Cas no 25055-92-9 (3H-Diazirine-3-propanamide, 3-methyl-)

3H-Diazirine-3-propanamide, 3-methyl-, is a versatile diazirine-based compound widely used in photoaffinity labeling and crosslinking applications. Its key advantage lies in its stable diazirine moiety, which, upon UV irradiation, generates highly reactive carbene intermediates capable of forming covalent bonds with proximal molecules. This property makes it valuable for studying protein-protein interactions, ligand-receptor binding, and other biomolecular processes. The methyl substitution enhances its stability and solubility in organic and aqueous media, facilitating its incorporation into diverse experimental systems. Its small molecular size minimizes steric interference, ensuring minimal disruption to native biological interactions. The compound is particularly useful in proteomics and structural biology research.
3H-Diazirine-3-propanamide, 3-methyl- structure
25055-92-9 structure
Product Name:3H-Diazirine-3-propanamide, 3-methyl-
CAS No:25055-92-9
MF:C5H9N3O
MW:127.144460439682
CID:5993870
PubChem ID:55282139
Update Time:2025-11-01

3H-Diazirine-3-propanamide, 3-methyl- Chemical and Physical Properties

Names and Identifiers

    • 3H-Diazirine-3-propanamide, 3-methyl-
    • EN300-6734561
    • SCHEMBL22769249
    • 25055-92-9
    • AKOS006342565
    • 3-(3-methyl-3h-diazirin-3-yl)propanamide
    • Inchi: 1S/C5H9N3O/c1-5(7-8-5)3-2-4(6)9/h2-3H2,1H3,(H2,6,9)
    • InChI Key: GFWDWZPUHOBTDB-UHFFFAOYSA-N
    • SMILES: N1C(C)(CCC(N)=O)N=1

Computed Properties

  • Exact Mass: 127.074561919g/mol
  • Monoisotopic Mass: 127.074561919g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 3
  • Complexity: 158
  • 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: -0.3
  • Topological Polar Surface Area: 67.8?2

Experimental Properties

  • Density: 1.37±0.1 g/cm3(Predicted)
  • Boiling Point: 281.0±32.0 °C(Predicted)
  • pka: 16.41±0.40(Predicted)

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Additional information on 3H-Diazirine-3-propanamide, 3-methyl-

3H-Diazirine-3-propanamide, 3-methyl- (CAS No. 25055-92-9): An Overview of Its Properties and Applications in Chemical Biology and Drug Discovery

3H-Diazirine-3-propanamide, 3-methyl- (CAS No. 25055-92-9) is a versatile compound that has gained significant attention in the fields of chemical biology and drug discovery due to its unique properties and potential applications. This compound, also known as 3-Methyl-3H-diazirine-3-propanamide, belongs to the class of diazirines, which are characterized by their reactivity and ability to form covalent bonds with biomolecules upon activation. This property makes it an invaluable tool in various biochemical and pharmaceutical research areas.

The chemical structure of 3H-Diazirine-3-propanamide, 3-methyl- consists of a diazirine ring attached to a propanamide moiety, with a methyl group substituent at the 3-position. The diazirine moiety is particularly reactive and can be photoactivated to generate highly reactive carbene intermediates. These intermediates can form covalent bonds with nearby biomolecules, such as proteins and nucleic acids, making 3H-Diazirine-3-propanamide, 3-methyl- an excellent candidate for bioconjugation and protein labeling studies.

Recent advancements in chemical biology have highlighted the importance of 3H-Diazirine-3-propanamide, 3-methyl- in understanding protein-protein interactions and post-translational modifications. For instance, a study published in the *Journal of the American Chemical Society* demonstrated the use of 3H-Diazirine-3-propanamide, 3-methyl- as a photoaffinity label to identify protein targets of small molecules. The researchers conjugated this compound to a known inhibitor and used it to probe the binding site on a target protein. The results provided detailed insights into the molecular interactions and helped refine the inhibitor's structure for improved potency.

In the context of drug discovery, 3H-Diazirine-3-propanamide, 3-methyl- has been utilized to develop novel therapeutics. A notable example is its application in PROTAC (PROteolysis TArgeting Chimeras) technology. PROTACs are bifunctional molecules that bring together a target protein and an E3 ubiquitin ligase, leading to the ubiquitination and subsequent degradation of the target protein. By incorporating 3H-Diazirine-3-propanamide, 3-methyl- into PROTACs, researchers can enhance the specificity and efficiency of protein degradation. This approach has shown promise in treating diseases such as cancer and neurodegenerative disorders.

The synthesis of 3H-Diazirine-3-propanamide, 3-methyl- involves several well-established chemical reactions. One common method involves the reaction of methylamine with diazirinyl acetonitrile, followed by hydrolysis to form the amide. The resulting compound can be further modified through various functional group transformations to tailor its properties for specific applications. For instance, introducing additional substituents or functional groups can alter its reactivity or solubility, making it more suitable for particular biological assays.

The safety profile of 3H-Diazirine-3-propanamide, 3-methyl- is an important consideration in its use. While diazirines are generally considered safe when handled properly, precautions should be taken to avoid exposure to high concentrations or prolonged contact with skin or eyes. Standard laboratory safety protocols should be followed when working with this compound to ensure safe handling and storage.

In conclusion, 3H-Diazirine-3-propanamide, 3-methyl- (CAS No. 25055-92-9) is a valuable compound with a wide range of applications in chemical biology and drug discovery. Its unique reactivity and versatility make it an essential tool for researchers aiming to understand complex biological systems and develop novel therapeutics. As research continues to advance, it is likely that new applications for this compound will emerge, further solidifying its importance in the scientific community.

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