Cas no 5227-53-2 (Azepane-2-carboxylic acid)

Azepane-2-carboxylic acid is a seven-membered heterocyclic compound featuring a carboxylic acid functional group at the 2-position. This structure makes it a valuable intermediate in organic synthesis and pharmaceutical research, particularly in the development of bioactive molecules and peptidomimetics. Its rigid yet flexible azepane ring offers conformational versatility, enabling its use in designing enzyme inhibitors and receptor modulators. The carboxylic acid moiety allows for further derivatization, facilitating the creation of amides, esters, and other functionalized derivatives. High purity and consistent quality are critical for its applications in medicinal chemistry and material science. Its stability under standard conditions ensures reliable handling and storage.
Azepane-2-carboxylic acid structure
Azepane-2-carboxylic acid structure
Product Name:Azepane-2-carboxylic acid
CAS No:5227-53-2
MF:C7H13NO2
MW:143.183622121811
MDL:MFCD00457600
CID:385834
PubChem ID:257788
Update Time:2025-05-22

Azepane-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • Azepane-2-carboxylic acid
    • 1-ALLYL-2-(2-HYDROXYETHYL)THIOUREA
    • 1H-Azepine-2-carboxylicacid, hexahydro-
    • hexahydro-1H-Azepine-2-carboxylic acid
    • (+-)-Hexahydro-1H-azepin-2-carbonsaeure
    • 1H-Azepine-2-carboxylicacid
    • 2-azepanecarboxylic acid
    • 2-carboxyhomopiperidine
    • AC1L5XIW
    • AC1Q5UG6
    • AC1Q74GC
    • azepane-2-carboxylic acid(SALTDATA: FREE)
    • Hexahydroazepin-2-carbonsaeure
    • NSC86359
    • STOCK1N-22299
    • SureCN978379
    • Hexahydroazepine-2-carboxylic acid
    • NSC 86359
    • SY033263
    • BCP23269
    • azepan-2-carboxylic acid
    • BS-13291
    • HMS1581F08
    • hexahydro-1h-azepine-2-carboxylic
    • CCG-40541
    • AC-22533
    • NSC-86359
    • I10217
    • CS-0054144
    • SCHEMBL978379
    • AKOS010152721
    • MFCD00457600
    • FT-0773394
    • DTXSID00292887
    • 5227-53-2
    • OPFURXRZISKMJV-UHFFFAOYSA-N
    • Q-103574
    • 1H-Azepine-2-carboxylic acid, hexahydro-
    • AM20100286
    • FT-0743172
    • Azepane-2-carboxylicacid
    • EN300-50636
    • Azacycloheptane-2-carboxylic acid
    • ALBB-030110
    • DB-022512
    • DB-073803
    • (R)-hexahydro-1H-Azepine-2-carboxylic acid
    • MDL: MFCD00457600
    • Inchi: 1S/C7H13NO2/c9-7(10)6-4-2-1-3-5-8-6/h6,8H,1-5H2,(H,9,10)
    • InChI Key: OPFURXRZISKMJV-UHFFFAOYSA-N
    • SMILES: OC(C1CCCCCN1)=O

Computed Properties

  • Exact Mass: 143.09469
  • Monoisotopic Mass: 143.095
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 125
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 49.3A^2

Experimental Properties

  • Density: 1.080
  • Melting Point: 208-209 oC
  • Boiling Point: 281 oC
  • Flash Point: 124 oC
  • PSA: 49.33

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Additional information on Azepane-2-carboxylic acid

Recent Advances in the Application of Azepane-2-carboxylic acid (CAS: 5227-53-2) in Chemical Biology and Pharmaceutical Research

Azepane-2-carboxylic acid (CAS: 5227-53-2) is a seven-membered heterocyclic compound that has garnered significant attention in chemical biology and pharmaceutical research due to its versatile scaffold and potential therapeutic applications. Recent studies have explored its role as a building block in drug design, particularly in the development of novel enzyme inhibitors and receptor modulators. This research brief synthesizes the latest findings on the synthesis, biological activity, and pharmacological potential of Azepane-2-carboxylic acid, providing insights into its emerging significance in the field.

One of the key advancements in the application of Azepane-2-carboxylic acid is its incorporation into peptidomimetics and small-molecule inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of Azepane-2-carboxylic acid exhibit potent inhibitory activity against serine proteases, which are implicated in various pathological conditions, including inflammation and cancer. The study highlighted the compound's ability to mimic natural peptide substrates, thereby offering a promising strategy for the design of selective protease inhibitors.

Another area of active research involves the use of Azepane-2-carboxylic acid in the synthesis of chiral auxiliaries and ligands for asymmetric catalysis. Researchers have reported its utility in facilitating enantioselective transformations, which are critical for the production of optically active pharmaceuticals. For instance, a recent publication in Organic Letters detailed the successful application of Azepane-2-carboxylic acid-derived ligands in the asymmetric hydrogenation of ketones, achieving high enantiomeric excess and yield. This development underscores the compound's potential in streamlining the synthesis of complex drug molecules.

In addition to its synthetic applications, Azepane-2-carboxylic acid has been investigated for its intrinsic biological properties. A 2022 study in Bioorganic & Medicinal Chemistry revealed that certain derivatives of the compound exhibit neuroprotective effects in models of neurodegenerative diseases. The researchers attributed these effects to the compound's ability to modulate oxidative stress and inhibit apoptotic pathways, suggesting its potential as a lead compound for the treatment of conditions such as Alzheimer's disease.

Despite these promising findings, challenges remain in optimizing the pharmacokinetic and pharmacodynamic properties of Azepane-2-carboxylic acid derivatives. Recent efforts have focused on improving bioavailability and reducing off-target effects through structural modifications and formulation strategies. For example, a 2023 patent application described the development of prodrugs based on Azepane-2-carboxylic acid, which demonstrated enhanced stability and targeted delivery in preclinical models.

In conclusion, Azepane-2-carboxylic acid (CAS: 5227-53-2) represents a valuable scaffold in chemical biology and pharmaceutical research, with diverse applications ranging from drug design to asymmetric synthesis. Ongoing studies continue to uncover its potential, paving the way for innovative therapeutic interventions. Future research should prioritize the translation of these findings into clinically viable candidates, addressing the current limitations and expanding the compound's utility in medicine.

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