Cas no 289472-80-6 (N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide)

N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide is a specialized organic compound featuring a pyrazinecarboxamide moiety linked to a phenylmethyl-substituted amino acid derivative. Its structural design combines a chiral center with both amide and carboxamide functional groups, making it a valuable intermediate in pharmaceutical and biochemical research. The compound’s rigid aromatic pyrazine ring and polar amide groups enhance its potential for selective binding interactions, particularly in drug discovery targeting enzyme inhibition or receptor modulation. Its well-defined stereochemistry and synthetic versatility further support its utility in the development of optically active compounds. Suitable for controlled reactions, it offers researchers a precise tool for exploring structure-activity relationships.
N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide structure
289472-80-6 structure
Product Name:N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide
CAS No:289472-80-6
MF:C14H14N4O2
MW:270.28656244278
MDL:MFCD26743605
CID:1030962
PubChem ID:67121778
Update Time:2025-10-31

N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide Chemical and Physical Properties

Names and Identifiers

    • (S)-N-(1-Amino-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide
    • N-[(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl]-2-pyrazinecarboxamide
    • N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]pyrazine-2-carboxamide
    • Bortezomib Impurity B
    • DTXSID80736476
    • UNII-N46QC2PY7V
    • 2-Pyrazinecarboxamide, N-((1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl)-
    • N46QC2PY7V
    • AKOS016844897
    • 2-Pyrazinecarboxamide, N-[(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl]-
    • KTQJEBWLYWKXRA-NSHDSACASA-N
    • Nalpha-(Pyrazine-2-carbonyl)-L-phenylalaninamide
    • DB-224821
    • 2-Pyrazinecarboxamide, N-[(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl]-; N-[(1S)-2-Amino-1-benzyl-2-oxo-ethyl]pyrazine-2-carboxamide
    • N-[(1S)-2-Amino-1-benzyl-2-oxoethyl]pyrazine-2-carboxamide
    • Pyrazinecarboxamide, N-[(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl]-
    • SCHEMBL1688075
    • N-((1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl)-pyrazinecarboxamide, (-)-
    • N-((1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl)-pyrazinecarboxamide
    • Bortezomib (m3)
    • (2S)-3-PHENYL-2-(PYRAZIN-2-YLFORMAMIDO)PROPANAMIDE
    • J-017332
    • 289472-80-6
    • N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide
    • MDL: MFCD26743605
    • Inchi: 1S/C14H14N4O2/c15-13(19)11(8-10-4-2-1-3-5-10)18-14(20)12-9-16-6-7-17-12/h1-7,9,11H,8H2,(H2,15,19)(H,18,20)/t11-/m0/s1
    • InChI Key: KTQJEBWLYWKXRA-NSHDSACASA-N
    • SMILES: O=C([C@H](CC1C=CC=CC=1)NC(C1C=NC=CN=1)=O)N

Computed Properties

  • Exact Mass: 270.11167570g/mol
  • Monoisotopic Mass: 270.11167570g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 6
  • Complexity: 342
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.3
  • Topological Polar Surface Area: 98?2

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Melting Point: NA
  • Boiling Point: 619.4±55.0 °C at 760 mmHg
  • Flash Point: 328.4±31.5 °C
  • Vapor Pressure: 0.0±1.8 mmHg at 25°C

N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide Security Information

N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide Pricemore >>

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Additional information on N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide

Professional Introduction to N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide (CAS No. 289472-80-6)

N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide, identified by its CAS number 289472-80-6, is a compound of significant interest in the field of pharmaceutical chemistry and biochemistry. This molecule, featuring a pyrazine core and an amide functional group, has garnered attention due to its structural complexity and potential biological activities. The stereochemistry at the 1S position adds an additional layer of interest, as enantiomeric purity can greatly influence pharmacological outcomes.

The< strong>pyrazine scaffold is a well-documented heterocyclic system, known for its presence in numerous bioactive molecules. Pyrazines exhibit a wide range of biological properties, including antimicrobial, antiviral, and anti-inflammatory effects. The incorporation of an amide group in this structure suggests potential interactions with biological targets such as enzymes and receptors, which are often modulated by amide-based pharmacophores.

In recent years, there has been a growing interest in the development of chiral drugs due to their improved efficacy and reduced side effects compared to their racemic counterparts. The specific stereochemistry of N-(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide makes it a valuable candidate for studying the impact of enantiomerism on biological activity. Studies have shown that the 1S configuration can significantly alter binding affinity and metabolic stability, making its synthesis and characterization crucial for drug development.

The< strong>phenylmethyl group, also known as benzyl, is another key feature of this compound. Benzyl groups are frequently used in medicinal chemistry due to their ability to enhance solubility, improve pharmacokinetics, and contribute to the overall stability of drug molecules. The presence of this group in conjunction with the pyrazine and amide moieties creates a complex molecular architecture that may confer unique biological properties.

Recent research has highlighted the importance of N-(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide in the development of novel therapeutic agents. For instance, studies have demonstrated its potential as a precursor in the synthesis of more complex molecules with targeted biological activities. The compound's ability to serve as a building block for larger scaffolds makes it particularly valuable in medicinal chemistry.

The< strong>amide functionality is known for its role in modulating protein-protein interactions and enzyme activity. In particular, amides have been extensively studied for their ability to act as hinge binders in drug design. The pyrazine-carboxamide moiety in N-(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide could potentially interact with specific residues in target proteins, leading to the development of highly selective drugs.

The synthesis of this compound involves multiple steps, each requiring careful optimization to ensure high yield and purity. Advanced synthetic techniques such as chiral resolution and asymmetric catalysis are often employed to achieve the desired stereochemical configuration. The complexity of the synthesis underscores the compound's significance in pharmaceutical research.

In conclusion, N-(1S)-2-Amino-2-oxo-1-(phenylmethyl)ethyl-2-pyrazinecarboxamide (CAS No. 289472-80-6) represents a promising candidate for further exploration in drug discovery. Its unique structural features, including the pyrazine core, amide group, and stereochemistry at the 1S position, make it a valuable asset for medicinal chemists. As research continues to uncover new biological activities and synthetic methodologies, this compound is poised to play a significant role in the development of next-generation therapeutics.

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