75154-69-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Aziridinecarboxylic Acid Methyl Ester is used as a precursor for the synthesis of azetidine-2-carboxylic acid derivatives, which are crucial in the development of various pharmaceuticals. Its chiral nature allows for the creation of enantiomerically pure compounds, enhancing the efficacy and selectivity of drugs.
Used in Agrochemical Industry:
(S)-2-Aziridinecarboxylic Acid Methyl Ester is employed as a building block in the synthesis of agrochemicals, contributing to the development of effective and targeted pesticides and other agricultural products.
Used in Asymmetric Synthesis:
(S)-2-Aziridinecarboxylic Acid Methyl Ester is used as a reagent in asymmetric synthesis, enabling the production of enantiomerically pure amino acids and other bioactive compounds. This application is vital for the creation of more effective and selective drugs, as well as for the development of novel agrochemicals.
Used in Drug Discovery and Development:
Due to its versatile nature and potential applications, (S)-2-Aziridinecarboxylic Acid Methyl Ester is utilized in drug discovery and development processes. Researchers and scientists in the chemical and pharmaceutical industries leverage its unique properties to design and synthesize new compounds with therapeutic potential.

InChI:InChI=1/C4H7NO2/c1-7-4(6)3-2-5-3/h3,5H,2H2,1H3/t3-/m0/s1

Upstream product

• 75154-68-6 methyl (2S)-N-tritylaziridine-2-carboxylate 
• 104597-98-0 (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine 
• 151910-17-7 methyl (2S)-(-)-1-butyrylaziridine-2-carboxylate 

Downstream Products

• 123557-03-9 (1R,2S)-1-acetyl-2-carbomethoxyaziridine 
• 100804-15-7 (1R,2S)-1-methylcarbamoyl-2-methoxycarbonylaziridine 
• 127700-57-6 1-p-toluensulfonylaziridine-(2S)-carboxylic acid tert-butyl ester 
• 105424-75-7 methyl (2S)-1-[(4-methylphenyl)sulfonyl]aziridine-2-carboxylate 
• 151910-16-6 methyl (2S)-(-)-1-acetylaziridine-2-carboxylate 
• 126496-79-5 (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester 
• 104597-98-0 (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine 
• 111193-37-4 1-(p-nitrobenzyloxycarbonyl)aziridine-2S-carboxylic acid methyl ester 
• 153381-07-8 (S)-N-methoxycarbonyl aziridine-2-carboxylatemethyl ester 

Relevant academic research and scientific papers

RAS INHIBITORS

The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.

Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035

The madurastatins are pentapeptide siderophores originally described as containing an unusual salicylate-capped N-terminal aziridine ring. Isolation of madurastatin C1 (1) (also designated MBJ-0034), from Actinomadura sp. DEM31376 (itself isolated from a

PHOSPHONATE COMPOUNDS FOR TREATMENT OF IMMUNE AND INFLAMMATORY DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D are provided comprising Formula I, I" and I''' or a pharmaceutically acceptable salt or composition thereof. The inhibitors described herein target Factor D and inhibit

Total synthesis and activity of the metallo-β-lactamase inhibitor aspergillomarasmine A

Resistance to β-lactam antibiotics is mediated primarily by enzymes that hydrolytically inactivate the drugs by one of two mechanisms: serine nucleophilic attack or metal-dependent activation of a water molecule. Serine β-lactamases are countered in the c

LUNG LOCALIZED INHIBITORS OF ALPHA(V)BETA 6

Described herein are compounds, compositions, and methods of their use treatment of a lung disease.

Selective cleavage of carbamate protecting groups from aziridines with otera's catalyst

Otera's distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selec

Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.

Synthesis of tryptophans by Lewis acid promoted ring-opening of aziridine-2-carboxylates: Optimization of protecting group and Lewis acid

The preparation of tryptophan derivatives through the Lewis acid promoted substitution of aziridine carboxylates with indole was found to be accompanied by a ring-expansion reaction to generate an oxazolidinone byproduct. The ratio of tryptophan to oxazol

Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates

Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs

Proteomic searches comparing two (R)-lacosamide affinity baits: An electrophilic arylisothiocyanate and a photoactivated arylazide group

We have advanced a novel strategy to search for lacosamide ((R)-1) targets in the brain proteome where protein binding is expected to be modest. Our approach used lacosamide agents containing "affinity bait" (AB) and "chemical reporter" (CR) units. The affinity bait moiety is designed to irreversibly react with the target, and the CR group permits protein detection and capture. In this study, we report the preparation and evaluation of (R)-N-(4-azido)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-3) and show that this compound exhibits potent anticonvulsant activities in the MES seizure model in rodents. We compared the utility of (R)-3 with its isostere, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-2), in proteomic studies designed to identify potential (R)-1 targets. We showed that despite the two-fold improved anticonvulsant activity of (R)-3 compared with (R)-2, (R)-2 was superior in revealing potential binding targets in the mouse brain soluble proteome. The difference in these agents' utility has been attributed to the reactivity of the affinity baits (i.e., (R)-2: aryl isothiocyanate moiety; (R)-3: photoactivated aryl azide intermediates) in the irreversible protein modification step, and we conclude that this factor is a critical determinant of successful target detection where ligand (drug) binding is modest. The utility of (R)-2 and (R)-3 in in situ proteome studies is explored.