85618-16-2

Usage

Uses

Used in Pharmaceutical Industry:
(2-Aminoethyl)phosphinic acid is used as a key intermediate in the synthesis of phosphinothricin analogs, which are potential inhibitors of glutamine synthetase. Glutamine synthetase is an enzyme that plays a crucial role in the metabolism of nitrogenous compounds in cells, and its inhibition can lead to the disruption of cellular processes, making it a target for the development of drugs against various diseases, including cancer.
In the preparation of phosphinothricin analogs, (2-Aminoethyl)phosphinic acid serves as a building block, providing the necessary structural elements for the formation of these bioactive compounds. By incorporating (2-AMINOETHYL)PHOSPHINIC ACID into the synthesis process, researchers can design and develop novel analogs with improved potency, selectivity, and pharmacological properties, ultimately leading to the discovery of new therapeutic agents with potential applications in the treatment of various diseases.
Furthermore, the versatility of (2-Aminoethyl)phosphinic acid allows for the exploration of its potential applications in other areas of pharmaceutical research, such as the development of enzyme inhibitors, antimicrobial agents, and other bioactive molecules. Its unique structure and reactivity make it a valuable tool for the design and synthesis of new compounds with diverse biological activities, contributing to the advancement of drug discovery and development efforts.

Upstream product

• 1075799-55-1 2-aminoethyl-H-phosphinic acid hydrochloride 
• 95879-70-2 2-carbamylethylphosphinic acid 
• 125742-17-8 (2-Amino-ethyl)-diethoxymethyl-phosphinic acid ethyl ester 

Downstream Products

• 868523-17-5 (2-benzyloxycarbonylamino-ethyl)-H-phosphinic acid 

Relevant academic research and scientific papers

Synthesis of P,N-heterocycles from ω-amino-H-phosphinates: Conformationally restricted α-amino acid analogs

(Chemical Equation Presented) P,N-Heterocycles (3-hydroxy-1,3- azaphospholane and 3-hydroxy-1,3-azaphosphorinane-3-oxide) are synthesized in moderate yield from readily available ω-amino-H-phosphinates and aldehydes or ketones via an intramolecular Kabachnik-Fields reaction. The products are conformationally restricted phosphinic analogs of α-amino acids. The multigram-scale syntheses of the H2N(CH2) nPO2H2 phosphinic precursors (n = 1, 2, 3) and some derivatives are also described.

Design, synthesis, and activity of analogues of phosphinothricin as inhibitors of glutamine synthetase

A new group of potent inhibitors of glutamine synthetase was designed and synthesized. The X-ray structure of bacterial glutamine synthetase complexed with phosphinothricin was used for computer-aided structure-based design of the inhibitors, in which the methyl group of phosphinothricin was chosen as the modification site. Amino and hydroxyl moieties were introduced into the phosphinic acid portion of the lead molecule to interact with ammonium binding site in the active cleft of the enzyme. Designed compounds were synthesized in enantiomerically pure form analogous to L-glutamic acid. In vitro kinetic studies with Escherichia coli glutamine synthetase confirmed the biological activity of the designed inhibitors, which with Ki values in the micromolar range (Ki = 0.59 μM for the most potent compound 2) appear to be slightly weaker inhibitors or equipotent to phosphinothricin.

DIETHOXYMETHYLPHOSPHONITES AND PHOSPHINATES. INTERMEDIATES FOR THE SYNTHESIS OF α,β- AND γ-AMINOALKYLPHOSPHONOUS ACIDS

New building blocks for the synthesis of functional alkyl phosphonous acids are described.Diethoxymethylphosphonites and phosphinates are readily prepared and undergo reactions typical of phosphites and phosphonates.The products are stable to chemical transformations, readily handled and purified, and easily transformed to the phosphonous acids.