4402-24-8

Usage

Uses

Used in Chemical Synthesis:
Diethyl (3-aminopropyl)phosphonate is used as a reagent in the preparation of various organic compounds. It plays a crucial role in the synthesis of complex molecules and pharmaceuticals.
Used in the Preparation of tert-Butyl (2-((diethoxyphosphoryl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)carbamate:
Diethyl (3-aminopropyl)phosphonate is used as a reactant for the synthesis of tert-Butyl (2-((diethoxyphosphoryl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)carbamate. Diethyl (3-aminopropyl)phosphonate is formed by reacting Diethyl (3-aminopropyl)phosphonate with tert-butyl (2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)carbamate, resulting in a new molecule with potential applications in various fields.

InChI:InChI=1/C7H18NO3P/c1-3-10-12(9,11-4-2)7-5-6-8/h3-8H2,1-2H3

Upstream product

• 10123-62-3 diethyl (2-cyanoethyl)phosphonate 
• 3986-95-6 diethyl (3-oxopropyl)phosphonate 
• 2526-67-2 diethyl 3-amino-3-oxopropylphosphonate 
• 100-46-9 benzylamine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 122-52-1 triethyl phosphite 
• 107257-50-1 [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)propyl]phosphonic acid diethyl ester 
• 260410-26-2 (3-azidopropyl)phosphonic acid diethyl ester 
• 762-04-9 Diethyl phosphonate 
• 107-11-9 1-amino-2-propene 
• 38318-52-4 α-bromovinylphosphonic acid diethyl ester 
• 63637-75-2 dibromo-1,2 ethyl phosphonate de diethyle 
• 2327-68-6 <3-Methoxycarbonyl-propyl>-phosphonsaeure-diaethylester 
• 1186-10-3 diethyl 3-(bromopropyl)phosphonic acid 

Downstream Products

• 113811-50-0 N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonic acid 
• 113811-57-7 diethyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonate 
• 113811-51-1 monoethyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-3-aminopropanephosphonate 
• 54008-28-5 Diaethyl 3(N-acetylamino)propylphosphonat 
• 55849-69-9 (3-hydroxypropyl)phosphonic acid diethyl ester 
• 1404216-49-4 (3-{[(benzyloxy)carbonyl]amino}propyl)(ethoxy)phosphinic acid triethylammonium salt 
• 1404216-50-7 C₁₃H₁₉ClNO₄P 
• 1404216-51-8 benzyl N-(3-{ethoxy[3-(octadecyloxy)propoxy]phosphoryl}propyl)carbamate 
• 1404216-53-0 ethyl 3-(octadecyloxy)propyl [3-({[4-(benzyloxy)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl}amino)propyl]phosphonate 
• 1404216-55-2 benzyl N-(3-{ethoxy[3-(hexadecyloxy)propoxy]phosphoryl}propyl)carbamate 
• 1404216-57-4 ethyl 3-(hexadecyloxy)propyl [3-({[4-(benzyloxy)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl}amino)propyl]phosphonate 
• 1404217-67-9 diethyl [3-({[4-(benzyloxy)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methyl}amino)propyl]phosphonate 

Relevant academic research and scientific papers

D-glucose-based azacrown ethers with a phosphonoalkyl side chain: Application as enantioselective phase transfer catalysts

Five chiral α-D-glucose-based monoaza-15-crown-5 ethers with a phosphonoalkyl side chain 5a-e have been synthesized. The substituent at the nitrogen atom has a major influence on the cation extraction ability of the azacrown. The new lariat ethers 5a-e show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone.

A fluorescent substrate for carbon-phosphorus lyase: Towards the pathway for organophosphonate metabolism in bacteria

Many species of bacteria can use naturally occurring organophosphonates as a source of metabolic phosphate by cleaving the carbon-phosphorus bond with a multi-enzyme pathway collectively called carbon-phosphorus lyase (CP-lyase). Very little is known about the fate of organophosphonates entering this pathway. In order to detect metabolic intermediates we have synthesized a fluorescently labelled organophosphonate and show that this is a viable substrate for the CP-lyase pathway in Escherichia coli and that the expected product of CP-bond cleavage is formed. The in vivo competence of one potential metabolic intermediate, 1-ethylphosphonate-α-d-ribofuranose, is also demonstrated.

PYRIMIDINE COMPOUNDS CONTAINING ACIDIC GROUPS

The present disclosure relates to a class of pyrimidine derivatives having immunomodulating properties that act via TLR7 which are useful in the treatment of viral infections and cancers.

Synthesis, antiviral, cytotoxic and cytostatic evaluation of N1-(Phosphonoalkyl)uracil derivatives

A series of N1-(phosphonoalkyl)uracils was prepared in a two-step reaction sequence from x- aminoalkylphosphonates and (E)-3-ethoxyacryloyl isocyanate followed by the uracil ring closure. Under standard conditions (NCS; NBS; I2/CAN) all N1-(phosphonoalkyl)uracils were transformed into the respective 5-halogeno derivatives to be later benzoylated at N3. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses. One compound was slightly active against human cytomegalovirus in HEL cell cultures (EC50 = 45 μM) while another showed weak activity against varicella-zoster virus (TK+ VZV strain OKA and TK- VZV strain 07-1) with EC50 = 43 and 53 μM, respectively. In addition, several compounds exhibited noticeable inhibitory effects on the proliferation of human cervical carcinoma cells (HeLa) at a concentration lower than 200 μM.

Cyclopropanation of 1,2-dibromoethylphosphonate: A synthesis of β-aminocyclopropylphosphonic acid and derivatives

Diethyl (1,2-dibromoethyl)phosphonate was found to undergo cyclopropanation with nitromethane in good yield. The resulting trans β-nitrocyclopropylphosphonate was converted to the trans N-protected aminocyclopropylphosphonate through a reduction-protection sequence. Subsequent hydrolysis gave the free β-aminocyclopropylphosphonic acid without any formation of ring-opening byproduct. Cyclopropanation of 1,2-dibromoethylphosphonates with nitroalkanes and their reduction are also discussed.

Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase

The pathogenic protozoa responsible for malaria lack enzymes for the de novo synthesis of purines and rely on purine salvage from the host. In Plasmodium falciparum (Pf), hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT) converts hypoxanthine to inosine monophosphate and is essential for purine salvage making the enzyme an anti-malarial drug target. We have synthesized a number of simple acyclic aza-C-nucleosides and shown that some are potent inhibitors of Pf HGXPRT while showing excellent selectivity for the Pf versus the human enzyme.

PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND USES THEREOF

The invention relates to compounds of formula (I) that are inhibitors of hypoxanthine and/or guanine purine phosphoribosyltransferases and to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and methods of treating diseases or conditions in which it is desirable to inhibit hypoxanthine and/or guanine purine phosphoribosyltransferases. Such diseases include malaria.

Design, synthesis, and miniemulsion polymerization of new phosphonate surfmers and application studies of the resulting nanoparticles as model systems for biomimetic mineralization and cellular uptake

Heterophase polymerizations have gained increasing attention in the past decades, especially as the decoration and functionalization of the particle surface for further applications gets more and more into focus. One promising approach for the functionalization exclusively on the particle surface is the use of surfmers (surfactant and monomer). Herein, we present the synthesis of a new family of surfmers and their use for decorating nanoparticles with phosphonate groups through miniemulsion polymerization. Furthermore the synthesis of a dye-labeled functional surfmer provided an elegant manner to evaluate and get deeper insights about its copolymerization. Additionally, potential applications of the synthesized particles in biological studies as well as their use as template for biomimetic mineralization are presented.

COMPOUNDS (CYSTEIN BASED LIPOPEPTIDES) AND COMPOSITIONS AS TLR2 AGONISTS USED FOR TREATING INFECTIONS, INFLAMMATIONS, RESPIRATORY DISEASES ETC.

The invention provides a novel class of compounds viz. generally lipopeptides like Pam3CSK4, immunogenic compositions and pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors 2. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness a vaccine.

PREPARATION OF AN INORGANIC SUBSTRATE HAVING ANTIMICROBIAL PROPERTIES

The invention relates to a process for modifying an inorganic substrate, directed toward giving it antimicrobial properties, said process consisting in grafting in one or more steps onto a surface of said substrate groups with intrinsic antimicrobial properties or groups capable of releasing species with antimicrobial properties. The grafting is performed by means of an organophosphorus coupling agent. A subject of the invention is similarly a substrate obtained by this process, as well as diverse uses of such a substrate.