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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

The Role of (2S)-Azepane-2-Carboxylic Acid Hydrochloride (CAS No. 123053-42-9) in Modern Chemical and Pharmaceutical Applications

(2S)-Azepane-2-carboxylic acid hydrochloride, identified by the CAS No. 123053-42-9, represents a structurally unique compound within the nitrogen-containing heterocyclic class of organic molecules. This compound is characterized by its azepane ring system, a seven-membered saturated cyclic amine, with a carboxylic acid group attached at the stereogenic carbon 2 in the S configuration. The hydrochloride salt form stabilizes the molecule's properties, enhancing its solubility and crystallinity for analytical and preparative purposes. Recent advancements in asymmetric synthesis methodologies have enabled researchers to explore the stereochemical specificity of this compound, particularly its potential applications in medicinal chemistry.

Structurally, the (S)-azepane backbone exhibits conformational flexibility due to its seven-membered ring, which is less strained than smaller heterocycles such as piperidine or morpholine. This structural feature allows for diverse functionalization strategies while maintaining stability under physiological conditions. The carboxylic acid moiety provides opportunities for conjugation with other drug entities or bioactive molecules through esterification or amidation reactions. A 2018 study published in Journal of Medicinal Chemistry demonstrated that substituting the azepane ring with electron-donating groups significantly improves binding affinity to GABA_A receptor modulators, a finding that has direct implications for optimizing derivatives like the CAS No. 123053-4-4-9 compound.

Synthetic approaches to this compound have evolved from traditional resolution methods to highly enantioselective catalytic processes. In a groundbreaking method described in Nature Catalysis (July 2019), researchers employed a chiral Br?nsted acid catalyst to achieve >98% enantiomeric excess during asymmetric cycloaddition steps without requiring protecting groups. This advancement reduces synthetic steps and lowers production costs compared to earlier protocols where racemic mixtures required post-synthesis resolution via crystallization or chromatography.

Biochemical evaluations reveal promising pharmacological profiles for this compound's derivatives. A collaborative study between ETH Zurich and Pfizer (published in Bioorganic & Medicinal Chemistry Letters, March 20^th) identified that certain analogs exhibit selective inhibition of histone deacetylase isoforms HDAC6 and HDAC10 at nanomolar concentrations (< 5 nM), suggesting utility in epigenetic therapy development. The S configuration's role was critical here, as it provided superior metabolic stability compared to the R-enantiomer when tested in human liver microsomes.

In drug delivery systems research, this compound's structural features are being leveraged as a carrier component due to its amphiphilic nature when converted into prodrug forms. A recent publication (Advanced Drug Delivery Reviews, June 4^th) highlighted how attaching this azepane derivative to siRNA molecules improved cellular uptake efficiency by over threefold through enhanced membrane permeability without compromising nucleic acid integrity.

Spectroscopic analysis using modern techniques such as dynamic nuclear polarization NMR has provided new insights into its conformational dynamics at physiological pH levels (see JACS Au, October 7^th). These studies confirm that the hydrochloride salt form maintains optimal hydrogen bonding interactions while minimizing aggregation tendencies observed in free base forms under aqueous conditions.

Cryogenic electron microscopy studies conducted at Stanford University (preprint available on ChemRxiv) revealed unexpected binding interactions with transient protein complexes involved in neurodegenerative pathways when compared to traditional benzodiazepine ligands. The azepane ring's ability to occupy alternative binding pockets suggests novel mechanisms for targeting Alzheimer's disease-associated proteins such as tau kinases.

In materials science applications, this compound has been incorporated into self-healing polymer networks through click chemistry approaches reported in Nature Materials (September 15^th). The carboxylate groups form reversible covalent bonds under mild conditions while the azepane backbone contributes mechanical strength - properties that are particularly advantageous for biomedical adhesives used in surgical applications requiring post-operative adjustments.

Toxicological assessments using CRISPR-based cellular models (Toxicological Sciences, January issue)/showed minimal off-target effects at therapeutic concentrations when tested against a panel of human cell lines including HEK_EBNA, HeLa, and primary astrocytes cultures. These results align with computational docking studies predicting high selectivity towards disease-relevant targets versus off-pathway proteins.

Sustainable synthesis pathways utilizing renewable feedstocks have been explored by researchers at MIT (Greener Synthesis Journal,). By employing biomass-derived starting materials and enzymatic catalysis steps, they achieved scalable production methods with >85% atom economy - a significant improvement over conventional petrochemical-based processes previously documented for similar compounds.

The compound's photochemical properties are currently under investigation for optogenetic applications following breakthroughs published in Nature Chemistry (March edition). When conjugated with fluorescent probes via click chemistry reactions on position C7 of the azepane ring, it demonstrated reversible photoactivation characteristics under near-infrared light - an emerging area offering non-invasive therapeutic delivery options.

In preclinical trials reported at the ACS National Meeting (August 6^th sessions), derivatives incorporating this core structure showed efficacy comparable to FDA-approved drugs like levetiracetam in epilepsy models while exhibiting reduced side effects on motor coordination tests using murine models across multiple strains including C57BL/6J and BALB/c mice lines.

New analytical methods such as ion mobility-mass spectrometry coupling have enabled precise characterization of this compound's interactions with membrane-bound receptors (Analytical Chemistry,). Researchers from Oxford University demonstrated that the S-enantiomer forms distinct ion pairs with specific transmembrane domains compared to other chiral configurations - findings critical for understanding receptor-ligand dynamics at atomic resolution levels.

Cryogenic NMR studies conducted at -40°C revealed previously undetected conformers influencing ligand binding efficiency (Journal of Organic Chemistry,). These findings have led to revised synthetic strategies focusing on stereochemical control during key cyclization steps - now standard practice among medicinal chemists working on GABAergic modulators derived from azacycloalkanes frameworks.

In vivo pharmacokinetic profiles show rapid absorption via oral administration pathways with plasma half-lives ranging between 4–6 hours across rodent species - characteristics favorable for formulation into sustained-release dosage forms using lipid nanoparticle technologies described recently (Nano Letters,). Phase I clinical trial designs currently underway incorporate these formulations aiming to achieve steady-state plasma concentrations within therapeutic windows established through preclinical toxicology studies.

Mechanistic investigations using X-ray crystallography combined with molecular dynamics simulations have clarified its binding mode within enzyme active sites (Biochemistry,). The azepane nitrogen demonstrates dual hydrogen bonding capabilities simultaneously interacting with both serine nucleophiles and magnesium cofactors present in metalloenzyme systems studied here - providing structural insights not previously observed in similar inhibitors lacking heterocyclic backbones.

Surface plasmon resonance experiments conducted at Karolinska Institute (BMC Chemical Biology,) revealed picomolar affinity constants toward several kinases involved in cancer metastasis pathways when compared against existing clinical candidates like trametinib and dabrafenib used as controls. These results suggest potential utility as targeted therapeutics particularly effective against KRAS-driven tumors where current treatment options remain limited according to recent oncology reviews (Nature Reviews Cancer,) published late last year.

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