6323-97-3

Usage

Uses

Used in Pharmaceutical Industry:
DL-1-(Aminoethyl)phosphonic acid is used as a building block for the synthesis of phosphonopeptides, which serve as antibacterial agents. These phosphonopeptides are designed to target and inhibit essential bacterial enzymes or processes, thereby combating bacterial infections effectively.
Additionally, DL-1-(Aminoethyl)phosphonic acid is utilized in the preparation of phosphorus amino acid analogs, which act as inhibitors of leucine aminopeptidase. Leucine aminopeptidase is an enzyme involved in various biological processes, and its inhibition can have therapeutic benefits in treating certain diseases by modulating the activity of this enzyme.

InChI:InChI=1/C2H8NO3P/c1-2(3)7(4,5)6/h2H,3H2,1H3,(H2,4,5,6)/p-1/t2-/m1/s1

Upstream product

• 54788-35-1 diethyl 1-aminoethylphosphonate 
• 917-64-6 methyl magnesium iodide 
• 60064-40-6 (diethoxyphosphoryl-ethylsulfanyl-methylene)-carbamic acid ethyl ester 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 64244-31-1 3-(diethoxyphosphinoyl)-1-phenyl-2-azabut-1-ene 
• 67532-84-7 dibenzyl acetylphosphonate 
• 52111-19-0 diethyl (1-carbamoylethyl)phosphonate 
• 60347-01-5 diethyl α-(ethylidenehydrazino)ethyl phosphonate 
• 67398-21-4 diphenyl 1-[(3-phenyl)thioureido]ethyl-phosphonate 
• 67398-22-5 {1-[3-(1-phenyl-ethyl)-thioureido]-ethyl}-phosphonic acid diphenyl ester 
• 75-07-0 acetaldehyde 
• 75-05-8 acetonitrile 
• 5335-91-1 1,1-bis-acetylamino-ethane 
• 539-71-9 diethyl ethane-1,1-diyldicarbamate 

Downstream Products

• 60668-25-9 N-benzyloxycarbonyl-α-aminoethylphosphonic acid 
• 59191-43-4 DL-<1-(phthaloylamino)ethyl>-phosphonic acid 
• 60668-26-0 1-R-1-[(N-benzyloxycarbonyl-L-alanyl)amino]ethanephosphonic acid 
• 60668-66-8 [(S)-1-((S)-2-Benzyloxycarbonylamino-propionylamino)-ethyl]-phosphonic acid 
• 60668-41-9 ethyl>phosphonic acid 
• 104513-48-6 Tri-N,O,O-(trimethylsilyl)-1-aminoethylphosphonsaeure 
• 6881-54-5 (1-oxoethyl)phosphonic acid 
• 60687-36-7 (R)-(1-aminoethyl)phosphonic acid 
• 66068-76-6 (S)-1-aminoethylphosphonic acid 
• 66794-08-9 N-Benzoyl-1-amino-ethyl-1-phosphonsaeure 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of phosphonopeptide derivatives incorporating single and dual inhibitors

In diagnostic microbiology, culture media are widely used for detection of pathogenic bacteria. Such media employ various ingredients to optimize detection of specific pathogens such as chromogenic enzyme substrates and selective inhibitors to reduce the presence of commensal bacteria. Despite this, it is rarely possible to inhibit the growth of all commensal bacteria, and thus pathogens can be overgrown and remain undetected. One approach to attempt to remedy this is the use of “suicide substrates” that can target specific bacterial enzymes and selectively inhibit unwanted bacterial species. With the purpose of identifying novel selective inhibitors, six novel phosphonopeptide derivatives based on D/L-fosfalin and β-chloro-L-alanine were synthesized and tested on 19 different strains of clinically relevant bacteria. Several compounds show potential as useful selective agents that could be exploited in the recovery of several bacterial pathogens including Salmonella, Pseudomonas aeruginosa, and Listeria.

1-(Acylamino)alkylphosphonic acids—alkaline deacylation

The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O?)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O?)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.

1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions

The 1-(N-acylamino)alkylphosphonic acids (AC)-AAP belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AAP on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media. In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AAP, including 1-(N-acetylamino)alkyl-phosphonic Ac-AAP, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AAP, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AAP, and 1-(N-benzoylamino)-alkylphosphonic Bz-AAP, derived from representative 1-aminoalkylphosphonic acids AAP (GlyP, AlaP, ValP, PglP, and PheP) in neutral and 2?M HCl solutions.

Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess

A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.

Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride

The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.

POLYMERIZABLE PHOSPHONIC ACID DERIVATIVE AND ADHESIVE COMPOSITION COMPRISING THE SAME

The present invention provides an adhesive composition comprising a polymerizable phosphonic acid derivative which is a composition having intramolecularly a polymerizable group and a phosphonic acid group, represented by the general formula [1]: wherein R represents a polymerizable group;A represents an oxygen atom or a sulfur atom;Xqs represent independently an oxygen atom or a sulfur atom;Yqs represent independently the same or different organic group;Zqs may be independently the same or different from each other and, a part of the Zqs optionally selected or all of the Zqs represent organic groups having a substituent which is an organic group other than a polymerizable group and a phosphonic acid group;p is an integer from 1 to 10;q is an integer from 1 to p; when p is 1, q is 1;X1 represents an oxygen atom or a sulfur atom;Y1 represents an organic group;Z1 represents an organic group having one or more of substituents which are organic groups other than an acidic group and a polymerizable group, or a salt thereof. The adhesive composition or the salt thereof according to the present invention improve a shelf life and adhesion properties of an adhesive composition comprising essentially a (meth)acrylate monomer having intramolecularly an acidic group and water in dental treatment.

Application of silicon-phosphorus based reagents in synthesis of aminophosphonates. Part 2: Reactions of N-(Triphenylmethyl)-aldimines with the silylated phosphorus acid esters

Reactions of silylated phosphorus acid esters with N-triphenylmethylaldimines (N-tritylaldimines) were investigated. N-Tritylmethaneimine reacts at room temperature with a mixture of P(OMe)3 and Me3SiBr forming the corresponding aminophosphonate derivatives in high yield. Other N-tritylimines are resistant toward the silylated reagents at room temperature, but undergo a similar phosphorylation reaction at elevated temperatures to form the expected aminophosphonic acids.

The formation of α-amino- and α-hydroxy-alkanephosphonic acids in the reactions of phosphite esters with aldehydes and alkyl carbamates

The preparation of α-aminoalkanephosphonic acids from triphenyl phosphite, an aldehyde, and ethyl or benzyl carbamate in glacial acetic acid, followed by hydrolysis, is accompanied by the formation of the corresponding α-hydroxyphosphonic acid. Reaction in toluene, using boron trifluoride-etherate as catalyst, affords an alternative preparative procedure but does not prevent the formation of α-hydroxyphosphonic acid. 31P nmr reveals the presence of numerous intermediates. The reactions are discussed.

A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.

Preparation of 1-aminoalkylphosphonic acids and 2-aminoalkylphosphonic acids by reductive amination of oxoalkylphosphonates

By reacting dialkyl 1-oxo- or 2-oxoalkylphosphonates with benzhydrylamine followed by reduction with triacetoxyborohydride and acid hydrolysis gave corresponding aminoalkylphosphonic acids with satisfactory yields. The use of benzylamine, α-methylbenzylamine and tritylamine was unsuccessful in the case of dialkyl 1-oxoalkylphosphonates whereas conversion of 2-oxoalkylphosphonates was also achieved although with lower yields.