25654-52-8

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-N-CBZ-AZETIDINE-2-CARBOXYLIC ACID is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the formation of stable intermediates, which are essential for the development of new drugs with improved efficacy and safety profiles.
Used in the Synthesis of Mugineic Acid Ammonium Salt:
(S)-N-CBZ-AZETIDINE-2-CARBOXYLIC ACID is used as a key intermediate for the synthesis of Mugineic Acid Ammonium Salt (M792005). Mugineic Acid is a potential phytosiderophore found in graminaceous plants, known for its iron chelation potency and antioxidant activity. The synthesis of (S)-N-CBZ-AZETIDINE-2-CARBOXYLIC ACID is important for understanding its role in plant nutrition and its potential applications in agriculture and human health.

Upstream product

• 174740-81-9 N-benzyloxycarbonyl-(S)-(-)-2-azetidine-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 2133-34-8 (2S)-azetidine-2-carboxylic acid 
• 352018-67-8 (R)-4-N-benzyloxycarbonylamino-2-chlorobutyric acid 
• 186593-56-6 (S)-1-benzyloxycarbonyl-2-azetidinemethanol 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 

Downstream Products

• 144062-00-0 N-benzyloxycarbonyl azetidine-2-carboxylate methyl ester 
• 153704-88-2 (S)-1-benzyl 2-tert-butyl azetidine-1,2-dicarboxylate 
• 186593-56-6 (S)-1-benzyloxycarbonyl-2-azetidinemethanol 
• 864951-51-9 (S)-Azetidine-1,2-dicarboxylic acid 1-benzyl ester 2-((S)-2-cyclohexyl-1-methyl-ethyl) ester 
• 1403954-15-3 C₃₈H₃₆N₄O₆ 
• 319918-73-5 (2S)-1-(Benzyloxycarbonyl)azetidine-2-carboxylic acid chloride 
• 144062-05-5 (S)-2-(Hydroxy-diphenyl-methyl)-azetidine-1-carboxylic acid benzyl ester 
• 144062-03-3 (S)-4,4-Diphenyl-3-oxa-1-aza-bicyclo[3.2.0]heptan-2-one 
• 88015-21-8 (S)-2-[(1S,2S)-2-Chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-azetidine-1-carboxylic acid benzyl ester 
• 477585-96-9 (2R)-3-((1-benzyloxycarbonyl)azetidin-2-yl)propanoic acid 
• 477585-76-5 methyl (2R)-3-((1-benzyloxycarbonyl)azetidin-2-yl)propanoate 
• 477585-75-4 (S)-2-((E)-2-Methoxycarbonyl-vinyl)-azetidine-1-carboxylic acid benzyl ester 
• 195607-10-4 (S)-2-Formyl-azetidine-1-carboxylic acid benzyl ester 
• 228867-83-2 (S)-1-(benzyloxycarbonyl)-2-azetidinemethanol-p-tosylate 

Relevant academic research and scientific papers

AZETIDOBENZODIAZEPINE DIMERS AND CONJUGATES COMPRISING THEM FOR USE IN THE TREATMENT OF CANCER

A compound of formula IV: as well as drug-linkers and conjugates comprising this compound, and the use of the conjugates in treating cancer.

Azetidine-Containing Alkaloids Produced by a Quorum-Sensing Regulated Nonribosomal Peptide Synthetase Pathway in Pseudomonas aeruginosa

Pseudomonas aeruginosa displays an impressive metabolic versatility, which ensures its survival in diverse environments. Reported herein is the identification of rare azetidine-containing alkaloids from P. aeruginosa PAO1, termed azetidomonamides, which are derived from a conserved, quorum-sensing regulated nonribosomal peptide synthetase (NRPS) pathway. Biosynthesis of the azetidine motif has been elucidated by gene inactivation, feeding experiments, and biochemical characterization in vitro, which involves a new S-adenosylmethionine-dependent enzyme to produce azetidine 2-carboxylic acid as an unusual building block of NRPS. The mutants of P. aeruginosa unable to produce azetidomonamides had an advantage in growth at high cell density in vitro and displayed rapid virulence in Galleria mellonella model, inferring functional roles of azetidomonamides in the host adaptation. This work opens the avenue to study the biological functions of azetidomonamides and related compounds in pathogenic and environmental bacteria.

FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

Synthesis of a Bicyclic Azetidine with in Vivo Antimalarial Activity Enabled by Stereospecific, Directed C(sp3)-H Arylation

The development of new antimalarial therapeutics is necessary to address the increasing resistance to current drugs. Bicyclic azetidines targeting Plasmodium falciparum phenylalanyl-tRNA synthetase comprise one promising new class of antimalarials, especially due to their activities against three stages of the parasite's life cycle, but a lengthy synthetic route to these compounds may affect the feasibility of delivering new therapeutic agents within the cost constraints of antimalarial drugs. Here, we report an efficient synthesis of antimalarial compound BRD3914 (EC50 = 15 nM) that hinges on a Pd-catalyzed, directed C(sp3)-H arylation of azetidines at the C3 position. This newly developed protocol exhibits a broad substrate scope and provides access to valuable, stereochemically defined building blocks. BRD3914 was evaluated in P. falciparum-infected mice, providing a cure after four oral doses.

NEW TETRACYCLINE DERIVATIVES AS ANTIINFECTIVE AGENTS

In accordance with one embodiment, the present invention provides a compound of general formula (I), stereoisomers thereof and/or its pharmaceutically acceptable salts thereof, which have antibacterial activity; with methods of treating infectious diseases in warm blooded animals employing these new compounds.

N-(5-MEMBERED AROMATIC RING)-AMIDO ANTI-VIRAL COMPOUNDS

Disclosed are compounds having Formula (I) and the compositions and methods thereof for treating or preventing a viral infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R2, m, R, V, W, T, Z, R

2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS

The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent "chemoattractant receptor-homologous molecule expressed on Th2 cells" antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

Synthesis of a new precursor to the nicotinic receptor tracer 5-IA-85380 precursor using trimethylsilyl iodide as deblocking agent

We describe the synthesis of a new precursor of 5-IA-85380, specific radiotracer for α4β2 nicotinic acetylcholine receptors. (S)-5-Trimethylstannyl-3-(2-azetidinylmethoxy)pyridine (4) was prepared in six steps and 62% overall yield starting from (S)-2- azetidinecarboxylic acid. The key step of this synthesis is selective release of the amine function without removing the stannyl moiety using trimethylsilyl iodine.

Process for preparation of optically active n-substituted azetidine-2-carboxylic acids

The object of the present invention is to produce an optically active N-substituted azetidine-2-carboxylic acid by an efficient, expedient and commercially profitable process. The present invention provides a production method of an optically active N-sub

Neurotrophic 2-azetidinecarboxylic acid derivatives, and related compositions and methods

This invention provides compounds having the following general structure: This invention also provides pharmaceutical compositions comprising same and methods of using these compositions to treat and prevent disorders characterized by neuronal damage.