2517-04-6

Basic information

• Product Name: AZETIDINE-2-CARBOXYLIC ACID
• Synonyms: Azetidinecarboxylic Acid;DL-H-Aze-OH;AZETIDINE-2-CARBO
• CAS NO: 2517-04-6
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 219-740-2
• Mol File: 2517-04-6.mol

Chemical Properties

• Melting Point: 217°C (rough estimate)
• Boiling Point: 189.47°C (rough estimate)
• Flash Point: 100.144 °C
• Appearance: /
• Density: 1.2245 (rough estimate)
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.4340 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.35±0.20(Predicted)
• CAS DataBase Reference: AZETIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: AZETIDINE-2-CARBOXYLIC ACID(2517-04-6)
• EPA Substance Registry System: AZETIDINE-2-CARBOXYLIC ACID(2517-04-6)

Safety Data

• Hazardous Substances Data: 2517-04-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Azetidine-2-carboxylic acid is used as a pharmaceutical intermediate for its potential in the development of drugs targeting various diseases. Its anti-tumor properties make it a candidate for cancer treatment, while its anti-viral characteristics suggest potential applications in antiviral therapies.
Used in Enzyme Inhibition:
Azetidine-2-carboxylic acid is used as a potent inhibitor of various enzymes, which can be leveraged in the development of treatments for enzyme-related disorders and conditions.
Used in Neurotransmitter Research:
As an intermediate in the biosynthesis of gamma-aminobutyric acid (GABA), a major inhibitory neurotransmitter in the central nervous system, azetidine-2-carboxylic acid is used in research to understand and potentially modulate GABAergic signaling, which could have implications for the treatment of neurological disorders.
Used in Tinnitus Treatment:
Azetidine-2-carboxylic acid is being investigated for its potential in the treatment of tinnitus, a condition characterized by the perception of sound without an external source, suggesting its use as a therapeutic agent for auditory disorders.
Used in Diabetes Management:
Research into the potential of azetidine-2-carboxylic acid in diabetes treatment highlights its use as a compound that could contribute to the management or treatment of this metabolic disease, possibly through its effects on insulin sensitivity or glucose metabolism.

InChI:InChI=1/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)

Upstream product

• 56-12-2 4-amino-n-butyric acid 
• 39897-13-7 1-(p-tolylsulfonyl)azetidine-2-carboxylic acid 
• 22742-42-3 DL-N-diphenylmethylazetidine-2-carboxylic acid benzyl ester 

Downstream Products

• 174740-81-9 N-benzyloxycarbonyl-(S)-(-)-2-azetidine-carboxylic acid 
• 161511-85-9 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 39897-13-7 1-(p-tolylsulfonyl)azetidine-2-carboxylic acid 
• 162698-26-2 azetidine-2-carboxylic acid methyl ester hydrochloride 
• 37712-76-8 1-acetyl-azetidine-2-carboxylic acid 
• 766483-76-5 azetidine-2-carboxylic acid ethyl ester 
• 1227243-20-0 1-{5-[8-(3-chloro-phenyl)-2-methyl-imidazo[1,2-a]pyridin-6-ylmethyl]-pyridin-2-yl}-azetidine-2-carboxylic acid 
• 1155877-43-2 1-[5-(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyrimidin-2-yl]-azetidine-2-carboxylic acid 
• 1155877-05-6 1-[5-(3'-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-azetidine-2-carboxylic acid 
• 1155286-71-7 1-{5-[4-(3-chloro-phenyl)-5-fluoro benzothiazol-6-ylmethyl]-pyridin-2-yl}-azetidine-2-carboxylic Acid 
• 51077-14-6 (S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid 
• 159749-28-7 1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid 
• 647854-63-5 methyl (2R)-azetidine-2-carboxylate hydrochloride 
• 228857-58-7 (R)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid 

Relevant articles and documents

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).

Solid-Liquid Biphasic Hydroformylation of Olefins Catalyzed by Rhodium Carhonyl Complexes

Some polymer-anchored alkenes have been hydroformylated by carrying out the reaction in a high-pressure reactor equipped with a suitably designed vial. The solid substrates are converted to the corresponding oxo-aldehydes in high yields. In all cases the regioselectivity was strongly shifted towards the linear aldehyde when the rhodium carbonyl complex was modified with xantphos (3:1 or 4:1 P/Rh molar ratio). Treatment with 5% of trifluoroacetine acid in dichloromethane at room temperature removed quantitatively the oxo-product from the polymer support, which can be purified and reused.

Anti-heparin peptides

The invention concerns a compound exhibiting an anti-heparin activity, of formula Z Bm ! (AXA)x Bn ! (AXA)y Bo (AXA)z Bp, the diagnostic reagents comprising it and the use of said compound in an in vitro diagnostic test of a medicine for anti-heparin activity.

Process for the production of enantiomerically-pure azetidine-2-carboxylic acid

The invention relates to a process for the production of enantiomerically-pure AzeOH which comprises selective crystallisation of a diastereomerically-pure tartrate salt thereof, followed by liberation of the free amino acid, as well as the compounds L-azetidine-2-carboxylic acid-D-tartrate and D-azetidine-2-carboxylic acid-L-tartrate.

Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors

Recent evidence indicating the therapeutic potential of cholinergic channel modulators for the treatment of central nervous system (CNS) disorders as well as the diversity of brain neuronal nicotinic acetylcholine receptors (nAChRs) have suggested an opportunity to develop subtype-selective nAChR ligands for the treatment of specific CNS disorders with reduced side effect liabilities. We report a novel series of 3-pyridyl ether compounds which possess subnanomolar affinity for brain nAChRs and differentially activate subtypes of neuronal nAChRs. The synthesis and structure-activity relationships for the leading members of the series are described, including A-85380 (4a), which possesses ca. 50 pM affinity for rat brain [3H]-(- )cytisine binding sites and 163% efficacy compared to nicotine to stimulate ion flux at human α4β2 nAChR subtype, and A-84543 (2a), which exhibits 84- fold selectivity to stimulate ion flux at human α4β2 nAChR subtype compared to human ganglionic type nAChRs. Computational studies indicate that a reasonable superposition of a low energy conformer of 4a with (S)-nicotine and (-)-epibatidine can be achieved.

Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole

Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.