74333-44-1

Usage

Uses

Used in Metal Ion Complexation and Extraction:
AEPA is utilized as a chelating agent for metal ion complexation and extraction processes. Its ability to form stable complexes with metal ions makes it an effective agent in these applications.
Used in Water Treatment:
In the water treatment industry, AEPA serves as a valuable component due to its chelating properties, which aid in the removal or sequestration of metal ions, thereby improving water quality.
Used in Corrosion Inhibition:
AEPA is employed as a corrosion inhibitor, leveraging its chelating capabilities to protect materials from the corrosive effects of metal ions in various industrial settings.
Used in Pharmaceutical Synthesis:
AEPA is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, AEPA is used in the synthesis of various agrochemicals, helping to create products that enhance crop protection and yield.
Given the wide range of applications and its low toxicity, AEPA is a chemical compound of significant interest in both research and industrial applications, offering solutions in various fields.

Upstream product

• 65577-30-2 1-(benzhydrylamino)ethylphosphinic acid 
• 62415-63-8 formylacetic acid oxime 
• 30148-50-6 bis(trimethylsilyl)phosphonite 
• 120060-76-6 Eth-(E)-ylidene-trityl-amine 
• 107-29-9 Acetaldehyde oxime 
• 125402-13-3 [1-(Benzhydrylidene-amino)-ethyl]-diethoxymethyl-phosphinic acid ethyl ester 

Downstream Products

• 6323-97-3 1-aminoethanephosphonic acid 
• 73336-73-9 C₁₃H₁₉N₂O₅P 
• 73336-74-0 C₁₃H₁₉N₂O₅P 
• 6323-97-3 (-)-1-aminoethylphosphonic acid 
• 145728-55-8 (L,D)-1-(N-phenylacetylamino)ethylphosphinic acid 
• 108327-37-3 [1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid 

Relevant academic research and scientific papers

Synthesis of alkyl hydrogen (1-aminoalkyl)phosphonates

Addition of hypophosphorous acid to aldoximes affords (1-aminoalkyl) phosphinic acids which on treatment with bromine in alkanols are transformed into alkyl hydrogen (1-aminoalkyl)phosphonates.

AMINOPHOSPHINIC DERIVATIVES THAT CAN BE USED IN THE TREATMENT OF PAIN

The present invention relates to a compound of the following general formula (I): R1—NH—CH(R2)—P(═O)(OR3)—CH2—C(R4)(R5)—CONH—CH(R6)—COOR7 (I) or a pharmaceutically acceptable salt of the latter, an isomer or a mixture of isomers in any proportions, especially a mixture of enantiomers, and in particular a racemic mixture, for which R1 represents a —C(═O)—O—C(R8)(R9)—OC(═O)—R10 group; R2 represents an optionally substituted hydrocarbon-based chain, an aryl or heteroaryl group or a methylene group substituted by a heterocycle; R3 represents a hydrogen atom or a —C(R12)(R13)—OC(═O)—R14 group; R4 and R5 form, together with the carbon that bears them, a saturated hydrocarbon-based ring or an optionally substituted piperidine ring or R4 represents a hydrogen atom and R5 represents a phenyl or a benzyl that is optionally substituted, a heteroaromatic ring or a methylene group substituted by a heterocycle; R6 represents an optionally substituted hydrocarbon-based chain or a phenyl or a benzyl that is optionally substituted; and R7 represents a hydrogen atom or a benzyl, alkyl, heteroaryl, alkylheteroaryl, —CHMe—COOR18, —CHR19—OC(═O)OR20 and —CHR19—OC(═O)OR20 group. The present invention also relates to the use of these compounds as a medicinal product, and in particular for the treatment of pain, more advantageously neuropathic and neuroinflammatory pain, to their method of synthesis and also to the compositions containing them.

Application of in situ silylation for improved, convenient preparation of fluorenylmethoxycarbonyl (Fmoc)-protected phosphinate amino acids

(Chemical Equation Presented) A convenient and efficient method has been developed for the preparation of 9-fluorenylmethoxycarbonyl (Fmoc)-protected 1-aminoalkylphosphinic acids. Reproducible procedures for the synthesis and purification of free α-amino H-phosphinates are provided. Protection of free amino phosphinates as the N-Fmoc derivative was achieved by in situ trimethylsilylation of aminoalkylphosphinic acids, which then reacted with Fmoc-Cl to provide corresponding products in excellent yields and in high purity after simple extractive isolation. Mechanistic aspects of the silylation are discussed, and the application of the procedure to another class of amino phosphorus acids is presented.

Design, synthesis and structure-activity relationships of new phosphinate inhibitors of MurD

A series of new phosphinate compounds were designed and synthesized as inhibitors of the d-glutamic acid-adding enzyme (MurD) involved in peptidoglycan biosynthesis. They were tested against the MurD enzyme from Escherichia coli, allowing initial structure-activity relationships to be deduced. Two compounds had IC50 values near 100 μM and constitute a promising starting point for further development.

Inhibition of the Staphylococcus aureus sortase transpeptidase SrtA by phosphinic peptidomimetics

During pathogenesis, Gram-positive bacteria utilize surface protein virulence factors such as the MSCRAMMs (microbial surface components recognizing adhesive matrix molecules) to aid the initiation and propagation of infection through adherence to host en

Synthesis of phosphinic and phosphonic analogs of aspartic acid

Approaches to the synthesis of 1-amino- and 2-amino-2-carboxyethylphosphinic and -phosphonic acids have been studied. A convenient method for the preparation of phosphinic acids is the reactions of ethyl diethoxymethylphosphonite with ethyl acetamidomethylenemalonate and ethyl 2-acetamidoacrylate.

A novel synthetic route to 1-aminoalkylphosphinic acids

A 'one-pot' synthesis of various 1-aminoalkylphosphinic acids is described. They were obtained in high yield by the deprotection of the corresponding bis(trimethylsilyl) N-tritylaminoalkylphosphites. The latter were prepared by addition of bis(trimethylsilyl) phosphonite to a N-tritylalkanimine.

Synthesis of 1-Aminoalkylphosphinic Acids. Part 2. An Alkylation Approach

Aminomethylphosphinic acid (7), protected at nitrogen as the imine derived from benzophenone and at phosphorus as the diethylacetal and ethyl ester , undergoes facile LDA-induced alkylation.Treatment with primary alkyl halides affords, on product hydrolysis, a versatile route to phosphinic analogues of α-amino carboxylic acids.Analogues of alanine, valine, leucine, phenylalanine, tyrosine, histidine, and aspartic and glutamic acids are thus prepared; the phosphonic histidine analogue (23b) can be prepared similarly from the imine phosphonate diester (21).Intra- and inter-molecular dialkylation reactions provide analogues of 1-aminocyclopropanecarboxylic acid (14) and 2,6-diaminoheptanedioic acid (16).Benzyl bromide alkylation of (25a) and (30a), where the nitrogen is protected as the imine of the 2-hydroxypinan-3-one chiral auxiliary (24) or (29), is diastereospecific leading to asymmetric synthesis of either (+)- or (-)-phenylalanine analogues; this selectivity is compared to that shown by the corresponding chiral imine phosphonate (25b) and imine carboxylate (25c).

1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.