28149-48-6

Basic information

• Product Name: 4-(Diethoxyphosphinylmethyl)benzoic Acid
• Synonyms: 4-(Diethoxyphosphinylmethyl)benzoic Acid;4-Carboxyphenyl Phosphonate;α-Phosphono-p-toluic Acid P,P-Diethyl Ester;4-((diethoxyphosphoryl)Methyl)benzoic acid;((Diethoxyphosphoryl)methyl)benzoic acid
• CAS NO: 28149-48-6
• Molecular Formula: C₁₂H₁₇O₅P
• Molecular Weight: 272.234141
• Product Categories: Aromatics;Inhibitors;Phosphorylating and Phosphitylating Agents
• Mol File: 28149-48-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(Diethoxyphosphinylmethyl)benzoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Diethoxyphosphinylmethyl)benzoic Acid(28149-48-6)
• EPA Substance Registry System: 4-(Diethoxyphosphinylmethyl)benzoic Acid(28149-48-6)

Safety Data

• Hazardous Substances Data: 28149-48-6(Hazardous Substances Data)

Usage

Uses

Used for the preparation of cholesterol acyltransferase-1 (ACAT-1) inhibitors suitable for use as antiarteriosclerotic and anticholesteremic agents.

Upstream product

• 6232-88-8 4-bromomethylbenzoic Acid 
• 122-52-1 triethyl phosphite 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 78-40-0 triethyl phosphate 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 71441-08-2 ethyl 4-(diethoxyphosphorylmethyl)benzoate 
• 1033780-39-0 diethyl 4-(4'-hexadecyloxy-2'-nitrobenzyloxycarbonyl) benzylphosphonate 
• 1373822-42-4 diethyl 4-(N-(4-amino-2-(benzylthio)-6-oxo-1,6-dihydropyrimidin-5-yl)-N-(2-(4-chlorophenoxy)ethyl)carbamoyl)benzylphosphonate 
• 1373822-43-5 methyl hydrogen 4-(2-(benzylthio)-7-(2-(4-chlorophenoxy)ethyl)-6-oxo-6,7-dihydro-1H-purin-8-yl)benzylphosphonate 
• 1373822-44-6 (4-(7-(2-(4-chlorophenoxy)ethyl)-2-(methylamino)-6-oxo-6,7-dihydro-1H-purin-8-yl)benzyl)phosphonic acid 
• 1373822-52-6 4-(2-(benzylthio)-7-(2-(4-chlorophenoxy)ethyl)-6-oxo-6,7-dihydro-1Hpurin-8-yl)benzylphosphonic acid 
• 125185-26-4 diethyl (4-(hydroxymethyl)benzyl)phosphonate 
• 166394-38-3 diethyl 4-(4-hydroxy-6,7-dimethoxyquinazolin-2-yl)benzylphosphonate 
• 133208-93-2 ibrolipim 

Relevant articles and documents

Identification of novel non-nucleoside vinyl-stilbene analogs as potent norovirus replication inhibitors with a potential host-targeting mechanism

Norovirus (NV), is the most common cause of acute gastroenteritis worldwide. To date, there is no specific anti-NV drug or vaccine to treat NV infections. In this study, we evaluated the inhibitory effect of different stilbene-based analogs on RNA genome replication of human NV (HNV) using a virus replicon-bearing cell line (HG23). Initial screening of our in-house chemical library against NV led to the identification of a hit containing stilbene scaffold 5 which on initial optimization gave us a vinyl stilbene compound 16c (EC50 = 4.4 μM). Herein we report our structure-activity relationship study of the novel series of vinyl stilbene analogs that inhibits viral RNA genome replication in a human NV-specific manner. Among these newly synthesized compounds, several amide derivatives of vinyl stilbenes exhibited potent anti-NV activity with EC50 values ranging from 1 to 2 μM. A trans-vinyl stilbenoid with an appended substituted piperazine amide (18k), exhibited potent anti-NV activity and also displayed favorable metabolic stability. Compound 18k demonstrated an excellent safety profile, the highest suppressive effect, and was selective for HNV replication via a viral RNA polymerase-independent manner. Its potential host-targeting antiviral mechanism was further supported by specific activation of heat shock factor 1-dependent stress-inducible pathway by 18k. These results suggest that 18k might be a promising lead compound for developing novel NV inhibitors with the novel antiviral mechanism.

Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonate diesters with benzyl halides. Synthetic and mechanistic studies

We have developed a new, efficient method for the synthesis of benzylphosphonate and benzylphosphonothioate diesters via a palladium(0)- catalyzed cross-coupling reaction between benzyl halides and H-phosphonate or H-phosphonothioate diesters, using Pd2(dba)3(CHCl 3) as a palladium source and Xantphos as a supporting ligand. Some mechanistic aspects of these reactions were investigated using 31P NMR spectroscopy.

NOVEL SAFRAMYCIN ANALOGS AS THERAPEUTIC AGENTS

The present invention is directed to saframcyin analogs that are useful in the treatment of cancer. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.