biology

5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid, identified by the chemical identifier CAS No. 1053164-76-3, is a heterocyclic compound that has garnered significant attention in the field of chemical biology due to its versatile structural framework and potential biological activities. This compound belongs to the pyrazole class, a scaffold that is widely recognized for its role in medicinal chemistry and pharmacological research. The presence of both amino and carboxylic acid functional groups in its molecular structure enhances its reactivity, making it a valuable intermediate in the synthesis of more complex molecules.

The< strong>1H-pyrazole core of this compound is a key feature that contributes to its unique chemical properties. Pyrazoles have been extensively studied for their antimicrobial, anti-inflammatory, and anticancer effects. The aromatic ring system and the electron-rich nature of the pyrazole moiety facilitate interactions with biological targets, making it an attractive candidate for drug discovery. Furthermore, the< strong>phenyl substituent at the 1-position introduces additional electronic and steric effects that can modulate the biological activity of the molecule.

The< strong>3-carboxylic acid group at the third position of the pyrazole ring provides a site for further functionalization, enabling the synthesis of derivatives with tailored properties. This carboxylic acid moiety can participate in various chemical reactions, such as esterification, amidation, or coupling reactions, which are commonly employed in drug development pipelines. The< strong>5-amino group also offers opportunities for modifications, allowing researchers to explore different pharmacophores and optimize binding interactions with biological targets.

In recent years, there has been a growing interest in leveraging computational methods and high-throughput screening to identify novel bioactive compounds. The< strong>5-amino-1-phenyl-1H-pyrazole-3-carboxylic acid scaffold has been utilized in virtual screening campaigns to identify potential inhibitors of enzymes and receptors involved in various diseases. For instance, studies have demonstrated its potential as a lead compound for developing treatments against inflammatory disorders by targeting cyclooxygenase (COX) enzymes.

One of the most compelling aspects of this compound is its role as a precursor in the synthesis of more complex molecules with enhanced biological activity. Researchers have successfully incorporated the< strong>5-amino-1-phenyl-1H-pyrazole-3-carboxylic acid core into peptidomimetics and small-molecule inhibitors. These derivatives have shown promise in preclinical studies, highlighting the compound's potential as a building block in drug discovery.

The< strong>CAS No. 1053164-76-3 registry number ensures that researchers can reliably source this compound for their experiments while maintaining consistency across different studies. This standardized identification system is crucial for reproducibility in scientific research and industrial applications.

The< strong>phenyl-substituted pyrazole derivative has also been explored for its antimicrobial properties. Studies have indicated that certain derivatives of< strong>5-amino-1-phenyl-1H-pyrazole-3-carboxylic acid exhibit activity against Gram-positive bacteria, making them candidates for developing novel antibiotics. The combination of structural features such as the< strong>amino,< strong>carboxylic acid, and< strong>phenyl groups contributes to its ability to disrupt bacterial cell wall synthesis or interfere with essential metabolic pathways.

In addition to its antimicrobial applications, this compound has been investigated for its potential role in cancer therapy. Preclinical studies have suggested that derivatives of< strong>5-amino-1-phenyl-1H-pyrazole-3-carboxylic acid can inhibit the growth of certain cancer cell lines by targeting specific kinases or other molecular pathways involved in tumor progression. The ability to modulate these pathways underscores the compound's significance as a pharmacological tool.

The< strong>CARs (Chiral Centers), if present, further enhance the complexity and potential diversity of derivatives derived from this scaffold. Chiral molecules often exhibit different biological activities depending on their stereochemistry, providing an additional layer of control over drug design.

The synthesis of< strong>5-amino-1-phenyl-1H-pyrazole-3-carboxylic acid< CAS No. 1053164-76 > involves multi-step organic reactions that highlight modern synthetic methodologies such as transition metal-catalyzed cross-coupling reactions and palladium-mediated transformations. These advanced techniques enable efficient access to complex heterocyclic structures while maintaining high yields and purity.

The growing body of research on< strong >5-amino - 1 - phenyl - 1 H - pyrazole - 3 - carbox y lic aci d underscores its importance as a versatile building block in medicinal chemistry . Its ability to serve as a precursor for biologically active molecules makes it an invaluable asset in drug discovery efforts aimed at addressing various therapeutic challenges . As research continues , it is likely that new applications and derivatives will emerge , further solidifying its role in chemical biology . p >

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